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WO1993012113A1 - 3-SUBSTITUTED IMIDAZO (1,5-a) AND IMIDAZO (1,5-a)-TRIAZOLO (1,5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY - Google Patents

3-SUBSTITUTED IMIDAZO (1,5-a) AND IMIDAZO (1,5-a)-TRIAZOLO (1,5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY Download PDF

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Publication number
WO1993012113A1
WO1993012113A1 PCT/US1992/010388 US9210388W WO9312113A1 WO 1993012113 A1 WO1993012113 A1 WO 1993012113A1 US 9210388 W US9210388 W US 9210388W WO 9312113 A1 WO9312113 A1 WO 9312113A1
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WIPO (PCT)
Prior art keywords
imidazo
triazol
methyl
quinazoline
quinoxalin
Prior art date
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PCT/US1992/010388
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French (fr)
Inventor
Ronald B. Gammill
Louis L. Skaletzky
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Pharmacia and Upjohn Co
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Upjohn Co
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Publication of WO1993012113A1 publication Critical patent/WO1993012113A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems

Definitions

  • Compounds of the present invention are therapeutically active compounds of imidazo-
  • U.S. Patent 4,440,929 and 4,866,065 discloses 4-thio, 4-imino, 4-hydroxyimino, 4- oxoimidazo(1,5-a)quinoxaline compounds containing nitrile, carboxaldehyde, carboxylic acid, ester, amide and methylalcohol substituents at the 3-position and H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy, and alkanoyl at the 5-position.
  • European Patent 202,441-A discloses imidazo(1,5-a)quinazoline compounds useful as anxiolytic and hypnotic agents, containing an oxadiazole at the 3-position and halogen, nitrile, methyl and trifluoromethyl groups at the 6-position.
  • U.S. Patent 4,968,682 and 4,999,354 discloses 4-oxoimidazo(1,5-a)quinoxaline compounds useful as anxiolytic and hypnotic agents, containing oxadiazole or ester substituents at the 3-position and hydrogen or halogen substituents at the 6-position.
  • the ring atom at position 6 may be carbon or nitrogen.
  • European Patent 283,162; U.S. Patents 4,902,686 and 4,873,244 disclose 4- oxoimidazo(1,50a)quinoxalines and 5-oxoimidazo(1,5-a)quinazolines having anticonvulsant and anxiolytic activity, with oxadiazoles, esters, and amides at position 3.
  • U.S. Patent 4,745,112 discloses imidazobenzodiazepines useful as anticonvulsants and anxiolytics containing an oxadiazole at the 3-position.
  • U.S. Patent 4,999,353 discloses 4-oxoimidazoquinoxalines useful as anxiolytics and hypnotics with an oxadiazole at position 3 and tert-butyl at position 5.
  • U.S. Patent 5,034,530 discloses imidazo(1,5-a)quinoxalines useful as anxiolytics and hypnotics with oxadiazoles at position 3 and no substitution at position 5 (imino) or 5 N-oxide-
  • U.S. Patent 4,939,139 discloses imidazo(1,5-a)benzodiazepines useful as anxiolytics containing an oxadiazole at position 3.
  • J. Med. Chem (1991) 34, 281-290 discloses 5-oxo(1,2,4)triazolo(1,5-c)quinazoIines with affinity for the benzodiazepine receptor, with phenyl, pyridinyl, CF 3 , ester, fiiranyl, thienyl, tetrahydrofuranyl at position 2.
  • J. Med. Chem. (198831 , 1098-1115 discloses 4-oxoimidazo(1,5-a)quinoxalines with an ester at position 3.
  • the subject of the paper is antiallergy agents.
  • EP 347.094A discloses imidazo(1,5-a)quinoxaline-4,5-enes useful for treating CNS disorders with no substitution at N 5 .
  • U.S. Patent 5,075,304 discloses certain imidazoquinoxaline, and U.S. Patent 5,100,895 discloses them as well with an additional fourth, fused heterocyclic ring.
  • the subject invention is a compound of Formula (I)
  • Z is -N(R 1 )-C(O)- or -C(O)-N(R 1 )-; where, R 1 is C 1-6 alkyl, C 3-7 cycloalkyl (optionally substituted with C 1-6 alkyls), C 1-6 alkyl-C 6-12 aryl, C 1-6 alkyI-C 6-12 heteroaryl, -(CH 2 ) n -R f , -(CH 2 ) n - CO-R d , -(CH 2 ) d -CHOH-R e , -CH 2 CH 2 OCH 3 , -CH(CH 3 )CH 2 OH, -CH(CH 3 )CH 2 OCH 3 , -CH 2 -(2- furan), -CH 2 -(3-furan) or -CH 2 -(2-pyran);
  • G is CH 2 , O, S, S(O) y , NR 6 and Q is -CHO, OH, NR, OR;
  • each R is independently choosen from H, F, Cl, Br, I, C 1-6 alkyl, CF 3 , CN, NO 2 , CONH 2 , CONH-R 6 , C(O)OR 6 , OR 6 ;
  • R 5 is H, F, Cl, Br, I, CF 3 , CN, -CH 2 CH 2 CF 3 , -CH 2 CH(CF 3 )CH 3 , C 3-6 cycloalkyl
  • R 6 are independently H, C 1-6 alkyl, C 6-12 aryl, C 1-6 alkyl-C 6-1 2 aryl, C 6-12 heteroaryl, C 1-6 alkyl-C 6-12 heteroaryl, -(CH 2 ) n -CO-(C 1-6 alkyl, -C 6-12 aryl or -C 6-12 heteroaryl), or when two -R 6 's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
  • R 9 is C 1-6 alkyl, C 6-12 aryl, C 1-6 alkyl-C 6-12 aryl, C 6-12 heteroaryl, C 1-6 alkyl-C 6-12 heteroaryl;
  • R a is -R 6 , CH(OH)R 9 , CO 2 R 9 , CON(R 6 ) 2 , (CH 2 ) n OR 6 , (CH 2 ) n SR 6 , (CH 2 ) n S(O) y R 9 , (CH 2 ) n N(R 6 ) 2 ;
  • R b is -(CH 2 ) d -OR 6 , -(CH 2 ) d -SR 6 , -(CH 2 ) n -OR 9 , -(CH 2 ) n -SR 9 , -(CH 2 ) d -S(O) y R 9 , - (CH 2 ) n N(R 6 ) 2 , -(CH 2 ) n -C 1-6 alkyl, -(CH 2 ) n -C 6-12 aryl, -(CH 2 ) n -C 6-12 heteroaryl;
  • R c is -(CH 2 ) d -OR 6 , -(CH 2 ) d -S(O) y R 9 , -(CH 2 ) d -NO 6 ) 2 , -(CH 2 ) n -C 1-6 -alkyl, -(CH 2 ) n -C 6-12 aryl, -(CH 2 ) n -C 6-12 heteroaryl, -(CH 2 ) n -C 6-12 heteroaryl;
  • R d is -(CH 2 ) d -OR 9 , -(CH 2 ) d -OR 6 , -(CH 2 ) d -SR 6 , -(CH 2 ) d -S(O) y R 9 , -(CH 2 ) n -N(R 6 ) 2 , (CH 2 ) n C 1-6 alkyl, -(CH 2 ) n -C 6-12 aryl, -(CH 2 ) n -C 6-12 heteroaryl;
  • R e is -(CH 2 ) 4 -OR 6 , -(CH 2 ) d -SR 6 , -(CH 2 ) d -S(O) y R 9 , -(CH 2 ) d -N(R 6 ) 2 , -(CH 2 ) d -N(O)(R 6 ) 2 , - (CH 2 ) n -C 1-6 alkyl, -(CH 2 ) n -C 6-12 aryl, -(CH 2 ) n -C 6-12 heteroaryl;
  • R f is -O-R 6 , -SR 6 ,-S(O) y R 9 , -O-(CH 2 )nN-R 6 , -S-(CH 2 ) n -R 6 , -S(O) y -(CH 2 ) n -R 9 , -N(R 6 ) 2 , -
  • R 1 cannot be C 1-6 alkyl, C 1-6 alkyl-C 6-12 aryl, C 1-6 alkyl-C 6-12 heteroaryl or -(CH 2 ) n -R f (to avoid the compounds disclosed in US Patent 4,440,929);
  • the subject invention is a compound of formula (II)
  • G is CH 2 , O, S, S(O) y , NR 6 ;
  • Q is -CHO, OH, NR, OR 1 ; and
  • n is 0-3;
  • R are each independently choosen from H, F, Cl, Br, I, C 1-6 alkyl, CF 3 , CN, NO 2 , CONH 2 , CONHR 6 , C(O)OR 6 , OR 6 ;
  • R 5 is H, F, Cl, Br, I, CF 3 , CN, -CH 2 CH 2 CF 3 , -CH 2 CH(CF 3 )CH 3 , C 3-6 cycloalkyl
  • R 6 are independently H, C 1-6 alkyl, C 6-12 aryl, C 1-6 alkyl -C 6-12 aryl, C 6 -12 heteroaryl, C 1-6 alkyl-C 6-12 heteroaryl, -(CH 2 ) n -CO-(C 1-6 alkyl, -C 6-12 aryl or -C 6-12 heteroaryl), or when two R 6 's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
  • R 9 is C 1-6 alkyl, C 6- 12 aryl, C 1-6 alkyl-C 6-12 aryl, C 6-12 heteroaryl, C 1-6 alkyl-C 6-12 heteroaryl;
  • R a is -R 6 , CH(OH)R 9 , CO 2 R 9 , CON(R 6 ) 2 , (CH 2 ) n OR 6 , (CH 2 ) n SR 6 , (CH 2 ) n S(O) y R 9 , (CH 2 ) n N(R 6 ) 2 ;
  • R b is -(CH 2 ) d -OR 6 , -(CH 2 ) d -SR 6 , -(CH 2 ) n -OR 9 , -(CH 2 ) n -SR 9 , -(CH 2 ) d -S(O) y R 9 ,
  • R c is -(CH 2 ) d -OR 6 , -(CH 2 ) d -S(O) y -R 9 , -(CH 2 ) d -N(R 6 ) 2 , -(CH 2 ) n -C 1-6 alkyl, -(CH 2 ) n -C 6-12 aryl, -(CH 2 ) n -C 6-12 heteroaryl;
  • the subject invention is a compound of an imidazo(1,5- a)quinoxaline of formula (III)
  • R are independentiy H, F, Cl, C 1-6 alkyl, CN, O-C 1-6 alkyl, CONH 2 , CONHR 6 , CO 2 R 6 , or OH;
  • R 5 is -(CH 2 ) P -N(R 6 ) 2 or C 3-7 cycloalkyl (substituted with F, Cl, C 2 -6 alkyl, or methyl provided at least one R is F or Cl);
  • R 6 is independently H, C 1-6 alkyl, C 6-12 aryl, C 6-12 heteroaryl, C 1-6 alkyl-C 6-12 aryl, C 1-6 alkyl-C 6-12 heteroaryl, or when two R 6 's are attached to the same nitrogen atom they can form a cyclic system, containing, in addition to the specified nitrogen atom, one other nitrogen or oxygen atom.
  • Preferred compounds of imidazo(1,5-a)quinoxaline of Formula III are where X is structure (a); R is H or F; and R 1 is a C 1 -6 alkyl.
  • Especially preferred compounds of Formula III are a. 3-(5-(1-Methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
  • the subject invention is a method or use of compounds from
  • Formula I, II or III for the preparation of a medicament useful in treating central nervous syste disorders associated with benzodiazepine receptors by administering to a subject in need of such treatment a therapeutically-effective amount of the compound to alleviate such disorder.
  • Alkyl are one to six carbon atoms or, as otherwise indicated, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, and isomeric forms thereof.
  • Aryl are six to twelve carbon atoms such as phenyl, ⁇ -naphthyl, ⁇ -naphthyl, m- methylphenyl, p-trifluoromethylphenyl and the like.
  • the aryl groups can also be substituted with one to 3 hydroxy, OR 8 , -OCOR 8 , fluoro, chloro, or bromo groups.
  • Cycloalkyl are three to seven carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Alkyl-aryl are alkyl chains of one to six carbon atoms and isomeric forms thereof which are substituted with aryl groups of six to twelve carbon atoms as described above.
  • Heteroaryl are six to twelve carbon atoms aryl, as described above, containing the heteroatoms nitrogen, sulfur or oxygen. Examples can include pyridine, thiophene, furan, pyrimidine, 2-pyridyI, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 3- pyridazinyl, 4-pyridazinyl, 3-pyrizinyl, 2-quinolyl, 3-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4- isoquinolyl, 2-quinazoIinyl, 4-quinazolinyl, 2-quinoxalinyl, 1-phthalazinyl, 2-imidazolyl, 4- imidazolyl, 3-isoxazoIyl, 4-isoxazolyl, 5-isoxazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- oxazolyl, 4-o
  • Pharmaceutically acceptable salts include salts of both inorganic and organic acids.
  • the pharmaceutically acceptable salts are preferred over the corresponding free amines since they produce compounds which are more water soluble.
  • the preferred pharmaceutically acceptable salts include salts of the following acids: methanesolfonic, hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, benzoic, citric, tartaric, fumaric or maleic.
  • the subject compounds are active orally or parenterally.
  • the compounds can be given in solid dosage forms as tablets or capsules, or can be given in liquid dosage forms such as elixirs, syrups or suspensions as is known to those skilled in the art. It is preferred that the compounds be given in solid dosage form and that it be a tablet.
  • the compound can be mixed with conventional ingredients such as talc, magnesium stearate, dicalcium phosphate, magnesium aluminum silicate, calcium sulfate, starch, lactose, acacia, methylcellulose, and functionally similar materials as pharmaceutical diluents or carriers.
  • Capsules are prepared by mixing the compound with an inert pharmaceutical diluent and filling the mixture into a hard gelatin capsule of appropriate size.
  • Soft gelatin capsules are prepared by machine encapsulation of a slunry of the compound with an acceptable vegetable oil, light liquid petrolatum or other insert oil.
  • Fluid unit dosage forms for oral administration such as syrups, elixirs, and suspensions can be prepared.
  • the forms can be dissolved in an aqueous vehicle together with sugar, aromatic flavoring agents and preservatives to form a syrup.
  • Suspensions can be prepared with an aqueous vehicle with the aid of a suspending agent such as acacia, tragacanth,
  • fluid unit dosage forms can be prepared utilizing the compound and a sterile vehicle.
  • the compound can be dissolved in water for injection and filter sterilized before filling into a suitable vial or ampoule and sealing.
  • Adjuvants such as a local anesthetic, preservative and buffering agents can be dissolved in the vehicle.
  • the composition can be frozen after filling into a vial and the water removed under vacuum.
  • the lyophilized powder can then be sealed in the vial and reconstituted prior to use.
  • the compounds should be given in amounts of about 0.25 mg to about 100 mg/person, one to three times a day. Preferably, about 10 to about 50 mg/day in divided doses.
  • the compounds should be given in the amount of about 0.25 mg to about 500 mg/person, preferrably at bedtime or when sedation is needed. It is preferred the sedative/hypnotic dose be from about 10 to about 100 mg/person.
  • the exact dosage and frequency of administration depends on the particular compound used, the particular condition being treated, the severity of the condition being treated, the age, weight, general physical condition of the particular patient, other medication the individual may be taking as is well known to those skilled in the art and can be more accurately determined by measuring the blood level or concentration of the compound in the patient's blood and/or the patient's response to the particular condition being treated.
  • the subject compounds along with a pharmaceutically-acceptable carrier, diluent o buffer can be administrated in a therapeutic or pharmacological amount effective to alleviate th central nervous system disorder with respect to the physiological condition diagnosed.
  • the compounds can be administered intravenously, intramuscularly, topically, transdermally such as by skin patches, bucally or orally to man or other vertebrates.
  • t-Butyl 4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxylate was treated with trifluoroacetic acid in methylene chloride to remove the tert-butyl ester group.
  • 4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaIine-3-carboxylic acid was treated with thionyl chloride followed by sodium azide to yield 4,5-dihydro-4-oxo-5-(1-methylethyl)- imidazo(1,5-a)-quinoxaline-3-carboxyI azide.
  • That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxycarbonyI)amino)-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5- a)-quinoxaline.
  • That carbamate was then decomposed with potassium hydroxide to yield 3- amino-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)-quinoxaline.
  • the dione (1.02 g) was dissolved in THF (10 mL) and cooled to 0°C.
  • Potassium t- butoxide (1.0 M in THF, 5.5 mL) was added, then the reaction was cooled to -20°C and diethylchlorophosphate (795uL) was added. The reaction was warmed to 23°C for 30 minutes, then cooled to -78°C and the isonitrile (800 uL) was added.
  • Potassium t-butoxide 1.0 M in THF, 5.5 mL was added and the reaction was warmed to 23°C for 3 hours.
  • Trifluoroacetic acid 500 uL was dissolved in methylene chloride (2.0 mL) and cooled to 0°C. A solution of the ester (650 mg) in methylene chloride (3.0 mL) was added and the reaction was allowed to warm to 23°C for 2.5 hours. The solvent was evaporated and the residue was dried in a vacuum oven for 17 hours at 45°C to give the extremely insoluble acid as a tan solid (542 mg, 99%).
  • the amine (2.42 g) was dissolved in water (4.0 mL) and concentrated HCI (2.3 mL) wa added. The mixture was cooled to 0°C and sodium nitrite (760 mg) was added. The reaction was stirred for 0°CC for 2 hours, then filtered. Sodium azide (716 mg) was added and gas evolution began immediately, followed by formation of a pale yellow precipitate. The reaction was stirred at 0°C for 2 hours, then extracted with ethyl acetate (3 x 175 mL). The combined extracts were washed with water (2 x 40 mL) and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to a yellow solid.
  • 1,2,3,4-tetrahydro-2,4-dioxo-quinazoline was reacted with t-butylisocyanate using reaction conditions as described in US Patent 4,771,051 to yield t-butyl 4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)-quinoxaline-3-carboxylate which was treated with trifluoroacetic acid in methylene chloride to remove the tert-butyl ester group.
  • 4,5-Dihydro-4-methyl-5-oxo- imidazo(1,5-a)-quinoxaline-3-carboxylic acid was treated with thionyl chloride followed by sodium azide to yield 4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline-3-carboxyl azide. That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxycarbonyl)amino)-4,5- dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaIine.
  • Ethyl imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylate was added to a mixture of water and methanol containing potassium carbonate.
  • the resulting acid, imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylic acid was then treated with thionyl chloride followed by sodium azide to yield imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxyl azide.
  • That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxy- carbonyl)ammino)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline.
  • That carbamate was then decomposed with potassium hydroxide to yield 3-amino-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline.

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Abstract

An oxoimidazo(1,5-a)quinoxaline and a oxoimidazo(1,5-a)quinazoline of formula (I), an imidazo(1,5-a)-1,2,4-triazolo-(4,3-c)quinazoline and an imidazo(1,5-a)-1,2,4-triazolo-(4,3-c)quinozoline of formula (II), and an imidazo(1,5-a)quinoxaline of formula (III). The R-groups and other variables are as defined herein. The compounds are useful in the treatment of central nervous system disorders associated with the benzodiazepine receptors in a subject in need of such treatment comprising administering to the subject a therapeutically-effective amount of a formula I, II, or III compound for alleviation of such disorder. Typically, the compound of formula I, II, or III is administered in the form of a pharmaceutical composition comprising a pharmaceutically-acceptable carrier or diluent.

Description

3-SUBSTITUTED IMIDAZO ( 1, 5-a) AND IMIDAZO ( 1, 5-a)-TRIAZOLO
( 1, 5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY
BACKGROUND OF THE INVENTION
1. Field of the Invention
Compounds of the present invention are therapeutically active compounds of imidazo-
(1,5-a)quinoxalines (Formula I), imidazo(1,5-a)-1,2,4-triazolo-(4,3-c)quinazoline (Formula II), and imidazo(1,5-a)-1,2,4-triazolo-(4,3-c)quinozoline (Formula II) useful in the treatment of central nervous system disorders. Pharmaceutical preparations of these compounds are useful in the treatment of anxiety, sleep disorders, panic disorders, convulsive disorders, muscle relaxant, cognitative disorders and/or depression.
2. Description of the Related Art
U.S. Patent 4,440,929 and 4,866,065 discloses 4-thio, 4-imino, 4-hydroxyimino, 4- oxoimidazo(1,5-a)quinoxaline compounds containing nitrile, carboxaldehyde, carboxylic acid, ester, amide and methylalcohol substituents at the 3-position and H, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxy, and alkanoyl at the 5-position.
