DE69835532D1 - Quinolin-enthaltende alpha-ketoamid-basierte inhibitoren von cystein- und serin protease - Google Patents

Quinolin-enthaltende alpha-ketoamid-basierte inhibitoren von cystein- und serin protease

Info

Publication number
DE69835532D1
DE69835532D1 DE69835532T DE69835532T DE69835532D1 DE 69835532 D1 DE69835532 D1 DE 69835532D1 DE 69835532 T DE69835532 T DE 69835532T DE 69835532 T DE69835532 T DE 69835532T DE 69835532 D1 DE69835532 D1 DE 69835532D1
Authority
DE
Germany
Prior art keywords
ketoamide
cystein
quinolin
containing alpha
based inhibitors
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 - Lifetime
Application number
DE69835532T
Other languages
English (en)
Other versions
DE69835532T2 (de
Inventor
Sankar Chatterjee
P Mallamo
Douglas Dunn
Allen Josef
Zi-Qiang Gu
A Daines
Dennis Kingsbury
Israel Pendrak
C Sham
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.)
Cephalon LLC
SmithKline Beecham Corp
Original Assignee
Cephalon LLC
SmithKline Beecham Corp
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 Cephalon LLC, SmithKline Beecham Corp filed Critical Cephalon LLC
Publication of DE69835532D1 publication Critical patent/DE69835532D1/de
Application granted granted Critical
Publication of DE69835532T2 publication Critical patent/DE69835532T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • A61P25/28—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
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • 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
    • C07D215/38—Nitrogen atoms
    • C07D215/40—Nitrogen atoms attached in position 8
    • 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biomedical Technology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Cardiology (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
DE69835532T 1997-10-07 1998-10-07 Chinolin-enthaltende alpha-Ketoamid-Cystein-und Serinproteaseinhibitoren Expired - Lifetime DE69835532T2 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US6126797P 1997-10-07 1997-10-07
US61267 1997-10-07
US09/167,193 US6083944A (en) 1997-10-07 1998-10-06 Quinoline-containing α-ketoamide cysteine and serine protease inhibitors
US167193 1998-10-06
PCT/US1998/021054 WO1999017775A1 (en) 1997-10-07 1998-10-07 QUINOLINE-CONTAINING α-KETOAMIDE CYSTEINE AND SERINE PROTEASE INHIBITORS

Publications (2)

Publication Number Publication Date
DE69835532D1 true DE69835532D1 (de) 2006-09-21
DE69835532T2 DE69835532T2 (de) 2007-02-15

Family

ID=26740894

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69835532T Expired - Lifetime DE69835532T2 (de) 1997-10-07 1998-10-07 Chinolin-enthaltende alpha-Ketoamid-Cystein-und Serinproteaseinhibitoren

Country Status (13)

Country Link
US (1) US6083944A (de)
EP (1) EP1032393B1 (de)
JP (1) JP2001518506A (de)
KR (1) KR100647177B1 (de)
CN (1) CN1190424C (de)
AT (1) ATE335485T1 (de)
AU (1) AU749099B2 (de)
CA (1) CA2304204C (de)
DE (1) DE69835532T2 (de)
ES (1) ES2270532T3 (de)
HK (1) HK1029936A1 (de)
NZ (1) NZ504024A (de)
WO (1) WO1999017775A1 (de)

