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WO1992022527A3 - 3-substituted pyrrolidine derivatives as calcium channel antagonists - Google Patents

3-substituted pyrrolidine derivatives as calcium channel antagonists Download PDF

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Publication number
WO1992022527A3
WO1992022527A3 PCT/GB1992/001088 GB9201088W WO9222527A3 WO 1992022527 A3 WO1992022527 A3 WO 1992022527A3 GB 9201088 W GB9201088 W GB 9201088W WO 9222527 A3 WO9222527 A3 WO 9222527A3
Authority
WO
WIPO (PCT)
Prior art keywords
calcium channel
channel antagonists
pyrrolidine derivatives
phenyl
substituted pyrrolidine
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/GB1992/001088
Other languages
French (fr)
Other versions
WO1992022527A2 (en
Inventor
Thomas Henry Brown
David Gwynn Cooper
Ronald Joseph King
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SmithKline Beecham Ltd
Original Assignee
SmithKline Beecham Ltd
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
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Priority to EP92912277A priority Critical patent/EP0589971A1/en
Priority to JP4511090A priority patent/JPH06508353A/en
Publication of WO1992022527A2 publication Critical patent/WO1992022527A2/en
Publication of WO1992022527A3 publication Critical patent/WO1992022527A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Addiction (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Compounds of structure (I), in which R is C1-8alkyl, C1-8alkyl(phenyl), C2-8alkenyl(phenyl)p, C2-8alkynyl(phenyl)p, C3-8cycloalkyl or C1-8alkylC3-8cycloalkyl; p is 0 to 2; n is 0 to 6; A is a bond, -CH=CH-, -C=C-, oxygen, sulphur or NR1; R1 is hydrogen, C¿1-8?alkyl or phenylC1-4alkyl; m is 0 to 3; and Ar is aryl or heteroaryl, each of which may be optionally substituted, and their pharmaceutically acceptable salts as calcium channel antagonists. Novel compounds of structure (I), processes for preparing them and pharmaceutical compositions containing them are also described.
PCT/GB1992/001088 1991-06-17 1992-06-17 3-substituted pyrrolidine derivatives as calcium channel antagonists Ceased WO1992022527A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP92912277A EP0589971A1 (en) 1991-06-17 1992-06-17 Compounds
JP4511090A JPH06508353A (en) 1991-06-17 1992-06-17 Compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9113031.0 1991-06-17
GB919113031A GB9113031D0 (en) 1991-06-17 1991-06-17 Compounds

Publications (2)

Publication Number Publication Date
WO1992022527A2 WO1992022527A2 (en) 1992-12-23
WO1992022527A3 true WO1992022527A3 (en) 1993-02-18

Family

ID=10696812

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1992/001088 Ceased WO1992022527A2 (en) 1991-06-17 1992-06-17 3-substituted pyrrolidine derivatives as calcium channel antagonists

Country Status (5)

Country Link
EP (1) EP0589971A1 (en)
JP (1) JPH06508353A (en)
AU (1) AU1975092A (en)
GB (1) GB9113031D0 (en)
WO (1) WO1992022527A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO300539B1 (en) * 1992-11-30 1997-06-16 Sankyo Co alpha, omega-diarylalkane derivatives, with therapeutic activity for the treatment and prevention of circulatory disorders and psychoses, and pharmaceutical preparations containing these derivatives
GB9226111D0 (en) * 1992-12-15 1993-02-10 Smithkline Beecham Plc Madicaments
GB9314973D0 (en) * 1993-07-20 1993-09-01 Smithkline Beecham Plc Medicaments
US5849760A (en) * 1993-12-09 1998-12-15 Institut De Recherche Jouveinal 2-(arylalkenyl)azacycloalkane derivatives as ligands for sigma receptors
WO1995024390A1 (en) * 1994-03-11 1995-09-14 Smithkline Beecham Plc Novel phenyl(-alkyl/alkoxy)-1-aminoalkyl-substituted piperidines and pyrrolidines as calcium channel antagonists
GB9411052D0 (en) * 1994-06-02 1994-07-20 Smithkline Beecham Plc Medicaments
GB9411045D0 (en) * 1994-06-02 1994-07-20 Smithkline Beecham Plc Compounds and use
GB9518572D0 (en) * 1995-09-12 1995-11-15 Smithkline Beecham Plc Compounds
EP0790235A1 (en) * 1996-02-15 1997-08-20 Sankyo Company Limited Diaryl alkane derivatives containing an alicyclic group, their preparation and their therapeutic and prophylactic uses
JP3593037B2 (en) * 1998-11-20 2004-11-24 エフ．ホフマン−ラ ロシュ アーゲー Pyrrolidine derivative CCR-3 receptor antagonist
GB0002100D0 (en) 2000-01-28 2000-03-22 Novartis Ag Organic compounds
EP1633343A1 (en) * 2003-05-30 2006-03-15 Neuromed Technologies, Inc. 3-aminomethyl-pyrrolidines as n-type calcium channel blockers
TW200825051A (en) 2006-08-09 2008-06-16 Smithkline Beecham Corp Pyrrolidinone anilines as progesterone receptor modulators
WO2008077089A1 (en) * 2006-12-19 2008-06-26 Smithkline Beecham Corporation Pyrrolidinanilines