A family of U.S. Patents 4,771,051; 4,774,245; 4,880,799; 4,886,797; 4,780,539;
4,795,749; and 4,870,073; disclose imidazo(1,5-a)quinoxaline and 4-oxoimidazo(1,5- a)quinoxalines compounds, useful as anxiolytic and hypnotic agents, having an oxadiazole substituent at the 3-position.
European Patent 202,441-A discloses imidazo(1,5-a)quinazoline compounds useful as anxiolytic and hypnotic agents, containing an oxadiazole at the 3-position and halogen, nitrile, methyl and trifluoromethyl groups at the 6-position.
U.S. Patent 4,968,682 and 4,999,354 discloses 4-oxoimidazo(1,5-a)quinoxaline compounds useful as anxiolytic and hypnotic agents, containing oxadiazole or ester substituents at the 3-position and hydrogen or halogen substituents at the 6-position. The ring atom at position 6 may be carbon or nitrogen.
European Patent 283,162; U.S. Patents 4,902,686 and 4,873,244 disclose 4- oxoimidazo(1,50a)quinoxalines and 5-oxoimidazo(1,5-a)quinazolines having anticonvulsant and anxiolytic activity, with oxadiazoles, esters, and amides at position 3.
South African Patent 8701,535, assigned to The Upjohn Company, discloses 5- oxoimidazo(1,5-a)quinazolines having anxiolytic activity, with oxadiazole and ester substituents at position 3 and Cl at position 6.
U.S. Patent 4,745,112 discloses imidazobenzodiazepines useful as anticonvulsants and anxiolytics containing an oxadiazole at the 3-position.
U.S. Patent 4,999,353 discloses 4-oxoimidazoquinoxalines useful as anxiolytics and hypnotics with an oxadiazole at position 3 and tert-butyl at position 5. U.S. Patent 5,034,530 discloses imidazo(1,5-a)quinoxalines useful as anxiolytics and hypnotics with oxadiazoles at position 3 and no substitution at position 5 (imino) or 5 N-oxide-
U.S. Patent 4,939,139 discloses imidazo(1,5-a)benzodiazepines useful as anxiolytics containing an oxadiazole at position 3.
J. Med. Chem (1991) 34, 281-290 discloses 5-oxo(1,2,4)triazolo(1,5-c)quinazoIines with affinity for the benzodiazepine receptor, with phenyl, pyridinyl, CF3, ester, fiiranyl, thienyl, tetrahydrofuranyl at position 2.
J. Med. Chem. (198831 , 1098-1115 discloses 4-oxoimidazo(1,5-a)quinoxalines with an ester at position 3. The subject of the paper is antiallergy agents.
PCT Publication, WO 91/07407; US Patent 5,116,841 assigned to Novo Nordisk, discloses 4-oxoimidazoquinoxaIines useful as anxiolytics and hypnotics with isoxazoles at position 3.
PCT Publication, WO 91/07408, assigned to Novo Nordisk, discloses 4- oxoimidazoquinoxalines useful as anxiolytics and hypnotics with ketones at position 3.
EP 347.094A discloses imidazo(1,5-a)quinoxaline-4,5-enes useful for treating CNS disorders with no substitution at N5.
U.S. Patent 5,075,304 discloses certain imidazoquinoxaline, and U.S. Patent 5,100,895 discloses them as well with an additional fourth, fused heterocyclic ring.
SUMMARY OF THE INVENTION
In one aspect, the subject invention is a compound of Formula (I)
Figure imgf000004_0001
or a pharmaceutically acceptable salt thereof wherein:
Z is -N(R1)-C(O)- or -C(O)-N(R1)-; where, R1 is C1-6 alkyl, C3-7 cycloalkyl (optionally substituted with C1-6 alkyls), C1-6 alkyl-C6-12 aryl, C1-6 alkyI-C6-12 heteroaryl, -(CH2)n-Rf, -(CH2) n- CO-Rd, -(CH2)d-CHOH-Re, -CH2CH2OCH3, -CH(CH3)CH2OH, -CH(CH3)CH2OCH3, -CH2-(2- furan), -CH2-(3-furan) or -CH2-(2-pyran);
Figure imgf000005_0001
h) -CH=CHRa or -C≡CRa,
i) -(CH2)n-G-(CH2)n-Q, or
j) -C(O)OR or -C(O)NR,
k) R5 (except for C6-12 aryl and C6-12 heteroaryl),
where, G is CH2, O, S, S(O)y, NR6 and Q is -CHO, OH, NR, OR;
each R is independently choosen from H, F, Cl, Br, I, C1-6 alkyl, CF3, CN, NO2, CONH2, CONH-R6, C(O)OR6, OR6;
R5 is H, F, Cl, Br, I, CF3, CN, -CH2CH2CF3, -CH2CH(CF3)CH3, C3-6 cycloalkyl
(substituted with a F, Cl, Br, I, C2-6 alkyl, C6-12 aryl, OH, NH2, OR6 or methyl provided at least one R is F or Cl), C1-6 alkyl-C3-6 cycloalkyl (substituted by F, Cl, Br. I, C1-6 alkyl, C6-12 aryl, OH, NH2 or OR6), C6-12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n- CO-Rb (except, n is at least 1 when Rb is C6-12 aryl), -(CH2)n-CHOH-Rc, 2- or 3- tetrahydrofurfuryl, 2- or 3-tetrahydrofuran (optionally substituted with H, C1-6 alkyl, OH, or C6-12 aryl), 2- or 3-tetrahydrothiophene, 2- or 3-tetrahydrothiophene sulfoxide, 2- or 3- tetrahydrothiophene sulfone (optionally substituted with H, C1-6 alkyl, OH, C6-12 aryl), -(CH2)n- (N-R6-pyrolidin-2-yl), -(CH2)n-N(R6)2, -C*(R9)(CH2)d-NH9-(C*H2)n, (where * indicates the atoms are bonded to each other);
R6 are independently H, C1-6 alkyl, C6-12 aryl, C1-6 alkyl-C6-1 2 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n-CO-(C1-6 alkyl, -C6-12 aryl or -C6-12 heteroaryl), or when two -R6's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
R9 is C1-6 alkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl, C1-6alkyl-C6-12 heteroaryl;
Ra is -R6, CH(OH)R9, CO2R9, CON(R6)2, (CH2)nOR6, (CH2)nSR6, (CH2)nS(O)yR9, (CH2)nN(R6)2;
Rb is -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)n-OR9, -(CH2)n-SR9, -(CH2)d-S(O)yR9, - (CH2)nN(R6)2, -(CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
Rc is -(CH2)d-OR6, -(CH2)d-S(O)yR9, -(CH2)d-NO6)2, -(CH2)n-C1-6-alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl, -(CH2)n-C6-12 heteroaryl;
Rd is -(CH2)d-OR9, -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)d-S(O)yR9, -(CH2)n-N(R6)2, (CH2)nC1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
Re is -(CH2)4-OR6, -(CH2)d-SR6, -(CH2)d-S(O)yR9, -(CH2)d-N(R6)2, -(CH2)d-N(O)(R6)2, - (CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
Rf is -O-R6, -SR6,-S(O)yR9, -O-(CH2)nN-R6, -S-(CH2)n-R6, -S(O)y-(CH2)n-R9, -N(R6)2, -
N(O)(R6)2;
d is 1-3; each n is independently 0-3; y is 1-2; and with the following provisos:
(1) when Z is -N(R1)-C(O)-, and -(CH2)n-X is defined as n is 0 and X is j then R1 cannot be C1-6 alkyl, C1-6 alkyl-C6-12 aryl, C1-6 alkyl-C6-12 heteroaryl or -(CH2)n-Rf (to avoid the compounds disclosed in US Patent 4,440,929);
(2) when Z is -C(O)-N(R1)-, and -(CR2)n-X is defined as X is a or b and n is 0 then R cannot be H, F, Cl, R1 cannot be C1-6 alkyl or C3-7 cycloalkyl, and R5 cannot be C1-6 alkyl, C3-7 cycloalkyl or C3-7 cycloalkylmethyl (to avoid the compounds disclosed in US Patent 4,771,051 and 4,780,539);
(3) when Z is -N(R1)-C(O)-, and (CH2)n-X is defined as X is a, b or -C(O)OR and n is 0 then R1 cannot be isopropyl, R5 cannot be C1-6 alkyl, C3-7 cycloalkyl or C1-6 alkoxymethyl (to avoid the compounds disclosed in US Patent 4,999,354).
In another aspect the subject invention is a compound of formula (II)
Figure imgf000006_0001
or a pharmaceutially acceptable salt thereof wherein:
Z is -N=CH- or -CH=N-;
Figure imgf000007_0001
h) -C=CHRa or -C≡Ra;
i) -(CH2)n-G-(CH2)n-Q,
j) -C(O)(NR, C1-6 alkyl, C6-12 aryl or C6-12 heteroaryl), or
k) C6-12 aryl or C6-12 heteroaryl,
O R5
where, G is CH2, O, S, S(O)y, NR6; Q is -CHO, OH, NR, OR1; and n is 0-3;
R are each independently choosen from H, F, Cl, Br, I, C1-6 alkyl, CF3, CN, NO2, CONH2, CONHR6, C(O)OR6, OR6;
R5 is H, F, Cl, Br, I, CF3, CN, -CH2CH2CF3, -CH2CH(CF3)CH3, C3-6 cycloalkyl
(substituted with a F, Cl, Br, I, C2-6 alkyl, C6- 12 aryl, OH, NH2, OR6 or methyl provided at least one R is F or Cl), C1-6 alkyl-C3-6 cycloalkyl (substituted by F, Cl, Br, I, C1-6 alkyl, C6-12 aryl, OH, NH2 or OR6), C6-12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n- CO-Rb (except, n is at least 1 when Rb is C6-12 aryl), -(CH2)n-CHOH-Rc, 2- or 3- tetrahydrofurfuryl, 2- or 3-tetrahydrofuran (optionally substituted with H, C1-6 alkyl, OH, or C6-12 aryl), 2- or 3-tetrahydrothiophene, 2- or 3-tetrahydrothiophene sulfoxide, 2- or 3- tetrahydrothiophene sulfone (optionally substituted with H, C1-6 alkyl, OH, C6-12 aryl), -(CH2)n- (N-R6-pyrolidin-2-yl), -(CH2)n-N(R6)2, -C*(R9)(CH2)d-NH9-(C*H2)n (where * indicates the atoms are bonded to each other);
R6 are independently H, C1-6 alkyl, C6-12 aryl, C1-6 alkyl -C6-12 aryl, C6 -12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n-CO-(C1-6 alkyl, -C6-12 aryl or -C6-12 heteroaryl), or when two R6's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
R9 is C1-6 alkyl, C6- 12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl, C1-6alkyl-C6-12 heteroaryl;
Ra is -R6, CH(OH)R9, CO2R9, CON(R6)2, (CH2)nOR6, (CH2)nSR6, (CH2)nS(O)yR9, (CH2)nN(R6)2;
Rb is -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)n-OR9, -(CH2)n-SR9, -(CH2)d-S(O)yR9,
(CH2)nN(R6)2, -(CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
Rc is -(CH2)d-OR6, -(CH2)d-S(O)y-R9, -(CH2)d-N(R6)2, -(CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
d is 1-3; y is 1-2.
Preferred compounds of Formula II where Z is -N=CH- are for example,
a. 7-Chloro-3-(5-t-butyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
h. 3-(p-Fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; or
c. 8-Chloro-3-(p-fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. Preferred compounds of Formula II where Z is -CH=N- are for example,
a. Ethyl Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate;
b. t-Butyl Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazolme-3-caιboxylate;
c. 3-(5-IsopropyI-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine; d. 3-(5-t-Butyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; e. 3-(5-Cyclopentyl-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
f. t-Butyl-7-Chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate;
g. 7-Chloro-3-(5-t-butyl-1,2,4-oxadiazol-3-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline; or
h. 7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline.
In yet another aspect, the subject invention is a compound of an imidazo(1,5- a)quinoxaline of formula (III)
Figure imgf000008_0001
or a pharmaceutically acceptable salt thereof wherein:
Figure imgf000009_0001
R are independentiy H, F, Cl, C1-6 alkyl, CN, O-C1-6 alkyl, CONH2, CONHR6, CO2R6, or OH;
R1 is C1-6 alkyl, C3-7 cycloalkyl (which can be substituted with C1-6 alkyl, C1-6 alkyl-C6-12 aryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)o-N(R6)2, -(CH2)pOR6, -CH2)p-S(O)mR6, -CH2)o-CON(R6)2, - CO-(CH2)o-NR6)2, or -(CH2)o--CO2R6 wherein p = 1-5, m = 0-2, o = 0-5;
R5 is -(CH2)P-N(R6)2 or C3-7 cycloalkyl (substituted with F, Cl, C2 -6 alkyl, or methyl provided at least one R is F or Cl); and
R6 is independently H, C1-6 alkyl, C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 aryl, C1-6 alkyl-C6-12 heteroaryl, or when two R6's are attached to the same nitrogen atom they can form a cyclic system, containing, in addition to the specified nitrogen atom, one other nitrogen or oxygen atom.
Preferred compounds of imidazo(1,5-a)quinoxaline of Formula III are where X is structure (a); R is H or F; and R1 is a C1 -6 alkyl. Especially preferred compounds of Formula III are a. 3-(5-(1-Methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
b. 7-Fluoro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
c. 7-Chloro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
d. 7-Fluoro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
e. 7-Chloro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
f. 3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
g. 7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
h. 7-Chloro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-(2- aminoethyl)pyrrolidinyl)y-imidazo(1,5-a)quinoxalin-4(5H)-one; i.7-ChIoro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-(2- aminoethyI)pyrrolidinyl)y-imidazo(1,5-a)quinoxalin-4(5H)-one; or
j. 7-Chloro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2- (aminoethyl)pyridinyI)y-imidazo(1,5-a)quinoxaIin-4(5H)-one.
In yet anther aspect, the subject invention is a method or use of compounds from
Formula I, II or III for the preparation of a medicament useful in treating central nervous syste disorders associated with benzodiazepine receptors by administering to a subject in need of such treatment a therapeutically-effective amount of the compound to alleviate such disorder.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of Formulas I, II and in are named and numbered following the
Chemical Abstracts ring system nomenclature system, see Ring Systems Handbook, Chemical Abstracts Service, Ring Systems File I, see RF 23543, 1988 Edition.
"Alkyl" are one to six carbon atoms or, as otherwise indicated, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, and isomeric forms thereof.
"Aryl" are six to twelve carbon atoms such as phenyl, α-naphthyl, β-naphthyl, m- methylphenyl, p-trifluoromethylphenyl and the like. The aryl groups can also be substituted with one to 3 hydroxy, OR8, -OCOR8, fluoro, chloro, or bromo groups.
"Cycloalkyl" are three to seven carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
"Alkyl-aryl" are alkyl chains of one to six carbon atoms and isomeric forms thereof which are substituted with aryl groups of six to twelve carbon atoms as described above.
"Heteroaryl" are six to twelve carbon atoms aryl, as described above, containing the heteroatoms nitrogen, sulfur or oxygen. Examples can include pyridine, thiophene, furan, pyrimidine, 2-pyridyI, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 3- pyridazinyl, 4-pyridazinyl, 3-pyrizinyl, 2-quinolyl, 3-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4- isoquinolyl, 2-quinazoIinyl, 4-quinazolinyl, 2-quinoxalinyl, 1-phthalazinyl, 2-imidazolyl, 4- imidazolyl, 3-isoxazoIyl, 4-isoxazolyl, 5-isoxazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2- oxazolyl, 4-oxazolyI, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-indoIyl, 3-indolyl, 3- indazolyl, 2-benzoxazoiyl, 2-benzothiazolyl, 2-benzimidazolyl, 2-benzofuranyl, 3-benzofuranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1,2,4-oxadiazol-3-yl, 1,2,4- oxadiazol-5-yl, 1,2,4-thiadiazoI-3-yl, 1,2,4-thiadiazoI-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazoI-5-yl, 1,2,3,4-tetrazol-5-yl, 5-oxazolyl, 1-pyιτolyl, 1-pyrazolyl, 1,2,3-triazol-1-yl, 1,2,4-triazol-1-yl, 1- tetrazolyl, 1-indolyl, 1-indazolyl, 2-isoindolyl, 1-purinyl, 3-isothiazolyl, 4-isothiazolyl, 5- isothiazolyl.
Pharmaceutically acceptable salts include salts of both inorganic and organic acids. The pharmaceutically acceptable salts are preferred over the corresponding free amines since they produce compounds which are more water soluble. The preferred pharmaceutically acceptable salts include salts of the following acids: methanesolfonic, hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, benzoic, citric, tartaric, fumaric or maleic.
The subject compounds are active orally or parenterally. Orally the compounds can be given in solid dosage forms as tablets or capsules, or can be given in liquid dosage forms such as elixirs, syrups or suspensions as is known to those skilled in the art. It is preferred that the compounds be given in solid dosage form and that it be a tablet.
For preparing solid compositions such as tablets, the compound can be mixed with conventional ingredients such as talc, magnesium stearate, dicalcium phosphate, magnesium aluminum silicate, calcium sulfate, starch, lactose, acacia, methylcellulose, and functionally similar materials as pharmaceutical diluents or carriers. Capsules are prepared by mixing the compound with an inert pharmaceutical diluent and filling the mixture into a hard gelatin capsule of appropriate size. Soft gelatin capsules are prepared by machine encapsulation of a slunry of the compound with an acceptable vegetable oil, light liquid petrolatum or other insert oil.
Fluid unit dosage forms for oral administration such as syrups, elixirs, and suspensions can be prepared. The forms can be dissolved in an aqueous vehicle together with sugar, aromatic flavoring agents and preservatives to form a syrup. Suspensions can be prepared with an aqueous vehicle with the aid of a suspending agent such as acacia, tragacanth,
methylcellulose and the like.
For parenteral administration, fluid unit dosage forms can be prepared utilizing the compound and a sterile vehicle. In preparing solutions the compound can be dissolved in water for injection and filter sterilized before filling into a suitable vial or ampoule and sealing.
Adjuvants such as a local anesthetic, preservative and buffering agents can be dissolved in the vehicle. The composition can be frozen after filling into a vial and the water removed under vacuum. The lyophilized powder can then be sealed in the vial and reconstituted prior to use.
For anxiolytic effect the compounds should be given in amounts of about 0.25 mg to about 100 mg/person, one to three times a day. Preferably, about 10 to about 50 mg/day in divided doses.
For sedative/hypnotic effect the compounds should be given in the amount of about 0.25 mg to about 500 mg/person, preferrably at bedtime or when sedation is needed. It is preferred the sedative/hypnotic dose be from about 10 to about 100 mg/person.
The exact dosage and frequency of administration depends on the particular compound used, the particular condition being treated, the severity of the condition being treated, the age, weight, general physical condition of the particular patient, other medication the individual may be taking as is well known to those skilled in the art and can be more accurately determined by measuring the blood level or concentration of the compound in the patient's blood and/or the patient's response to the particular condition being treated.
Thus, the subject compounds along with a pharmaceutically-acceptable carrier, diluent o buffer can be administrated in a therapeutic or pharmacological amount effective to alleviate th central nervous system disorder with respect to the physiological condition diagnosed. The compounds can be administered intravenously, intramuscularly, topically, transdermally such as by skin patches, bucally or orally to man or other vertebrates.
Other definitions are used as follows: All temperatures are in degrees Centigrade. THF refers to tetrahydrofuran, DMF is dimethylformamide, DMSO is dimethylsulfoxide and CDCl3 i deuteriochloroform. Saline refers to an aqueous saturated sodium chloride solution. IR refers t infrared spectroscopy. NMR refers to nuclear (proton) magnetic resonance spectroscopy, chemical shifts are reported in ppm (δ) downfield from tetramethylsilane. MS refers to mass spectrometry expressed as m/e or m/z. (M + H)+ refers to the positive ion of a parent plus a hydrogen atom. El refers to electron impact. Cl refers to chemical ionizatioa FAB refers to fast atom bombardment. Ether refers to diethyl ether. Pharmaceutically acceptable refers to those properties and/or substances which are acceptable to the patient from a
pharmacological/toxicological point of view and to the manufacturing pharmaceutical chemist from a physical/chemical point of view regarding composition, formulation, stability, patient acceptance and bϊoavailability. When solvent pairs are used, the ratios of solvents used are volume/volume (v/v).
