AU709330B2 - Serine protease inhibitors - Google Patents

Serine protease inhibitors Download PDF

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Publication number
AU709330B2
AU709330B2 AU18775/97A AU1877597A AU709330B2 AU 709330 B2 AU709330 B2 AU 709330B2 AU 18775/97 A AU18775/97 A AU 18775/97A AU 1877597 A AU1877597 A AU 1877597A AU 709330 B2 AU709330 B2 AU 709330B2
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AU
Australia
Prior art keywords
alkyl
compound
pro
chr
side chain
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
AU18775/97A
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English (en)
Other versions
AU1877597A (en
Inventor
Anton Egbert Peter Adang
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.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
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 Akzo Nobel NV filed Critical Akzo Nobel NV
Publication of AU1877597A publication Critical patent/AU1877597A/en
Application granted granted Critical
Publication of AU709330B2 publication Critical patent/AU709330B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • 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
    • 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
    • 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
    • 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Hematology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
AU18775/97A 1996-03-01 1997-02-26 Serine protease inhibitors Ceased AU709330B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP96200543 1996-03-01
EP96200543 1996-03-01
PCT/EP1997/000938 WO1997031937A1 (en) 1996-03-01 1997-02-26 Serine protease inhibitors

Publications (2)

Publication Number Publication Date
AU1877597A AU1877597A (en) 1997-09-16
AU709330B2 true AU709330B2 (en) 1999-08-26

Family

ID=8223736

Family Applications (1)

Application Number Title Priority Date Filing Date
AU18775/97A Ceased AU709330B2 (en) 1996-03-01 1997-02-26 Serine protease inhibitors

Country Status (25)

