CA2268886A1 - Aminothiophenecarboxamides - Google Patents

Aminothiophenecarboxamides

Info

Publication number
CA2268886A1
CA2268886A1 CA002268886A CA2268886A CA2268886A1 CA 2268886 A1 CA2268886 A1 CA 2268886A1 CA 002268886 A CA002268886 A CA 002268886A CA 2268886 A CA2268886 A CA 2268886A CA 2268886 A1 CA2268886 A1 CA 2268886A1
Authority
CA
Canada
Prior art keywords
aminothiophenecarboxamides
phosphodiesterase
potency
disturbances
demonstrate
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.)
Granted
Application number
CA002268886A
Other languages
French (fr)
Other versions
CA2268886C (en
Inventor
Rochus Jonas
Pierre Schelling
Franz-Werner Kluxen
Maria Christadler
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.)
Merck Patent GmbH
Original Assignee
Merck Patent Gesellschaft Mit Beschraenkter Haftung
Rochus Jonas
Pierre Schelling
Franz-Werner Kluxen
Maria Christadler
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 Merck Patent Gesellschaft Mit Beschraenkter Haftung, Rochus Jonas, Pierre Schelling, Franz-Werner Kluxen, Maria Christadler filed Critical Merck Patent Gesellschaft Mit Beschraenkter Haftung
Publication of CA2268886A1 publication Critical patent/CA2268886A1/en
Application granted granted Critical
Publication of CA2268886C publication Critical patent/CA2268886C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Gynecology & Obstetrics (AREA)
  • Cardiology (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)

Abstract

Aminothiophene carboxylic acid amides having formula (I) and their physiologically harmless salts, wherein R1, R2, R3, R4, R5, A and n have the meaning given in claim 1, demonstrate phosphodiesterase V inhibition and can be used to treat cardiovascular diseases and in therapy for disturbances of potency.
CA002268886A 1996-10-15 1997-10-08 Aminothiophenecarboxamides Expired - Fee Related CA2268886C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19642451A DE19642451A1 (en) 1996-10-15 1996-10-15 Aminothiophene carboxamides
DE19642451.8 1996-10-15
PCT/EP1997/005531 WO1998016521A1 (en) 1996-10-15 1997-10-08 Aminothiophene carboxylic acid amides and the use thereof as phosphodiesterase inhibitors

Publications (2)

Publication Number Publication Date
CA2268886A1 true CA2268886A1 (en) 1998-04-23
CA2268886C CA2268886C (en) 2008-05-20

Family

ID=7808775

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002268886A Expired - Fee Related CA2268886C (en) 1996-10-15 1997-10-08 Aminothiophenecarboxamides

Country Status (26)

Country Link
US (1) US6143777A (en)
EP (1) EP0934301B1 (en)
JP (1) JP4243352B2 (en)
KR (1) KR100479811B1 (en)
CN (1) CN1110493C (en)
AR (1) AR009985A1 (en)
AT (1) ATE202347T1 (en)
AU (1) AU725741B2 (en)
BR (1) BR9712321A (en)
CA (1) CA2268886C (en)
CZ (1) CZ297253B6 (en)
DE (2) DE19642451A1 (en)
DK (1) DK0934301T3 (en)
ES (1) ES2159851T3 (en)
GR (1) GR3036341T3 (en)
HK (1) HK1020724A1 (en)
HU (1) HUP9904703A3 (en)
NO (1) NO991776L (en)
PL (1) PL192109B1 (en)
PT (1) PT934301E (en)
RU (1) RU2184731C2 (en)
SI (1) SI0934301T1 (en)
SK (1) SK283807B6 (en)
TW (1) TW438791B (en)
WO (1) WO1998016521A1 (en)
ZA (1) ZA979199B (en)