General Method for the Synthesis of 3-(1,2,3-TriazoI-1-yI)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one Compounds of Formula I where Z is -N(R1)-C(O)- and X is a 1,2,3- triazole (e, f, g)
t-Butyl 4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxylate was treated with trifluoroacetic acid in methylene chloride to remove the tert-butyl ester group. 4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaIine-3-carboxylic acid was treated with thionyl chloride followed by sodium azide to yield 4,5-dihydro-4-oxo-5-(1-methylethyl)- imidazo(1,5-a)-quinoxaline-3-carboxyI azide. That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxycarbonyI)amino)-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5- a)-quinoxaline. That carbamate was then decomposed with potassium hydroxide to yield 3- amino-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)-quinoxaline. Treatment of 3-amino- 4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline with sodium nitrate in an acidic medium followed by treatment of sodium azide and finally treatment with water afforded 3- azido-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaIine. Treatment of 3-asido- 4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)-qquinoxaIine with acetylenes in an organic solvent such as toluene afforded the triazole final products.
Preparation of Intermediates
t-Butyl 4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,50a)-quinoxaIine-3- carboxylate
The dione (1.02 g) was dissolved in THF (10 mL) and cooled to 0°C. Potassium t- butoxide (1.0 M in THF, 5.5 mL) was added, then the reaction was cooled to -20°C and diethylchlorophosphate (795uL) was added. The reaction was warmed to 23°C for 30 minutes, then cooled to -78°C and the isonitrile (800 uL) was added. Potassium t-butoxide (1.0 M in THF, 5.5 mL) was added and the reaction was warmed to 23°C for 3 hours. The reaction mixture was poured into ethyl acetate (200 mL), washed with water (2 x 50 mL) and brine, then dried over magnesium sulfate. The organic layer was filtered and concentrated in vacuo to a yellow oil. THe product was purified by column chromatography over silica gel (250 g), eluting with 15% acetonitrile in methylene chloride to give a white solid (1.3 g, 80%). MP = 150-1ºC.
4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxylic acid
Trifluoroacetic acid (500 uL) was dissolved in methylene chloride (2.0 mL) and cooled to 0°C. A solution of the ester (650 mg) in methylene chloride (3.0 mL) was added and the reaction was allowed to warm to 23°C for 2.5 hours. The solvent was evaporated and the residue was dried in a vacuum oven for 17 hours at 45°C to give the extremely insoluble acid as a tan solid (542 mg, 99%).
4,5-Dihydro-4-oxo-5(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxyl chloride The carboxylic acid (1.0 g) was dispersed in toluene (3.0 mL) and thionyl chlroide (1.3 mL) was added. The reaction was fitted with a reflux condensed and heated to reflux for 5 hours, until all the acid dissolved. The reaction mixture was then cooled and concentrated in vacuo and the residue recrystaliized from toluene to give the acid chloride as fluffy white crystals (1.02 g, 96%). MP = 220- 1°C.
4,5-Dihydro-4-oxo-5(1-methyIethyl)-imidazo(1,5-a)-quinoxaline-3-carboxyl azide Sodium azide (252 mg) was dissolved in water (2.0 mL) and acetone (12 mL) was added. The acid chloride (neat, 1.02 g) was added slowly at 23°C and the reaction was stirred for 1 hour. The mixture was poured into ethyl acetate (200 mL) and washed with water and brine. The organic layer was dried over magnewium sulfate, filtered, and concentrated in vacuo to a white solid (1.02 g, 98%). MP = 1140C.
3-(MethoxycarbonyI)amino)-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5- a)quinoxaline
The acyl azide (1.0 g) was mixed with toluene (250 mL) and heated to 105°C. Gas evolution begins at 80°C. The reaction was heated for 1 hour, then cooled and concentrated in vacuo to a white solid which was recrystaliized from methanol giving white crystals (750 mg, 74%). MP = 238-41°C.
3-Amino-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxaline
The carbamate (600 mg) was dispersed in methanol (12 mL) and potassium hydroxide (10% aqueous solution, 8.0 mL) was added. The reaction was stirred at 25°C for 1 hour and add carbamate dissolved, the reaction was stored at -10°C for 17 hours, then concentrated in vacuo and chromatographed over silica gel (100 g), eluting with 5% methanol in methylene chloride. The white product was recrystallized from ethyl acetate giving white crystals (264 mg 54%). MP = 178-80°C.
3-Azido-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxaline
The amine (2.42 g) was dissolved in water (4.0 mL) and concentrated HCI (2.3 mL) wa added. The mixture was cooled to 0°C and sodium nitrite (760 mg) was added. The reaction was stirred for 0°CC for 2 hours, then filtered. Sodium azide (716 mg) was added and gas evolution began immediately, followed by formation of a pale yellow precipitate. The reaction was stirred at 0°C for 2 hours, then extracted with ethyl acetate (3 x 175 mL). The combined extracts were washed with water (2 x 40 mL) and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to a yellow solid. The product was purified by silica gel chromatography, eluting with 5% methanol in methylene chloride to give a white solid which was recrystallized from ethyl acetate (1.43 g, 53%). MP = 140°C.
Preparation of 1,2,3-TriazoI-1-yl (e) Compounds
3-(1-2-3-Triazol-1-yI)-5-(1-methylethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one
The azide (268 mg) and propiolic acid (58 uL) were mixed in toluene (5 mL) and the reaction heated to reflux for 3 hours. The reaction was then cooled and concentrated in vacuo to a black tarry looking material. This residue was chromatographed over silica gel, eluting with 5% methanol in methylene chloride. Recrystallization from ethyl acetate gave white crystals (175 mg, 60%). MP = 235-7°C.
3-(4-Phenyl-1-2,3-triazol-1-yl)-5-(1-methylethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one
The azide (500 mg) was dissolved in toluene (10 mL) and the acetylene (3.0 mL) was added. The reaction was heated to reflux for 17 hours, then the solvent removed in vacuo. The residue was chromatographed over silica gel (300 g), eluting with 5% methanol in methylene chloride. The product was recrystallized from methanol/ethyl acetate to give a fluffy white solid (382 mg, 55%). MP=236-8°C.
3-(4,5-Dicarbomethoxy-1,2-3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1-5-a)quinoxaIin-4(5H)- one
The azide (268 mg) was dissolved in toluene (4.0 mL) and
dimethylacetylenedicarboxylate (123 uL) was added. The reaction mixture was heated to reflux for 5 hours, until all starting material was consumed by TLC. The reaction was cooled and concentrated in vacuo, filtered through silica gel and recrystaliized from ethyl acetate giving a white solid (154 mg, 38%). MP = 155-8°C.
3-(4-Carbomethoxy-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one The azide (500 mg) was dissolved in warm toluene (15 mL) and the acetylene (2.5 mL) was added. The reaction mixture was heated to reflux for 3 hours. The reaction was cooled and concentrated in vacuo to a yellow solid which was chromatographed over silica gel (500 g), eluting with 5% methanol in methylene chloride to give a white solid which was triturated with methanol (567 mg, 86%). MP = 275-8°C.
The following compounds can be made using the basic procedures described above.
3-(4-Carbomethoxy-5-methyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-7-methyl- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Carbomethoxy-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-7-methyl-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Carbomethoxy-5-methyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Carbomethoxy-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Carbomethoxy-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Carbomethoxy-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Morpholinyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-7-methyl-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)- imidazo(1,5a)quinoxalin-4(5H)-one;
3-(4-Morpholinylmethyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)- imidazo(1 ,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(4-(4-N-methylpiperazinyl)methyl)-1,2,3-triazol-1-yl)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-chlorobenzyl}-methyI-1,2,3-triazol-1-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(m-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-MethyI-N-(3,4-dichlorobenzyl}-methyl-1,2,3-triazol-1-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-MethyI-N-(3,4-difluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methyIethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-fluorobenzyI}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(p-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-trifluoromethyIbenzyI}-methyl-1,2,3-triazoI-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(p-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)qurnoxalin-4(5H)-one;
3-(4-{N-MethyI-N-(o-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-clorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Ethyl-N-(m-clorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-clorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(3,4-diclorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(3,4-difluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one ;
3-(4-{N-Ethyl-N-(p-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(3,4-dichlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Methyl-N-(3,4-difluorophenyl}-methyl-1,2,3-triazol-1-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-fluorophenyI}-methyl-1,2,3-triazol-1-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-fluorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-fluorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-trifluoromethylphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-MethyI-N-(m-trifluoromethylphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(o-trifluoromethyIphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(p-methoxyphenyl}-methyl-1 ,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(m-methoxyphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(o-methoxyphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-chlorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(3,4-dichlorophenyl}-methyl-1,2,3-triazol-1-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(3,4-difluorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-fluorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-fluorophenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Ethyl-N-(o-fluorophenyl)-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-trifluoromethylphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-trifluoromethylphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-trifluoromethylphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(p-methoxyphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(m-methoxyphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(o-methoxyphenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(p-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(m-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(o-chlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(3,4-dichlorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(3,4-difluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(p-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(m-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(o-fluorobenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(p-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(m-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(o-trifluoromethylbenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Isopropyl-N-(p-methoxybenzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-IsopropyI-N-(m-methoxybenzyl}-methyl-1,2,3-triazoI-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Isopropyl-N-(o-methoxybenzyI}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin~4(5H)-one;
3-(4-{N-Methyl-N-(cyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(1-methylcyclopropyI}-methyl-1,2,3-triazoI-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin~4(5H)-one;
3-(4-{N-Methyl-N-(2-methylcyclopropyl}-methyI-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(1-methoxycyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-{N-Ethyl-N-(cyclopropyl}-methyl-1,2,3-triazoI-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(1-methylcyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-EthyI-N-(2-methylcyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(1-methoxycyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Phenyl-N-(cyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Phenyl-N-(1-methyIcycIopropyI}-methyl-1,2,3-triazol-1-yl)-5-(1-methyIethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Phenyl-N-(2-methylcycIopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Phenyl-N-(1-m-thoxycyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Benzyl-N-(cycIopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-BenzyI-N-(1-methylcyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methyIethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Benzyl-N-(2-methylcyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one; 3-(4-{N-Benzyl-N-(1-methoxycyclopropyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl)-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Morpholinylmethyl)-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Morpholinyl)-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-{N-Methyl-N-(phenyl) -methyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-Morpholinylmethyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Morpholinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-{N-Methyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2- methyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-MorpholinylmethyI)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Morpholinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-{N-Methyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(2-morpholinyIethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-{N-Methyl-N-benzyI}-methyl-1,2,3-triazol-1-yI)-5-(2-morpholinyIethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-{N-EthyI-N-benzyl}-methyl-1,2,3-triazol-1-yI)-7-fluoro-5-(2-morpholinylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Bromomethyl)-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-MorphoIinylmethyl)-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-MorphoIinyI)-1,2,3-triazoI-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5-a)quinoxalϊn-
4(5H)-one;
3-(4-Cyclopropyl-1,2,3--riazol-1-yl)-5-(1-methyIethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(4-CycIopropyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(4-CycIopropyI-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-Cyclopropyl-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
3-(4-Cyclopropyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5 - a)quinoxalin-4(5H)-one;
3-(4-Carboxymethyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Carboxymethyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one; 3-(4-Carboxymethyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Carboxymethyl-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Carboxymethyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2,3-Dimethylcyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2,3-Dimethylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2,3-Dimethylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2,3-Dimethylcyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2,3-Dimethylcyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(4-(2-MethyIcyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(2-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-MethylcyclopropyI)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(2-MethylcyclopropyI)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(1-Methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Me-hoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-MethoxycycIopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-MethoxycycIopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-HydroxycyclopropyI)-1,2,3-triazol-1-yl)-5-(1-Hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Hydroxycyclopropyl)-1,2,3-triazoI-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Hydroxycyclopropyl)-1,2,3-rriazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Hydroxycyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Hydroxycyclopropyl)-1,2,3-triazol-1-yl)-5-(tetr--hydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Aminocyclopropyl)-1,2,3-triazol-1-yl)-5-(1-Hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-AminocycIopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-AmmocycIopropyI)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(4-(1-Aminocyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Aminocyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tefrahydrofuran)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofurfuryl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofurfuryl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofurfuryl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5 H)-one;
3-(4-(2-Tetrahydrofurfuryl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofurfuryl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(3-Tefrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one; 3-(4-(3-Tetrahydrofurn)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofurn)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yI)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofiιrfuryl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyI)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyI)-1,2,3-triazol-1-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrroIidinyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-AcetyI-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(1-Methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yI)-5-(1-methylethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(t-ButyI)-1,2,3-triazoI-1-yI)-5-(2-methoxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxa!in-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxaIin-
4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxaIin-
4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tettahydrofuran)-1,2,3-triazol-1-yI)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(1-mel-hylethyI)-imidazo(1,5-a)quinoxalin- (5H)-one;
3-(5-(2-PyrroIidinyI)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- n (5H)-one; 3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofiιrfuryl)-imidazo(1,5-a)quinoxalin 4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin 4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1- Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Methyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Bromomethyl)-1,2,3-triazol-1-yl)-5-(1-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one; 3-(5-MorpholinyImethyl)-1,2,3-triazol-1-yl)-5-(1-methoxyethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Morpholmyl)-1,2,3-triazol-1-yI)-5-(1-methoxyethyl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
3-(5-{N-Methyl-N-(phenyl}-methyI-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
3-(5-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Bromometfryl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
3-(5-Morpholinylmethyl)-1,2,3-triazol-1-yl)-5-(2-tettahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Morpholinyl)-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfiιryI)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-{N-MethyI-N-(phenyl}-methyl-1,2,3-triazol-1-yI)-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-{N-Methyl-N-benzyl}-methyl-1,2,3-triazoI-1-yl)-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2- methyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Bromomethyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-Morpholinylmethyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Morpholinyl)-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-{N-Methyl-N-(phenyI}-methyl-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-(phenyl}-methyl-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one; 3-(5-{N-Methyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-{N-Ethyl-N-benzyl}-methyl-1,2,3-triazol-1-yl)-7-fluoro-5-(2-morpholinylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Bromomethyl)-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-Morpholinylmethyl)-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Morpholinyl)-1,2,3-triazol-1-yl)-5-(2-morpholinylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetxahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5 H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-((4-(2-methyIcyclopropyI)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yI)-7-fluoro-5-(1-Methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-MethoxycycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-MethoxycycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-tiiazol-1-yI)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyI)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2- tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(t-ButyI)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(t-ButyI)-1,2,3-triazoI-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-(1-Methyl-2-pyrroIidinyl)-1,2,3-triazoI-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazoI-1-yI)-7-fluoro-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrroIidinyl)-1,2,3-triazol-1-yl)-7-fIuoro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazoI-1-yI)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-AcetyI-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrroIidinyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-CycIopropyl)-1,2,3-triazoI-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methyIcycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-methyIcycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazo -1-yl)-7-fluoro-5-(1-Methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazo -1-yl)-7-fluoro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazo -1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazo -1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methoxycyclopropyl)-1,2,3-triazol -1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxatin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazoI-1-yl)-7-fluoro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yI)-7-fluoro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tefrahydrofuran)-1,2,3-triazol-1-yl)-7-fluoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazoI-1-yl)-7-fluoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-CycIopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chIoro-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-((4-CyclopropyI)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-CyclopropyI)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(1-methylcycIopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-methylcycIopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(2-methyIcycIopropyl)-1,2,3-triazol-1-yl)-6-c-iloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one; 3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-Methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(t-Bulyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazoI-1-yl)-6-chloro-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazol-1-yI)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIϊn-4(5H)-one;
3-(4-(3-Tetrahydrofuran)-1,2,3-triazoI-1-yI)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chIoro-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chIoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazoI-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazoI-1-yl)-6-chIoro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyI)-1,2,3-triazol-1-yI)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5-(2-methylcyclopropyI)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-methyIcyclopropyl)-1,2,3-triazol-1-yI)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-methyIcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-methylcyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(1-Methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,3-triazoI-1-yI)-6-chloro-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,3-triazol-1-yI)-6-chloro-5-(tetrahydropyran-2-methyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(t-ButyI)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yI)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(t-ButyI)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tefrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yI)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tefrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(3-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-5-(tetrahydropyran-2-methyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Metiιoxymethyl-1,2,3-triazol-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(4-MethoxymethyI-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymethyl-1,2,3-triazol-1-yl)-6-chloro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(4-Methoxymeth yl-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazoI-1-yl)-6-chloro-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-6-chloro-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-6-chloro-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,3-triazol-1-yl)-6-cWoro-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-5-(tetrahydropyran-2-methyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; General Method for the Synthesis of 3-(1,2,3-Triazol-1-yI)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinoxaline Compounds of Formula I where Z is -C(O)-N(R1)- and X is 1,2-3-triazole (e,f,g).
1,2,3,4-tetrahydro-2,4-dioxo-quinazoline was reacted with t-butylisocyanate using reaction conditions as described in US Patent 4,771,051 to yield t-butyl 4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)-quinoxaline-3-carboxylate which was treated with trifluoroacetic acid in methylene chloride to remove the tert-butyl ester group. 4,5-Dihydro-4-methyl-5-oxo- imidazo(1,5-a)-quinoxaline-3-carboxylic acid was treated with thionyl chloride followed by sodium azide to yield 4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline-3-carboxyl azide. That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxycarbonyl)amino)-4,5- dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaIine. That carbamate was then decomposed with potassium hydroxide to yield 3-amino-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline. Treatment of 3-amino-4,5-dihydro-4-methyI-5-oxo-imidazo(1,5-a)-quinoxaline with sodium nitrate in an acidic medium followed by treatment of sodium azide and finally treatment with water afforded 3-azido-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline. Treatment of 3- azido-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline with acetylenes in an organic solvents such as toluene afforded the triazole final products.
The following compounds can be made using the above described procedure.
3-((4-{N-Methyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5 -dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-methoxybenzyl} -methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-
5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Ethyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline; 3-((4-{N-EthyI-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazoI-1-yl)-4,5-dihydro-4-methyI- 5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Ethyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yI)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-EthyI-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyI-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-EthyI-N-(p-trifluoromethyIbenzyI}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(m-trifluoromethyIbenzyI}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyI-5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Ethyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-EthyI-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoIine;
3-((4- {N-Ethyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyI-5- oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Methyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyI-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-MethyI-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-cmorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(3,4-dichlorophenyl}-methyI)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyI-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-MethyI-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-fluorophenyl}-methyI)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoIine; 3-((4-{N-Methyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-meth yl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(m-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-
5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4- {N-Ethyl-N-(o-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(3,4-dichlorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-
5-oxo-imidazo(1,5-a)quinazoline;
3-((4- {N-Ethyl-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4- {N-Ethyl-N-(p-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(p-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-{N-Ethyl-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethyIphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-EthyI-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Ethyl-N-(m-methoxyphenyI}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(o-methoxyphenyl}-methyl)-1,2,3-triazoI-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(p-chlorobenzyl}-methyI)-1,2,3-triazoI-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Isopropyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-IsopropyI-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-
5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Isopropyl-N-(3,4-dichlorobenzyl}-methyI)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyI-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyI- 5-oxo-imidazo(1,5-a)quinazoIine;
3-((4-{N-Isopropyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yI)-4,5-dihydro-4-methyl- 5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyI-
5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(p-trifluoromethyIbenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro- 4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yI)-4,5-dihydro- 4-methyI-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(o-trifluoromethylbenzyl}-methyl)-12,3-triazol-1-yl)-4,5-dihydro- 4-methyI-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Isopropyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yI)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-{N-Isopropyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-4.5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5- oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Phenyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Phenyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Phenyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Phenyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Benzyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Benzyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Benzyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Benzyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline.
