NZ336046A - Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives - Google Patents

Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives

Info

Publication number
NZ336046A
NZ336046A NZ336046A NZ33604697A NZ336046A NZ 336046 A NZ336046 A NZ 336046A NZ 336046 A NZ336046 A NZ 336046A NZ 33604697 A NZ33604697 A NZ 33604697A NZ 336046 A NZ336046 A NZ 336046A
Authority
NZ
New Zealand
Prior art keywords
aryl
alkyl
amino
optionally substituted
alkenyl
Prior art date
Application number
NZ336046A
Inventor
Albert Gyorkos
Lyle W Spruce
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 US08/762,381 external-priority patent/US5891852A/en
Priority claimed from US08/984,884 external-priority patent/US6001811A/en
Priority claimed from US08/984,881 external-priority patent/US6015791A/en
Priority claimed from US08/985,056 external-priority patent/US5998379A/en
Priority claimed from US08/985,201 external-priority patent/US6150334A/en
Application filed by Cortech Inc filed Critical Cortech Inc
Publication of NZ336046A publication Critical patent/NZ336046A/en

Links

Classifications

    • 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

Landscapes

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

Abstract

The pyrrole derivative has the formula (I) wherein: X is O and Y is N; R1 is isopropyl, n-butyl, tert-butyl, or is alkyl substituted with one or more carboxyl, carboalkoxy, amino, alkylamino or dialkylamino groups or is alkyl fused aryl, alkyl fused arylcycloalkyl, alkyl(aryl)2 or a,a-dialkyl-arylalkyl optionally comprising 1-4 heteroatoms selected from O, S and N, and optionally substituted with halo, cyano, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, aryl, -O-aryl, arylcarboxamide, alkylthio or haloalkylthio or R1 is aryl or arylalkyl substituted with alkyl, amino, alkylamino, dialkylamino, optionally substituted aryl or aryloxy or is aryl or arylalkyl substituted with two more halo, cyano, nitro, hydroxyl, haloalkyl, amino, amino alkyl, dialkylamino, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, alkylthio, haloalkylthio, arylcarboxamide or optionally substituted aryl or -O-aryl or R1 is aryl or arylalkyl comprising one or more heteroatoms selected from O, S and N or cycloalkyl or alkylcycloalkyl optionally comprising one or more heteroatoms selected from O, S and N; R2 and R3 are independently or together H, alkyl or alkenyl optionally substituted with 1-3 halo, hydroxyl, thio, alkylthio, amino, alkylamino, dialkylamino, alkylguanidinyl, dialkylguanidinyl, guanidinyl, or amidylguanidine or are -RCOR', RCOOR', -RNR'R"R" or -RC(O)NR'R"; R is alkyl or alkenyl; R', R" and R" are independently H, alkyl, alkenyl, cycloalkyl or aryl or are cycloalkyl, alkylcycloalkyl, alkenylcycloalkyl, alkyloxyaryl, alkylthioaryl, alkylaminoaryl, aryl, arylalkyl or (cs-cl2)arylalkenyl optionally comprising 1-4 heteroatoms selected from N, O and S, and optionally substituted with halo, cyano, keto, nitro, hydroxyl, haloalkyl, amino, aminoalkyl, dialkylamino, amidine, alkylamidine, dialkylamidine, alkyl, alkenyl, alkylenedioxy, alkynyl, alkoxy, haloalkoxy, carboxyl, carboalkoxy, alkylcarboxamide, aryl, -O-aryl, arylcarboxamide, alkylthio or haloalkylthio; A is a direct bond, -NHC(O) or is proline, isoleucine, cyclohexylalanine, optionally substituted cysteine, phenylalanine, homophenylalanine, dehydrophenylalanine, indoline-2-carboxylic acid, optionally substituted tetrahydrosioquinoline-2-carboxylic acid, tryptophan, tyrosine, serine, threonine, histidine, methionine, valine, norvaline, norleucine, octahydroindole-2-carboxylic acid, asparagine, glutamine, ornithine or lysine and R4 is benzyl. A pharmaceutical composition thereof is useful for inhibiting serine proteases.
NZ336046A 1996-12-06 1997-12-05 Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives NZ336046A (en)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
US08/762,381 US5891852A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-cycloheptane derivatives
US08/771,317 US5801148A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-proline analogs
US08/761,190 US5807829A (en) 1994-11-21 1996-12-06 Serine protease inhibitor--tripeptoid analogs
US08/760,916 US5861380A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-keto and di-keto containing ring systems
US08/761,313 US5869455A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-N-substituted derivatives
US98529897A 1997-12-04 1997-12-04
US08/984,884 US6001811A (en) 1994-11-21 1997-12-04 Serine protease inhibitors--N-substituted derivatives
US08/984,881 US6015791A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-cycloheptane derivatives
US08/985,056 US5998379A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-proline analogs
US08/985,201 US6150334A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-tripeptoid analogs
PCT/US1997/021636 WO1998024806A2 (en) 1996-12-06 1997-12-05 Substituted oxadiazole, thiadiazole and triazole serine protease inhibitors

Publications (1)

Publication Number Publication Date
NZ336046A true NZ336046A (en) 2000-10-27

Family

ID=27581319

Family Applications (1)

Application Number Title Priority Date Filing Date
NZ336046A NZ336046A (en) 1996-12-06 1997-12-05 Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives

