NZ336046A - Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives - Google Patents
Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivativesInfo
- 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
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.
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)
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 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
1997
- 1997-12-05 CA CA002272548A patent/CA2272548A1/en not_active Abandoned
- 1997-12-05 EP EP97952232A patent/EP0954526A2/en not_active Withdrawn
- 1997-12-05 AU AU55894/98A patent/AU734615B2/en not_active Ceased
- 1997-12-05 NZ NZ336046A patent/NZ336046A/en unknown
- 1997-12-05 JP JP52565698A patent/JP3220169B2/en not_active Expired - Fee Related
- 1997-12-05 WO PCT/US1997/021636 patent/WO1998024806A2/en not_active Application Discontinuation
- 1997-12-05 TR TR1999/01681T patent/TR199901681T2/en unknown
- 1997-12-05 HU HU0100669A patent/HUP0100669A3/en unknown
- 1997-12-05 CN CN97180392A patent/CN1247542A/en active Pending
- 1997-12-05 TR TR2001/03270T patent/TR200103270T2/en unknown
- 1997-12-05 RU RU99114606/04A patent/RU2217436C2/en not_active IP Right Cessation
-
1999
- 1999-06-04 NO NO992734A patent/NO992734L/en not_active Application Discontinuation
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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