AU2001278479B2 - Pyrrolidine derivatives as metalloprotease inhibitors - Google Patents

Pyrrolidine derivatives as metalloprotease inhibitors Download PDF

Info

Publication number
AU2001278479B2
AU2001278479B2 AU2001278479A AU2001278479A AU2001278479B2 AU 2001278479 B2 AU2001278479 B2 AU 2001278479B2 AU 2001278479 A AU2001278479 A AU 2001278479A AU 2001278479 A AU2001278479 A AU 2001278479A AU 2001278479 B2 AU2001278479 B2 AU 2001278479B2
Authority
AU
Australia
Prior art keywords
pyrrolidine
ester
acid
mmol
carboxylic acid
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
AU2001278479A
Other languages
English (en)
Other versions
AU2001278479A1 (en
Inventor
Johannes Aebi
Daniel Bur
Alexander Chucholowski
Henrietta Dehmlow
Eric Argirios Kitas
Ulrike Obst
Hans Peter Wessel
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of AU2001278479A1 publication Critical patent/AU2001278479A1/en
Application granted granted Critical
Publication of AU2001278479B2 publication Critical patent/AU2001278479B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • 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
    • A61P9/06—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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—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
    • C07D207/46—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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • 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
    • 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
    • C07D417/12—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 linked by a chain containing hetero atoms as chain links
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Immunology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (AREA)
  • Reproductive Health (AREA)
  • Endocrinology (AREA)
  • Transplantation (AREA)
  • Gynecology & Obstetrics (AREA)
  • Neurology (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Neurosurgery (AREA)
  • Pregnancy & Childbirth (AREA)
  • Pain & Pain Management (AREA)
  • Dermatology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2001278479A 2000-07-19 2001-07-10 Pyrrolidine derivatives as metalloprotease inhibitors Ceased AU2001278479B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00114949.1 2000-07-19
EP00114949 2000-07-19
PCT/EP2001/007951 WO2002008185A1 (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as metalloprotease inhibitors

Publications (2)

Publication Number Publication Date
AU2001278479A1 AU2001278479A1 (en) 2002-05-02
AU2001278479B2 true AU2001278479B2 (en) 2007-06-21

Family

ID=8169226

Family Applications (2)

Application Number Title Priority Date Filing Date
AU2001278479A Ceased AU2001278479B2 (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as metalloprotease inhibitors
AU7847901A Pending AU7847901A (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as metalloprotease inhibitors

Family Applications After (1)

Application Number Title Priority Date Filing Date
AU7847901A Pending AU7847901A (en) 2000-07-19 2001-07-10 Pyrrolidine derivatives as metalloprotease inhibitors

Country Status (15)

Country Link
US (3) US20020040146A1 (enExample)
EP (1) EP1303486A1 (enExample)
JP (1) JP3983663B2 (enExample)
KR (1) KR100613196B1 (enExample)
CN (1) CN100406439C (enExample)
AR (1) AR037990A1 (enExample)
AU (2) AU2001278479B2 (enExample)
BR (1) BR0112655A (enExample)
CA (1) CA2415740A1 (enExample)
MX (1) MXPA03000368A (enExample)
PA (1) PA8522301A1 (enExample)
PE (1) PE20020333A1 (enExample)
UY (1) UY26846A1 (enExample)
WO (1) WO2002008185A1 (enExample)
ZA (1) ZA200300170B (enExample)

Families Citing this family (12)

* 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
US7405234B2 (en) * 2002-05-17 2008-07-29 Bristol-Myers Squibb Company Bicyclic modulators of androgen receptor function
EP1558591B1 (en) 2002-10-07 2014-05-07 The Regents of The University of California Modulation of anxiety through blockade of anandamide hydrolysis
US7388027B2 (en) * 2004-03-04 2008-06-17 Bristol-Myers Squibb Company Bicyclic compounds as modulators of androgen receptor function and method
CN101376656A (zh) * 2007-08-30 2009-03-04 山东轩竹医药科技有限公司 培南衍生物
EP2234608A2 (en) 2007-12-11 2010-10-06 Viamet Pharmaceuticals, Inc. Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties
US8404866B2 (en) * 2008-09-03 2013-03-26 Florida State University Research Foundation Substituted heterocyclic mercaptosulfonamide metalloprotease inhibitors
RU2766579C2 (ru) 2015-07-02 2022-03-15 ХОРАЙЗОН ОРФАН ЭлЭлСи Цистеаминдиоксигеназа-резистентные аналоги цистеамина и их применение
BR112020014561A2 (pt) * 2018-01-17 2020-12-08 Migal - Galilee Research Institute Ltd. Nibidores inovadores da via metabólica da metionina
CN111825582B (zh) * 2020-08-12 2022-04-08 江西理工大学 一种以芳基磺酰氯为硫源合成β-硫代羰基化合物的方法
JP7904556B2 (ja) * 2022-11-25 2026-08-13 Ｎｔｔ株式会社 ベンゼンヘキサチオールの作製方法
CN120801563A (zh) * 2025-08-14 2025-10-17 陕西圣济康泽中药研究科技有限公司 一种检测西洋参中皂苷类物质的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998008814A1 (en) * 1996-08-28 1998-03-05 The Procter & Gamble Company Bidentate metalloprotease inhibitors
WO1998008815A1 (en) * 1996-08-28 1998-03-05 The Procter & Gamble Company Substituted cyclic amine metalloprotease inhibitors

