[go: up one dir, main page]

DE69706874T2 - Substituierte 4-arylbutyrsäurederivate als matrix metalloprotease inhibitoren - Google Patents

Substituierte 4-arylbutyrsäurederivate als matrix metalloprotease inhibitoren

Info

Publication number
DE69706874T2
DE69706874T2 DE69706874T DE69706874T DE69706874T2 DE 69706874 T2 DE69706874 T2 DE 69706874T2 DE 69706874 T DE69706874 T DE 69706874T DE 69706874 T DE69706874 T DE 69706874T DE 69706874 T2 DE69706874 T2 DE 69706874T2
Authority
DE
Germany
Prior art keywords
phenyl
oxo
butyric acid
phthalimidoethyl
group
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.)
Expired - Fee Related
Application number
DE69706874T
Other languages
English (en)
Other versions
DE69706874D1 (en
Inventor
R. Brittelli
R. Dixon
C. Kluender
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.)
Bayer AG
Bayer Corp
Original Assignee
Bayer AG
Bayer Corp
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 Bayer AG, Bayer Corp filed Critical Bayer AG
Publication of DE69706874D1 publication Critical patent/DE69706874D1/de
Application granted granted Critical
Publication of DE69706874T2 publication Critical patent/DE69706874T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/04—1,2,3-Triazines

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Oncology (AREA)
  • Immunology (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Neurology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (13)

1. Verbindungen mit Matrix-Metalloprotease-Inhibitoraktivität der allgemeinen Formel:
worin gilt:
R¹ stellt einen Substituent dar, unabhängig ausgewählt aus der Gruppe, bestehend aus einem
C&sub6;&submin;&sub1;&sub2;-Alkylkrest,
C&sub5;&submin;&sub1;&sub2;-Alkoxyrest,
C&sub5;&submin;&sub1;&sub2;-Alkylthiorest,
einem Polyether der Formel R²O(C&sub2;H&sub2;O)a-, worin
a 1 oder 2 und
R² ein C&sub1;&submin;&sub5;-Alkyl-, Phenyl- oder Benzylrest sind, und aus
einem substituierten Alkinylrest der Formel R³(CH&sub2;)b-C C-, worin b 1 bis 10 und
R³ H-, HO- oder R&sup4;O- sind, worin
R&sup4; ein C&sub1;&submin;&sub3;-Alkyl-, Pheny- oder Benzylrest ist,
wobei die Alkyl-, Phenyl- und Benzylreste von R¹ gegebenenfalls mindestens einen pharmazeutisch zulässigen Substituent aufweisen;
der Index n ist 2-4;
R&sup5; stellt einen Substituent dar, unabhängig ausgewählt aus der Gruppe, bestehend aus einem
Phenyl-,
Imidoyl- mit 4 bis 12 Kohlenstoffatomen,
(3H)-Henzo-1,2,3-triazin-4-on-3-yl-,
N-Saccharinyl-,
(2H)-Phthalazin-1-on-2-yl-,
2-Benzoxazolin-2-on-3-yl-,
5,5-Dimethyloxazolidin-2,4-dion-3-yl- und aus einem
Thiazolidin-2,4-dion-3-yl-Rest,
wobei die Phenyl- und Benzo-Reste von R&sup5; gegebenenfalls mindestens einen pharmazeutisch zulässigen Substituent aufweisen;
sowie pharmazeutisch zulässige Salze davon.
2. Verbindung gemäß Anspruch 1, worin R¹ eine Alkylgruppe darstellt.
3. Verbindung gemäß Anspruch 1, worin R¹ eine Alkoxy- oder Alkylthiogruppe darstellt.
4. Verbindung gemäß Anspruch 1, worin R¹ eine Polyethergruppe darstellt.
