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EA200300206A1 - PHENOXYBENZYLAMINE DERIVATIVES AS A SEROTONIN REPEATED ABSORPTION INHIBITORS - Google Patents

PHENOXYBENZYLAMINE DERIVATIVES AS A SEROTONIN REPEATED ABSORPTION INHIBITORS

Info

Publication number
EA200300206A1
EA200300206A1 EA200300206A EA200300206A EA200300206A1 EA 200300206 A1 EA200300206 A1 EA 200300206A1 EA 200300206 A EA200300206 A EA 200300206A EA 200300206 A EA200300206 A EA 200300206A EA 200300206 A1 EA200300206 A1 EA 200300206A1
Authority
EA
Eurasian Patent Office
Prior art keywords
alkyl
heterocyclic ring
serotonin
general formula
phenoxybenzylamine
Prior art date
Application number
EA200300206A
Other languages
Russian (ru)
Inventor
Мевис Дайан Адам
Марк Дэвид Эндрюс
Марк Леонард Эллиотт
Джеффри Эдвард Гаймер
Дэвид Хепворт
Гэрри Ральф мл. Ховард
Дональд Стюарт Миддлтон
Алан Стоби
Original Assignee
Пфайзер Инк.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB0021593A external-priority patent/GB0021593D0/en
Priority claimed from GB0107116A external-priority patent/GB0107116D0/en
Application filed by Пфайзер Инк. filed Critical Пфайзер Инк.
Publication of EA200300206A1 publication Critical patent/EA200300206A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Reproductive Health (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Addiction (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Quinoline Compounds (AREA)

Abstract

Соединение общей формулы (I), где Rи Rпредставляют собой H, C-Cалкил или (CH)(C-Cциклоалкил), где d = 0, 1, 2 или 3; или Rи Rвместе с атомом азота, к которому они присоединены, образуют азетидиновое кольцо; один из Z и Y представляет собой -SR, а другой представляет собой галоген или -R; где Rнезависимо представляет собой C-Cалкил, необязательно замещенный фтором; при условии, что Rне является CF; или Z и Y соединены так, что вместе с соединяющими их атомами образуют конденсированное 5-7-членное карбоциклическое или гетероциклическое кольцо, и когда Z и Y образуют гетероциклическое кольцо, оно помимо атомов углерода содержит один или два гетероатома, независимо выбранных из кислорода, серы и азота; Rи R, которые могут быть одинаковыми или разными, представляют собой A-X, где A = -CH=CH- или -(CH)-, где p равно 0, 1 или 2; X представляет собой водород, F, Cl, Br, I, CONRR, SONRR, SONHC(=O)R, OH, Cалкокси, NRSOR, NO, NRR, CN, COR, CHO, SR, S(O)Rили SORили 5- или 6-членное гетероциклическое кольцо, содержащее 1, 2 или 3 гетероатома, выбранных из N, S и O, и необязательно независимо замещенное одним или несколькими R; где Rпредставляет собой гидроксильную группу, C-Cалкоксигруппу, F, C-Cалкил, галогеналкил, галогеналкоксигруппу, -NH, -NH(C-Cалкил) или -N(C-Cалкил). Соединения общей формулы (I) ингибируют повторное поглощение моноаминов, в частности, проявляют активность в качестве ингибиторов повторного поглощения серотонина.Международная заявка была опубликована вместе с отчетом о международном поиске.The compound of general formula (I), where R 1 and R 5 is H, C 1 -C 6 alkyl or (CH) (C 1 -C 5 cycloalkyl), where d = 0, 1, 2 or 3; or R and R together with the nitrogen atom to which they are attached, form an azetidine ring; one of Z and Y is -SR, and the other is halogen or -R; wherein R independently is C 1 -C 6 alkyl optionally substituted with fluorine; with the proviso that R is not CF; or Z and Y are connected so that together with the atoms connecting them form a fused 5-7-membered carbocyclic or heterocyclic ring, and when Z and Y form a heterocyclic ring, it contains, in addition to carbon atoms, one or two heteroatoms independently selected from oxygen, sulfur and nitrogen; R and R, which may be the same or different, are A-X, where A = -CH = CH- or - (CH) -, where p is 0, 1 or 2; X represents hydrogen, F, Cl, Br, I, CONRR, SONRR, SONHC (= O) R, OH, Salkoxy, NRSOR, NO, NRR, CN, COR, CHO, SR, S (O) R or SOR or 5- or a 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected from N, S and O, and optionally independently substituted with one or more R; where R 1 is a hydroxyl group, a C 1 -C 6 alkoxy group, F, C 1 -C 6 alkyl, haloalkyl, a halogenoalkoxy group, -NH, -NH (C 1 -C 6 alkyl) or -N (C 1 -C 6 alkyl). The compounds of general formula (I) inhibit the reuptake of monoamines, in particular, are active as serotonin reuptake inhibitors. The international application was published along with an international search report.

EA200300206A 2000-08-31 2001-08-22 PHENOXYBENZYLAMINE DERIVATIVES AS A SEROTONIN REPEATED ABSORPTION INHIBITORS EA200300206A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0021593A GB0021593D0 (en) 2000-08-31 2000-08-31 Diphenyl ether compounds useful in therapy
GB0107116A GB0107116D0 (en) 2001-03-21 2001-03-21 Novel compounds
PCT/IB2001/001521 WO2002018333A1 (en) 2000-08-31 2001-08-22 Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors

Publications (1)

Publication Number Publication Date
EA200300206A1 true EA200300206A1 (en) 2003-06-26

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EP (1) EP1313701A1 (en)
JP (1) JP2004507523A (en)
KR (1) KR20030029889A (en)
CN (1) CN1449380A (en)
AP (1) AP2001002265A0 (en)
AR (1) AR031867A1 (en)
AU (1) AU2001278650A1 (en)
BG (1) BG107544A (en)
BR (1) BR0113610A (en)
CA (1) CA2420969A1 (en)
CZ (1) CZ2003467A3 (en)
DO (1) DOP2001000242A (en)
DZ (1) DZ3414A1 (en)
EA (1) EA200300206A1 (en)
EE (1) EE200300084A (en)
HN (1) HN2001000191A (en)
HR (1) HRP20030141A2 (en)
HU (1) HUP0303385A2 (en)
IL (1) IL154343A0 (en)
IS (1) IS6704A (en)
MA (1) MA26945A1 (en)
MX (1) MXPA03001848A (en)
NO (1) NO20030842L (en)
NZ (1) NZ523951A (en)
OA (1) OA12372A (en)
PA (1) PA8526701A1 (en)
PE (1) PE20020346A1 (en)
PL (1) PL360743A1 (en)
SK (1) SK2012003A3 (en)
TN (1) TNSN01131A1 (en)
UY (1) UY26924A1 (en)
WO (1) WO2002018333A1 (en)

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DOP2001000242A (en) 2002-05-15
PE20020346A1 (en) 2002-05-08
IS6704A (en) 2003-01-30
PL360743A1 (en) 2004-09-20
HUP0303385A2 (en) 2004-03-01
WO2002018333A1 (en) 2002-03-07
HRP20030141A2 (en) 2003-04-30
CN1449380A (en) 2003-10-15
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