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US6410584B1 (en) 1998-01-14 2002-06-25 Cell Pathways, Inc. Method for inhibiting neoplastic cells with indole derivatives
JP2002518471A (en) * 1998-06-19 2002-06-25 ノバルティス アクチエンゲゼルシャフト Preparation of pyrimidinone derivatives
US6200771B1 (en) 1998-10-15 2001-03-13 Cell Pathways, Inc. Method of using a novel phosphodiesterase in pharmaceutical screeing to identify compounds for treatment of neoplasia
US6133271A (en) * 1998-11-19 2000-10-17 Cell Pathways, Inc. Method for inhibiting neoplastic cells and related conditions by exposure thienopyrimidine derivatives
US6187779B1 (en) 1998-11-20 2001-02-13 Cell Pathways, Inc. Method for inhibiting neoplastic cells and related conditions by exposure to 2,8-disubstituted quinazoline derivatives
US6369092B1 (en) 1998-11-23 2002-04-09 Cell Pathways, Inc. Method for treating neoplasia by exposure to substituted benzimidazole derivatives
US6486155B1 (en) 1998-11-24 2002-11-26 Cell Pathways Inc Method of inhibiting neoplastic cells with isoquinoline derivatives
US6034099A (en) * 1998-11-24 2000-03-07 Cell Pathways, Inc. Method for inhibiting neoplastic lesions by administering 4-(arylmethylene)- 2, 3- dihydro-pyrazol-3-ones
US6077842A (en) * 1998-11-24 2000-06-20 Cell Pathways, Inc. Method of inhibiting neoplastic cells with pyrazolopyridylpyridazinone derivatives
US6020379A (en) * 1999-02-19 2000-02-01 Cell Pathways, Inc. Position 7 substituted indenyl-3-acetic acid derivatives and amides thereof for the treatment of neoplasia
US6479493B1 (en) 2001-08-23 2002-11-12 Cell Pathways, Inc. Methods for treatment of type I diabetes
WO2003027093A1 (en) * 2001-09-21 2003-04-03 Smithkline Beecham Corporation Chemical compounds
DE60229975D1 (en) * 2001-10-04 2009-01-02 Smithkline Beecham Corp NF-KB INHIBITORS
US7208516B2 (en) 2002-03-20 2007-04-24 Celgene Corporation Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
US6962940B2 (en) 2002-03-20 2005-11-08 Celgene Corporation (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof
US7893101B2 (en) 2002-03-20 2011-02-22 Celgene Corporation Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof
US7276529B2 (en) 2002-03-20 2007-10-02 Celgene Corporation Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
US7196207B2 (en) * 2002-07-24 2007-03-27 Mitsui Chemicals, Inc. Method for producing 2-alkyl-3-aminothiophene derivative
US7179836B2 (en) * 2002-09-20 2007-02-20 Smithkline Beecham Corporation Chemical compounds
FR2875807B1 (en) 2004-09-30 2006-11-17 Servier Lab ALPHA CRYSTALLINE FORM OF STRONTIUM RANELATE, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
EP2258357A3 (en) 2005-08-26 2011-04-06 Braincells, Inc. Neurogenesis with acetylcholinesterase inhibitor
JP2009506069A (en) 2005-08-26 2009-02-12 ブレインセルス，インコーポレイティド Neurogenesis through modulation of muscarinic receptors
AU2006304787A1 (en) 2005-10-21 2007-04-26 Braincells, Inc. Modulation of neurogenesis by PDE inhibition
US20070112017A1 (en) 2005-10-31 2007-05-17 Braincells, Inc. Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en) 2006-03-08 2010-08-26 Braincells, Inc. Modulation of neurogenesis by nootropic agents
JP2009536667A (en) 2006-05-09 2009-10-15 ブレインセルス，インコーポレイティド 5HT receptor-mediated neurogenesis
EP2021000A2 (en) 2006-05-09 2009-02-11 Braincells, Inc. Neurogenesis by modulating angiotensin
US7998971B2 (en) * 2006-09-08 2011-08-16 Braincells Inc. Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en) 2006-09-19 2010-07-22 Braincells, Inc. Modulation of neurogenesis by ppar agents
MX2011002149A (en) * 2008-08-27 2011-04-05 Calcimedica Inc Compounds that modulate intracellular calcium.
WO2010099217A1 (en) 2009-02-25 2010-09-02 Braincells, Inc. Modulation of neurogenesis using d-cycloserine combinations
US20150119399A1 (en) 2012-01-10 2015-04-30 President And Fellows Of Harvard College Beta-cell replication promoting compounds and methods of their use
RU2503671C1 (en) * 2012-07-31 2014-01-10 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" (Z)-2-[(3-CARBAMOYL-4,5,6,7-TETRAHYDROBENZO[b]THIEN-2-YL)AMINO]-4-(4-R-PHENYL)-4-OXOBUT-2-ENOIC ACIDS, HAVING ANALGESIC ACTIVITY
RU2501795C1 (en) * 2012-10-01 2013-12-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Пермский государственный национальный исследовательский университет" N-R-AMIDES OF (Z)-2[(3-ETHOXYCARBONYL)-4,5,6,7-TETRAHYDROBENZO [b]THIEN-2-YL)AMINO]-4-PHENYL-4-OXOBUT-2-ENOIC ACIDS, HAVING ANALGESIC ACTIVITY
EP3157520B1 (en) 2014-06-23 2019-09-04 Celgene Corporation Apremilast for the treatment of a liver disease or a liver function abnormality
RU2722176C1 (en) * 2019-09-06 2020-05-28 Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (z)-2-((4-r1-5-r2-3-(ethoxycarbonyl)thiophen-2-yl)amino)-4-oxo-4-r3-but-2-ene acids, having antimicrobial activity

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Also Published As

Publication number Publication date
US6143777A (en) 2000-11-07
CZ297253B6 (en) 2006-10-11
ZA979199B (en) 1998-05-11
PT934301E (en) 2001-10-31
CZ124099A3 (en) 1999-07-14
DE19642451A1 (en) 1998-04-16
HK1020724A1 (en) 2000-05-19
PL332802A1 (en) 1999-10-11
SI0934301T1 (en) 2001-12-31
TW438791B (en) 2001-06-07
SK43299A3 (en) 2000-04-10
NO991776D0 (en) 1999-04-14
CN1110493C (en) 2003-06-04
AU725741B2 (en) 2000-10-19
EP0934301A1 (en) 1999-08-11
ATE202347T1 (en) 2001-07-15
DK0934301T3 (en) 2001-10-08
WO1998016521A1 (en) 1998-04-23
JP2001501957A (en) 2001-02-13
HUP9904703A2 (en) 2001-05-28
GR3036341T3 (en) 2001-11-30
JP4243352B2 (en) 2009-03-25
HUP9904703A3 (en) 2001-06-28
CA2268886C (en) 2008-05-20
NO991776L (en) 1999-06-09
KR100479811B1 (en) 2005-03-30
AR009985A1 (en) 2000-05-17
CN1233246A (en) 1999-10-27
DE59703869D1 (en) 2001-07-26
KR20000049154A (en) 2000-07-25
EP0934301B1 (en) 2001-06-20
BR9712321A (en) 1999-08-31
RU2184731C2 (en) 2002-07-10
PL192109B1 (en) 2006-08-31
SK283807B6 (en) 2004-02-03
ES2159851T3 (en) 2001-10-16
AU4945197A (en) 1998-05-11

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