1a. II General Method for the Synthesis of 3-(1,2,3-Triazol-1-yl)-4,5-dihydro-
4-methyl-5-oxo-imidazo(1,5-a)quinazoline Compounds. 3-((4,5-Dicarbomethoxy)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinoxatine;
3-((4-Carbomethoxy-5-methyl)-1,2,3-triazol-1-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
3-((4-Carbomethoxymethyl)-1,2,3-triazol-1-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
3-((4-Morpholinyl)-1,2,3-triazoI-1-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-((4-Bromomethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-MorpholinylmethyI)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-benzyl}-methyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Ethyl-N-benzyI}-methyl)-1,2,3--riazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-{N-Methyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-(2,3-DimethyIcyclopropyl)-1,2,3-triazoI-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-MethyI{2-tetrahydrofuran})-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yI)-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(2-Methyl)cyclopropyI)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(1-MethoxyI)cyclopropyl)-1,2,3-triazol-1-yl)-4-meth yl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yI)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(1-Methyl)cycIopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoiine;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinoxaline;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline
3-(4-(1-Acetyl -2-pyrrolidinyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-4-methyI-5-oxo-imidazo(1,5-a)quinazoline; 3-((5-(3-Tetxahydrofuran))-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazoI-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-TetrahydrofurfuryI))-1,2,3-triazol-1-yI)-4-metiiyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-4-methyI-5-oxo-imidazo(1,5-a)quinazoline; 3-(5-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5-a)quinoxaIine;
3-(5-(1-Methyl-2-pyrroIidinyl)-1,2,3-triazoI-1-yl)-4-methyI-5-oxo-imidazo(1,5- a)quinoxaline;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-((4-CyclopropyI)-1,2,3-triazoI-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(2-Methyl)cycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazoI-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Hydroxyl)cycIopropyI)-1,2,3-triazoI-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(2-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyI-5-oxo- imidazo(1,5-a)quinazolϊne;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazoI-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quuιazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yI)-7-fluoro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-(4-(1-Acetyl -2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(1-Methylcyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yI)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-7-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-CyclopropyI)-1,2,3-triazol-1-yl)-7-chIoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methyl)cycIopropyI)-1,2,3-triazol-1-yl)-7-chloro--4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(2-Methyl)cycIopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-MethoxyI)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(1-HydroxyI)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-CyclopropylmethyI)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(2-Methyl)cycIopropylmethyl)-1,2,3-triazol-1-yI)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chIoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-(1-Hydroxyl)cycIopropylmethyI)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-t-Butyl)-1,2,3-triazol-1-yI)-7-chloro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(3-Tetrahydrofurfuιyl))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-(4-(1-Methyl -2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinoxaline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyI-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5-a)quinazoIine;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-7-chloro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-MethyI)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1-5- a)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-(2-Methyl)cyclopropyImethyI)-1,2,3-triazol-1-yI)-6-chIoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(1-Methoxyl)cycIopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yI)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-t-Butyl)-1,2,3-triazoI-1-yI)-6-chloro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yI)-6-chloro-4-methyl-5-oxo-imidazo( 1 ,5 - a)quinazoline;
3-((4-(3-Tetrahydrofu rfuryl))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropyI)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-CycIopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazoI-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(1-Methoxyl)cycIopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((4-(1-HydroxyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyI-5-oxo-imidazo(1,5-a)quinazoline; 3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-4-metfryl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazoI-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fIuoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyI-5-oxo-imidazo(1,5- a)quinazoIine;
3-((5-Cyclopropyl)-1,2,3-triazoI-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-((5-(1-MethyI)cycIopropyl)-1,2,3-triazoI-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-((5-(2-Methyl)cyclopropyI)-1,2,3-triazoI-1-yI)-6-fluoro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-MethoxyI)cycIopropyl)-1,2,3-triazol-1-yl)-6-fIuoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yI)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(1-Methyl)cyclopropyImethyI)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-((5-Metiιoxymethyl)-1,2,3-triazol-1-yl)-6-fluoro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
General Method for the Synthesis of 3-(1,2,3-TriazoI-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazolines, Compounds of Formula II where Z is -N =CH- and X is 1,2,3- triazole (e,f,g).
Ethyl imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylate was added to a mixture of water and methanol containing potassium carbonate. The resulting acid, imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylic acid, was then treated with thionyl chloride followed by sodium azide to yield imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxyl azide. That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxy- carbonyl)ammino)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. That carbamate was then decomposed with potassium hydroxide to yield 3-amino-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline. Treatment of 3-amino-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline with sodium nitrate in an acidic medium followed by treatment of sodium azide and finally treatment with water afforded 3-azido-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. Treatment of 3- azido-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline with acetylenes in an organic solvents such as toluene afforded the triazole final products described below.
3-(1,2,3-Triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-Phenyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4,5-Dicarbomethoxy)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline; 3-((4-Carbomethoxy)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-benzyI}-methyl)-1,2,3-triazoI-1-yI)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Bromomethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine; 3-((4-Piperazinyl)methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((4-{N-MethyI-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-tιiazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(p-fluorobenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-MethyI-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-((4-{N-Metfιyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-MethyI-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-Methyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-((4-{N-Methyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-Ethyl-N-(p-chlorobenzyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline; 3-((4-{N-Ethyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-{N-Methyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(o-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-dichlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline; 3-((4-{N-Methyl-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4 triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(p-fluorophenyl}-methyl)-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-Methyl-N-(o-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-MethyI-N-(p-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-Methyl-N-(m-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Methyl-N-(o-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-{N-Ethyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-EthyI-N-(3,4-dichlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-EthyI-N-(p-fluorophenyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline; 3-((4-{N-Ethyl-N-(o-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(p-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(m-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(o-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline; 3-((4-{N-Isopropyl-N-(p-methoxybenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-IsopropyI-N-(m-methoxybenzyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-methyl-N-(cyclopropyl)-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((4-{N-MethyI-N-(1-methylcycIopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-MethyI-N-(2-methyIcycIopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-MethyI-N-(1-methoxycyclopropyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-Ethyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quuιazoIine;
3-((4-{N-Ethyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-EthyI-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-EthyI-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Phenyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-{N-Phenyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Phenyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-((4-{N-PhenyI-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Benzyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-{N-Benzyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-((4-{N-Benzyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline; 3-((4-{N-Benzyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
1a. Ill General Method for the Synthesis of 3-(1,2,3-Triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazolines
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-Methyl {2-tetrahydrofuran})-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(4-(2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline 3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3--triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((5-(1-Methyl)cyclopropyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-MethoxyI)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-CycIopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoline;
3-((5-(1-Methyl)cycIopropylmethyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Tetrahydrofurforyl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(3-Tetrahydrofurforyl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-MethoxymethyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline; 3-((5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,(5-triazolo((5,3-c)quinazoline 3-((5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,(5-triazolo((5,3- c)quinazoline 3-((5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,(5-triazolo((5,3- c)quinazoline
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-(4-(1-Acetyl-2-pyrrolidinyI)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-(1-Methyl)cycIopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yI)-7-fIuoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-CyclopropyImethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazoI-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-MethyI)cyclopropyImethyl)-1,2,3-triazoI-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazoI-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yI)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoline; 3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-Methyl)cyclopropyI)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyI)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-CycIopropylmethyl)-1,2,3-triazoI-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoIine;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(2-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-t-ButyI)-1,2,3-triazoI-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-MethyI)cyclopropyl)-1,2,3-triazol-1-yl)-6-chIoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,44 triazoIo(4,3-c)quinazoline; 3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(2-PyrroIidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(1-Methoxyl)cycIopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazoI-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazoi-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyI)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazoI-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-((4-(2-Methyl)cycIopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline; 3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)qumazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazoI-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quύιazoIine;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline.
General Method for the Synthesis of 3-(1,2,3-TriazoI-1-yI)-iιnidazo(1,5-a)-1-2,4- triazoIo(1,5-c)quinazoIines, Compounds of Formula II where Z is -CH=N- and X is 1,2,3- triazole (e,f,g).
1,2,4-Triazolo(4,3-a)quinazoline-5-one; (US Patent 3,850,932) was heated with a mixture of POCl3/PCL5 at 130°C to yield 5-chloro-1,2,4-triazolo(4,3-a)quinazoIine. Treatment of 5- chloro-1,2,4-triazolo(4,3-a)quinazoIine with acetic acid results in rearrangement of the triazole ring to yield 5-oxo-1,2,4-triazolo(1,5-a)quinazoline. Conversion of 5-oxo-1,2,4-triazolo(1,5- a)quinazoline or 5-chloro-1,2,4-triazolo(1,5-a)quinazoline to ethyl imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline-3-carboxyIate was effected under standard reaction conditions. Ethyl imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate was added to a mixture of water and methanol containing potassium carbonate. The resulting acid, imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline-3-carboxylic acid, was then treated with thionyl chloride followed by sodium azide to yield imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxyl azide. That compound was heated in a hydrocarbon solvent to effect molecular rearrangement followed by trapping of the unstable intermediate with methanol to yield 3-((methoxycarbonyl)amino)- imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. That carbamate was then decomposed with potassium hydroxide to yield 3-amino-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline with sodium nitrate in an acidic medium followed by treatment of sodium azide and finally treatment with water afforded 3-azido-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. Treatment of 3- azido-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline with acetylenes in an organic solvents such as toluene afforded the triazole final products described below.
3-(1 ,2,3-Triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-Phenyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4,5-Dicarbomethoxy)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-Carbomethoxy)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((4-{N-Methyl-N-benzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-Bromomethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-Piperazinyl)methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-{N-Methyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4. {N-Methyl-N-(o-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethyIbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-methoxybenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-{N-Methyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-iιnidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(p-chlorobenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(m-chlorobenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(o-chlorobenzyI}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(p-fluorobe-ιzyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-{N-Ethyl-N-(o-fluorobenzyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(p-trifluoromethylbenzyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(m-trifIuoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethyIbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-{N-EthyI-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-EthyI-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-{N-Methyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-dichlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(m-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-. triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(o-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(phenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-{N-Ethyl-N-(p-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(m-chlorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(o-chlorophenyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(3,4-dichlorophenyl}-methyl)-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-EthyI-N-(3,4-difluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(p-fluorophenyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(m-fluorophenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-{N-Ethyl-N-(o-fluorophenyI}-methyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-EthyI-N-(p-trifluoromethyIphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-EthyI-N-(m-trifluoromethylphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(o-trifluoromethylphenyI}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(p-methoxyphenyl}-methyl)-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(m-methoxyphenyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-{N-Ethyl-N-(o-methoxyphenyl}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-{N-Isopropyl-N-(m-chlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-chlorobenzyl}-methyI)-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-{N-IsopropyI-N-(3,4-dichlorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(3,4-difluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-fluorobenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-trifluoromethylbenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5- a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(p-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(m-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Isopropyl-N-(o-methoxybenzyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Methyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Ethyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Phenyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-{N-Phenyl-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- - 1,2,4-triazoIo(1,5-c)quinazoline;
3-((4-{N-Phenyl-N-(2-methylcyclopropyI}-methyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Phenyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Benzyl-N-(cyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-{N-BenzyI-N-(1-methylcyclopropyl}-methyl)-1,2,3-triazoI-1-yI)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Be-ιzyI-N-(2-methylcyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-((4-{N-Benzyl-N-(1-methoxycyclopropyl}-methyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoline. 1 a. IV General Method for the Synthesis of 3-(1,2,3-Triazol-1-yl)-imidazo(1,5-a)-1,1,4- triazoIo(1,5-c)quinazolines
3-((4-Cyciopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((4-MethyI{2-tetrahydrofuran})-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazoI-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Methyl)cycIopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(2-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazolines
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(2-TetrahydrofurfuryI))-1,2,3-triazol-1-yI)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(3-TetrahydrofurfuryI))-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-Me-hoxymethyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(5-(2-PyrrolidinyI)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazolines
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIines
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-iιnidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(2-Methyl)cyclopropyI)-1,2,3-triazol-1-yI)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(2-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yI)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-Triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yI)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(3-Tefrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- tria2θlo(1,5-c)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazoI-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIines
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazoI-1-yl)-7-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-((4-CyclopropyI)-1,2,3-triazoI-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-(2-Methyl)cycIopropyI)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-CyclopropyImethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(2-Metiιyl)cyclopropylmethyl)-1,2,3-triazoI-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline; 3-((4-t-Butyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-t-ButyI)-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazoI-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((5-(2-TetrahydrofurfuryI))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-7-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-Methoxymethyl)-1,2,3-triazoI-1-yI)-7-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yI)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(2-MethyI)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(1-HydroxyI)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(1-Methyl)cyclopropylmethyI)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(2-MethyI)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-t-Butyl)-1,2,3-triazoI-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo((1,5-a-)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(3-TetrahydrofurfuryI))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(4-(2-Pyrrplidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo( 1 ,5 -c)quinazolines
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline; 3-((5-(3-Tetrahydrofuran))-1,2,3-triazoI-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((5-(3-TetrahydrofurfuryI))-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-(5-(2--PyrroIidinyl)-1,2,3-triazol-1-yI)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIines
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-((5-Methoxymethyl)-1,2,3-triazol-1-yl)-6-chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-Cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoIine;
3-((4-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(1-Methoxyl)cyclopropyI)-1,2,3-triazoI-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-((4-(1-HydroxyI)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-CyclopropyImethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((4-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-((4-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((4-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-((4-(2-Tetrahydrofuran)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(3-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((4-(2-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((4-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(4-(2-Pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazolines
3-(4-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-(4-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines
3-((4-Methoxymethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-Cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-Cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(1-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(2-Methyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Methoxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(1-Hydroxyl)cyclopropylmethyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-t-Butyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-((5-(2-Tetrahydrofuran))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-((5-(3-Tetrahydrofuran))-1,2,3-triazoI-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-((5-(2-Tetrahydrofurfuιyl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-((5-(3-Tetrahydrofurfuryl))-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
3-((5-Methoxymethyl)-1,2,3-triazol-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)qyuinazoIine;
3-(5-(2-Pyrrolidinyl)-1,2,3-triazol-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(5-(1-Methyl-2-pyrrolidinyl)-1,2,3-triazol-1-yI)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-(5-(1-Acetyl-2-pyrrolidinyl)-1,2,3-triazol-1-yl)-6-fluoro-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine.
General Method for the Synthesis of 3-(1-5-disubstituted-1,2,3-Triazol-4-yl)-5-(1- methylethyI)-imidazo(1,5-a)quinoxalin-4(5H)-ones, 3-(1,4-disubstituted-1,2,3-TriazoI-5-yl)-5- (1-methyIethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-ones and 3-Acetylenic-5-(1-methyIethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-ones, Compounds of formula I where Z is -N(R1)-C(O)- and X is 1,2,3-triazoIe (e,f,g).
4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxylic acid was heated to 290-300° in a metal bath until the CO2 cleavage had finished. The melt was dissolved in methylene chloride and ethanol and the solution was concentrated until methylene chloride no longer distilled over. 4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline crystallized from this solution. 4,5-Dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline was heated to 95° for several hours with iodine in a mixtare of DMF and water. Standard aqueous workup afforded 3-iodo-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaline. 3-Iodo-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline was heated at reflux for several hours with propargyl alcohol, bis(triphenylphosphine)-palladium (II) chloride and copper (I) iodide in diethylamine to afford 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4- oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline. Reaction of 3-(3-hydroxy-1-propynyl)-4,5- dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline with phenylazide afforded at elevated temperatures afforded a mixture of 3-((1-phenyl-5-hydroxymethyl)-1,2,3-triazol-4-yl)- 4,5-dih ydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxaline and 3-((1-phenyl-4- hydroxymethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline.
The following compounds can be made from the above procedure.
3-(1-Cyano-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones; 3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Cyano-4-methyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-phenyl-1,2,3-triazol -4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol -4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Methyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones; 3-(1-Methyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Phenyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Phenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones; 3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-(p-Methoxyphenyl)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-4-yI)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-(o-Methoxypheny)l-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-p-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-m-Methoxyphenyl-1,2,3-triazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-o-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-cyclopropyI-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyI-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-qιιinoxalin-
4(5H)-ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazoI-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxaIin-4(5H)-ones;
3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methoxy)cyclopropyl)-1,2,3-triazol -5-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-methyl- l,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-Cyano-5-phenyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-phenyI-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-mιidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazoI-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-mιidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Methyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Methyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Phenyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Phenyl-1,2,3-Mazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-(p-Methoxyphenyl)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-(o-Methoxypheny)l-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-p-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-m-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-o-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-Mazol-4-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methyI)cyclopropyl)-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((2-methyl)cyciopropyl)-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methoxy)cycIopropyl)-1,2,3-triazoI-5-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tettahydrofuran)-1,2,3-triazol-4-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxaIin-4(5H)-ones;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yI)-5-(3-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxaIin-4(5H)-ones;
3-(1-Cyano-1,2,3-triazol-4-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Cyano-1,2,3-triazoI-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imιdazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-methyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-phenyl-1,2,3-triazol-4-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5 -carbomethoxy-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Carbomethoxy- l,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Methyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Methyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Phenyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Phenyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-(p-MethoxyphenyI)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-4-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-(o-Methoxypheny)I-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-p-MethoxyphenyI-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-m-MethoxyphenyI-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-o-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-cycIopropyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazoI-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-carbometfroxy-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-isopropyI-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-5-((1-methyI)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methyI)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxaIin-4(5H)-ones; 3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methoxy)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-4-methyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5 -phenyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones; 3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(2-picoIyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yI)-5-(2-picolyI)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yI)-5-(2-picolyl)-imidazo(1,5-a)-quinoxaIin-
4(5H)-ones;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-5-(2-picoIyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Carbomethoxy-1,2,3-triazoI-5-yI)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Methyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones; 3-(1-Methyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxaIin-4(5H)-ones; 3-(1-Phenyl-1,2,3-triazol-4-yl)-5-(2-picolyI)-imidazo(1,5-a)-quinoxaIin-4(5H)-ones; 3-(1-p-FIuorophenyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-m-FluorophenyI-1,2,3-triazol-4-yl)-5-(2-picoIyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-o-FluorophenyI-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Phenyl-1,2,3-triazol-5-yI)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)-ones;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quύιoxalin-4(5H)- ones;
3-(1-p-Fluorophenyl-1,2,3-triazoI-5-yI)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-(p-Methoxyphenyl)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-(o-Methoxypheny)1-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-p-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(2-picoIyl)--midazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-m-Methoxyphenyl-1,2,3-triazoI-5-yl)-5-(2-picoIyl)-imidazo(1,5-a)-quinoxaIin-4(5H)- ones; 3-(1-o-Methoxyphenyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-
4(5H)-ones;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin- 4(5H)-ones;
3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)-quinoxalin-4(5H)- ones;
3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-((1-methoxy)cyclopropyl)-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones; 3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-5-(2-picolyI)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-triazol-4-yl)-5-(2-picolyI)-imidazo(1,5-a)- quinoxalin-4(5H)-ones;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxa!in-4(5H)-ones;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yI)-5-(2-picolyl)-imidazo(1,5-a)- quinoxaIin-4(5H)-ones;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)- quinoxalin-4(5H)-ones.
General Method for the Synthesis of 3-(1-5-disubstituted-1,2-3-TriazoI-4-yl)-4,5- dihydro-4-methyI-5-oxo-imidazo(1,5-a)quinazoIine, 3-(1,4-disubstituted-1,2,3-TrϊazoI-5-yI)- 4,5-dihydro-4-methyI-5-oxo-imidazo(1,5-a)quinazolϊne and 3-AcetyIenic-4,5-dihydro-4- methyl-5-oxo-imidazo(1,5-a)quinazoline, Compounds of formula I where Z is -C(O)-N(R1)- and X is 1,2,3-triazoIe (e,f,g).
4,5-Dihydro-4-methyI-5-oxo-imidazo(1,5-a)-quinazoline-3-carboxylic acid was heated to 290-300° in a metal bath until the CO2 cleavage had finished. The melt was dissolved in methylene chloride and ethanol and the solution was concentrated until methylene chloride no longer distilled over. 4-5-Dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline was isolated from that solution. 4,5-Dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline was heated to 95° for several hours with iodine in a mixture of DMF and water. Standard aqueous workup afforded 3-iodo-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline. 3-Iodo-4,5-dihydro-5-oxo-4- methyI-imidazo(1,5-a)-quinoxaline was heated at reflux for several hours with propargyl alcohol, bis(triphenyIphosphine)-palladium (II) chloride and copper (I) iodide in diethylamine to afford 3- (3-hydroxy-1-propynyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaIine. Reaction of 3- (3-hydroxy-1-propynyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline with phenylazide afforded at elevated temperatures afforded a mixture of 3-((1-phenyI-5-hydroxymethyl)-1,2,3- triazol-4-yl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline and 3-((1-phenyl-4- hydroxymethyl)-4-5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline.
Compounds of the following structures can be made by the above procedure.