5. Verbindung gemäß Anspruch 1, worin R¹ eine substituierte Alkinylgruppe darstellt.
6. Verbindung gemäß Anspruch 1, worin R&sup5; eine Phenylgruppe darstellt.
7. Verbindung gemäß Anspruch 1, worin R&sup5; eine Imidoyl- oder (3H)- Benzo-1,2,3-triazin-4-on-3-yl-Gruppe darstellt.
8. Verbindung gemäß Anspruch 1, worin R&sup5; aus der Gruppe ausgewählt ist, bestehend aus einer N-Saccharinyl-, (2H)-Phthalazin-1-on-2-yl-, 2- Benzoxazolin-2-on-3-yl-, 5,5-Dimethyloxazolidin-2,4-dion-3-yl- und aus einer Thiazolidin-2,4-dion-3-yl-Gruppe.
9. Verbindung gemäß Anspruch 1, ausgewählt aus der Gruppe, bestehend aus:
4-(4-(3-Hydroxyprop-1-inyl)phenyl)-4-oxo-2-(3- phenylpropyl)buttersäure,
4-(4-(Hex-1-inyl)phenyl)-4-oxo-2-(3-phenylpropyl)buttersäure,
4-(4-(6-Hydroxyhex-1-inyl)phenyl)-4-oxo-2-(3-phenylpropyl)buttersäure,
4-(4-(Hex-1-inyl)phenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure,
4-(4-(6-Hydroxyhex-1-inyl)phenyl)-4-oxo-2-(2- phthalimidoethyl)buttersäure,
4-(4-(3-Hydroxyprop-1-inyl)phenyl)-4-oxo-2-(2- phthalimidoethyl)buttersäure,
4-(4-Hexylphenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure,
4-(4-(Dec-1-inyl)phenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure,
4-(4-(3-Phenoxyprop-1-inyl)phenyl)-4-oxo-2-(2- phthalimidoethyl)buttersäure,
4-(4-Heptyloxyphenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure,
4-(4-Hexyloxyphenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure,
4-(4-Decyloxyphenyl)-4-oxo-2-(2-phthalimidoethyl)buttersäure, und aus
4-(4-(2-Benzyloxyethyoxy)phenyl)-4-oxo-2-(2- phthalimidoethyl)buttersäure.
10. Zusammensetzung mit Matrix-Metalloprotease-Inhibitoraktivität, umfassend eine Verbindung gemäß Anspruch 1 und einen pharmazeutisch zulässigen Träger.
11. Verwendung einer Verbindung gemäß Anspruch 1 zur Herstellung eines Medikaments zur Behandlung eines Matrix-Metalloprotease-mediierten Zustands in einem Säugetier, um eine Wirkung zu erzielen.
12. Verwendung gemäß Anspruch 11, wobei das genannte Säugetier ein Mensch ist.
13. Verwendung gemäß Anspruch 11, wobei die genannte Wirkung ist: Linderung von Osteoarthritis, rheumatoider Arthritis, septischer Arthritis, Periodontalkrankheiten, Kornealgeschwüren, Proteinurie, aneurysmaler Aortakrankheiten, dystrophober Epidermolysebullosa, Zuständen, die zu Entzündungsreaktionen führen, von durch MMP-Aktivität mediierten Osteopenien, Temperomandibular-Gelenkkrankheiten oder von Demyelatierkrankheiten des Nervensystems, Verzögerung von Tumor-Metastase oder von degenerativem Knorpelverlust nach einer traumatischen Gelenksverletzung, Verringerung einer Koronarthrombose aus atherosklerotischem Plaque-Bruch oder verbesserte Geburtenkontrolle.
DE69706874T 1996-05-15 1997-05-12 Substituierte 4-arylbutyrsäurederivate als matrix metalloprotease inhibitoren Expired - Fee Related DE69706874T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64768296A 1996-05-15 1996-05-15
PCT/US1997/007951 WO1997043237A1 (en) 1996-05-15 1997-05-12 Subsitute 4-arylbutyric acid derivatives as matrix metalloprotease inhibitors

