AR034309A1 - PHENYL PHONYLAMINOPHENYLAMINE DERIVATIVES, PROCEDURE FOR PREPARATION, MEDICATIONS AND THE USE OF SUCH DERIVATIVES FOR THE PREPARATION OF ANTIVIRAL MEDICINES - Google Patents
PHENYL PHONYLAMINOPHENYLAMINE DERIVATIVES, PROCEDURE FOR PREPARATION, MEDICATIONS AND THE USE OF SUCH DERIVATIVES FOR THE PREPARATION OF ANTIVIRAL MEDICINESInfo
- Publication number
- AR034309A1 AR034309A1 ARP020101392A ARP020101392A AR034309A1 AR 034309 A1 AR034309 A1 AR 034309A1 AR P020101392 A ARP020101392 A AR P020101392A AR P020101392 A ARP020101392 A AR P020101392A AR 034309 A1 AR034309 A1 AR 034309A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- hydroxyl
- amino
- alkyl
- different
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 4
- 239000003814 drug Substances 0.000 title abstract 3
- 229940079593 drug Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 230000000840 anti-viral effect Effects 0.000 title 1
- -1 amino, amino, hydroxyl Chemical group 0.000 abstract 9
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical class 0.000 abstract 9
- 125000001424 substituent group Chemical group 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 abstract 1
- 241000701022 Cytomegalovirus Species 0.000 abstract 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000002483 medication Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- NLEOEXCPIKOHJB-UHFFFAOYSA-N n'-phenylbenzenesulfonohydrazide Chemical class C=1C=CC=CC=1S(=O)(=O)NNC1=CC=CC=C1 NLEOEXCPIKOHJB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Derivados fenilsulfonilaminofenilamina, que comprenden compuestos de fórmula general (1), en la que: R2 y R3 son iguales o distintos y representan hidrógeno, hidroxilo, halógeno, nitro, ciano, trifluormetilo, trifluormetoxi, alquilo C1-6, alcoxi C1-6 o representan un grupo de fórmulas (2) ó (3) en la que R5, R6 y R7 son iguales o distintos y representan cada uno hidrógeno o alquilo C1-6, que puede estar sustituido por su parte con uno o dos sustituyentes seleccionados del grupo que consiste de hidroxilo, halógeno, ciano, trifluormetilo y trifluormetoxi; A representa un heteroarilo de 5 ó 6 miembros unido a través de un átomo de C con el anillo fenilo adyacente, con 1 a 3 heteroátomos seleccionados del grupo que consiste de N, O y S; R1 representa arilo C6-10, heteroarilo de 5 a 10 miembros o heterociclilo de 5 a 10 miembros, cada uno con 1 a 3 heteroátomos seleccionados del grupo que consiste de N, O y S, pudiendo estar sustituido R1 con hasta 3 sustituyentes seleccionados del grupo que consiste de hidroxilo, amino, monoalquil(C1-6)amino, dialquil(C1-6)amino, halógeno, nitro, ciano, oxo, alquilo C1-6, que puede estar sustituido por su parte con amino o hidroxilo, alcoxi C1-6, fenilo, heterociclilo de 5 ó 6 membros con hasta 2 heteroátomos seleccionados del grupo que consiste de N, O y S, heteroarilo de 5 ó 6 miembros con uno o más heteroátomos seleccionados del grupo que consiste de N, O y S, -C(O)-O-R8, -C(O)-NR9R10, -NH-C(O)R11, -NH-C(O)-C-(O)-R12 y -NH-SO2-R13; en las que R8, R9 y R10 son iguales o distintos y representan cada uno hidrógeno o alquilo C1-6; o R9 y R10 junto con el átomo de nitrógeno al que están unidos, forman un heterociclo de 5 ó 6 miembros que contiene otro heteroátomo de nitrógeno u oxígeno y que puede estar sustituido de 1 a 2 veces con sustituyentes iguales o distintos del grupo que consiste de alquilo C1-4, que está sustituido por su parte