WO1991002716A3 - Inhibiteurs de collagenase a base d'acide hydroxamique - Google Patents

Inhibiteurs de collagenase a base d'acide hydroxamique Download PDF

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Publication number
WO1991002716A3
WO1991002716A3 PCT/GB1990/001117 GB9001117W WO9102716A3 WO 1991002716 A3 WO1991002716 A3 WO 1991002716A3 GB 9001117 W GB9001117 W GB 9001117W WO 9102716 A3 WO9102716 A3 WO 9102716A3
Authority
WO
WIPO (PCT)
Prior art keywords
hydroxamic acid
acid based
collagenase inhibitors
based collagenase
disease
Prior art date
Application number
PCT/GB1990/001117
Other languages
English (en)
Other versions
WO1991002716A2 (fr
Inventor
Colin Campion
Alan Hornsby Davidson
Jonathan Philip Dickens
Michael John Crimmin
Original Assignee
British Bio Technology
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 British Bio Technology filed Critical British Bio Technology
Priority to DE69012575T priority Critical patent/DE69012575T2/de
Priority to US07/820,664 priority patent/US5453438A/en
Priority to KR1019920700412A priority patent/KR927003624A/ko
Priority to EP90911398A priority patent/EP0489032B1/fr
Publication of WO1991002716A2 publication Critical patent/WO1991002716A2/fr
Publication of WO1991002716A3 publication Critical patent/WO1991002716A3/fr
Priority to NO92920702A priority patent/NO920702L/no
Priority to FI920771A priority patent/FI920771A0/fi

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • 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
    • C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—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 two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Composés de la formule générale (I) où R1 représente un atome d'hydrogène ou un groupe alkyle C¿1?-C6, alkényle C1-C6, phényle, phényle(C1-C6)alkyle, alkylthiométhyle C1-C6, phénylthiométhyle, phénylthiométhyle substitué, phényl(C1-C6)alkylthiométhyle ou hétérocyclylthiométhyle; ou R?1¿ représente -S-Rx où Rx représente un groupe α; R2 représente un atome d'hydrogène ou un alkyle C¿1?-C6, un alkényle C1-C6, un phényl(C1-C6)-alkyle, un cycloalkyl(C1-C6) alcoyle, ou cycloalkényl(C1-C6)alkyle; R?3¿ représente une chaîne latérale d'aminoacide ou un groupe alcoyle C¿1?-C6, benzyle, (C1-C6)alkoxybenzyle, benzyloxy(C1-C6)alkyle ou benzyloxybenzyle; R?4¿ représente un atome d'hydrogène ou un groupe méthyle; R5 représente un groupe (CH¿2?)nA; ou R?4 et R5¿ ensemble représentent un groupe β; Q représente CH¿2? ou CO; m est un entier entre 1 et 3; n est un entier entre 1 et 6; et A représente un groupe hydroxy, (C1-C6) alkoxy, (C2-C7)alkoxy, (C1-C6)alkylthio, phénylthio, (C2-C7)acylamino ou N-pyrrolidone ou un sel et/ou N-oxyde et/ou (si le composé est un composé thio) un oxyde sulfonique ou une sulfone de celui-ci. Ces composés présentent une activité d'inhibition de collagenase et sont utiles pour le traitement de maladies comprenant la dégénérescence de tissus et/ou pour stimuler la guérison de plaies. Les maladies comportant la dégénérescence de tissus comprennent l'arthropathie (en particulier la polyarthrite rhumatoïde), l'inflammation, les maladies dermatologiques, les maladies de résorption osseuse et l'invasion tumorale.
PCT/GB1990/001117 1989-08-24 1990-07-20 Inhibiteurs de collagenase a base d'acide hydroxamique WO1991002716A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE69012575T DE69012575T2 (de) 1989-08-24 1990-07-20 Auf hydroxaminsäure basierte kollagenaseinhibitoren.
US07/820,664 US5453438A (en) 1989-08-24 1990-07-20 Hydroxamic acid based collagenase inhibitors
KR1019920700412A KR927003624A (ko) 1989-08-24 1990-07-20 화합물
EP90911398A EP0489032B1 (fr) 1989-08-24 1990-07-20 Inhibiteurs de collagenase a base d'acide hydroxamique
NO92920702A NO920702L (no) 1989-08-24 1992-02-21 Hydroksaminsyrebaserte kollagenaseinhibitorer
FI920771A FI920771A0 (fi) 1989-08-24 1992-02-21 Hydroxylamidbaserade kollagenasinhibitorer.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB898919251A GB8919251D0 (en) 1989-08-24 1989-08-24 Compounds
GB8919251.2 1989-08-24

Publications (2)

