WO1998024806A3 - Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors - Google Patents

Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors Download PDF

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Publication number
WO1998024806A3
WO1998024806A3 PCT/US1997/021636 US9721636W WO9824806A3 WO 1998024806 A3 WO1998024806 A3 WO 1998024806A3 US 9721636 W US9721636 W US 9721636W WO 9824806 A3 WO9824806 A3 WO 9824806A3
Authority
WO
WIPO (PCT)
Prior art keywords
thiadiazole
triazole
protease inhibitors
serine protease
substituted oxadiazole
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
PCT/US1997/021636
Other languages
French (fr)
Other versions
WO1998024806B1 (en
WO1998024806A2 (en
Inventor
Albert Gyorkos
Lyle W Spruce
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.)
Cortech Inc
Original Assignee
Cortech Inc
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
Priority claimed from US08/760,916 external-priority patent/US5861380A/en
Priority claimed from US08/984,881 external-priority patent/US6015791A/en
Priority claimed from US08/985,201 external-priority patent/US6150334A/en
Priority claimed from US08/985,056 external-priority patent/US5998379A/en
Priority claimed from US08/984,884 external-priority patent/US6001811A/en
Priority to BR9713684-0A priority Critical patent/BR9713684A/en
Priority to AU55894/98A priority patent/AU734615B2/en
Priority to EP97952232A priority patent/EP0954526A2/en
Priority to CA002272548A priority patent/CA2272548A1/en
Priority to HU0100669A priority patent/HUP0100669A3/en
Priority to JP52565698A priority patent/JP3220169B2/en
Application filed by Cortech Inc filed Critical Cortech Inc
Priority to NZ336046A priority patent/NZ336046A/en
Publication of WO1998024806A2 publication Critical patent/WO1998024806A2/en
Publication of WO1998024806A3 publication Critical patent/WO1998024806A3/en
Publication of WO1998024806B1 publication Critical patent/WO1998024806B1/en
Priority to NO992734A priority patent/NO992734L/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • 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
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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
    • C07K5/04—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
    • 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
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-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
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052—Val-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
    • C07K5/06008—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
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • 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
    • 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
    • C07K5/06156—Dipeptides with the first amino acid being heterocyclic and Trp-amino acid; Derivatives thereof
    • 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
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, 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
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The present invention relates to certain substituted oxadiazole, thiadiazole and triazole peptoids which are useful as inhibitors of serine proteases.
PCT/US1997/021636 1996-12-06 1997-12-05 Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors Ceased WO1998024806A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002272548A CA2272548A1 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
AU55894/98A AU734615B2 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
JP52565698A JP3220169B2 (en) 1996-12-06 1997-12-05 Serine protease inhibitor
BR9713684-0A BR9713684A (en) 1996-12-06 1997-12-05 Serine protease inhibitors
NZ336046A NZ336046A (en) 1996-12-06 1997-12-05 Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives
HU0100669A HUP0100669A3 (en) 1996-12-06 1997-12-05 Peptide derivatives as serine protease inhibitors, their use and pharmaceutical compositions comprising thereof
EP97952232A EP0954526A2 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
NO992734A NO992734L (en) 1996-12-06 1999-06-04 Serine protease inhibitors

Applications Claiming Priority (20)

Application Number Priority Date Filing Date Title
US08/760,916 US5861380A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-keto and di-keto containing ring systems
US08/760,916 1996-12-06
US08/762,381 1996-12-06
US08/771,317 US5801148A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-proline analogs
US08/761,313 US5869455A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-N-substituted derivatives
US08/762,381 US5891852A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-cycloheptane derivatives
US08/761,313 1996-12-06
US08/771,317 1996-12-06
US08/761,190 1996-12-06
US08/761,190 US5807829A (en) 1994-11-21 1996-12-06 Serine protease inhibitor--tripeptoid analogs
US98529897A 1997-12-04 1997-12-04
US08/984,884 1997-12-04
US08/984,884 US6001811A (en) 1994-11-21 1997-12-04 Serine protease inhibitors--N-substituted derivatives
US08/984,881 1997-12-04
US08/985,298 1997-12-04
US08/985,056 1997-12-04
US08/985,056 US5998379A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-proline analogs
US08/985,201 1997-12-04
US08/985,201 US6150334A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-tripeptoid analogs
US08/984,881 US6015791A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-cycloheptane derivatives

Publications (3)

Publication Number Publication Date
WO1998024806A2 WO1998024806A2 (en) 1998-06-11
WO1998024806A3 true WO1998024806A3 (en) 1998-10-15
WO1998024806B1 WO1998024806B1 (en) 1999-05-20

Family

ID=27581319

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/021636 Ceased WO1998024806A2 (en) 1996-12-06 1997-12-05 Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors

Country Status (11)

Country Link
EP (1) EP0954526A2 (en)
JP (1) JP3220169B2 (en)
CN (1) CN1247542A (en)
AU (1) AU734615B2 (en)
CA (1) CA2272548A1 (en)
HU (1) HUP0100669A3 (en)
NO (1) NO992734L (en)
NZ (1) NZ336046A (en)
RU (1) RU2217436C2 (en)
TR (2) TR199901681T2 (en)
WO (1) WO1998024806A2 (en)

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US6004933A (en) * 1997-04-25 1999-12-21 Cortech Inc. Cysteine protease inhibitors
US6656910B2 (en) * 1997-12-04 2003-12-02 Cortech, Inc. Serine protease inhibitors
KR20010078725A (en) * 1998-06-03 2001-08-21 존 더블류. 갈루치 2세 Peptoid and Nonpeptoid Containing Alpha-Keto Oxadiazoles as Serine Protease Inhibitors
EP1105412A1 (en) * 1998-08-17 2001-06-13 Cortech, Inc. Serine protease inhibitors comprising alpha-keto heterocycles
FR2782997A1 (en) * 1998-09-08 2000-03-10 Hoechst Marion Roussel Inc NOVEL BENZODIAZEPINONE DERIVATIVES, PREPARATION METHOD AND INTERMEDIATES THEREOF, MEDICAMENT APPLICATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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
AU3719100A (en) * 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Inhibitors of serine protease activity, methods and compositions for treatment of viral infections
AU3731400A (en) * 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Methods and compositions useful in inhibiting apoptosis
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JPWO2002014310A1 (en) * 2000-08-10 2004-01-15 小野薬品工業株式会社 2- [5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidyl] -N- [1- (2- [5-t-butyl-1,3,4-oxadiazolyl] carbonyl ) -2- (R, S) -Methylpropyl] acetamide hydrochloride compound
KR20030027119A (en) * 2000-09-08 2003-04-03 오노 야꾸힝 고교 가부시키가이샤 Novel crystals of 1,3,4-oxadiazole derivative, process for producing the crystals and medicines containing the same as the active ingredient
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WO2003006014A1 (en) * 2001-07-10 2003-01-23 Ono Pharmaceutical Co., Ltd. Medicine comprising combination of five-membered heterocyclic compound and drug compensating for or enhancing its activity
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IL148924A (en) * 2002-03-26 2015-06-30 Mor Research Applic Ltd Use of agents that inhibit the activity of intracellular elastase in the preparation of a medicament for treating and/or preventing necrosis of cells and diseases associated therewith
PL2520654T3 (en) 2003-08-26 2017-08-31 The Regents Of The University Of Colorado, A Body Corporate Inhibitors of serine protease activity and their use in methods and compositions for treatment of bacterial infections
EP1533306A1 (en) 2003-11-04 2005-05-25 Ajinomoto Co., Inc. Azlactone compound and method for preparation thereof
RU2421451C2 (en) * 2004-12-14 2011-06-20 Астразенека Аб Oxadiazole compounds, use thereof in preparing medicinal agent and method of inhibiting dgat1 activity
US7951823B2 (en) 2006-05-23 2011-05-31 Irm Llc Compounds and compositions as channel activating protease inhibitors
TWI389899B (en) * 2006-08-08 2013-03-21 Msd Oss Bv An orally active thrombin inhibitor
KR20090108131A (en) 2007-02-09 2009-10-14 아이알엠 엘엘씨 Compounds and Compositions as Channel Activating Protease Inhibitors
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KR20200044138A (en) 2011-06-24 2020-04-28 더 리젠츠 오브 더 유니버시티 오브 콜로라도, 어 바디 코포레이트 Compositions, methods and uses for alpha-1 antitrypsin fusion molecules
JP2015504675A (en) 2012-01-10 2015-02-16 ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド，ア ボディー コーポレイトＴＨＥ ＲＥＧＥＮＴＳ ＯＦ ＴＨＥ ＵＮＩＶＥＲＳＩＴＹ ＯＦ ＣＯＬＯＲＡＤＯ，ａ ｂｏｄｙ ｃｏｒｐｏｒａｔｅ Compositions, methods, and uses of alpha-1 antitrypsin fusion molecules
CN105263901B (en) * 2013-05-08 2017-06-23 橘生药品工业株式会社 α substituted glycyl amine derivatives
JP2017523213A (en) * 2014-08-06 2017-08-17 ノバルティス アーゲー Quinolone derivatives as antibacterial agents

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WO1993021212A1 (en) * 1992-04-16 1993-10-28 Zeneca Limited Lactam dipeptides having hle inhibiting activity
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WO1993021212A1 (en) * 1992-04-16 1993-10-28 Zeneca Limited Lactam dipeptides having hle inhibiting activity
FR2694295A1 (en) * 1992-07-28 1994-02-04 Adir Novel peptides derived from trifluoromethylketones, process for their preparation and pharmaceutical compositions containing them
WO1995033762A1 (en) * 1994-06-02 1995-12-14 Merrell Pharmaceuticals Inc. Perfluoroalkyl ketone inhibitors of elastase and processes for making the same
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Title
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SKILES J W ET AL: "ELASTASE INHIBITORS CONTAINING CONFORMATIONALLY RESTRICTED LACTAMS AS P3-P2 DIPEPTIDE REPLACEMENTS", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 3, no. 4, 1993, pages 773 - 778, XP000673137 *

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TR200103270T2 (en) 2003-03-21
AU5589498A (en) 1998-06-29
NO992734L (en) 1999-08-02
WO1998024806B1 (en) 1999-05-20
EP0954526A2 (en) 1999-11-10
CA2272548A1 (en) 1998-06-11
NZ336046A (en) 2000-10-27
JP2001507679A (en) 2001-06-12
JP3220169B2 (en) 2001-10-22
AU734615B2 (en) 2001-06-21
WO1998024806A2 (en) 1998-06-11
CN1247542A (en) 2000-03-15
HUP0100669A2 (en) 2001-08-28
TR199901681T2 (en) 2000-03-21
RU2217436C2 (en) 2003-11-27
NO992734D0 (en) 1999-06-04
HUP0100669A3 (en) 2001-12-28

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