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1964511A1 (en) * 1968-12-23 1970-07-09 Robins Co Inc A H 1-substituted-3-phenoxypyrrolidines and process for their preparation
EP0030526A1 (en) * 1979-12-05 1981-06-17 Astra Läkemedel Aktiebolag New phenyl-azacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds
EP0218249A2 (en) * 1985-10-11 1987-04-15 Tokyo Kasei Kogyo Co., Ltd Process for the production of 3-aminopyrrolidines
EP0229623A2 (en) * 1986-01-09 1987-07-22 Hoechst Aktiengesellschaft Diaryl-substituted alkylamines, procedure for their preparation, their application and medicaments containing them
EP0244739A2 (en) * 1986-05-02 1987-11-11 BASF Aktiengesellschaft N-substituted pyrrolidine and piperidine derivatives and their salts
EP0290958A2 (en) * 1987-05-12 1988-11-17 Hoechst Aktiengesellschaft Diarylalkyl-substituted alkylamines, process for their preparation, their use as well as medicaments containing them
EP0309913A2 (en) * 1987-09-30 1989-04-05 BASF Aktiengesellschaft Fungicidal N-substituted 3-aryl-pyrrolidine derivatives
EP0360685A1 (en) * 1988-09-23 1990-03-28 Lipha, Lyonnaise Industrielle Pharmaceutique 1-[(Diaryl methoxy)alkyl] pyrrolidines and piperidines, process for their preparation and pharmaceutical compounds containing them
EP0466585A1 (en) * 1990-07-10 1992-01-15 Adir Et Compagnie Novel piperidin, tetrahydropyridine and pyrrolidine derivatives, process for their preparation and pharmaceutical compositions containing them

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1964511A1 (en) * 1968-12-23 1970-07-09 Robins Co Inc A H 1-substituted-3-phenoxypyrrolidines and process for their preparation
EP0030526A1 (en) * 1979-12-05 1981-06-17 Astra Läkemedel Aktiebolag New phenyl-azacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds
EP0218249A2 (en) * 1985-10-11 1987-04-15 Tokyo Kasei Kogyo Co., Ltd Process for the production of 3-aminopyrrolidines
EP0229623A2 (en) * 1986-01-09 1987-07-22 Hoechst Aktiengesellschaft Diaryl-substituted alkylamines, procedure for their preparation, their application and medicaments containing them
EP0244739A2 (en) * 1986-05-02 1987-11-11 BASF Aktiengesellschaft N-substituted pyrrolidine and piperidine derivatives and their salts
EP0290958A2 (en) * 1987-05-12 1988-11-17 Hoechst Aktiengesellschaft Diarylalkyl-substituted alkylamines, process for their preparation, their use as well as medicaments containing them
EP0309913A2 (en) * 1987-09-30 1989-04-05 BASF Aktiengesellschaft Fungicidal N-substituted 3-aryl-pyrrolidine derivatives
EP0360685A1 (en) * 1988-09-23 1990-03-28 Lipha, Lyonnaise Industrielle Pharmaceutique 1-[(Diaryl methoxy)alkyl] pyrrolidines and piperidines, process for their preparation and pharmaceutical compounds containing them
EP0466585A1 (en) * 1990-07-10 1992-01-15 Adir Et Compagnie Novel piperidin, tetrahydropyridine and pyrrolidine derivatives, process for their preparation and pharmaceutical compositions containing them

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF MEDICINAL CHEMISTRY, Vol. 12, No. 3, May 1969, pages 442-444; R.L. DUNCAN et al., "Synthesis and Biological Properties of Some 1-Substituted 3-(o-Methoxyphenoxy)Pyrrolidines", Compounds of Formula III, page 442. *

Also Published As

Publication number Publication date
WO1992022527A2 (en) 1992-12-23
AU1975092A (en) 1993-01-12
JPH06508353A (en) 1994-09-22
EP0589971A1 (en) 1994-04-06
GB9113031D0 (en) 1991-08-07

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