opcionalmente con hidroxilo o amino, amino, hidroxilo, alcoxi C1-4, oxo, carboxilo y con alcoxi(C1-4)carbonilo; R11 y R12 son iguales o distintos y representan cada uno trifluormetilo, alcoxi C1-6, hidroxilo o alquilo C1-6, que está sustituido opcionalmente 1 ó 2 veces con sustituyentes iguales o distintos del grupo que consiste de amino, alcoxi(C1-6)carbonilamino, monoacil(C1-6)amino, hidroxilo, amidino, guanidino, alcoxi(C1-6)carbonilo, carboxilo y fenilo; y R13 representa alquilo C1-6 o arilo C1-6, que pueden estar sustituidos cada uno con halógeno, amino, hidroxilo, alcoxi C1-4 o alquilo C1-4; R4 representa alquilo C1-6, que puede estar sustituido hasta 3 veces con sustituyentes iguales o diferentes del grupo que consiste de amino, hidroxilo, halógeno, alcoxi C1-6, alcanoil(C1-5)oxi y fenilo, que por su parte está sustituido opcionalmente 1 ó 2 veces con sustituyentes iguales o distintos del grupo que consiste de halógeno, nitro, ciano, amino e hidroxilo; o representa cicloalquilo C3-7, que puede estar sustituido hasta 3 veces con sustituyentes iguales o distintos del grupo consistente de amino, hidroxilo, halógeno, alcoxi C1-6 y alquilo C1-6, que por su parte está sustituido opcionalmente hasta 3 veces con sustituyentes iguales o distintos del grupo que consiste de amino, hidroxilo, halógeno y alcoxi C1-6; o representa arilo C6-10 que está sustituido opcionalmente 1 ó 2 veces con sustituyentes iguales o distintos del grupo que consiste de halógeno, nitro, ciano, amino e hidroxilo; y en la que X representa oxígeno o azufre; y en la que los heterociclos que contienen nitrógeno también pueden estar presentes en forma de N-óxidos; así como sus tautómeros, estereoisómeros, mezclas estereoisoméricas y sales farmacológicamente aceptables; así como a procedimientos para su preparación y a su uso para la preparación de medicamentos como agentes antivirales, especialmente frente a citomegalovirus.Phenylsulfonylaminophenylamine derivatives, comprising compounds of general formula (1), in which: R2 and R3 are the same or different and represent hydrogen, hydroxyl, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, C1-6 alkyl, C1-6 alkoxy or they represent a group of formulas (2) or (3) in which R5, R6 and R7 are the same or different and each represent hydrogen or C1-6 alkyl, which may be substituted on its part with one or two substituents selected from the group consisting of hydroxyl, halogen, cyano, trifluoromethyl and trifluoromethoxy; A represents a 5- or 6-membered heteroaryl linked through a C atom with the adjacent phenyl ring, with 1 to 3 heteroatoms selected from the group consisting of N, O and S; R1 represents C6-10 aryl, 5-10 membered heteroaryl or 5-10 membered heterocyclyl, each with 1 to 3 heteroatoms selected from the group consisting of N, O and S, and R1 may be substituted with up to 3 substituents selected from the group consisting of hydroxyl, amino, mono- (C1-6) alkyl, dialkyl (C1-6) amino, halogen, nitro, cyano, oxo, C1-6 alkyl, which may be substituted on the other hand with amino or hydroxyl, alkoxy C1-6, phenyl, 5- or 6-membered heterocyclyl with up to 2 heteroatoms selected from the group consisting of N, O and S, 5- or 6-membered heteroaryl with one or more heteroatoms selected from the group consisting of N, O and S , -C (O) -O-R8, -C (O) -NR9R10, -NH-C (O) R11, -NH-C (O) -C- (O) -R12 and -NH-SO2-R13 ; wherein R8, R9 and R10 are the same or different