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Publication number Priority date Publication date Assignee Title
US6150378A (en) * 1997-10-07 2000-11-21 Cephalon, Inc. Peptidyl-containing α-ketoamide cysteine and serine protease inhibitors
IL138402A0 (en) 1998-04-20 2001-10-31 Basf Ag Heterocyclically substituted amides used as calpain inhibitors
EP1150977B1 (de) * 1999-02-12 2004-08-25 SmithKline Beecham plc Phenylharnstoffe und phenylthioharnstoffe als orexinrezeptorantagonisten
EP1465862A1 (de) 2002-01-17 2004-10-13 SmithKline Beecham Corporation Cycloalkyl-ketoamiden derivate und ihre verwendung als cathepsin-k-inhibitoren
AU2003209297A1 (en) * 2002-01-18 2003-09-02 Massachusetts Eye And Ear Infirmary Methods and compositions for preserving the viability of photoreceptor cells
WO2003091202A1 (fr) * 2002-04-25 2003-11-06 Ono Pharmaceutical Co., Ltd. Composes derives de dicetohydrazine et medicaments contenant ces composes comme ingredient actif
EP1682511A2 (de) * 2003-11-10 2006-07-26 Wyeth Verfahren und zusammensetzungen zur inhibierung von selectin
WO2005077969A2 (en) * 2004-02-04 2005-08-25 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly hcv ns3-ns4a protease
WO2006124494A1 (en) * 2005-05-13 2006-11-23 Virginia Tech Intellectual Properties, Inc. TRANSITION-STATE INHIBITORS OF PIN1, α-KETOAMIDE-CONTAINING PEPTIDOMIMETICS, AND SYNTHESES THEREOF
WO2007019427A2 (en) * 2005-08-08 2007-02-15 Massachusetts Eye & Ear Infirmary Methods and compositions for preserving the viability of photoreceptor cells
BRPI0721298A2 (pt) 2006-12-29 2014-03-25 Abbott Gmbh & Co Kg Composto de carboxamida e seus usos como inibidores de calpaína
TWI453019B (zh) 2007-12-28 2014-09-21 Abbvie Deutschland 甲醯胺化合物
TWI519530B (zh) 2009-02-20 2016-02-01 艾伯維德國有限及兩合公司 羰醯胺化合物及其作為鈣蛋白酶（ｃａｌｐａｉｎ）抑制劑之用途
US8236798B2 (en) 2009-05-07 2012-08-07 Abbott Gmbh & Co. Kg Carboxamide compounds and their use as calpain inhibitors
US9051304B2 (en) 2009-12-22 2015-06-09 AbbVie Deutschland GmbH & Co. KG Carboxamide compounds and their use as calpain inhibitors V
US8598211B2 (en) 2009-12-22 2013-12-03 Abbvie Inc. Carboxamide compounds and their use as calpain inhibitors IV
CA2819087A1 (en) 2010-12-09 2012-06-14 AbbVie Deutschland GmbH & Co. KG Carboxamide compounds and their use as calpain inhibitors v
JP2015512427A (ja) 2012-04-03 2015-04-27 アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー カルボキサミド化合物およびそれのカルパイン阻害薬ｖとしての使用
EP3426674A4 (de) 2016-03-09 2019-08-14 Blade Therapeutics, Inc. Cyclische keto-amid-verbindungen als calpain-modulatoren sowie verfahren zur herstellung und verwendung davon
AU2017292646A1 (en) 2016-07-05 2019-02-07 Blade Therapeutics, Inc. Calpain modulators and therapeutic uses thereof
SG10201912574WA (en) 2016-09-28 2020-02-27 Blade Therapeutics Inc Calpain modulators and therapeutic uses thereof
RU2020130022A (ru) * 2018-03-28 2022-05-04 Блэйд Терапьютикс, Инк. Модуляторы кальпаина и их терапевтическое применение

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EP0423358A4 (en) * 1989-04-15 1992-05-06 Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai Postostatin and related compound thereof, or their salts
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US5444042A (en) * 1990-12-28 1995-08-22 Cortex Pharmaceuticals Method of treatment of neurodegeneration with calpain inhibitors
JPH06504547A (ja) * 1990-12-28 1994-05-26 ジョージア・テック・リサーチ・コーポレーション ペプチドケトアミド、ケト酸およびケトエステル
US5650508A (en) * 1991-12-27 1997-07-22 Georgia Tech Research Corporation Peptide ketoamides
JP2525552B2 (ja) * 1992-01-23 1996-08-21 東レ株式会社 モルヒナン誘導体および医薬用途
US5514694A (en) * 1992-09-21 1996-05-07 Georgia Tech Research Corp Peptidyl ketoamides
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US5563127A (en) * 1993-03-24 1996-10-08 The Dupont Merck Pharmaceutical Company Boronic acid and ester inhibitors of thrombin
US5658885A (en) * 1993-04-27 1997-08-19 The Dupont Merck Pharmaceutical Company Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes
US5541290A (en) * 1993-06-24 1996-07-30 Harbeson; Scott L. Optically pure calpain inhibitor compounds
DE4331134A1 (de) * 1993-09-14 1995-03-16 Bayer Ag Neue antiviral wirksame Pseudopeptide
HU226535B1 (en) * 1994-05-27 2009-03-30 Glaxosmithkline Spa Quinoline derivatives as tachykinin nk3 receptor antagonists, pharmaceutical compositions containing them, and their use
US5614649A (en) * 1994-11-14 1997-03-25 Cephalon, Inc. Multicatalytic protease inhibitors
JPH08208462A (ja) * 1994-11-24 1996-08-13 Takeda Chem Ind Ltd カテプシンｌ阻害剤
ATE205477T1 (de) * 1995-06-06 2001-09-15 Pfizer Substituierte n-(indol-2-carbonyl)-amide und derivate als glycogen phosphorylase inhibitoren
EP1491533A3 (de) * 1997-03-14 2005-01-19 Cephalon, Inc. Chinolin- und Naphthalincarboxamide, deren pharmazeuitische Zubereitungen und Verwendung als Calpain Inhibitoren

Also Published As

Publication number Publication date
EP1032393A1 (de) 2000-09-06
CA2304204C (en) 2010-05-18
NZ504024A (en) 2002-09-27
AU749099B2 (en) 2002-06-20
JP2001518506A (ja) 2001-10-16
US6083944A (en) 2000-07-04
HK1029936A1 (en) 2001-04-20
EP1032393A4 (de) 2002-06-12
WO1999017775A1 (en) 1999-04-15
CA2304204A1 (en) 1999-04-15
ES2270532T3 (es) 2007-04-01
KR20010024432A (ko) 2001-03-26
ATE335485T1 (de) 2006-09-15
CN1190424C (zh) 2005-02-23
KR100647177B1 (ko) 2006-11-17
EP1032393B1 (de) 2006-08-09
AU9788298A (en) 1999-04-27
DE69835532T2 (de) 2007-02-15
CN1274283A (zh) 2000-11-22

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