CA2414311C - Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme - Google Patents

Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme Download PDF

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Publication number
CA2414311C
CA2414311C CA002414311A CA2414311A CA2414311C CA 2414311 C CA2414311 C CA 2414311C CA 002414311 A CA002414311 A CA 002414311A CA 2414311 A CA2414311 A CA 2414311A CA 2414311 C CA2414311 C CA 2414311C
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CA
Canada
Prior art keywords
pyrrolidine
methyl
sulfonyl
naphthalene
mercapto
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.)
Expired - Fee Related
Application number
CA002414311A
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English (en)
French (fr)
Other versions
CA2414311A1 (en
Inventor
Johannes Aebi
Denise Blum
Daniel Bur
Alexander Chucholowski
Henrietta Dehmlow
Eric Argirios Kitas
Bernd Michael Loeffler
Ulrike Obst
Sabine Wallbaum
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F Hoffmann La Roche AG
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F Hoffmann La Roche AG
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Filing date
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Publication of CA2414311A1 publication Critical patent/CA2414311A1/en
Application granted granted Critical
Publication of CA2414311C publication Critical patent/CA2414311C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • C07D207/10—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 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
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • C07D207/10—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 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
    • C07D207/16—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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hospice & Palliative Care (AREA)
  • Reproductive Health (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Biochemistry (AREA)
  • Psychiatry (AREA)
  • Hematology (AREA)
  • Toxicology (AREA)
  • Transplantation (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
CA002414311A 2000-07-19 2001-07-10 Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme Expired - Fee Related CA2414311C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00114947 2000-07-19
EP00114947.5 2000-07-19
PCT/EP2001/007950 WO2002006222A1 (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme

Publications (2)

Publication Number Publication Date
CA2414311A1 CA2414311A1 (en) 2002-01-24
CA2414311C true CA2414311C (en) 2008-01-08

Family

ID=8169224

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002414311A Expired - Fee Related CA2414311C (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme

Country Status (16)

Country Link
US (1) US6541638B2 (enExample)
EP (1) EP1303485A1 (enExample)
JP (1) JP4068452B2 (enExample)
KR (1) KR100568841B1 (enExample)
CN (1) CN1620433A (enExample)
AR (1) AR033984A1 (enExample)
AU (1) AU2001270627A1 (enExample)
BR (1) BR0112580A (enExample)
CA (1) CA2414311C (enExample)
GT (1) GT200100145A (enExample)
MX (1) MXPA03000223A (enExample)
PA (1) PA8522501A1 (enExample)
PE (1) PE20020294A1 (enExample)
UY (1) UY26847A1 (enExample)
WO (1) WO2002006222A1 (enExample)
ZA (1) ZA200300167B (enExample)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0112655A (pt) * 2000-07-19 2003-06-24 Hoffmann La Roche Derivados de pirrolidino como inibidores de metaloproteases
CA2430978C (en) * 2000-12-28 2012-05-15 Daiichi Pharmaceutical Co., Ltd. Vla-4 inhibitors
WO2003074478A1 (en) 2002-03-05 2003-09-12 Sumitomo Chemical Company, Limited Process for the preparation of biaryl compounds
WO2004089294A2 (en) 2003-04-04 2004-10-21 Incyte Corporation Compositions, methods and kits relating to her-2 cleavage
MXPA05010883A (es) 2003-04-10 2006-01-23 Amgen Inc Derivados de amina ciclica y su uso en el tratamiento de trastornos inflamatorios relacionados mediados por bradiquinina.
WO2004092116A1 (en) 2003-04-10 2004-10-28 Amgen, Inc. Bicyclic compounds having bradykinin receptors affinity and pharmaceutical compositions thereof
RU2006101541A (ru) 2003-06-20 2006-06-10 Амген Инк. (US) Производные пиперазина и способ их применения
JP4676884B2 (ja) 2003-07-24 2011-04-27 第一三共株式会社 シクロヘキサンカルボン酸類
CN1294120C (zh) * 2003-10-21 2007-01-10 山东大学 吡咯烷类基质金属蛋白酶抑制剂及其应用
WO2007119214A2 (en) * 2006-04-13 2007-10-25 Actelion Pharmaceuticals Ltd Endothelin receptor antagonists for early stage idiopathic pulmonary fibrosis
ES2350548B1 (es) * 2009-06-25 2011-09-29 Institut Univ. De Ciència I Tecnologia, S.A. N-fenil-1-sulfonil-2-pirrolidinacarboxamidas para la identificacion de actividad biologica y farmacologica.
EP2730571A1 (en) * 2012-11-12 2014-05-14 Universitat De Barcelona 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives
WO2017168174A1 (en) 2016-04-02 2017-10-05 N4 Pharma Uk Limited New pharmaceutical forms of sildenafil
WO2019009317A1 (ja) * 2017-07-05 2019-01-10 日産化学株式会社 ベンジル化合物
CN110078593A (zh) * 2018-11-15 2019-08-02 南通正达农化有限公司 一种苹果蠹蛾性信息素的合成方法
CN122374291A (zh) 2023-12-12 2026-07-10 爱杜西亚药品有限公司 作为食欲素受体调节剂的芳基砜及砜酮衍生物
WO2025132542A1 (en) 2023-12-19 2025-06-26 Idorsia Pharmaceuticals Ltd Macrocyclic orexin agonists
CN119661387B (zh) * 2024-12-18 2025-12-16 长沙普济生物科技股份有限公司 一种烷基胺与3-卤代丙酸酯合成N-烷基-β-氨基丙酸钠的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1283906C (en) * 1983-05-09 1991-05-07 Makoto Sunagawa .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF
AU644008B2 (en) * 1990-08-10 1993-12-02 Sumitomo Pharmaceuticals Company, Limited Beta-lactam compounds, and their production and use
JP3091297B2 (ja) * 1992-01-10 2000-09-25 住友製薬株式会社 ピロリジン誘導体およびその製造方法
BR9712792A (pt) * 1996-08-28 1999-12-14 Procter & Gamble Inibidores de metaloprotease bidentada.
BR9713465A (pt) * 1996-08-28 2000-03-28 Procter & Gamble Inibidores metalotprotease de amina cìclica sibstituìda
CA2294341C (en) * 1997-07-10 2007-09-25 Merck & Co., Inc. Crystalline forms of antibiotic side chain intermediates
SK16382000A3 (sk) * 1998-05-01 2001-05-10 Kyoto Pharmaceutical Industries, Ltd. Karbapénové deriváty, ich vyžitie a ich medziproduktové zlúčeniny

Also Published As

Publication number Publication date
AU2001270627A1 (en) 2002-01-30
PA8522501A1 (es) 2002-09-17
WO2002006222A1 (en) 2002-01-24
US20020049243A1 (en) 2002-04-25
US6541638B2 (en) 2003-04-01
UY26847A1 (es) 2002-01-31
KR20030016416A (ko) 2003-02-26
AR033984A1 (es) 2004-01-21
JP4068452B2 (ja) 2008-03-26
CA2414311A1 (en) 2002-01-24
EP1303485A1 (en) 2003-04-23
KR100568841B1 (ko) 2006-04-10
MXPA03000223A (es) 2003-06-06
CN1620433A (zh) 2005-05-25
PE20020294A1 (es) 2002-04-17
JP2004504297A (ja) 2004-02-12
GT200100145A (es) 2002-05-16
ZA200300167B (en) 2004-04-07
BR0112580A (pt) 2003-06-17

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