Country Link
US (1) US6410684B1 (OSRAM)
EP (1) EP0886647B1 (OSRAM)
JP (1) JP2000506837A (OSRAM)
KR (1) KR19990087415A (OSRAM)
CN (1) CN1212704A (OSRAM)
AR (1) AR006310A1 (OSRAM)
AT (1) ATE221080T1 (OSRAM)
AU (1) AU709330B2 (OSRAM)
BR (1) BR9707808A (OSRAM)
CA (1) CA2246246A1 (OSRAM)
CZ (1) CZ277898A3 (OSRAM)
DE (1) DE69714222T2 (OSRAM)
DK (1) DK0886647T3 (OSRAM)
ES (1) ES2180933T3 (OSRAM)
HU (1) HUP9900390A3 (OSRAM)
IL (1) IL120310A (OSRAM)
NO (1) NO983991L (OSRAM)
NZ (1) NZ331484A (OSRAM)
PL (1) PL328875A1 (OSRAM)
PT (1) PT886647E (OSRAM)
RU (1) RU2178419C2 (OSRAM)
TR (1) TR199801704T2 (OSRAM)
TW (1) TW442452B (OSRAM)
WO (1) WO1997031937A1 (OSRAM)
ZA (1) ZA971667B (OSRAM)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU719216B2 (en) * 1996-02-13 2000-05-04 Akzo Nobel N.V. Serine protease inhibitors
JP2001525823A (ja) 1997-05-15 2001-12-11 イーライ・リリー・アンド・カンパニー 抗血栓化合物
KR20010043004A (ko) 1998-04-30 2001-05-25 개리 이. 프라이드만 피코르나 바이러스 억제 화합물, 그의 제조 방법 및 용도
EP1105412A1 (en) * 1998-08-17 2001-06-13 Cortech, Inc. Serine protease inhibitors comprising alpha-keto heterocycles
AU3731400A (en) 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Methods and compositions useful in inhibiting apoptosis
US6849605B1 (en) 1999-03-05 2005-02-01 The Trustees Of University Technology Corporation Inhibitors of serine protease activity, methods and compositions for treatment of viral infections
US6489308B1 (en) 1999-03-05 2002-12-03 Trustees Of University Of Technology Corporation Inhibitors of serine protease activity, methods and compositions for treatment of nitric-oxide-induced clinical conditions
CN1372566A (zh) 1999-08-04 2002-10-02 阿格罗尼制药公司 抗细小核糖核酸病毒的化合物和组合物,它们的药物用途,及其合成原料
NZ523134A (en) 2000-06-14 2004-08-27 Agouron Pharma Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
US7244721B2 (en) 2000-07-21 2007-07-17 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
WO2002008187A1 (en) 2000-07-21 2002-01-31 Schering Corporation Novel peptides as ns3-serine protease inhibitors of hepatitis c virus
MXPA03000627A (es) 2000-07-21 2004-07-30 Schering Corp Nuevos peptidos como inhibidores de proteasa serina-ns3 del virus de la hepatitis c.
HUP0304058A2 (hu) 2001-01-30 2004-04-28 Bristol-Myers Squibb Company Xa faktor szulfonamid-laktám inhibitorok és alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények
US7405210B2 (en) * 2003-05-21 2008-07-29 Osi Pharmaceuticals, Inc. Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
ES2353309T3 (es) 2004-03-08 2011-03-01 Prosidion Ltd. Hidrazidas del ácido pirrolopiridin-2-carboxílico como inhibidores de glucógeno fosforilasa.
ATE424821T1 (de) 2004-12-02 2009-03-15 Prosidion Ltd Pyrrolopyridin-2-karbonsäureamide
RU2509776C2 (ru) * 2008-10-15 2014-03-20 ДАНИСКО ЮЭс ИНК. МОДИФИЦИРОВАННЫЕ ВАРИАНТЫ ИНГИБИТОРОВ ПРОТЕАЗ Bowman Birk
EP4257191A3 (en) 2016-06-21 2023-11-22 Orion Ophthalmology LLC Heterocyclic prolinamide derivatives
WO2017222914A1 (en) 2016-06-21 2017-12-28 Inception 4, Inc. Carbocyclic prolinamide derivatives
WO2022013684A1 (en) 2020-07-11 2022-01-20 Pfizer Inc. Antiviral heteroaryl ketone derivatives
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556655A (en) * 1984-09-24 1985-12-03 Schering Corporation Antihypertensive compounds having both diuretic and angiotensin converting enzyme inhibitory activity
CA2008116C (en) * 1989-02-23 2001-11-20 Thomas Weller Glycine derivatives
ZW11290A1 (en) 1989-07-14 1990-10-31 Smithkline Beecham Corp Hemoregulatory peptides
US5672582A (en) * 1993-04-30 1997-09-30 Merck & Co., Inc. Thrombin inhibitors
WO1994025051A1 (en) * 1993-04-30 1994-11-10 Merck & Co., Inc. Thrombin inhibitors
SE9301916D0 (sv) 1993-06-03 1993-06-03 Ab Astra New peptides derivatives
ZA951618B (en) 1994-03-04 1996-08-27 Lilly Co Eli Antithrombotic agents
ZA951617B (en) 1994-03-04 1997-02-27 Lilly Co Eli Antithrombotic agents.
US5561146A (en) 1994-06-10 1996-10-01 Bristol-Myers Squibb Company Modified guanidino and amidino thrombin inhibitors
JPH10503176A (ja) * 1994-06-17 1998-03-24 コーバス インターナショナル， インコーポレイテッド 酵素インヒビターとしての３−アミノ−２−オキソ−１−ピペリジン酢酸誘導体
JPH0820597A (ja) * 1994-07-07 1996-01-23 Meiji Seika Kaisha Ltd トロンビン阻害作用を有する複素環カルボニル化合物
JPH11508535A (ja) * 1994-12-22 1999-07-27 バイオケム ファーマ インコーポレイテッド 低分子量２環式トロンビン阻害剤

Also Published As

Publication number Publication date
DE69714222D1 (de) 2002-08-29
BR9707808A (pt) 1999-07-27
PL328875A1 (en) 1999-03-01
CZ277898A3 (cs) 1999-06-16
WO1997031937A1 (en) 1997-09-04
HUP9900390A2 (hu) 1999-06-28
IL120310A (en) 2002-02-10
IL120310A0 (en) 1997-06-10
HK1021541A1 (en) 2000-06-16
ES2180933T3 (es) 2003-02-16
TW442452B (en) 2001-06-23
KR19990087415A (ko) 1999-12-27
PT886647E (pt) 2002-12-31
AU1877597A (en) 1997-09-16
AR006310A1 (es) 1999-08-25
DE69714222T2 (de) 2003-02-20
CA2246246A1 (en) 1997-09-04
EP0886647B1 (en) 2002-07-24
US6410684B1 (en) 2002-06-25
JP2000506837A (ja) 2000-06-06
HUP9900390A3 (en) 2000-11-28
ATE221080T1 (de) 2002-08-15
DK0886647T3 (da) 2002-11-04
CN1212704A (zh) 1999-03-31
RU2178419C2 (ru) 2002-01-20
NZ331484A (en) 2000-01-28
NO983991L (no) 1998-10-30
EP0886647A1 (en) 1998-12-30
ZA971667B (en) 1997-09-10
TR199801704T2 (xx) 1998-12-21
NO983991D0 (no) 1998-08-31

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Legal Events

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