and each represent hydrogen or C1-6 alkyl; or R9 and R10 together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocycle containing another nitrogen or oxygen heteroatom and which may be substituted 1 to 2 times with substituents the same or different from the group consisting C1-4 alkyl, which is optionally substituted with hydroxyl or amino, amino, hydroxyl, C1-4 alkoxy, oxo, carboxyl and with (C1-4) alkoxycarbonyl; R11 and R12 are the same or different and each represent trifluoromethyl, C1-6 alkoxy, hydroxy or C1-6 alkyl, which is optionally substituted 1 or 2 times with the same or different substituents of the group consisting of amino, (C1-6 alkoxy) ) carbonylamino, mono-acyl (C1-6) amino, hydroxyl, amidino, guanidino, (C1-6) alkoxycarbonyl, carboxyl and phenyl; and R13 represents C1-6 alkyl or C1-6 aryl, which may each be substituted with halogen, amino, hydroxyl, C1-4 alkoxy or C1-4 alkyl; R4 represents C1-6 alkyl, which may be substituted up to 3 times with the same or different substituents of the group consisting of amino, hydroxyl, halogen, C1-6 alkoxy, (C1-5) alkanoyl, oxy and phenyl, which in turn is optionally substituted 1 or 2 times with substituents the same or different from the group consisting of halogen, nitro, cyano, amino and hydroxyl; or represents C3-7 cycloalkyl, which may be substituted up to 3 times with substituents the same or different from the group consisting of amino, hydroxyl, halogen, C1-6 alkoxy and C1-6 alkyl, which in turn is optionally substituted up to 3 times with substituents the same or different from the group consisting of amino, hydroxyl, halogen and C1-6 alkoxy; or represents C6-10 aryl that is optionally substituted 1 or 2 times with substituents the same or different from the group consisting of halogen, nitro, cyano, amino and hydroxyl; and in which X represents oxygen or sulfur; and wherein the nitrogen-containing heterocycles may also be present in the form of N-oxides; as well as its tautomers, stereoisomers, stereoisomeric mixtures and pharmacologically acceptable salts; as well as procedures for its preparation and its use for the preparation of medications as antiviral agents, especially against cytomegalovirus.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10119137 | 2001-04-19 | ||
| DE10148598A DE10148598A1 (en) | 2001-04-19 | 2001-10-02 | New N-(acylaminophenyl)-heteroaryl-benzenesulfonamide derivatives, useful as antiviral agents, especially effective against human cytomegalovirus infections |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR034309A1 true AR034309A1 (en) | 2004-02-18 |
Family
ID=7681939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020101392A AR034309A1 (en) | 2001-04-19 | 2002-04-17 | PHENYL PHONYLAMINOPHENYLAMINE DERIVATIVES, PROCEDURE FOR PREPARATION, MEDICATIONS AND THE USE OF SUCH DERIVATIVES FOR THE PREPARATION OF ANTIVIRAL MEDICINES |
Country Status (9)
| Country | Link |
|---|---|
| KR (1) | KR20030088509A (en) |
| AR (1) | AR034309A1 (en) |
| CO (1) | CO5540388A2 (en) |
| DE (1) | DE10148598A1 (en) |
| EC (1) | ECSP034813A (en) |
| GT (1) | GT200200075A (en) |
| PE (1) | PE20021061A1 (en) |
| SV (1) | SV2003000995A (en) |
| ZA (1) | ZA200307892B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7482366B2 (en) * | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| HRP20050168A2 (en) | 2002-08-23 | 2005-10-31 | Rigel Pharmaceuticals | Pyridyl substituted heterocycles useful for treating or preventing hcv infection |