3-(1-Cyano-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-(1-Cyano-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline; 3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-4-,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-4-methyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-(1-Cyano-5-phenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5 -carbomethoxy-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Carbomethoxy-1,2,3-triazol -5-yl)-4,5-dihydro-4-methyl -5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Methyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-(1-Methyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-(1-Phenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-m-Fluorophenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Phenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline; 3-(1-p-Methoxyphenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-m-Methoxyphenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-o-Methoxyphenyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-p-Methoxyphenyl-1,2,3-triazol-5-yI)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-m-Methoxyphenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyI-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-o-Methoxyphenyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoIine;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)quinazoline;
3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-triazoI-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-4-((1-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-5-((2-methyl)cycIopropyl)-1,2,3-triazoI-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoIine;
3-(1-Cyano-4-((1-methoxy)cyclopropyI)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1-5-a)quinazoline; 3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)quinazoline;
General Method for the Synthesis of 3-(1,5-disubstituted-1,2,3-triazoI-4-yl)- imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline, 3-(1,4-disubstituted-1,2,3-triazol-5-yl)- imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline, and 3-Acetylenic-imidazo(1,5-a)-1-2,4- triazolo-(4,3-c)quinazoline, Compounds of Formula II where Z is -N=CH- and X is 1,2,3- triazole (e,f,g).
Imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylic acid was heated to 290-300° in a metal bath until the CO2 cleavage had finished. The melt was dissolved in methylene chloride and ethanol and the solution was concentrated until methylene chloride no longer distilled over. Imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline crystallized from this solution. Imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline was heated to 95° for several hours with iodine in a mixture of DMF and water. Standard aqueous workup afforded 3-iodo-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline. 3-Iodo-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline was heated at reflux for several hours with propargyl alcohol, bis(triphenylphosphine)-palladium (II) chloride and copper (I) iodide in diethylamine to afford 3-(3-hydroxy-1-propynyl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline. Reaction of 3-(3-hydroxy-1-propynyl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline with phenylazide afforded at elevated temperatures afforded a mixture of 3-((1-phenyl-5-hydroxymethyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline and 3-((1-phenyl-4-hydroxymethyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline.
Compounds of the following structures can be made using the above procedure.
3-(1-Cyano-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Cyano-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Cyano-5-methyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-methyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Cyano-5-phenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline; 3-(1-Cyano-4-cyclopropyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-Cyano-4-t-butyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yI)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-Carbomethoxy-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
3-(1-Methyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Methyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-Phenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine; 3-(1-m-Fluorohenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-PhenyI-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(1-(p-MethoxyphenyI)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-(m-MethoxyphenyI)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-(o-Methoxyphenyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-(p-Methoxyphenyl)-1,2,3-triazol-5-yI)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoIine;
3-(1-(o-Methoxyphenyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-5-trifluoromethyI-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
3-(1-Cyano -4-trifluoromethyI-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoline; 3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-((1-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-5 -((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-((1-methoxy)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)--midazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline.
General Method for the Synthesis of 3-(1,5-disubstituted-1,2,3-triazol-4-yl)- imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline, 3-(1,4-disubstituted-1,2,3-triazol-5-yl)- imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline, and 3-Acetylenic-imidazo(1,5-a)-1,2,4- triazolo-(1,5-c)quinazoline, Compounds of Formula II where Z is -CH=N- and X is 1,2,3- triazole (e,f,g).
Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylic acid was heated to 290-300 in a metal bath until the CO2 cleavage had finished. The melt was dissolved in methylene chloride and ethanol and the solution was concentrated until methylene chloride no longer distilled over. Imidazo(1,5-a)-1,2,4-triazolo(1-5-c)quinazoline crystallized from this solution. Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine was heated to 95° for several hours with iodine in a mixture of DMF and water. Standard aqueous workup afforded 3-iodo-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine. 3-Iodo-imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoline was heated at reflux for several hours with propargyl alcohol, bis(triphenylphosphine)-palladium (II) chloride and copper (I) iodide in diethylamine to afford 3-(3-hydroxy-1-propynyI)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline. Reaction of 3-(3-hydroxy-1-propynyl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine with phenylazide afforded at elevated temperatures afforded a mixture of 3-((1-phenyI-5-hydroxymethyl)-1,2,3-triazoI-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine and 3-((1-phenyl-4-hydroxymethyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline.
Compounds of the following structures can be made using the above procedure.
3-(1-Cyano-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-Cyano-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(1-Cyano-5-methyI-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(1-Cyano-4-methyI-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-Cyano-5-phenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-Cyano-4-phenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine; 3-(1-Cyano-5-cyclopropyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-(1-Cyano-4-cycIopropyl-1,2,3-triazoI-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-5-t-butyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-Cyano-4-t-butyl-1,2,3-triazoI-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-Cyano-5-carbomethoxy-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline;
3-(1-Cyano-4-carbomethoxy-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Carbomethoxy-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine; 3-(1-Carbomethoxy-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(1-Methyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-MethyI-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoIine;
3-(1-Phenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-p-Fluorophenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-m-Fluorohenyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-4-yl)-iιmdazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-Phenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-o-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-m-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(1-p-Fluorophenyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 3-(1-(p-Methoxyphenyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-(o-Methoxyphenyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-(p-Methoxyphenyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-(m-Methoxyphenyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-(o-Methoxyphenyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-5-trifluoromethyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-4-trifluoromethyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-5-isopropyl-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-4-isopropyl-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-5-((1-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-4-((1-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-5-((2-methyl)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-4-((2-methyl)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-5-((1-methoxy)cyclopropyl)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-4-((1-methoxy)cyclopropyl)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline; 3-(1-Cyano-5-(2-tetrahydrothiophene)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(1-Cyano-4-(2-tetrahydrothiophene)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-(1-Cyano-5-(2-tetrahydrofuran)-1,2,3-Mazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
3-(1-Cyano-4-(2-tetrahydrofuran)-1,2,3-triazol-5-yl)-imidazo( 1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline;
3-(1-Cyano-5-(3-tetrahydrofuran)-1,2,3-triazol-4-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
3-(1-Cyano-4-(3-tetrahydrofuran)-1,2,3-triazol-5-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline;
Synthesis of 1,2,4-Oxadiazol-3-yl Analogues (Formula I, Z is -N(R1)-C(O)- and X is 1,2,4-oxadizole (a).
3-(5-(1-MethylcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(1-MethylcycIopropyI)-1,2,4-oxadiazol-3-yl)-5-(1-meth yl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-CycIopropyl-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcycIopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycycIopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1- methyIethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-FIuoro-3-(5-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyI)- imidazo(1 ,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5 (2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5 (2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Cmoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5 ,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-FIuoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-FIuoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methyIfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(5-methyIfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5-(2-methylcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-FIuoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyI)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycycIopropyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyI-2- hydroxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadιazol-3-yl)-5-(1-methyl-2-hydroxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5 (2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5 (3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyanq-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl- 2-hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyI-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1- methyl-2-hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl -2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one ;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-MethoxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-hydroxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyI)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-MethyIfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-hydroxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- hydroxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-((5-Cyclopropyl-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-(1-MethylcyclopropyI)-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fIuoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methyIcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiaz.ol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl -2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-me-hy0ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- me-hoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2- methoxyethyl)-imidazo(13-a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-TetrahydrofuιyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuι-yl)-1,2,4oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dunethyl-2-tefrahydrof-ιryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl 2-methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1- methyl-2-methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-methoxyethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(3-tetrahydrotiiiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-cyclopentyI-1,2,4-oxadiazol-3-yI)-5-(1-metiiyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl-2- methoxyetfryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1-5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fIuoro-3-(5-(1-methoxycyclopentyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-metiiyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one ;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-met-hyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyI-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(1-methyl-2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-((5-Cyclopropyl-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methyIpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-((5-(1-MethylcycIopropyl)-1,2,4-oxadiazol-3-yl)methyl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylpropyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyI)-1,2,4-oxadiazol-3-yI)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalϊn-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIpropyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-metiiylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyI)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5 (2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyI-2-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(1- methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1- methylpropyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yI)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(1-methyIpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yI)-5-(1-methyIpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoror3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-HydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycycIopentyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyIpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIpropyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1-5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazoI-3-yl)-5-(1-metiiylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl )-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5-(5-metfrylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyIpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyIpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylpropyl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(1-methylpropyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol.-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-MethoxycyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-ox--diazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(3-Tetrahydrofuιyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyeithyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyI-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)-imidazo(1,5 a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-cyclopentyI-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2- methoxyethyI)-imidazo(1,5-a)quinoxahn-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(1-hydroxycyclopentyI)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-Metiιylfuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5 a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5 a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcycIopropyl)-1,2,4-oxadiazol-3-yI)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-MethyIcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-metfryIcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methyIcyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1 -methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuιyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5-((1-hydroxy-1-methyl)etlιyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryI)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4- oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5 (3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Cmoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5t(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofύrfuryl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imldazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,4-oxadiazoI-3-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- (5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(5-(2-Pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo( 1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(2-Pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-Pyrrolidinyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-morpholinoethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-morphoIinoethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxa!in-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yI)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one:
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quiιloxaIin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetralιydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5 (3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yI)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5 (3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrotiιiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)-imidazo(1,5- a)quinoxaIin-4(5-(H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(1-methoxycycIopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyI)-1,2,4-oxadiazol-3-yl)-5-(2- morphoIinoethyI)-imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-ChIoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
3-(5-(1-HydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
3-(5-(5-MethyIfuιy0-1,2,4-oxadiazol-3-yl)-5-(2-morpholmoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5 -(H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one; 6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-fIuoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyI)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-ChIoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methyIcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fIuoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(1-methyIcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-3~yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fIuoro-3-(5-(1-hydroxycycIopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)--midazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 7-ChIoro-3-(5(2-tetiahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-FIuoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxγpiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-5-(2-(3-hydroxypiperdinyl)ethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one:
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdϊnyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-CycIopentyl-1,2,4-oxadiazol-3-yI)-5-(2-(3-hydroxypiperdinyl)ethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-cycIopentyI-1,2,4-oxadiazol-3-yI)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-cycIopentyl-1,2,4-oxadiazol-3-yI)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyI)ethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyI)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyI)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one; 7-Fluoro-3-(5-(4-fluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-(3- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-ChIoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3-hydroxypiperdinyI)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
7-ChIoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1-5-a)quinoxalin-4(5-(H)-one:
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(3- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H )-one:
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycycIopropyl)-1,2,4-oxadϊazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-metfιoxycyclopropyI)-1-2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-HydroxycyclopropyI)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl )-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol- 3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H )-one;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yI)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yI)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyI)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrotiιiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H )-one; 7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyI)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazoI-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-FIuoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one:
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one:
6-Chloro-3-(5-cycIopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yI)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one:
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)-imidazo(1,5- a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one; 6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyI)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazoI-3-yI)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(4-fIuorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxaIin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4-hydroxypiperdinyl)ethyl)- imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazoI-3-yl)-5-(2-(4- hydroxypiperdinyI)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Chloro-3-(5-(2,4-difluorophenyI)-1,2,4-oxadiazol-3-yI)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5-(H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-(4- hydroxypiperdinyl)ethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2-methylcycIopropyI)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Fluoro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yI)-5-(2-picoIyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-ChIoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(5(3-TetrahydrofuryI)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5 H)-one;
3-(5(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H )-one;
7-Fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2- picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxalin-4(5H)-one:
7-Chloro-3-(5(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- 5 a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(5(2-tetrahydrotiiiophene)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrot hiophene)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Fluoro-3-(5-cycIopen-yl-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
7-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1-5-a)quinoxalin-
4(5H)-one;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picoiyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-cycIopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one: 6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H )-one;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-picoIyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(5-(4-fluorophenyI)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyI)-1,2,4-oxadiazol-3-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-ChIoro-3-(5-(4-fIuorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(2,4-DifluorophenyI)-1,2,4-oxadiazoI-3-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(5-(2,4-difluorophenyl)- 1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(5-(2,4-difluoroplιenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one: 6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-t-Butyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
7-Fluoro-3-(5-t-butyl-1,2,4-oxadiazol-3-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methyletlιyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-Methoxymethyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxaIin- 4(5H)-one;
6-Chloro-3-(5-methoxymethyl-1,2,4-oxadiazol-3-yI)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5-methoxymethyl-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(5(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(5-tert-butyl-1,2,4-oxadiazol-3-yI)-5-(2-picolyl)-imidazo(1,5-a)quinoxaIin-
4(5H)-one;
7-Fluoro-3-(5(2-tetrahydrofuryI)-1,2,4-oxadiazol-3-yI)-5-(allyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
7-Chloro-3-(5)2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-(2-pyrrolydinyIethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5 {(1,1-Dimethyl-1-methoxy)methyl}-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(5 {(1,1-Dimethyl-1-methoxy)methyl)-1,2,4-oxadiazol-3-yl)-5-(2- pyrroIydinylethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5 {(1,1-Dimethyl-1-methoxy)methyl}-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(5(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(5(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one: 7-Fluoro-3-(5(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo( 1,5- a)quinoxalin-4(5H)-one;
3-(5(2-Pyridyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one.
Synthesis of 1,2,4-Oxadiazol-3-yl Analogues (Formula I, Z is -C(O)-N(R1)- and X is 1,2,4- oxadizole (a).
The 1,2,4-oxadiazol-3-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(5-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(2 -Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(2-methylcycIopropyI)-1,2,4-oxadiazol-3-yl)-5 -oxo-4-methyI- imidazo(1,5-a)quinoxalϊne;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(1-MethoxycycIopropyl)-1,2,4-oxadiazol-3-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(1-methoxycyclopropyI)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxa!ine;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline:
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline; 7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline;
3-(5-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyI- imidazo(1,5-a)quinoxaline;
6-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaIine;
3-(5-(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl - imidazo(1,5-a)quinoxaIine;
3-(5-(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline; 7-Fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl))1,2,4-oxadiazol-3-yl)-5-oxo -4- methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline;
3-(5-(2-Tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-fluoro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yI)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
7-ChIoro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-Chloro-3-(5-(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(3-Tetrahydrofurfuryl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline:
6-Fluoro-3-(5-(3-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-FIuoro-3-(5-(3-tetrahydrofurfuryl)-1 ,2,4-oxadiazol-3-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaIine:
6-Cyano-7-fluoro-3-(5-(3-tetrahydrofurfuryI)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(3-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(3-tetrahydrofurfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(3-tetrahydrofurfuryl)-1-2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline; 6-Fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Fluoro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(3-tetrahydrothiophene)- 1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-((5-Cyclopen-yl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-((5-cyclopentyl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-((5-cycIopentyl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-fluoro-3-((5-cyclopentyl)-1,2,4-oxadiazol-3-yI))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Chloro-3-((5-cycIopentyl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-((5-cyclopentyl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-ChIoro-3-((5-cyclopentyl)-1,2,4-oxadiazol-3-yl))-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-FIuoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(1-methoxycyclopentyl)- 1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-ChIoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(5-(5-metiiylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo( 1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazoI-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(5-(2,4-difluorophenyI)-1,2,4-oxadiazol-3-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine:
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)-5-oxo-4-methyI- imidazo(1,5-a)quinoxaline:
2a.III The 1,2,4-oxadiazol-3-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(5-(-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- tri azolo(4, 3-c)quinazoline ;
7-Chloro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-(-(2-Methylcyclopropyl)- 1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline:
6-Fluoro-3-(5-(-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-5)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-(2-metlιylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(5-(-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline; 6-Cyano-7-Chloro-3-(5-(-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
3-(5-(-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
6-Fluoro-3-(5-(-(1-methoxycycIopropyl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-(-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(4,3-c)quinazoIine;
7-Chloro-3-(5-(-(1-methoxycyclopropyl)-! ,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoIine;
3-(5-(-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoline;
6-FIuoro-3-(5-(-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
7-Fluoro-3-(5-(-(1-hydroxycyclopropyl)- 1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4-.3-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-(-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yI)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
7-Chloro-3-(5-(-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
3-(5-(-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a) 1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(5-(-((1-metiioxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
3-(5-(-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline:
6-Cyano-7-fluoro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline; 7-Chloro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
6-Cyano-7-Chloro-3-(5-(-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(4,3-c)quinazoline;
3-(5-((2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-((2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
7-Fluoro-3-(5-((2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)-imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
6-Cyano-7-fluoro-3-(5-((2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)-midazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-((2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazoIo(4,3- c)quinazoIine;
7-Chloro-3-(5-((2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazoIo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-((2-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
3-(5-((3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
7-Fluoro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- clquinazoline;
6-Cyano-7-fluoro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-((5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4- triazolo(4,3-c)quinazoline;
6-Fluoro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3- yl)imidazo(1,5-a)1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-((5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3- yl)imidazo(1,5-a)1,2,4-triazolo(4,3-c)quinazoline;
3-(5-((2-Tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline; 6-Chloro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoIine;
7-ChIoro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-((2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a) 1,2,4-triazolo(4,3-c)quinazoline;
3-(5-((3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-((3-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yl)imidazo(1,5- a)1,2,4-triazoIo(4,3-c)quinazolϊne;
3-(5-CyclopentyI-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3-c)quinazoIine; 6-Fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Fluoro-(5-cycIopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
6-Cyano-7-fluoro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline; 6-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Clιloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- tri azolo(4, 3-c)quinazoline ;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4, 3-c)quinazoline ;
7-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3-c)quinazoline; 6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
7-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(5-methyIfuryl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoIine;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-y0imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoIine;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-y0imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(4,3-c)quinazoline;
Compounds of Formula II, Z is -CH=N- and X is 1,2,4-oxadizole (a).
The 1,2,4-oxadiazol-3-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(5-(-(1-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)immdazo(1,5-a) 1,2,4- triazoIo(1,5-c)quinazoline;
7-Fluoro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-(1-methylcycIopropyl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,55a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(2-Methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(5-(2-methylcyclopropyI)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
7-Fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(2-methylcyclopropyl)-1,2,4-oxadiazoI-3-yl)-midazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoIine;
3-(5-(1-Metiioxycyclopropyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline; 6-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(1,5-c)quinazoline;
6-ChIoro-3-(5-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-ChIoro-3-(5-((1-methoxy-1-methyl)ethyl)-12.4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
6-Cyano-7-Chloro-3-(5-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5- a)1,2,4-triazolo(1,5-c)quinazoline;
3-(5-((1-Hydroxy-1-met-hyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-y0imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)-midazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-((1-hydroxy-1-methyI)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a) 1,2,4-triazolo(1,5-c)quinazoline;
6-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
7-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoIine;
6-Cyano-7-ChIoro-3-(5-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazoIo(1,5-c)quinazoline; 3-(5-(2-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(3-Tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-y0imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(5-((3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(3-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)qu-nazoline;
7-Fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazoI-3-yI)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryI)-1,2,4-oxadiazol-3-yl)imidazo(1,5- a)1,2,4-triazolo(1,5-c)quinazoline;
6-ChIoro-3-(5-(5-5-dimethyl-2-tetrahydrofuryl)- 1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-ChIoro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-3- yI)imidazo(1,5-a)1,2,4-triazolo(1,5-c)quinazoline;
3-(5-(2-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazoI-3-yI)imidazo(1,5-a) 1,2,4- triazolo(1,5-c)quinazoIine;
7-Fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
6-Cyano-7-fluoro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoline:
6-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoline; 6-Cyano-7-Chloro-3-(5-(2-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(3-Tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(3-tetrahydrothiophene)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(Cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a) 1,2,4-triazolo(1,5-c)quinazoline; 6-Fluoro-3-(5-(cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Fluoro-3-(5-(cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(cyclopentyl-1,2,4-oxadiazoI-3-yl)imid azo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Chloro-3-(5-(cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(5-(cyclopentyl-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline; 6-Cyano-7-Chloro-3-(5-(cycIopentyl-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoIine;
3-(5-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoline;
7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazoIo(1,5- c)quinazoline;
6-Fluoro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(5-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazoIo(1,5-c)quinazoline;
6-Cyano-7-fIuoro-3-(5-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoIine;
7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(5-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(5-Methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5-c)quinazoline; 6-Fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Fluoro-3-(5-(5-metiιylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-ChIoro-3-(5-(5-methylfuryl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(4-Fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Cyano-7-ChIoro-3-(5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(2,4-Difluorophenyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazoIo(1,5- c)quinazoIine;
7-Fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-fluoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
6-ChIoro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazoI-3-yI)imidazo(1,5-a)1,2,4-triazolo(1,5- c)cjuinazoline;
7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano-7-Chloro-3-(5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl)imidazo(1,5-a)1,2,4- triazolo(1,5-c)quinazoline;
3-(5-(1-(t-ButyldiphenyIsiloxy)cyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazoI-3-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(5-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(5-(1-(t-ButyldiphenyIsiloxy)cyclopropyl)-1,2,4-oxadiazol-3-yl)-7-fluoro-5-(2- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-fluoro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-fluoro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-fluoro-5-(5-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-(t-Butyldiphenylsiloxy)cyclopropyl)-1,2,4-oxadiazol-3-yl)-7-chloro-5-(2- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-chloro-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-7-chloro-5-(5-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-(t-Butyldiphenylsiloxy)cyclopropyl)-1,2,4-oxadiazol-3-yl)-6-chloro-5-(2- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-6-chloro-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-6-chloro-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(5-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-3-yl)-6-chloro-5-(5-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
Synthesis of 1,2,4-Oxadiazol-5-yl Analogues (Formula I, Z is -N(R1)-C(O)- and X is 1,2,4-oxadizole (b).