Publication Number Publication Date
WO1991002716A2 WO1991002716A2 (fr) 1991-03-07
WO1991002716A3 true WO1991002716A3 (fr) 1991-06-27

Family

ID=10662057

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1990/001117 WO1991002716A2 (fr) 1989-08-24 1990-07-20 Inhibiteurs de collagenase a base d'acide hydroxamique

Country Status (16)

Country Link
US (2) US5453438A (fr)
EP (1) EP0489032B1 (fr)
JP (1) JP2871849B2 (fr)
KR (1) KR927003624A (fr)
AT (1) ATE111443T1 (fr)
AU (1) AU639706B2 (fr)
CA (1) CA2064786A1 (fr)
DE (1) DE69012575T2 (fr)
DK (1) DK0489032T3 (fr)
ES (1) ES2063975T3 (fr)
FI (1) FI920771A0 (fr)
GB (1) GB8919251D0 (fr)
NO (1) NO920702L (fr)
NZ (1) NZ235050A (fr)
TW (1) TW202456B (fr)
WO (1) WO1991002716A2 (fr)

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GB8827308D0 (en) * 1988-11-23 1988-12-29 British Bio Technology Compounds
US5268384A (en) * 1990-11-21 1993-12-07 Galardy Richard E Inhibition of angiogenesis by synthetic matrix metalloprotease inhibitors
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GB9211707D0 (en) * 1992-06-03 1992-07-15 Celltech Ltd Peptidyl derivatives
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US5326760A (en) * 1992-06-29 1994-07-05 Glaxo, Inc. Aminobutanoic acid compounds having metalloprotease inhibiting properties
GB9215665D0 (en) * 1992-07-23 1992-09-09 British Bio Technology Compounds
GB9223904D0 (en) * 1992-11-13 1993-01-06 British Bio Technology Inhibition of cytokine production
US5646167A (en) * 1993-01-06 1997-07-08 Ciba-Geigy Corporation Arylsulfonamido-substituted hydroxamix acids
GB2290543B (en) * 1993-03-16 1996-05-22 British Biotech Pharm Hydroxamic acid derivatives as metalloproteinase inhibitors
AU6575394A (en) * 1993-04-27 1994-11-21 Celltech Therapeutics Limited Peptidyl derivatives as metalloproteinase inhibitors
GB9308695D0 (en) * 1993-04-27 1993-06-09 Celltech Ltd Peptidyl derivatives
ES2075797B1 (es) * 1993-08-18 1996-05-16 British Bio Technology Derivados de acidos hidroxamicos terapeuticamente activos, procedimiento para su preparacion, composiciones farmaceuticas que los contienen y el uso de dichos compuestos en medicina.
ES2075798B1 (es) * 1993-08-18 1996-03-01 British Bio Technology Derivados de aminoacidos naturales como inhibidores de metaloproteinasas, procedimiento para su preparacion, composiciones farmaceuticas que los contienen y el uso de dichos compuestos en medicina.
US6037472A (en) 1993-11-04 2000-03-14 Syntex (U.S.A.) Inc. Matrix metalloprotease inhibitors
BR9506535A (pt) * 1994-01-20 1997-09-16 British Biotech Pharm Inibidores de metaloproteinases
GB9501737D0 (en) * 1994-04-25 1995-03-22 Hoffmann La Roche Hydroxamic acid derivatives
US5831004A (en) 1994-10-27 1998-11-03 Affymax Technologies N.V. Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use
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GB9423914D0 (en) * 1994-11-26 1995-01-11 British Biotech Pharm Polyether derivatives as metalloproteinase inhibitors
US5639746A (en) * 1994-12-29 1997-06-17 The Procter & Gamble Company Hydroxamic acid-containing inhibitors of matrix metalloproteases
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US5672598A (en) * 1995-03-21 1997-09-30 The Procter & Gamble Company Lactam-containing hydroxamic acids
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HUP9903863A3 (en) 1995-11-23 2000-11-28 British Biotech Pharm Metalloproteinase inhibitors
DE69716934T2 (de) * 1996-08-28 2003-07-31 The Procter & Gamble Company, Cincinnati 1,3-diheterozyklische metalloprotease inhibitoren
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KR100326611B1 (ko) * 1996-08-28 2002-03-02 데이비드 엠 모이어 스피로시클릭 메탈로프로테아제 저해제
DE69716615T2 (de) 1996-08-28 2003-06-18 The Procter & Gamble Company, Cincinnati Heterozyklische metalloproteaseinhibitoren
RU2170232C2 (ru) * 1996-08-28 2001-07-10 Дзе Проктер Энд Гэмбл Компани Амиды фосфиновых кислот и способ предупреждения или лечения заболевания, связанного с нежелательной активностью металлопротеазы
ES2181021T3 (es) * 1996-09-10 2003-02-16 British Biotech Pharm Derivados citostaticos del acido hidroxamico.
US6462023B1 (en) 1996-09-10 2002-10-08 British Biotech Pharmaceuticals, Ltd. Cytostatic agents
US5840974A (en) * 1996-12-04 1998-11-24 Britisch Biotech Pharmaceuticals, Ltd. Metalloproteinase inhibitors
US5952320A (en) * 1997-01-07 1999-09-14 Abbott Laboratories Macrocyclic inhibitors of matrix metalloproteinases and TNFα secretion
US5985911A (en) * 1997-01-07 1999-11-16 Abbott Laboratories C-terminal ketone inhibitors of matrix metalloproteinases and TNFα secretion
JP2001513484A (ja) 1997-07-31 2001-09-04 ザ プロクター アンド ギャンブル カンパニー 非環式メタロプロテアーゼ阻害剤
GB9810464D0 (en) * 1998-05-16 1998-07-15 British Biotech Pharm Hydroxamic acid derivatives
US6288261B1 (en) 1998-12-18 2001-09-11 Abbott Laboratories Inhibitors of matrix metalloproteinases
HUP0202199A2 (en) 1999-03-03 2002-10-28 Procter & Gamble Alkenyl- and alkynyl-containing metalloprotease inhibitors
JP2003506438A (ja) * 1999-08-10 2003-02-18 ブリティッシュ バイオテック ファーマシューティカルズ リミテッド 抗菌剤
GB9929527D0 (en) * 1999-12-14 2000-02-09 Smithkline Beecham Plc Novel compounds
US6797820B2 (en) * 1999-12-17 2004-09-28 Vicuron Pharmaceuticals Inc. Succinate compounds, compositions and methods of use and preparation
US6987104B2 (en) 2001-06-15 2006-01-17 Vicuron Pharmaceuticals Inc. Pyrrolidine bicyclic compounds and its derivatives, compositions and methods of use
AR036053A1 (es) 2001-06-15 2004-08-04 Versicor Inc Compuestos de n-formil-hidroxilamina, un proceso para su preparacion y composiciones farmaceuticas