Publications (2)

Publication Number Publication Date
DE69706874D1 DE69706874D1 (en) 2001-10-25
DE69706874T2 true DE69706874T2 (de) 2002-03-28

Family

ID=24597888

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69706874T Expired - Fee Related DE69706874T2 (de) 1996-05-15 1997-05-12 Substituierte 4-arylbutyrsäurederivate als matrix metalloprotease inhibitoren

Country Status (21)

Country Link
EP (1) EP0923529B1 (de)
JP (1) JP3354941B2 (de)
CN (1) CN1225620A (de)
AR (1) AR007101A1 (de)
AT (1) ATE205822T1 (de)
AU (1) AU727468B2 (de)
BR (1) BR9709075A (de)
CA (1) CA2253795C (de)
CO (1) CO5011113A1 (de)
DE (1) DE69706874T2 (de)
ES (1) ES2160955T3 (de)
HR (1) HRP970247B1 (de)
ID (1) ID17326A (de)
MY (1) MY116903A (de)
PA (1) PA8429501A1 (de)
SV (1) SV1997000033A (de)
TN (1) TNSN97086A1 (de)
TW (1) TW442468B (de)
WO (1) WO1997043237A1 (de)
YU (1) YU18897A (de)
ZA (1) ZA974033B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6288063B1 (en) 1998-05-27 2001-09-11 Bayer Corporation Substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives as matrix metalloprotease inhibitors
FR2832925B1 (fr) * 2001-12-03 2006-07-14 Lipha Utilisation de derives de l'acide 4-oxobutanoique dans le traitement de l'inflammation
JP2012087113A (ja) * 2010-09-22 2012-05-10 Daicel Corp フェニル酢酸化合物
WO2015150362A2 (de) 2014-04-03 2015-10-08 Bayer Pharma Aktiengesellschaft Chirale 2,5-disubstituierte cyclopentancarbonsäure-derivate und ihre verwendung
WO2015150350A1 (de) 2014-04-03 2015-10-08 Bayer Pharma Aktiengesellschaft 2,5-disubstituierte cyclopentancarbonsäuren zur behandlung von atemwegserkrankungen
US20170022171A1 (en) 2014-04-03 2017-01-26 Bayer Pharma Aktiengesellschaft 2,5-disubstituted cyclopentanecarboxylic acids and their use
WO2015150364A1 (de) * 2014-04-03 2015-10-08 Bayer Pharma Aktiengesellschaft Substituierte benzotriazinonbutansäuren und ihre verwendung
WO2015189117A1 (de) * 2014-06-12 2015-12-17 Bayer Pharma Aktiengesellschaft Heterobicyclisch substituierte 4-oxobutansäure-derivate und ihre verwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE650081A (de) * 1963-07-03
FR2378741A1 (fr) * 1977-02-01 1978-08-25 Fabre Sa Pierre Acides garyl goxo isovaleriques doues de proprietes antiphlogistiques et antalgiques

Also Published As

Publication number Publication date
PA8429501A1 (es) 2000-05-24
HRP970247B1 (en) 2002-02-28
HRP970247A2 (en) 1998-04-30
CO5011113A1 (es) 2001-02-28
JPH11510518A (ja) 1999-09-14
ES2160955T3 (es) 2001-11-16
DE69706874D1 (en) 2001-10-25
WO1997043237A1 (en) 1997-11-20
JP3354941B2 (ja) 2002-12-09
CA2253795C (en) 2002-10-15
AU2938997A (en) 1997-12-05
CA2253795A1 (en) 1997-11-20
CN1225620A (zh) 1999-08-11
ID17326A (id) 1997-12-18
BR9709075A (pt) 1999-08-03
EP0923529B1 (de) 2001-09-19
SV1997000033A (es) 1999-01-14
AU727468B2 (en) 2000-12-14
TW442468B (en) 2001-06-23
EP0923529A1 (de) 1999-06-23
ATE205822T1 (de) 2001-10-15
YU18897A (en) 1999-11-22
ZA974033B (en) 1998-02-19
AR007101A1 (es) 1999-10-13
TNSN97086A1 (fr) 2005-03-15
MY116903A (en) 2004-04-30

Similar Documents

Publication Publication Date Title
DE69730508T2 (de) Hemmung von matrixmetalloproteasen durch 2-substituierte-4-(4-substituiertphenyl)-4-oxobutansäuren
EP0586537A1 (de) Substituierte n-carboxylalkylpeptidylderivate als antidegenerativ-aktive agentien
DE69708909T2 (de) Substituierte 4-biphenyl-4-hydroxybuttersäurederivate als matrix metallprotease inhibitoren
US20020042418A1 (en) Inhibition of matrix metalloproteases by substitued biaryl oxobutyric acides
DE69706874T2 (de) Substituierte 4-arylbutyrsäurederivate als matrix metalloprotease inhibitoren
US5863915A (en) Substituted 4-arylbutyric acid derivatives as matrix metalloprotease
DE69717811T2 (de) Substituierte phenethyl-derivate als matrx-metalloprotease-inhibitoren
US5968795A (en) Biaryl acetylenes as inhibitors of matrix metalloproteases
CA2253796C (en) Inhibition of matrix metalloproteases by acetylene containing compounds
DE69715619T2 (de) Inhibition der matrix metalloproteasen durch 2-(omega-aroylalkyl)-4-biaryl-4-oxobutansäuren
JP3417951B2 (ja) マトリックスメタロプロテアーゼ阻害剤としての置換されたオキシ酪酸
US5804581A (en) Inhibition of matrix metalloproteases by substituted phenalkyl compounds
US5932577A (en) Substituted oxobutyric acids as matrix metalloprotease inhibitors
WO1997043238A9 (en) Substituted oxobutyric acids as matrix metalloprotease inhibitors
US5932763A (en) Inhibition of matrix metalloproteases by 2-(ω-arolalkyl)-4-biaryl-4-oxobutyric acids
NZ335433A (en) Substituted 4-biphenyl-4-hydroxybutyric acid derivatives as matrix metalloprotease inhibitors and their use and manufacture as medicaments

Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee