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
Application number
PCT/US1997/021636
Other languages
French (fr)
Other versions
WO1998024806A2 (en
WO1998024806B1 (en
Inventor
Albert Gyorkos
Lyle W Spruce
Original Assignee
Cortech Inc
Albert Gyorkos
Lyle W Spruce
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 US08/761,190 external-priority patent/US5807829A/en
Priority claimed from US08/984,881 external-priority patent/US6015791A/en
Priority claimed from US08/984,884 external-priority patent/US6001811A/en
Priority claimed from US08/985,056 external-priority patent/US5998379A/en
Priority claimed from US08/985,201 external-priority patent/US6150334A/en
Priority to JP52565698A priority Critical patent/JP3220169B2/en
Priority to EP97952232A priority patent/EP0954526A2/en
Priority to BR9713684-0A priority patent/BR9713684A/en
Priority to AU55894/98A priority patent/AU734615B2/en
Application filed by Cortech Inc, Albert Gyorkos, Lyle W Spruce filed Critical Cortech Inc
Priority to HU0100669A priority patent/HUP0100669A3/en
Priority to CA002272548A priority patent/CA2272548A1/en
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

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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

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 WO1998024806A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NZ336046A NZ336046A (en) 1996-12-06 1997-12-05 Serine protease inhibitors containing substituted oxadiazole, thiadiazole and triazole peptide derivatives
CA002272548A CA2272548A1 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
HU0100669A HUP0100669A3 (en) 1996-12-06 1997-12-05 Peptide derivatives as serine protease inhibitors, their use and pharmaceutical compositions comprising thereof
JP52565698A JP3220169B2 (en) 1996-12-06 1997-12-05 Serine protease inhibitor
AU55894/98A AU734615B2 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
EP97952232A EP0954526A2 (en) 1996-12-06 1997-12-05 Serine protease inhibitors
BR9713684-0A BR9713684A (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
US08/761,190 1996-12-06
US08/762,381 1996-12-06
US08/761,190 US5807829A (en) 1994-11-21 1996-12-06 Serine protease inhibitor--tripeptoid analogs
US08/771,317 US5801148A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-proline analogs
US08/761,313 1996-12-06
US08/760,916 US5861380A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-keto and di-keto containing ring systems
US08/762,381 US5891852A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-cycloheptane derivatives
US08/771,317 1996-12-06
US08/760,916 1996-12-06
US08/761,313 US5869455A (en) 1994-11-21 1996-12-06 Serine protease inhibitors-N-substituted derivatives
US98529897A 1997-12-04 1997-12-04
US08/984,881 1997-12-04
US08/985,201 US6150334A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-tripeptoid analogs
US08/985,298 1997-12-04
US08/984,884 1997-12-04
US08/985,056 US5998379A (en) 1994-11-21 1997-12-04 Serine protease inhibitors-proline analogs
US08/984,884 US6001811A (en) 1994-11-21 1997-12-04 Serine protease inhibitors--N-substituted derivatives
US08/985,056 1997-12-04
US08/985,201 1997-12-04
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 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) TR200103270T2 (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
KR20010078725A (en) * 1998-06-03 2001-08-21 존 더블류. 갈루치 2세 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
AU3511500A (en) * 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Inhibitors of serine protease activity, methods and compositions for treatment of nitric oxide-induced clinical conditions
AU3864000A (en) * 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Inhibitors of serine protease activity, methods and compositions for treatment of herpes viruses
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
WO2000051624A2 (en) 1999-03-05 2000-09-08 The Trustees Of University Technology Corporation Methods and compositions useful in inhibiting apoptosis
CN1350525A (en) * 1999-03-12 2002-05-22 小野药品工业株式会社 1,3,4-oxadiazole derivatives and process for producing the same
CA2375229A1 (en) 1999-06-17 2000-12-28 Source Precision Medicine, Inc. Method and compounds for inhibiting activity of serine elastases
US7122627B2 (en) 1999-07-26 2006-10-17 Bristol-Myers Squibb Company Lactam inhibitors of Hepatitis C virus NS3 protease
EP1206449A1 (en) * 1999-07-26 2002-05-22 Bristol-Myers Squibb Company Lactam inhibitors of hepatitis c virus ns3 protease
CN1399632A (en) * 1999-09-27 2003-02-26 小野药品工业株式会社 Pyrimidine derivatives, process for preparing the derivatives and drugs containing the same 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
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
AU2001230570A1 (en) * 2000-02-03 2001-08-14 Ono Pharmaceutical Co. Ltd. 1,3,4-oxadiazole derivatives and process for producing the same
CA2401240A1 (en) * 2000-02-03 2001-08-09 Toshihide Horiuchi 1,3,4-oxadiazole derivatives and process for the preparation thereof
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
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
AU2001292305A1 (en) * 2000-09-29 2002-04-08 Ono Pharmaceutical Co. Ltd. Airway mucus secretion inhibitors
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
MXPA04000293A (en) * 2001-07-11 2004-05-04 Vertex Pharma 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
EP1660094A4 (en) 2003-08-26 2009-09-16 Univ Colorado 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
CA2651762A1 (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
EP2152674B1 (en) 2007-05-22 2011-08-03 Boehringer Ingelheim International GmbH Benzimidazolone chymase inhibitors
JP6216921B2 (en) 2011-06-24 2017-11-01 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 for alpha-1 antitrypsin fusion molecules
EP2802653A4 (en) 2012-01-10 2015-09-02 Univ Colorado Regents Compositions, methods and uses for alpha-1 antitrypsin fusion molecules
SG11201509244XA (en) * 2013-05-08 2015-12-30 Kissei Pharmaceutical Α-substituted glycineamide derivative
WO2016020836A1 (en) * 2014-08-06 2016-02-11 Novartis Ag Quinolone derivatives as antibacterials

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528633A1 (en) * 1991-08-15 1993-02-24 Zeneca Limited Pyrimidinyl acetamides as elastase inhibitors
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
WO1996016080A1 (en) * 1994-11-21 1996-05-30 Cortech, Inc. Human neutrophil elastase inhibitors

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528633A1 (en) * 1991-08-15 1993-02-24 Zeneca Limited Pyrimidinyl acetamides as elastase inhibitors
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
WO1996016080A1 (en) * 1994-11-21 1996-05-30 Cortech, Inc. Human neutrophil elastase inhibitors

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BROWN E.A.: "Design of orally active, non-peptidic inhibitors of HLE", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 9, 1994, WASHINGTON US, pages 1259 - 1261, XP002069592 *
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 *

Also Published As

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

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