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Publication number Priority date Publication date Assignee Title
DE3341610A1 (de) * 1982-11-18 1984-05-24 E.R. Squibb & Sons, Inc., Princeton, N.J. Carboxy- und substituierte carboxyalkanoyl- und cycloalkanoylpeptide
EP0167936A2 (fr) * 1984-07-03 1986-01-15 Microbial Chemistry Research Foundation Utilisation d'actinonine comme immunopotentiateur
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EP0236872B1 (fr) * 1986-03-11 1992-11-25 F. Hoffmann-La Roche Ag Dérivés hydroxylamine, leur préparation et emploi comme médicaments

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DE3341610A1 (de) * 1982-11-18 1984-05-24 E.R. Squibb & Sons, Inc., Princeton, N.J. Carboxy- und substituierte carboxyalkanoyl- und cycloalkanoylpeptide
EP0167936A2 (fr) * 1984-07-03 1986-01-15 Microbial Chemistry Research Foundation Utilisation d'actinonine comme immunopotentiateur
EP0214639A2 (fr) * 1985-09-10 1987-03-18 G.D. Searle & Co. Inhibiteurs de collagénase dérivés d'acides hydroxamique
EP0236872B1 (fr) * 1986-03-11 1992-11-25 F. Hoffmann-La Roche Ag Dérivés hydroxylamine, leur préparation et emploi comme médicaments
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Also Published As

Publication number Publication date
US5910609A (en) 1999-06-08
ES2063975T3 (es) 1995-01-16
GB8919251D0 (en) 1989-10-04
US5453438A (en) 1995-09-26
EP0489032A1 (fr) 1992-06-10
JP2871849B2 (ja) 1999-03-17
NZ235050A (en) 1991-12-23
NO920702L (no) 1992-04-23
FI920771A0 (fi) 1992-02-21
ATE111443T1 (de) 1994-09-15
DE69012575D1 (de) 1994-10-20
CA2064786A1 (fr) 1991-02-25
NO920702D0 (no) 1992-02-21
EP0489032B1 (fr) 1994-09-14
AU6045490A (en) 1991-04-03
DK0489032T3 (da) 1995-01-30
DE69012575T2 (de) 1995-03-30
TW202456B (fr) 1993-03-21
JPH05501864A (ja) 1993-04-08
KR927003624A (ko) 1992-12-18
AU639706B2 (en) 1993-08-05
WO1991002716A2 (fr) 1991-03-07

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