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3579888D1 (de) * 1984-11-08 1990-10-31 Sumitomo Pharma Carbapenemverbindungen und deren herstellung.
US4925838A (en) * 1988-03-18 1990-05-15 Fujisawa Pharmaceutical Company, Ltd. 3-pyrrolidinylthio-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid compounds
US5317016A (en) * 1991-08-20 1994-05-31 Shionogi Seiyaku Kabushiki Kaisha Pyrrolidylthiocarbapenem derivative
GB9301276D0 (en) * 1993-01-22 1993-03-17 Fujisawa Pharmaceutical Co Bicyclic compounds and their preparation
JP4182545B2 (ja) * 1994-02-25 2008-11-19 萬有製薬株式会社 カルバペネム誘導体
PT888340E (pt) * 1996-02-13 2002-12-31 Abbott Lab Derivados de acido 4-(benzo-1,3-dioxolil)pirrolidino-3-carboxilico como antagonistas de endotelina
BR0112580A (pt) * 2000-07-19 2003-06-17 Hoffmann La Roche Compostos, composições farmacêuticas que contêm os mesmos, utilização desses compostos, processo para tratamento terapêutico e/ou profilático e processo para a preparação desses compostos
BR0112655A (pt) * 2000-07-19 2003-06-24 Hoffmann La Roche Derivados de pirrolidino como inibidores de metaloproteases

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998008814A1 (en) * 1996-08-28 1998-03-05 The Procter & Gamble Company Bidentate metalloprotease inhibitors
WO1998008815A1 (en) * 1996-08-28 1998-03-05 The Procter & Gamble Company Substituted cyclic amine metalloprotease inhibitors

Also Published As

Publication number Publication date
ZA200300170B (en) 2004-04-07
US6790860B2 (en) 2004-09-14
MXPA03000368A (es) 2004-09-13
US20040242672A1 (en) 2004-12-02
AU7847901A (en) 2002-02-05
EP1303486A1 (en) 2003-04-23
US20030199569A1 (en) 2003-10-23
JP2004504379A (ja) 2004-02-12
CN100406439C (zh) 2008-07-30
PE20020333A1 (es) 2002-05-10
BR0112655A (pt) 2003-06-24
KR20030024792A (ko) 2003-03-26
JP3983663B2 (ja) 2007-09-26
UY26846A1 (es) 2002-01-31
CN1443164A (zh) 2003-09-17
KR100613196B1 (ko) 2006-08-18
CA2415740A1 (en) 2002-01-31
WO2002008185A1 (en) 2002-01-31
AR037990A1 (es) 2004-12-22
US20020040146A1 (en) 2002-04-04
PA8522301A1 (es) 2002-11-18
US7189756B2 (en) 2007-03-13

Similar Documents

Publication Publication Date Title
SK160697A3 (en) Substituted derivatives of (sulfinic acid, sulfonic acid, sulfonylamino or sulfinylamino)-n- -[(aminoiminomethyl)phenylalkyl]-azaheterocyclylamide compounds
WO2002030890A1 (en) Nitrogenous five-membered ring compounds
KR100568841B1 (ko) 엔도텔린-전환 효소의 억제제로서의 피롤리딘 유도체
SK16252001A3 (sk) Aromatická sulfónhydroxámová kyselina ako inhibítor metaloproteiázy
US6790860B2 (en) Pyrrolidine derivatives
US6569847B1 (en) Substituted azetidin-2-ones as cysteine protease inhibitors
AU2001278479A1 (en) Pyrrolidine derivatives as metalloprotease inhibitors
EP2814822B1 (en) Novel pyrrolidine derivatives
EP1317428B1 (en) Pyrrolidine-2-carboxylic acid hydrazide derivatives for use as metalloprotease inhibitors
AU2005229666A1 (en) Nitrogen-containing 5-membered ring compound

Legal Events

Date Code Title Description
MK14 Patent ceased section 143(a) (annual fees not paid) or expired