| CN100364531C (en) * | 2002-12-18 | 2008-01-30 | 西托维亚公司 | 3,5-disubstituted-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| DE10300109A1 (en) * | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Method for inhibiting replication of herpes viruses |
| US7326790B2 (en) | 2003-05-02 | 2008-02-05 | Rigel Pharmaceuticals, Inc. | Diphenylisoxazole compounds and hydro isomers thereof |
| US8580842B2 (en) | 2003-09-30 | 2013-11-12 | Abbott Gmbh & Co. Kg | Heteroaryl-substituted 1,3-dihydroindol-2-one derivatives and medicaments containing them |
| WO2005049065A2 (en) | 2003-11-19 | 2005-06-02 | Rigel Pharmaceuticals, Inc. | Synergistic combinations of dihaloacetamide with interferon or ribavirin for treatment hcv infections |
| US7514434B2 (en) | 2004-02-23 | 2009-04-07 | Rigel Pharmaceuticals, Inc. | Heterocyclic compounds having an oxadiazole moiety and hydro isomers thereof |
| JP2008540425A (en) | 2005-05-02 | 2008-11-20 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Heterocyclic antiviral compounds containing metabolizable moieties and uses thereof |
| US8486979B2 (en) | 2006-12-12 | 2013-07-16 | Abbvie Inc. | 1,2,4 oxadiazole compounds and methods of use thereof |
| UY30846A1 (en) | 2006-12-30 | 2008-07-31 | Abbott Gmbh & Amp | OXINDOL DERIVATIVES REPLACED, MEDICINES THAT UNDERSTAND AND USE THEMSELVES |
| US20080255203A1 (en) * | 2007-04-12 | 2008-10-16 | Abbott Laboratories | Heterocyclic compounds and their methods of use |
| ES2455197T3 (en) | 2007-12-07 | 2014-04-14 | Abbvie Deutschland Gmbh & Co Kg | 5,6-disubstituted oxindole derivatives and their use for the preparation of a medicine for the treatment of vasopressin-dependent diseases |
| BRPI0820668A2 (en) | 2007-12-07 | 2017-08-22 | Abbott Gmbh & Co Kg | 5-HALOGEN SUBSTITUTED OXINDOL DERIVATIVES AND THEIR USE TO TREAT VASOPRESSIN DEPENDENT DISEASES |
| CA2707667C (en) | 2007-12-07 | 2016-02-23 | Abbott Gmbh & Co. Kg | Amidomethyl-substituted oxindole derivatives and the use thereof for the treatment of vasopressin-dependent illnesses |
| WO2010009775A1 (en) | 2007-12-07 | 2010-01-28 | Abbott Gmbh & Co. Kg | Carbamate-substituted oxindole derivatives and use thereof for the treatment of vasopressin-dependent diseases |
| US9040568B2 (en) | 2009-05-29 | 2015-05-26 | Abbvie Inc. | Pharmaceutical compositions for the treatment of pain |
-
2001
- 2001-10-02 DE DE10148598A patent/DE10148598A1/en not_active Withdrawn
-
2002
- 2002-04-08 KR KR10-2003-7013617A patent/KR20030088509A/en not_active Withdrawn
- 2002-04-17 AR ARP020101392A patent/AR034309A1/en unknown
- 2002-04-18 SV SV2002000995A patent/SV2003000995A/en not_active Application Discontinuation
- 2002-04-18 PE PE2002000323A patent/PE20021061A1/en not_active Application Discontinuation
- 2002-04-18 GT GT200200075A patent/GT200200075A/en unknown
-
2003
- 2003-10-09 ZA ZA200307892A patent/ZA200307892B/en unknown
- 2003-10-17 EC EC2003004813A patent/ECSP034813A/en unknown
- 2003-11-19 CO CO03102172A patent/CO5540388A2/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CO5540388A2 (en) | 2005-07-29 |
| DE10148598A1 (en) | 2002-10-24 |
| ECSP034813A (en) | 2003-12-01 |
| KR20030088509A (en) | 2003-11-19 |
| PE20021061A1 (en) | 2002-12-12 |
| ZA200307892B (en) | 2004-10-11 |
| GT200200075A (en) | 2002-12-24 |
| SV2003000995A (en) | 2003-03-18 |
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