The 1,2,4-oxadiazol-5-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
6-Chloro-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
8-Chloro-3-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(3-Isopropyl-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
7-Fluoro-3-(3-isopropyI-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(3(2-PyridyI)-1,2,4-oxadiazol-5-yl)-5-(1-metJιylethyl)-imidazo(1,5-a)quinoxaIin-4(5H)- one;
3-(3(3-Pyridyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(3(4-PyridyI)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(3(2-Thienyl)-1,2,4-oxadiazol-5-yl)-5-(1-methyIethyl)-imidazo(1,5-a)quinoxalin-4(5H)- one;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(3(N,N-Dimethylamino)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
3-(3-PyrroIidinyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- (5H)-one;
3-(3-PhenyI-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(t-ButyI-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(p-Chlorobenzyl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- (5H)-one; 3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-ox-idiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycycIopropyl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-HydroxycycIopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one; 6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(1- methyIethyl)-iιnidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-TetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3(2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(1- methylethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetι^ydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3(3-Tettrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-CyclopentyI-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxa!in-4(5H)-one; 6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-me-hylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3-(5-Metiιylfuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazoI-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yI)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Cyano-7-fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methyl ethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2,4-difluorophenyI)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-)2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methylcycIopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyI)- ύnidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazoI-5-yI)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2- morphoIinoethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol -5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fIuoro-3-(3-((1-methoxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(2- morphoIinoethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yI)-5-(2- morphoIinoethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Hydroxy-1-methyI)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalϊn~4(5H)-one;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-Tetrahydrofuιy0-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrofuryl)-l;2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholmoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrofiiryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryI)-1,2,4-oxadiazoI-5-yI)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(5,5-dimethyI-2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(5,5-dimethyl-2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyI)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin^l(5H)-one; 3-(3(3-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-Cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopehtyI)-1,2,4-oxadiazol-5-yI)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycycIopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- morpholinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yI)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycycIopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- morphoIinoethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazoI-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yI)-5-(2- morpholinoethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopentyI)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- morphol-noethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(5-Methylfuryl)-1,2,4-oxadiazoI-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(5-methyl--uryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5 H)-one ;
6-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxa!in-4(5H)-one;
7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol -5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazoI-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yI)-5-(2-morpholinoethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(2,4-dϊfluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxalϊn-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2,4-difluorophenyI)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morpholinoethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-morphoIinoethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methylcyclopropyl)-1-2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one; 7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yI)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyI)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyI)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-ChIoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxatin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-hydroxy-1-methy0ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- 5 a)quinoxaIin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrofiιryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyI)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinpxalin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(3-Tetrahydrotiιiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- midazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-Cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Cyano-7-fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-cycIopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(3-(1-MethoxycycIopentyl)-1,2,4-oxadiazoI-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazoo1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(5-Methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a,quinoxalin-4(5H)- one;
6-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazoI-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-(4-fIuorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyI)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-ChIoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picoIyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-me-hoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-metiiylcyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one; 6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2-methylcyclopropyI)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2-methylcycIopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-ChIoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3-(1-MethoxycycIopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycycIopropyl)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-((1-Methoxy-1-metiιy0ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-methoxy-1-methy0ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one; 3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyI)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(2-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Cyano-7-ChIoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)quinoxaIin-4(5H)-one;
3-(3(2-Tetrahydrot-hiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1 ,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(3-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrotiιiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3(-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo((,5- a)quinoxalin-4(5H)-one; 7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-methoxycyclopentyI)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopentyI)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- methoxyethyl)-imidazo(1,5-a)qumoxalin-4(5H)-one;
3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycycIopentyI)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin- 4(5H)-one;
6-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(5-metfrylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(5-metiιylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5-a)quinoxalin-
4(5H)-one;
6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one; 6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Chloro-3-(3-(4-fluoropphenyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazoI-5-yI)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
6-Cyano-7-fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
6-Cyano-7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyI)- imidazo(1,5-a)quinoxaIin-4(5H)-one.
3-(3-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(2,3-Dimethylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-((3-Cyclopropyl-1,2,4-oxadiazol-5-yl)methyl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
3-((3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)methyl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydroftιrfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrorurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one; 7-ChIoro-3-(3-(2-methylcyclopropyI)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)-imidazo(1,5 a)quinoxalin-4(3H)-one;
6-FIuoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-ChIoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyI)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurluryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(1-Hydroxycyclopropyl)- 1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo (1,5-a)quuιoxalin-4(3H)-one;
3-(3-((1 -Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-((1 -methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)- midazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one; 6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo (1,5-a)quinoxalin-4(3H)-one;
3-(3(2-Tetrahydrofuιyl)-1,2,4-oxadiazol -5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuιyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl) -1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3(2-Tetrahydrothiophene)- 1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one; 6-Cyano-7-fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
7-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4- oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
6-Cyano-7-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin-4(3H )-one;
3-(3(3-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-ChIoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
7-ChIoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-CycIopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin- 4(3H)-one;
6-Fluoro-3-(3-cyclopentyI-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
7-Fluoro-3-(3-cycIopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(1-methoxycyclopentyI)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-ChIoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one; 7-Fluoro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryI)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-ChIoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-ChIoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(3-Methylfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(3-methylfuryl)- 1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(3-methylfuryl )-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5- a)quinoxahin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(3-methylfuryl )-1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-ChIoro-3-(3-(3-methylfuryl) -1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin-4(3H)-one;
7-ChIoro-3-(3-(3-methyIfuryl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(3-methylfuryl) -1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryI)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-ChIoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
7-ChIoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
6-Cyano-7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-(2- tetrahydrofurfuryl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(2-Pyrrolidinyl)-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxalin- 4(3H)-one; 3-(3-(2-PyrroIidinyl)-1,2,4-oxadiazol-5-yI)-5-(2-methoxyethyI)-imidazo(1,5-a)quinoxalin- 4(3H)-one;
3-(3-(2-PyrroIidinyl)-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(2-Pyrrolidinyl)-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(3H)- one;
3-(3-(2-PyrroIidinyl)methyl-1,2,4-oxadiazol-5-yl)-5-(1-methyIethyI)-imidazo(1,5-a)quinoxaIin- 4(3H)-one;
3-(3-(2-Pyrrolidinyl)methyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(2-PyrroIidinyl)methyl-1,2,4-oxadiazoI-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(2-PyrroIidinyl)methyl-1,2,4-oxadiazoI-5-yl)-5-(2-picoIyI)-imidazo(1,5-a)quinoxalin- 4(3H)-one;
3-(3-(N-MethyI-2-pyrrolidinyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
3-(3-(N-MethyI-2-pyrroIidinyl-1,2,4-oxadiazoI-5-yl)-5-(2-methoxyethyI)-imidazo(1,5- a)quinoxaIin-4(3H)-one;
3-(3-(N-Methyl-2-pyrrolidinyl-1,2,4-oxadiazol-5-yl)-5-(2-tetrahydrofurfuryl)-imidazo(1,5-a)quinoxaIin-4(3H)-one;
3-(3-(N-Methyl-2-pyrrolidinyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(N-Methyl-2-pyrroIidinyl)methyl-1,2,4-oxadiazol-5-yl)-5-(1-methylethyl)-imidazo(1,5-a)quinoxaIin-4(3H)-one;
3-(3-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-5-yl)-5-(2-methoxyethyl)- imidazo(1,5-a)quinoxaIin-4(3H)-one;
3-(3-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazoI-5-yI)-5-(2-tetrahydrofurfuryl)- imidazo(1,5-a)quinoxalin-4(3H)-one;
3-(3-(N-Methyl-2-pyrrolidinyl)methyl-1,2,4-oxadiazol-5-yl)-5-(2-picolyl)-imidazo(1,5- a)quinoxalin-4(3H)-one;
Synthesis of 1,2,4-Oxadiazol-5-yl Analogues (Formula I, Z is -C(O)-N(R1)- and X is 1,2,4-oxadizole (b).
The 1,2,4-oxadiazol-5-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxalin;
6-Fluoro-3-(3-(1-methylcyclopropyI)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline; 6-Cyano-7-fIuoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-ChIoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI- imidazo(1,5-a)quinoxaIine;
3-(3-(1-methoxycyclopropyl)-1,2-4-oxadiazoI-5-yl)-5-oxo-4-methyl -imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5 a)quinoxaline;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5 a)quinoxaIine;
6-Cyano-7-fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI- imidazo(1,5-a)quinoxaIine;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-Cyano-7-ChIoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-Fluoro-3-(3-(1-hydroxycyclopropyI)-1,2,4-oxadiazoI-5-yI)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yI)-5-oxo-4- methyI-imidazo(1,5-a)quinoxaIine;
3-(3(2-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(14-a)quinoxaline; 6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3(2-tetrahydrofuryl )-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(3(2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine;
6-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-metthyI-imidazo(1,5- a)quinoxaline;
6-Cyano-7-(Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine;
3-(3(2-Tetrahydrofurfuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine; 6-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3(5,5-dimethyl -2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-ChIoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5 a)quinoxaIine;
7-Fluoro-3-(3(2-tetrahyrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
6-Cyano-7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
6-ChIoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(3(3-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-ChIoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
3-(3-Cyylopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3-cyclopentyI-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine;
6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4- methyl- imidazo(1,5-a)quinoxaline;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Fluoro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaIine;
7-Fluoro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI-imidazo(1,5- a)quinoxaline;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaIine;
3-(3-(5-Methylfuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(3-(5-methylfuryl )-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine;
6-Cyano-7-Fluoro-3-(3-(5-methyIfuryl)-1,2,4-oxadiazoI-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-ChIoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyI-imidazo(1,5-a)quinoxaIine;
7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yI)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaIine;
6-Cyano-7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(3-(4-fluorophenyI)-1,2,4-oxadiazol-5-yl)-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline; 6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
6-Cyano-7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline;
Synthesis of 1,2,4-Oxadiazol-5-yl Analogues (Formula II, Z is -N=CH-, and X is 1,2,4- oxadizole.
The 1,2,4-oxadiazol-5-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(3-(1-MethyIcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoline;
6-Fluoro-3-(3-(1-methyIcycIopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
7-Fluoro-3-(3-(1-methyIcycIopropy)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-methyIcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-Cyano-7-Chloro-3-(3-(1-methylcycIopropyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)qumazoline;
3-(3-(2-Methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3-(2-methylcycIopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
7-Fluoro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(2-methylcyclopropyI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline; 7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(3-(1-Methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)-midazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(3-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5 -yl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-ChIoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazoI-5-yl)midazo (1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
6-Cyano-7-Chloro-3-(3-(1-hydroxycycIopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1-5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Fluoro-3-(3-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoIine;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(3-((1-methoxy-1-methyI)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazoIo(4,3-c)quinazoline;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Fluoro-3-(3-((1-hydroxy-1-metthyl)ethyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline; 6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-me-hy0ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoIine;
3-(3(2-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(3(2-Tetrahydrofurfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano -7-Fluoro-3-(3(2-tetrahydrofurfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-112,4- triazolo(4,3-c)quinazoline;
6-ChIoro-3-(3(2-tetrahydrofurfuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(3(2-tetrahydrofurfuryI)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3(2-tetrahydrofurfuιyI)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoline;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoIine;
6-Cyano-7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-ChIoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
7-ChIoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Cyano-7-ChIoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoIine;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1-2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline; 6-Cyano-7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-ChIoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(3(3-Tetrahydrothiophene )-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-tri--zolo(4,3-c)quinazoline;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
7-ChIoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
3-(3-C-yclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3-cycIopentyl-1,2,4-oxadiazol-5-yl)imidazo(1-5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
7-Fluoro-3-(3-cycIopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-Chloro-3-(3-cycIopentyl-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo (4,3-c)quinazoline;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(3-(5-Methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; 6-Fluoro-3-(3-(5-methylfuryl)-1-2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
6-ChIoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
7-ChIoro-3-(3-(5-methyIfuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-ChIoro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoIine;
6-Fluoro-3-(3-(4-fluorophenyI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(4,3- c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoIine;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(4,3-c)quinazoIine;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline; 7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline;
6-Cyano-7-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
Synthesis of 1,2,4-Oxadiazol-5-yl Analogues (Formula II, where Z is -CH=N- and X is 1,2,4-oxadizole (b).
The 1,2,4-oxadiazol-5-yl analogues were prepared as described in EP 202-441. The isonitrile oxadiazole starting materials were also prepared by standard means.
3-(3-(1-Methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(1-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
3-(3-(2-MethyIcyclopropyI)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(3-(2-methylcycIopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(2-methylcyclopropyI)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(2-methylcycIopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)- 1,2,4- triazoIo(1,5-c)quinazoline;
6-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(2-methylcyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
3-(3-(1-MethoxycyclopropyI)-1,2,4-oxadiazol-5-yl)-midazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoline;
6-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 6-Cyano-7-Chloro-3-(3-(1-methoxycyclopropyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-(3-(1-Hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
6-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(3-((1-Methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-((1-methoxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-(3-((1-Hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline;
6-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoIine;
6-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-((1-hydroxy-1-methyI)ethyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-((1-hydroxy-1-methyl)ethyl)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline;
3-(3(2-TetrahydrofuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(3(2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoIine;
6-ChIoro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Cyano -7-Chloro-3-(3(2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(3(3-Tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3(3-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(3(5,5-Dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(3(5,5-dimethyl-2-tetrahydrofuryl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3(5-5-dimethyl-2-tetrahydrofuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5- a)-1,2,4-triazoIo(1,5-c)quinazoline;
3-(3(2-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
6-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
6-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoIine;
7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3(2-tetrahydrothiophene)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(3(3-Tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 6-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3(3-tetrahydrothiophene)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
3-(3-Cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 6-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-cyclopentyl-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(3-(1-Methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; 6-Chloro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-ChIoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
6-Cyano-7-ChIoro-3-(3-(1-methoxycyclopentyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoline;
3-(3-(1-Hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline;
6-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazoI-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline;
6-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline;
7-Chloro-3-(3-(1-hydroxycyclopentyl)-1,2,4-oxadiazol-5-yI)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
6-Cyano-7-ChIoro-3-(3-(1-hydroxycycIopentyl)-1,2,4-oxadiazol-5-yl)-midazo(1,5-a)- l,2,4-triazolo(1,5-c)quinazoline;
3-(3-(5-Methylfuryl )-1,2,4-oxadiazol -5-yl)imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoline; 6-Fluoro-3-(3-(5-methylfuryl )-1,2,4-oxadiazol -5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(5-methylfuryl )-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
6-Cyano-7-Fluoro-3-(3-(5-methylfuryI)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine; 6-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(5-methylfuryl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Chloro-3-(3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(3-(2,4-Difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
6-Cyano-7-Fluoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoIine;
6-Chloro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
7-ChIoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazoI-5-yI)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine;
6-Cyano-7-ChIoro-3-(3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl)imidazo(1,5-a)-1,2,4- triazoIo(1,5-c)quinazoline.
Synthesis of Compounds of Formula I, where Z is -N(R1)-C(O)- and X is SCHO (i), such as 3-carboxaIdehyde-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxaIine.
4,5-Dihydro-4-oxo-5-(1-methyIethyI)-imidazo(1,5-a)-quinoxaline-3-carboxylic acid was treated with thionyl chloride to afford the corresponding acid chloride (4,5-dihydro-4-oxo-5-(1- methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxyl chloride). That acid chloride was then reduced with sodium borohydride in a mixture of THF and water to afford the alcohol 3- (hydroxymethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline. 3- (Hydroxymethyl)-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)-quinoxaline was oxidized with MnO2 to yield 3-carboxaldehyde-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)- quinoxaline.
Synthesis of Compounds of Formula I, where Z is -C(O)-N(R1)- and X is SCHO (i), such as 3-carboxaldehyde-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline.
4,5-Dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline-3-carb oxylic acid was treated with thionyl chloride to afford the corresponding acid chloride (4,5-dihydro-5-oxo-4-methyl- imidazo(1,5-a)-quinoxaline-3-carboxyl chloride). That acid chloride was then reduced with sodium borohydride in a mixture of THF and water to afford the alcohol 3-(hydroxymethyl)-4,5- dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline. 3-(Hydroxymethyl)-4,5-dihydro-5-oxo-4- methyl-imidazo(1,5-a)-quinoxaline was oxidized with MnO2 to yleld 3-carboxaldehyde-4,5- dihydro-5-oxo-4-methyl-imidazo(1,5-a)-quinoxaline.
Synthesis of Compounds of Formula II, where Z is -N=CH- and X is SCHO (i), such as 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline.
Imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylic acid was treated with thionyl chloride to afford the corresponding acid chloride (imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline-3-carboxyl chloride). That acid chloride was then reduced with sodium
borohydride in a mixture of THF and water to afford the alcohol 3-(hydroxymethyl)- imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. 3-(Hydroxymethyl)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline.
Synthesis of Compounds of Formula II, where Z is -CH=N- and X is SCHO (i), such as 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoIine.
Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylic acid was treated with thionyl chloride to afford the corresponding acid chloride (imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoline-3-carboxyl chloride). That acid chloride was then reduced with sodium
borohydride in a mixture of THF and water to afford the alcohol 3-(hydroxymethyl)- imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. 3-(Hydroxymethyl)-imidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazoline was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)- 1,2,4-triazolo(1,5-c)quinazoline.
Synthesis of Compounds of Formula II, where Z is -CH= N- and X is -C(O)-alkyl, heteroaryl or aryl (j).
Treatment of imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxyl chloride with benzene in the presence of a Lewis acid (such as AlCl3) afforded the corresponding C-3 aryl ketone 3-benzoyl-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. 3-(p-Fluorobenzoyl)- imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline was prepared in the following manner. 3- (Hydroxymethyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol which was in turn oxidized with MnO2 to yield the title compound 3-(p-fluorobenzoyl)-imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline;
3-Benzoyl-imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline;
3-(p-FluorobenzoyI)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline.
Synthesis of Compounds of Formula II, where Z is -N=CH- and X is -C(O)-aIkyI, heteroaryl or aryl (j).
Treatment of imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoIine-3-carboxyI chloride with benzene in the presence of a Lewis acid (such as AlCI3) afforded the corresponding C-3 aryl ketone 3-benzoyI-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine. 3-(p-Fluorobenzoyl)- imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline was prepared in the following manner. 3- (Hydroxymethyl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol which was in mm oxidized with MnO2 to yield the title compound 3-(p-fluorobenzoyl)-imidazo(1-5-a)- 1,2-4-triazoIo(1,5-c)quinazoline;
3-Benzoyl-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(p-Fluorobenzoyl)-imidazo(1,5 -a)-1,2,4-triazolo(1,5-c)quinazoIine.
Examples of Compounds of Formula I, where Z is -N(R,)-C(O)- and X is -C(O)-OR
(j).
t-Butyl 4,5-dihydro-4-oxo-5-(2-morphoIinoethyI)-imidazo(1,5-a)-quinoxaline-3- carboxylate;
t-Butyl 4,5-dihydro-4-oxo-7-fluoro-5-(2-morpholinoethyI)-imidazo(1,5-a)-quinoxaIine-3- carboxylate.
Examples of Compounds of Formula I, where Z is -N(R1)-C(O)- and X is -C(O)-NR
(j).
Prepared from the corresponding acid using standard coupling conditions known to those skillful in the art.
5-(1-Methylethyl)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-(2-pyridinyl) carboxamide MP 276-81
5-(1-MethyIethyl)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-cyclopropylmethyl carboxamide MP 290-3
5-(1-MethylethyI)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-isopropyl carboxamide 5-(1-MethylethyI)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-t-butyI carboxamide
5-(1-Methylethyl)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-piperdinyl
carboxamide
5-(1-Methylethyl)-4,5-dihydro-4-oxo-imidazo(1,5-a)quinoxaline-3-(4-methylpiperazinyl) carboxamide
Examples of Compounds of formula I, where Z is -C(O)-N(R-)- and X is -C(O)-NR
(j).
Prepared from the corresponding acid using standard coupling conditions known to those skillful in the art.
4,5-dihydro-4-methyl-5-oxo-imidazo(1,,-a)quinoxaline-3-(2-pyridinyl) carboxamide MP 276-81 C;
4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinoxaline-3-cyclopropylmethyl carboxamide MP 290-3 C;
4.5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinoxaline-3-isopropyl carboxamide
4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinoxaline-3-t-butyl carboxamide
4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quinoxaline-3-piperdinyl carboxamide
4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)quuioxaline-3-(4-methylpiperazinyl) carboxamide
Examples of Compounds of formula II, where Z is -N=CH- and X is -C(O)-NR (j).
Ethyl imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylate was added to a mixtare of water and methanol containing potassium carbonate. The resulting acid, imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxylic acid, was then treated with CDI in DMF followed by the addition of 3,4-dichlorobenzylamine to yield the title compound, imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline-3-((3,4-dichlorobenzyl)carboxamide).
Examples of Compounds of formula II, where Z is -CH=N- and X is -C(O)-NR (j). Ethyl imidazo(1-5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate was added to a mixtare of water and methanol containing potassium carbonate. The resulting acid, imidazo(1,5- a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylic acid, was then treated with CDI in DMF followed by the addition of 3,4-dichlorobenzylamine to yield the compound. imidazo(1,5-a)- 1,2-4-triazolo(1,5-c)quinazoline-3-((3-4-dichlorobenzyl)carboxamide ).
Examples of Compounds of Formula I, where Z is -N(R1)-C(O)- and X is -CH2-OH
(i).
Treatment of 4,5-dmydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline-3-carboxyI chloride with benzene in the presence of a Lewis acid (such as AlCl3) afforded the
corresponding C-3 aryl ketone 3-benzoyl-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaline. Reduction of that ketone with NaBH4 afforded 3-(1-hydroxybenzyl-4,5-dihydro-4- oxo-5-(1-methyIethyl)-imidazo(1,5-a)-quinoxaline. 3-(p-Fluorobenzoyl)-4,5,-dihydro-4-oxo-5-(1- methylethyl)-imidazo(1,5-a)-quinoxaIine was prepared in the following manner. 3-
(Hydroxymethyl)-4,5-dihydro-4-oxo-5-(1-methyIethyI)-imidazo(1,5-a)-quinoxaIine was oxidized with MnO2 to yield 3-carboxaIdehyde-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)- quinoxaline. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol.
3-(1-HydroxybenzyI)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline;
3-((1-Hydroxy)p-fluorobenzyl)-4,5-dihydro-4-oxo-5-(1-methyIethyl)-imidazo(1,5-a)- quinoxaline.
Examples of Compounds of formula I, where Z is -C(O)-N(R1)- and X is -CH2-OH
(i).
Treatment of 4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaIine-3-carboxyl chloride with benzene in the presence of a Lewis acid (such as AlCI3) afforded the corresponding C-3 aryl ketone 3-benzoyl-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline. Reduction of that ketone with NaBH4 afforded 3-(1-hydroxybenzyl-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)- quinoxaline. 3-(p-FluorobenzoyI)-4,5,-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline was prepared in the following manner. 3-(HydroxymethyI)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)-quinoxaline was oxidized with MnO2 to yield 3-carboxaldehyde-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)-quinoxaline. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol.
3-(1-Hydroxybenzyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline;
3-((1-Hydroxy)p-fluorobenzyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline. Examples of Compounds of Formula II, where Z is -N-CH- and X is -CH2-OH (i). Treatment of imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline-3-carboxyl chloride with benzene in the presence of a Lewis acid (such as AlCl3) afforded the corresponding C-3 aryl ketone 3-benzoyl-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. Reduction of that ketone with NaBH4 afforded 3-(1-hydroxybenzyl-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. 3-(p- Fluorobenzoyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline was prepared in the following manner. 3-(Hydroxymethyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol.
3-(1-Hydroxybenzyl-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-((1-Hydroxy )p-fluorobenzyI)-imidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazoline.
Examples of Compounds of Formula II, where Z is -CH=N- and X is -CH2-OH (i).
Treatment of imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxyl chloride with benzene in the presence of a Lewis acid (such as AlCl3) afforded the corresponding C-3 aryl ketone 3-benzoyl-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. Reduction of that ketone with NaBH4 afforded 3-(1-hydroxybenzyl-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. 3-(p- FluorobenzoyI)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline was prepared in the following manner. 3-(Hydroxymethyl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline was oxidized with MnO2 to yield 3-carboxaldehyde-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. Treatment of that aldehyde with p-fluorophenylmagnesium bromide afforded the corresponding alcohol. 3-(1-Hydroxybenzyl-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-((1-Hydroxy)p-fluorobenzyl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline.
Examples of Formula I, where Z is -N(R1)-C(O)- and X is -CH2-OR or -CH2-NR (i). Treatment of 3-(hydroxymethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaIine with benzoyl chloride in piyidine afforded 3-(benzoyloxomethyl)-4,5-dihydro-4- oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline. Altematively, 3-(hydroxymethyl)-4,5-dihydro- 4-oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline can be treated with thionyl chloride to yield the corresponding 3-(chloromethyl)-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5- a)quinoxaline which when treated with sodium isopropoxide affords 3-(isopropoxymethylether)- 4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline. 3-(ChIoromethyl)-4-5-dihydro- 4-oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline can also be reacted with amines to yield compounds such as: 3-(isopropylaminomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline, 3-(N,N-diethylaminomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline, 3-(morpholinomethyI)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline.
3-(HydroxymethyI)-4,5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)quinoxaline; 3-(Benzoyloxomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline; 3-(ChloromethyI)-4-5-dihydro-4-oxo-5-(1-methylethyI)-imidazo(1,5-a)quinoxaline;
3-(Isopropoxymethylether)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline;
3-(Isopropylaminomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline;
3-(N,N-DiethyIaminomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5- a)quinoxaline;
3-(Morpholinomethyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)quinoxaline. Examples of Formula I, where Z is -C(O)-N(R1 )- and X is -CH2-OR or -CH2-NR (i). Treatment of 3-(hydroxymethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline with benzoyl chloride in pryidine afforded 3-(benzoyloxomethyl)-4,5-dihydro-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline. Altematively, 3-(hydroxymethyl)-4,5-dihydro-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline can be treated with thionyl chloride to yield the corresponding 3- (chloromethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline which when treated with sodium isopropoxide affords 3-(Isopropoxymethylether)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5- a)quinoxaline. 3-(Chloromethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline can also be reacted with amines to yield compounds such as: 3-(isopropylaminomethyl)-4,5-dihydro-5- oxo-4-methyl-imidazo(1,5-a)quinoxaline, 3-(N,N-diethylaminomethyl)-4,5-dihydro-5-oxo-4- methyl-imidazo(1,5-a)quinoxaline, 3-(morpholinomethyl)-4,5-dihydro-5-oxo-4-methyl- imidazo(1,5-a)quinoxaline.
3-(Hydroxymethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(Benzoyloxomethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(Chloromethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(Isopropoxymethylether)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(Isopropylaminomethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline;
3-(N,N-Diethylaminomethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline; 3-(Morpholinomethyl)-4,5-dihydro-5-oxo-4-methyl-imidazo(1,5-a)quinoxaline.
Examples of Formula II where Z is -N=CH- and X is CH2-OR or CH2-NR (i).
Treatment of 3-(hydroxymethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline with benzoyl chloride in pryidine afforded 3-(benzoyloxomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline. Alternatively, 3-(hydroxyme-hyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline can be treated with thionyl chloride to yield the corresponding 3-(chloromethyl)imidazo(1,5-a)- 1,2,4-triazolo(4,3-c)quinazoline which when treated with sodium isopropoxide affords 3- (isopropoxymethylether)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline. 3-
(Chloromethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline can also be reacted with amines to yield compounds such as 3-(isopropylaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoline, 3-(NN-diethyIaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline, 3- (morphoIinomethyI)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline.
3-(Hydroxymethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(Benzoyloxomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
3-(Chloromethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(Isopropoxymethylether)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine;
3-(Isopropylaminomethyl)imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline;
3-(RN-Diethylaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
3-(Morpholinomethyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine.
Examples of Formula II where Z is -CH=N- and X is CH2-OR or CH2-NR (i).
Treatment of 3-(hydroxymethyl)imidazo(1,5-a)-1,2,4-triazolo(1-5-c)quinazoline with benzoyl chloride in pryidine afforded 3-(benzoyloxomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline. Alternatively, 3-(hydroxymethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline can be treated with thionyl chloride to yield the corresponding 3-(chloromethyl)imidazo(1,5-a)- 1,2,4-triazoIo(1,5-c)quinazoline which when treated with sodium isopropoxide affords 3- (isopropoxymethylether)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. 3- (Chloromethyl)imidazo(1,5-a)-1,2,4-triazoIo(1,5-c)quinazoline can also be reacted with amines to yield compound such as: 3-(isopropylaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoline, 3-(N,N-diethyIaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline, 3- (morpholinomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine.
3-(HydroxymethyI)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(BenzoyIoxomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(Chloromethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine;
3-(Isopropoxymethylether)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(IsopropyIaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(N,N-Diethylaminomethyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
3-(MorpholinomethyI)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. Examples of Compounds of Formula I, where Z is -N(R1-C(O)-, and X is -CH=CH2 (h).
3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)- quinoxaline was treated with sodium in ammonia (see Synthesis (1972) 391 and for a review see Synthesis (1973) 457) to yield 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-oxo-5-(1-methylethyI)- imidazo(1,5-a)-quinoxaline. Altematively, 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-oxo-5-(1- methylethyl)-imidazo(1,5-a)-quinoxaline can be converted to the 3-(3-t-butoxycarbonyloxy-1- propynyl) derivative under standard conditions and that material treated with a borohydride reducing agent such as those reported in: J. Am. Chem. Soc. (1971), 93, 6309; J. Am. Chem. Soc (1972) 94, 6560; Synthesis (1972) 557; J. Org. Chem. (1973) 38, 1617; J. Am. Chem. Soc.
(1972) 94, 4370. Altematively, direct reduction of 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-oxo- 5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline with PhMe2SiZnEt2Li/CuCN/THF as described in Tetrahedron Letters (1985) 26, 4629 yields 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-oxo-5-(1- methylethyl)-imidazo(1,5-a)-quinoxaline. These olefinic compounds can also be prepared from 3-iodo-4,5-dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxaline or other 3-halo-4,5- dihydro-4-oxo-5-(1-methylethyl)-imidazo(1,5-a)-quinoxalines using a Pd(OAc)2 catalyzed procedure as described in J. Org. Chem. (1972) 37, 2320.
Examples of Compounds of Formula I, where Z is -C(O)-N(R,)-, and X is -CH=CH2
(h).
3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline was treated with sodium in ammonia (see Synthesis (1972) 391 and for a review see Synthesis
(1973) 457) to yield 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)- quinoxaline. Altematively, 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5- a)-quinoxaline can be converted to the 3-(3-t-butoxycarbonyloxy-1-propynyI) derivative under standard conditions and that material treated with a borohydride reducing agent such as those reported in: J. Am. Chem. Soc. (1971), 93, 6309; J. Am. Chem. Soc (1972) 94, 6560; Synthesis (1972) 557; J. Org. Chem. (1973) 38, 1617; J. Am. Chem. Soc. (1972) 94, 4370. Alternatively, direct reduction of 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)- quinoxaline with PhMe2SiZnEt2Li/CuCN/THF as described in Tetrahedron Letters (1985) 26, 4629 yields 3-(3-hydroxy-1-propynyl)-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)-quinoxaline. These olefϊnic compounds can also be prepared from 3-iodo-4,5-dihydro-4-methyl-5-oxo- imidazo(1,5-a)-quinoxaline or other 3-halo-4,5-dihydro-4-methyl-5-oxo-imidazo(1,5-a)- quinoxalines using a Pd(OAc)2 catalyzed procedure as described in J. Org. Chem. (1972) 37, 2320.
Examples of Compounds of Formula II, where Z is -N=CH-, and X is -CH=CH, (h).
3-(3-Hydroxy-1-propynyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine was treated with sodium in ammonia (see Synthesis (1972) 391 and for a review see Synthesis (1973) 457) to yield 3-(3-hydroxy-1-propynyl)imidazo(1,5-a)-1,2,4-triazoIo(4,3-c)quinazoline. Altematively, 3-(3-hydroxy-1-propynyI)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline can be converted to the 3-(3-t-butoxycarbonyloxy-1-propynyl) derivative under standard conditions and that material treated with a borohydride reducing agent such as those reported in: J. Am. Chem. Soc. (1971), 93, 6309; J. Am. Chem. Soc (1972) 94, 6560; Synthesis (1972) 557; J. Org. Chem. (1973) 38, 1617; J. Am. Chem. Soc. (1972) 94, 4370. Altematively, direct reduction of 3-(3-hydroxy-1- propynyl)imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline with PhMe2SiZnEt2Li/CuCN/THF as described in Tetrahedron Letters (1985) 26, 4629 yields 3-(3-hydroxy-1-propynyl)imidazo(1,5- a)-1,2,4-triazolo(4,3-c)quinazoIine. These olefinic compounds can also be prepared from 3- iodoimidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline or other 3-haloimidazo(1,5-a)-1,2,4- triazolo(4,3-c)quinazolines using a Pd(OAc)2 catalyzed procedure as described in J. Org. Chem. (1972) 37, 2320.
Examples of Compounds of Formula II, where Z is -CH=N-, and X is -CH=CH2 (h).
3-(3-Hydroxy-1-propynyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline was treated with sodium in ammonia (see Synthesis (1972) 391 and for a review see Synthesis (1973) 457) to yield 3-(3-hydroxy-1-propynyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline. Alternatively, 3-(3-hydroxy-1-propynyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline can be converted to the 3-(3-t-butoxycarbonyloxy-1-propynyl) derivative under standard conditions and that material treated with a borohydride reducing agent such as those reported in: J. Am. Chem. Soc. (1971), 93, 6309; J. Am. Chem. Soc (1972) 94, 6560; Synthesis (1972) 557; J. Org. Chem. (1973) 38, 1617; J. Am. Chem. Soc. (1972) 94, 4370. Altematively, direct reduction of 3-(3-hydroxy-1- propynyl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline with PhMe2SiZnEt2Li/CuCN/THF as described in Tetrahedron Letters (1985) 26, 4629 yields 3-(3-hydroxy-1-propynyl)imidazo(1,5- a)-1,2,4-triazolo(1,5-c)quinazoline. These olefinic compounds can also be prepared from 3-iodoimidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline or other 3-haloimidazo(1,5-a)-1,2,4- triazolo(1,5-c)quinazolines using a Pd(OAc)2 catalyzed procedure as described in J. Org. Chem. (1972) 37, 2320.
Examples of Compounds of Formula II, where Z is -N=CH-, and X is an Aryl or heteroaryl (k).
Potassium t-butoxide was added to a THF solution of p-fluorobenzyisonitrile below room temperature. To that solution was added 5-chloro-1,2,4-triazolo(4,3-a)quinazoline and stirring continued for several hours. The solvent was evaporated and the compound isolated by recrystallization from a mixture of alcohol/pentane. Using this procedure the following compounds are prepared.
3-(p-Huorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline;
8-Chloro-3-(p-fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline.
Examples of Compounds of Formula II, where Z is -CH=N-, and X is an Aryl or heteroaryl (k).
Potassium t-butoxide was added to a THF solution of p-fluorobenzyisonitrile below room temperature. To that solution was added 5-chloro-1,2,4-triazolo(1,5-a)quinazoline and stirring continued for several hours. The solvent was evaporated and the compound isolated by recrystallization from a mixture of alcohol/pentane. Using this procedure the following compounds are prepared.
3-(p-Fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline;
8-ChIoro-3-(p-fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine.
With respect to compounds of Formula III , preferred embodiments are those where R is hydrogen or fluorine, R1 is a C1- 6 lkyl, and R5 is a C3-7 cycloalkyl substituted with a F, Cl, C2-6 alkyl, O-C1-6 alkyl or OH. More preferred is where X is the oxadiazyl group (a). Even more preferred is where one R is fluorine and the other is hydrogen; and R1 is C2-C4 alkyl (more preferred R1 is i-propyl). cycloalkyl.
Since the imidazo(1,5-a)quinoxalines (III) are amines, many do not form salts, but some do. If salts can be made, they are preferred because of their increased water solubility. When salts of the imidazo(1,5-a)quinoxalines (III) are made they are produced by reaction with acids of sufficient strength.
The pharmaceutical properties of the invention are demonstrated by determining their ability to displace radioactive labelled flunitrazepam from benzodiazepine receptors. In the following Table, Ki values are shown for Examples 1, 2 and 4 compounds and a comparative compound which is not a compound of the subject invention but is structurally similar. The comparative example, "Comparative" in Table, is 3-((2-methylcyclopropyl)-1,2,4-oxadiazol-3-yl)- 5-(1-methyIethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-one prepared by A/S Ferrosan, Soborg, Denmark. Calculation of K: values for CNS activity described in Sethy, V.H. et al., J. Pharm Pharmacol. 34:115-16 (1982).
The Ki value is determined from a concentration response curve obtained in the presence and absence of a fixed concentration of competitive antagonist, flunitrazepam.
Comparison of the agonist concentrations required to produce identical degrees of effect reveals the Ki. The lower Ki value indicates a higher affinity for benzodiazepine.
TABLE
Figure imgf000301_0001
* In all compounds, R is H; and R1 is isopropyl.
The imidazo(1,5-a)quinoxalines (I) are produced by a number of processess, as described above, depending on the variable substitutents involved. The process to produce the imidazo(1,5-a)quinoxalines (I) can be viewed as a three "sequence" process. The first part is the formation of an appropiately substituted 1,2-diamino aromatic/heteroaromatic compound from some appropiately substituted nitro aromatic. The second transformation is the conversion of to the appropriately substituted 1,2-diamino aromatic/heteroaromatic compound which is subsequently converted to the bicyclic amide "quinoxaline". The final step is the addition of the appropriately substituted imidazol group through the reaction of the quinoxaline and an isonitrile oxadiazole.
The diamino compounds can then be transformed to the corresponding bicyclic amides. The diamino compound starting materials are known to those skilled in the art or can be readily prepared by methods known to those skilled in the ait The diamino compounds are reacted with oxalyl chloride in a solvent such methylene chloride to yield bicyclic amides.
The bicyclic amide can then be transformed to the corresponding imidazo(1,5- a)quinoxaIine. The imidazole ring is formed by known methods (see J. Med. Chem., 32, 2282 (1989), US Patent 4,774,245, EP 344,943 A, EP 347,094A, EP320.136, EP 368,652A and EP 283,102A).
When the final product is other than a 1-substituted cycloalkyl, the compound will contain an asymmetric center and therefore produce two enantiomers one "S" and the other "R", either of which can be (+/d) and the other (-/1). Both enantiomers (+) and (-) are useful in the same way as the optically impure (racemic, +) mixture. Hence, they may be utilized in the racemic form without separating them. However, if it is desired to utilize one of the enantiomers, two methods are available to produce optically pure forms (see for example, Optical Resolution Procedures for Chemical Compounds, Vol 1,: Amines and Related Compounds, Paul Newman, Optical Resolution Information Center, Manhattan College, Riverdale, NY, 10471, 1978).
The following examples describe how to prepare the various compounds of Formula in.
PREPARATION 1 5-(2-Methylcyclopropyl)-3-N-formylaminomethyl-1,2,4- oxadiazole
2-Methyl cyclopropane carboxylic acid (50g) was added to toluene (500 mL) and oxalyl chloride (46.3 mL) at 0°C. To that mixture was added dimethylformamide (DMF; 1 mL) and the resulting reaction stirred for eight hours. Approximately one third of the solvent was removed in vacuo and the resulting solution added to a pressure equalizing addition funnel.
That solution was added dropwise to a suspension of 2-formylaminoethanamidoxime (140 g, prepared from N-formylaminoacetonitrile and hydroxylamine), triethylamine (83.4 mL) and dichloromethane (1000 ml) at 0°. The reaction was stirred for 18 hours and the solvent was removed under reduced pressure. Water (500 ml) was added to the residue and the mixtare heated at reflux for seventy six hours. After cooling the mixture was partitioned between ethyl acetate and water. The organic layer is separated, dried (NaSO4) and solvent removed in vacuo to afford the crude product (17.8 g). NMR (CDCL3, δ) 8.3, 6.6, 4.5, 1.9, 1.8, 1.6, 1.4. 1.2, 1.1.