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)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP1135151A4 (en) * 1998-06-03 2002-01-02 Cortech Inc Peptoid and nonpeptoid containing alpha-keto oxadiazoles as serine protease inhibitors
WO2000009542A1 (en) * 1998-08-17 2000-02-24 Cortech, Inc. SERINE PROTEASE INHIBITORS COMPRISING α-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
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
WO2000051625A1 (en) * 1999-03-05 2000-09-08 The Trustees Of University Technology Corporation Inhibitors of serine protease activity, methods and compositions for treatment of herpes viruses
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
AU3731400A (en) 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Methods and compositions useful in inhibiting apoptosis
AU2941200A (en) * 1999-03-12 2000-10-04 Ono Pharmaceutical Co. Ltd. 1,3,4-oxadiazole derivatives and process for producing the same
AU5625900A (en) * 1999-06-17 2001-01-09 Cortech, Inc. Method and compounds for inhibiting activity of serine elastases
WO2001007407A1 (en) * 1999-07-26 2001-02-01 Bristol-Myers Squibb Pharma Company Lactam inhibitors of hepatitis c virus ns3 protease
US7122627B2 (en) 1999-07-26 2006-10-17 Bristol-Myers Squibb Company Lactam inhibitors of Hepatitis C virus NS3 protease
MXPA02003186A (en) * 1999-09-27 2002-10-31 Ono Pharmaceutical Co Pyrimidine derivatives, process for preparing the derivatives and drugs containing the same as the active ingredient.
US6797720B2 (en) 1999-12-03 2004-09-28 Ono Pharmaceutical Co., Ltd. 1,3,4-oxadiazoline derivative and an agent comprising its derivative as active ingredient
AU1556601A (en) * 1999-12-03 2001-06-12 Ono Pharmaceutical Co. Ltd. 1,3,4-oxadiazolin-2-one derivatives and drugs containing these derivatives as the active ingredient
EP1253143A4 (en) * 2000-02-03 2003-03-26 Ono Pharmaceutical Co 1,3,4-oxadiazole derivatives and process for producing the same
KR20020072303A (en) * 2000-02-03 2002-09-14 오노 야꾸힝 고교 가부시키가이샤 1,3,4-oxadiazole derivatives and process for producing the same
AU2001277736A1 (en) * 2000-08-10 2002-02-25 Ono Pharmaceutical Co. Ltd. 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidyl)-n-(1-(2-( -t-butyl-1,3,4-oxadiazolyl)carbonyl)-2-(r,s)-methylpropyl) acetamide hydrochloride
US20040023998A1 (en) * 2000-09-08 2004-02-05 Tsutomu Kojima Novel crystals of 1,3,4-oxadiazole derivatives, process for producing the crystals and medicines containing the same as the active ingredient
CA2423945A1 (en) * 2000-09-29 2003-03-27 Atsushi Nagai Restrainers of airway mucus secretion
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
WO2003006490A1 (en) * 2001-07-11 2003-01-23 Vertex Pharmaceuticals Incorporated Bridged bicyclic serine protease inhibitors
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
EP3192872A1 (en) 2003-08-26 2017-07-19 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
US7358368B2 (en) 2003-11-04 2008-04-15 Ajinomoto Co., Inc. Azlactone compound and method for preparation thereof
WO2007137080A2 (en) 2006-05-23 2007-11-29 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
JP2010518099A (en) 2007-02-09 2010-05-27 アイアールエム・リミテッド・ライアビリティ・カンパニー Compounds and compositions as channel activating protease inhibitors
CA2687821C (en) * 2007-05-22 2015-04-14 Boehringer Ingelheim International Gmbh Benzimidazolone chymase inhibitors
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
WO2013106589A1 (en) 2012-01-10 2013-07-18 The Regents Of The University Of Colorado, A Body Corporate Compositions, methods and uses for alpha-1 antitrypsin fusion molecules
JP6200495B2 (en) * 2013-05-08 2017-09-20 キッセイ薬品工業株式会社 α-Substituted glycinamide derivatives
EP3177593A1 (en) * 2014-08-06 2017-06-14 Novartis AG Quinolone derivatives as antibacterials

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GB9216272D0 (en) * 1991-08-15 1992-09-09 Ici Plc Substituted heterocycles
GB9307555D0 (en) * 1992-04-16 1993-06-02 Zeneca Ltd Heterocyclic compounds
FR2694295B1 (en) * 1992-07-28 1994-09-02 Adir New peptides derived from trifluoromethyl ketones, their preparation process and the pharmaceutical compositions containing them.
DE69513167T2 (en) * 1994-06-02 2000-06-15 Merrell Pharmaceuticals Inc., Cincinnati PERFLUOROALKYLL KETONES, INHIBITORS OF ELASTASE AND PROCESS FOR THEIR PRODUCTION
US5618792A (en) * 1994-11-21 1997-04-08 Cortech, Inc. Substituted heterocyclic compounds useful as inhibitors of (serine proteases) human neutrophil elastase

Also Published As

Publication number Publication date
JP3220169B2 (en) 2001-10-22
AU734615B2 (en) 2001-06-21
HUP0100669A3 (en) 2001-12-28
AU5589498A (en) 1998-06-29
NO992734D0 (en) 1999-06-04
RU2217436C2 (en) 2003-11-27
EP0954526A2 (en) 1999-11-10
WO1998024806A3 (en) 1998-10-15
JP2001507679A (en) 2001-06-12
WO1998024806B1 (en) 1999-05-20
TR200103270T2 (en) 2003-03-21
CN1247542A (en) 2000-03-15
WO1998024806A2 (en) 1998-06-11
HUP0100669A2 (en) 2001-08-28
CA2272548A1 (en) 1998-06-11
NO992734L (en) 1999-08-02
TR199901681T2 (en) 2000-03-21

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