PREPARATION 2 5-(2-methylcyclopropyl)-3-isocyanomethyl-1,2,4-oxadiazole
To 5-(2-methylcycIopropyl)-3-N-formylaminomethyl-1,2,4-oxadiazole (PREPARATION 1, 17.8 g), triethylamine (45 mL) and dichloromethane (200 ml) at 0° is added, dropwise, phosphorus oxychloride (96 mL). The reaction is stirred and slowly allowed to warm to room temperatare over 2.5 hours. A sodium bicarbonate (15 g) in water (300 ml) was added slowly. The reaction was stirred for 2 hours and then partitioned between dichloromethane and saline. The phases are separated, the organic phase is dried over sodium sulfate, concentrated, and the residue chromatographed on silica gel (300 ml) eluting with 50% ethyl acetate/hexane (1/3). The appropriate fractions are pooled and concentrated to give the title compound (13.6 g; 85%) as an oil. NMR (CDCL3, δ) 4.7, 1.95, 1.6, 1.5, 1.4, 1.2, 1.0.
PREPARATION 3 5-(1-Methylcyclopropyl)-3-N-formylaminomethyI-1,2,4- oxadiazole
Following the general procedure for preparation 1 and making non-critical variations but using
1-methylcyclopropane carboxylic acid the title compound was prepared. NMR (CDCL3, δ) 8.3,
7.1, 4.6, 1.5, 1.4, 1.0.
PREPARATION 4 5-(1-Methylcyclopropyl)-3-isocyanomethyl-1,2,4-oxadiazole
Following the general procedure for Preparation 2 and making non-critical variations but using
5-(1-methylcyclopropyl)-3-N-formylaminomethyl-1,2,4-oxadiazole the title compound was prepared. NMR (CDCL3, δ) 4.7, 1.6, 1.5, 1.1.
PREPARATION 5 5-(1-Methoxycyclopentpyl)-3-N-formylaminomethyl-1,2,4- oxadiazole
Following the general procedure for preparation 1 and making non-critical variations but using 1-methoxycyclopentane carboxylic acid (prepared according to the method described in Zhurnal Organicheskoi Khimii (1972) 9, 1841-44) the title compound was prepared.
PREPARATION 6 5-(1-Methoxycyclopentyl)-3-isocyanomethyl-1,2,4-oxadiazole
Following the general procedure for Preparation 2 and making non-critical variations but using 5-(1-methoxycyclopentpyl)-3-N-formylaminomethyl-1,2,4-oxadiazole the title compound was prepared. NMR (CDCL3, δ) 4.77, 3.24, 2.35, 1.75.
Example 1: (Formula III) 3-(5-(1-Methycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(1-methyl- ethyl)-imidazo(1,5-a)-quinoxalin-4(5H)-one.
Potassium tert-butoxide (1M, 3.8 ml) was added to 1,2,3,4-tetrahydro-1-(1-methylethyl)-2,3- dioxoquinoxaline (1.0 g) at 0°C in THF (10 ml). The mixtare was stirred for 20 min and then diethylchlorophosphate (0.73 ml) was added. The reaction was stirred for 1 hr at 0°, then cooled to -78°C. The 1 -methylcyclopropyl isocyanoacetate (0.86 g) was added, followed by potassium tert-butoxide (1 M, 5.5 ml). The reaction was stirred at 0°C for 1 hour and then partitioned between ethyl acetate and water. The organic layers are dried over sodium sulfate and concentrated. The crude product was chromatographed over silica gel eluting with 25% ethyl acetate/dichloromethane. The appropriate fractions were pooled, concentrated and recrystallized from ethyl acetate/hexane to give the title compound; Mp 195°C.
Example 2: (Formula III) 7-Fluoro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1- methylethyl)-imidazo(1,5-a)-quinoxaIin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-fluoro-1,2,3,4-tetrahydro-1-(1-methyIethyl)-2,3-dioxoquinoxaline the title compound was prepared Mp 220°C.
Example 3: (Formula III) 7-ChIoro-3-(5-(1-methycyclopropyI)-1,2,4-oxadiazol-3-yI)-5-(1- methylethyl)-imidazo(1-5-a)-quinoxalin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-chloro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2,3-dioxoquinoxaline the title compound was prepared.
Example 4: (Formula III) 7-Fluoro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazoI-3-yI)-5-(1- methylethyI)-imidazo(1,5-a)-quinoxalin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-fIuoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2,3-dioxoquinoxaline and 5-(2-methylcycIopropyl)- 3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared, Mp 197°C.
Example 5: (Formula III) 7-ChIoro-3-(5-(2-methycycIopropyl)-1,2,4-oxadiazoI-3-yI)-5-(1- methylethyI)-imidazo(1-5-a)-quinoxaIin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-chloro-1,2 ,3,4-tetrahydro-1-(1-methylethyl)-2,3-dioxoquinoxaline and 5-(2-methylcycIopropyl)- 3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared.
Example 6: (Formula III) 3-(5-(1-MethoxycycIopentyI)-1,2,4-oxadiazoI-3-yl)-5-(1- methylethyI)-imidazo(1-5-a)-quinoxalin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 5-(1-methoxycyclopentyl)-3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared. Example 7: (Formula III) 7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5- (1-methylethyI)-imidazo(1,5-a)-quinoxaIin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-fluoro-1,2,3,4-tetrahydro-1-(1-methylethyl)-2,3-dioxoquinoxaline and 5-(1- methoxycyclopentyl)-3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared.
Example 8: (Formula III) 7-Chloro-3-(5-(2-methycycIopropyI)-1,2,4-oxadiazoI-3-yl)-5-(1- (2-aminoethyl)pyrroIidinyI)-imidazo(1,5-a)-quinoxalin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-chIoro-1,2,3,4-tetrahydro-1-(1-(2-aminoethyl)Pyrrolidinyl)-2,3-dioxoquinoxaline and 5-(2- methyIcyclopropyl)-3-isocyanomethyl-1,2,4-oxadiazoIe the title compound was prepared, Mp 201-2°C.
Example 9: (Formula III) 7-ChIoro-3-(5-(1-methycyclopropyI)-1,2,4-oxadiazol-3-yI)-5-(1- (2-aminoethyl)pyrrolidinyl)-imidazo(1,5-a)-quinoxaIin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-chIoro-1,2,3,4-tetrahydro-1-(1-(2-aminoethyl)pyrroIidinyI)-2,3-dioxoquinoxaline and 5-(1- methylcyclopropyl)-3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared, Mp
218-9°C.
Example 10: (Formula III) 7-Chloro-3-(5-(1-methycycIopropyl)-1,2,4-oxadiazol-3-yl)-5-(2-
(aminomethyl)pyridinyI)-imidazo(1-5-a)-quinoxalin-4(5H)-one.
Following the general procedure of EXAMPLE 1 and making non-critical variations but using 7-chloro-1,2,3,4-tetrahydro-1-(2-(aminomethyl)pyridinyl)-2,3-dioxoquinoxaline and 5-(1- methylcyclopropyl)-3-isocyanomethyl-1,2,4-oxadiazole the title compound was prepared, Mp 258-60°C.

Claims

WHAT IS CLAIMED:
1. A compound of formula (I)
Figure imgf000306_0001
or a pharmaceutically acceptable salt thereof wherein:
Z is -N(R1)-C(O)- or -C(O)-N(R1)-;
where, R1 is C1-6 alkyl, C3-7 cycloalkyl (optionally substituted with C1-6 alkyls), C1-6 alkyl- C6-12 aryl, C1-6 alkyl- C6-12 heteroaryl, -(CH2)n -Rf, -(CH2)n-CO-Rd, -(CH2)d-CHOH-Re, -CH2CH2OCH3, -CH(CH3)CH2OH, -CH(CH3)CH2OCH3, -CH2-(2-furan), -CH2-(3-furan) or -CH2-(2-pyran);
X is
Figure imgf000306_0002
h) -CH=CHRa or -OCR.,
i) -(CH2)n-G Q, or
j) -C(O)OR
Figure imgf000306_0003
)NR,
k) R5 (except for C6-12 aryl and C1-12 heteroaryl),
where, G is CH2, O, S, S(O)y, NR6 and
Q is -CHO, OH, NR, OR;
R are independently H, F, Cl, Br, I, C1-6 alkyl, CF3, CN, NO2, CONH2, CONHR6, C(O)OR6, OR6; R5 is H, F, Cl, Br, I, CF3, CN, -CH2CH2CF3, -CH2CH(CF3)CH3, C3-6 cycloalkyl (substitated with a F, Cl, Br, I, C2-6 alkyl, C6-12 aryl, OH, NH2, OR6 or methyl provided at least one R is F or Cl), C1-6 alkyl- C3-6 cycloalkyl (substituted by F, Cl, Br, I, C1-6 alkyl, C6-12 aryl, OH, NH2 or OR6), C6- 12 aryl, C1-6 alkyl- C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl- C6-12 heteroaryl, -(CH2)n-CO-Rb (except, n is at least 1 when Rb is C6-12 aryl), -(CH2)n-CHOH-Rc,
2- or 3-tetrahydrofurfuryl,
2- or 3-tetrahydrofuran (optionally, substituted with H, C1-6 alkyl, OH, or C6-12 aryl), 2- or 3-tetrahydrothiophene,
2- or 3-tetrahydrothiophene sulfoxide,
2- or 3-tetrahydrothiophene sulfone (optionally substitated with H, C1-6 alkyl, OH, C6-12 aryl),
-(CH2)n-(N-R6-pyrolidin-2-yl),
-(CH2)n-N(R6)2,
-C*(R9)(CH2)d-NH9-(C*H2)n (where * indicates the atoms are bonded to each other);
R6 are independently H, C1-6 alkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl- C6-12 heteroaryl, -(CH2)n-CO-(C1-6 alkyl, -C(6-12 aryl or - C6-12 heteroaryl), or when two R6's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
R9 is C1-6 alkyl, C6-12 aryl, C1-6 alkyl- C6-12 aryl, C6-12 heteroaryl,
C1-6alkyl-C6-12 heteroaryl;
Ra is -R6, CH(OH)R9, CO2R9, CON(R6)2, (CH2)nOR6, (CH2) nSR6,
(CH2 )nS(O)y, (CH2)nN(R6)2;
Rb is -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)n-OR9, -(CH2)n-SR9, -(CH2)d-S(O)yR9,
-(CH2)nN(R6)2, -(CH2)n- C1-6 alkyl, -(CH2)n-C6-12 aryl,
-(CH2)n-C6-12 heteroaryl;
Rc is -(CH2)d-OR6, -(CH2)d-S(O)yR9, -(CH2) d -N(R6)2, -(CH2)n-C1-6-alkyl,
-(CH2)n-C6-12 aryl, -(CH2)n- C6-12 heteroaryl,
-(CH2)n-C6-12 heteroaryl;
Rd is -(CH2)d-OR9, -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)d-S(O)yR9, -(CH2)n- N(R6)2, -(CH2)nC1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl;
Re is -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)d-S(O)yR9, -(CH2)d-N6)2,
-(CH2)d-N(O)(R6)2, -(CH2)n- C1-6 alkyl, -(CH2)n- C6-12 aryl,
-(CH2)n-C6-12 heteroaryl;
Rf is -OR6, -SR6, -S(O)yR9, -O-(CH2)nN-R6, -S-(CH2)n-R6, -S(O)y-(CH2)n-R9,
-N(R6)2, -N(O)(R6)2;
d is 1-3; each n is independently 0-3; y is 1-2; and with the following provisos:
(1) when Z is -N(R1)-C(O)-, -(CH2)n-X is defined as n is 0 and X is j then R1 cannot be C1-6 alkyl, C1-6 alkyl- C1-12 aryl, C1-6 alkyl- C1-12 heteroaryl or -(CH2)n-Rf;
(2) when Z is -C(O)-N(R1)-, -(CH2)n-X is defined as X is a or b and n is 0 then R cannot be H, F, Cl, R1 cannot be C1-6 alkyl or C3-7 cycloalkyl, and R5 cannot be C1-6 alkyl, C3-7 cycloalkyl or C3-7 cycloalkylmethyl;
(3) when Z is -N(R1)-C(O)-, (CH2)n-X is defined as X is a, b or -C(O)OR and n is 0 then R1 cannot be isopropyl, R5 cannot be C1-6 alkyl, C3-7 cycloalkyl or C1-6 alkoxymethyl. 2. The compound of Claim 1 wherein Z is -N(R1)-C(O)-.
3. The compound of Claim 1 wherein Z is -C(O)-N(R1)-.
4. A compound of foimula (II)
Figure imgf000308_0001
or a pharmaceutially acceptable salt thereof wherein:
Z is -N=CH- or -CH=N-;
X is
Figure imgf000308_0002
h) -C=CHR3 or -C≡Ra;
i) -(CH2)n-G-(CH2)n-Q,
j) -C(O)(NR, C1-6 alkyl, C6-12 aryl or C6-12 heteroaryl), or
k) C6-12 aryl or C6-12 heteroaryl,
l) R5
where, G is CH2, O, S, S(O)y, NR6;
Q is -CHO, OH, NR, OR1; and
n is 0-3;
R are independently H, F, Cl, Br, I, C1-6 alkyl, CF3, CN, NO2, CONH2, CONHR6, C(O)OR6, OR6;
R5 is H, F, Cl, Br, I, CF3, CN, -CH2CH2CF3, -CH2CH(CF3)CH3, C3-6 cycloalkyl (substitated with a F, Cl, Br, I, C2-6 alkyl, C6-12 aryl, OH, NH2, OR6 or methyl provided at least one R is F or Cl), C1-6 alkyl-C3-6 cycloalkyl (substituted by F, Cl, Br, I, C1-6 alkyl, C6-12 aryl, OH, NH2 or OR6), C6- 12 aryl, C1-6 aIkyl- C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n-CO-Rb (except, n is at least 1 when Rb is C6-12 aryl), -(CH2)n-CHOH-Rc,
2- or 3-tetrahydrofurfuryl,
2- or 3-tetrahydrofuran (optionally substituted with H, C1-6 alkyl, OH, or C6-12 aryl), 2- or 3-tetrahydrothiophene,
2- or 3-tetrahydrothiophene sulfoxide,
2- or 3-tetrahydrothiophene sulfone (optionally substitated with H, C1-6 alkyl, OH, C6-12 aryl),
-(CH2)n-(N-R6-pyrolidin-2-yl),
-(CH2)n-N(R6)2,
-C*(R9)(CH2)d-NH9-(C*H2)n (where * indicates the atoms are bonded to each other);
R6 are independently H, C1-6 alkyl, C6-12 aryl, C1-6 alkyl- C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 heteroaryl, -(CH2)n-CO-( C1-6 alkyl, -C6-12 aryl or -C6-12 heteroaryl), or when two R6's are attached to the same nitrogen atom they can form a cyclic system containing, in addition to the specified nitrogen atom, one other oxygen or nitrogen atom;
R9 is C1-6 alkyl, C6-12 aryl, C1-6 alkyl-C6-12 aryl, C6-12 heteroaryl,
C1-6alkyl-C6-12 heteroaryl;
Ra is -R6, CH(OH)R9, CO2R9, CON(R6)2 , (CH2)nOR6, (CH2)nSR6,
(CH2)nS(O)yR9, (CH2)nN(R6);
Rb is -(CH2)d-OR6, -(CH2)d-SR6, -(CH2)n-OR9, -(CH2)n-SR9, -(CH2)d-S(O)yR9,
-(CH2)nN(R6)2, -(CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl,
-(CH2)n-C6-12 heteroaryl;
Rc is -(CH2)d-OR6, -(CH2)d-S(O)yR9, -(CH2)d-N(R6)2, -(CH2)n-C1-6 alkyl, -(CH2)n-C6-12 aryl, -(CH2)n-C6-12 heteroaryl,
d is 1-3; y is 1-2.
5. The compound of Claim 4 wherein Z is -N=CH-.
6. The compound of Claim 5 which is
a. 7-ChIoro-3-(5-t-butyl-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)-1,2,4-triazolo(4,3- c)quinazoIine;
b. 3-(p-Fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoline; or
c. 8-ChIoro-3-(p-fluorophenyl)-imidazo(1,5-a)-1,2,4-triazolo(4,3-c)quinazoIine.
7. The compound of Claim 4 wherein Z is -CH=N-.
8. The compound of Claim 7 which is
a. ethyl Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoIine-3-carboxylate;
b. t-Butyl Imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate;
c. 3-(5-Isopropyl-1-2,4-oxadiazol-3-yl)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; d. 3-(5-t-Butyl-1,2,4-oxadiazol-3-yI)imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline; e. 3-(5-Cyclopentyl-1,2,4-oxadiazoI-3-yl)imidazo(1,5-a)-1,2,4-triazolo(1-5-c)quinazoline; f. t-Butyl-7-Chloro-imidazo(1,5-a)-1,2,4-triazolo(1,5-c)quinazoline-3-carboxylate;
g. 7-Chloro-3-(5-t-butyl-1,2,4-oxadiazoI-3-yl)-imidazo(1,5-a)-1,2,4-triazoIo(1,5- c)quinazoIine; or
h. 7-Chloro-3-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)-imidazo(1,5-a)-1,2,4-triazolo(1,5- c)quinazoIine.
9. An imidazo(1,5-a)quinoxaline of formula (III)
Figure imgf000310_0001
or a pharmaceutically acceptable salt thereof wherein:
Figure imgf000311_0001
R are independently H, F, Cl, C1-6 alkyl, CN, O-C1-6 alkyl, CONH2, CONHR6, CO2R6, or OH;
R1 is C1-6 alkyl, C3-7 cycloalkyl (which can be substituted with C1-6 alkyl, C1-6 alkyl-C6-12 aryl, C1-6 alkyl-C1-12 heteroaryl, -(CH2)o-N(R6)2, -(CH2)pOR6, -CH2)p-S(O)mR6, -CH2)o-CON(R6)2, - CO-(CH2)o-NR6)2, or -(CH2)o--CO2R6 wherein p = 1-5, m = 0-2, o = 0-5;
R5 is -(CH2)p-N(R6)2 or C3-7 cycloalkyl (substitated with F, Cl, C2-6 alkyl, or methyl provided at least one R is F or Cl); and
R6 is independently H, C1-6 alkyl, C6-12 aryl, C6-12 heteroaryl, C1-6 alkyl-C6-12 aryl, C1-6 alkyl-C6-12 heteroaryl, or when two R6's are attached to the same nitrogen atom they can form a cyclic system, containing, in addition to the specified nitrogen atom, one other nitrogen or oxygen atom.
10. The imidazo(1,5-a)quinoxaline in of Claim 9 where X is structure (a).
11. The imidazo(1,5-a)quinoxaline in of Claim 9 where R is H or F.
12. The imidazo(1,5-a)quinoxaline III of Claim 9 where R1 is a C1-6 alkyl.
13. The imidazo(1,5-a)quinoxaline III of Claim 9 which is
a. 3-(5-(1-Methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)-imidazo(1,5- a)quinoxalin-4(5H)-one;
b. 7-Fluoro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
c. 7-Chloro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
d. 7-Fluoro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
e. 7-Chloro-3-(5-(2-methycyclop-Opyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
f.3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazoI-3-yl)-5-(1-methyIethyl)-imidazo(1,5- a)quinoxaIin-4(5H)-one;
g. 7-Fluoro-3-(5-(1-methoxycyclopentyl)-1,2,4-oxadiazol-3-yl)-5-(1-methylethyl)- imidazo(1,5-a)quinoxalin-4(5H)-one;
h. 7-Chloro-3-(5-(2-methycyclopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-(2- aminoethyl)pyrrolidinyI)y-imidazo(1,5-a)quinoxalin-4(5H)-one;
i. 7-Chloro-3-(5-(1-methycycIopropyl)-1,2,4-oxadiazol-3-yl)-5-(1-(2- aminoethyl)pyrroIidinyl)y-imidazo(1,5-a)quinoxalin-4(5H)-one; or
j. 7-Chloro-3-(5-(1-methycyclopropyl)-1,2,4-oxadiazol-3-yI)-5-(2-
(aminoethyl)pyridinyI)y-imidazo(1,5-a)qmnoxalin-4(5H)-one.
14. A use of compounds from Formula I, II or III for the preparation of a medicament useful in treating central nervous system disorders associated with benzodiazepine receptors by administering to a subject in need of such treatment a therapeutically-effective amount of the compound to alleviate such disorder.
PCT/US1992/010388 1991-12-17 1992-12-07 3-SUBSTITUTED IMIDAZO (1,5-a) AND IMIDAZO (1,5-a)-TRIAZOLO (1,5-c) QUINOXALINES AND QUINAZOLINES WITH CNS ACTIVITY Ceased WO1993012113A1 (en)

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