CA2253869A1 - Substituted oxobutyric acids as matrix metalloprotease inhibitors - Google Patents
Substituted oxobutyric acids as matrix metalloprotease inhibitorsInfo
- Publication number
- CA2253869A1 CA2253869A1 CA002253869A CA2253869A CA2253869A1 CA 2253869 A1 CA2253869 A1 CA 2253869A1 CA 002253869 A CA002253869 A CA 002253869A CA 2253869 A CA2253869 A CA 2253869A CA 2253869 A1 CA2253869 A1 CA 2253869A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- matrix metalloprotease
- metalloprotease inhibitors
- carbons
- alkyl
- 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.)
- Granted
Links
- 239000011159 matrix material Substances 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 title 1
- 102000005741 Metalloproteases Human genes 0.000 abstract 2
- 108010006035 Metalloproteases Proteins 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
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
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- 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
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (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)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Enzymes And Modification Thereof (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides pharmaceutical compositions and methods for treating certain conditions associated with matrix metalloproteases, comprising administering an amount of a compound or composition of the invention which is effective to inhibit the activity of at least one matrix metalloprotease, resulting in achievement of the desired effect. The compounds of the present invention are either of the formula:
wherein y is 0, 2 or 3, r is 0-6, Z is (CH2)7 or (CH2)e-C6H4-(CH2)f, wherein, a is 0-1 and f is 0-5 and R 15 is -H, -Cl, -OMe or wherein n is 0-4, R 17 is C2H5, allyl, benzyl, and R 16 is
wherein y is 0, 2 or 3, r is 0-6, Z is (CH2)7 or (CH2)e-C6H4-(CH2)f, wherein, a is 0-1 and f is 0-5 and R 15 is -H, -Cl, -OMe or wherein n is 0-4, R 17 is C2H5, allyl, benzyl, and R 16 is
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64838496A | 1996-05-15 | 1996-05-15 | |
| US08/648,384 | 1996-05-15 | ||
| PCT/US1997/007975 WO1997043238A1 (en) | 1996-05-15 | 1997-05-12 | Substituted oxobutyric acids as matrix metalloprotease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2253869A1 true CA2253869A1 (en) | 1997-11-20 |
| CA2253869C CA2253869C (en) | 2003-04-22 |
Family
ID=24600568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253869A Expired - Fee Related CA2253869C (en) | 1996-05-15 | 1997-05-12 | Substituted oxobutyric acids as matrix metalloprotease inhibitors |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0912487A1 (en) |
| JP (1) | JP3417951B2 (en) |
| CN (1) | CN1163466C (en) |
| AR (1) | AR007096A1 (en) |
| AU (1) | AU727648B2 (en) |
| CA (1) | CA2253869C (en) |
| CO (1) | CO4990925A1 (en) |
| HR (1) | HRP970246B1 (en) |
| ID (1) | ID20291A (en) |
| MY (1) | MY132470A (en) |
| PA (1) | PA8429401A1 (en) |
| PE (1) | PE65998A1 (en) |
| SV (1) | SV1997000034A (en) |
| TN (1) | TNSN97085A1 (en) |
| TW (1) | TW467892B (en) |
| WO (1) | WO1997043238A1 (en) |
| YU (1) | YU18797A (en) |
| ZA (1) | ZA974032B (en) |
Families Citing this family (6)
| 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 |
| GB0321538D0 (en) | 2003-09-13 | 2003-10-15 | Glaxo Group Ltd | Therapeutically useful compounds |
| US20100324081A1 (en) * | 2007-08-15 | 2010-12-23 | Kyorin Pharmaceutical Co., Ltd. | Preventive, inhibitor or remedy for cerebral aneurysm comprising ibudilast as an active ingredient |
| EP3126339A1 (en) | 2014-04-03 | 2017-02-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids and use thereof |
| JP2017509665A (en) | 2014-04-03 | 2017-04-06 | バイエル ファーマ アクチエンゲゼルシャフト | 2,5-Disubstituted cyclopentanecarboxylic acids for the treatment of airway diseases |
| JP2017511319A (en) | 2014-04-03 | 2017-04-20 | バイエル ファーマ アクチエンゲゼルシャフト | Chiral 2,5-disubstituted cyclopentanecarboxylic acid derivatives and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69529100T2 (en) * | 1994-01-22 | 2003-07-17 | British Biotech Pharm | metalloproteinase |
-
1997
- 1997-05-09 ZA ZA9704032A patent/ZA974032B/en unknown
- 1997-05-09 MY MYPI97002045A patent/MY132470A/en unknown
- 1997-05-09 CO CO97025164A patent/CO4990925A1/en unknown
- 1997-05-09 TN TNTNSN97085A patent/TNSN97085A1/en unknown
- 1997-05-09 HR HR970246A patent/HRP970246B1/en not_active IP Right Cessation
- 1997-05-12 AR ARP970101976A patent/AR007096A1/en unknown
- 1997-05-12 TW TW086106284A patent/TW467892B/en not_active IP Right Cessation
- 1997-05-12 PA PA19978429401A patent/PA8429401A1/en unknown
- 1997-05-12 JP JP54100297A patent/JP3417951B2/en not_active Expired - Fee Related
- 1997-05-12 CN CNB971964599A patent/CN1163466C/en not_active Expired - Fee Related
- 1997-05-12 AU AU31219/97A patent/AU727648B2/en not_active Ceased
- 1997-05-12 YU YU18797A patent/YU18797A/en unknown
- 1997-05-12 CA CA002253869A patent/CA2253869C/en not_active Expired - Fee Related
- 1997-05-12 SV SV1997000034A patent/SV1997000034A/en not_active Application Discontinuation
- 1997-05-12 WO PCT/US1997/007975 patent/WO1997043238A1/en not_active Application Discontinuation
- 1997-05-12 EP EP97926454A patent/EP0912487A1/en not_active Withdrawn
- 1997-05-12 PE PE1997000362A patent/PE65998A1/en not_active Application Discontinuation
- 1997-05-14 ID IDP971607A patent/ID20291A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2253869C (en) | 2003-04-22 |
| ID20291A (en) | 1998-11-19 |
| TW467892B (en) | 2001-12-11 |
| TNSN97085A1 (en) | 2005-03-15 |
| YU18797A (en) | 1999-11-22 |
| PA8429401A1 (en) | 2000-05-24 |
| HRP970246B1 (en) | 2002-04-30 |
| WO1997043238A1 (en) | 1997-11-20 |
| JP3417951B2 (en) | 2003-06-16 |
| CN1225622A (en) | 1999-08-11 |
| ZA974032B (en) | 1998-02-19 |
| PE65998A1 (en) | 1998-10-20 |
| JPH11509870A (en) | 1999-08-31 |
| CO4990925A1 (en) | 2000-12-26 |
| MY132470A (en) | 2007-10-31 |
| AR007096A1 (en) | 1999-10-13 |
| CN1163466C (en) | 2004-08-25 |
| EP0912487A1 (en) | 1999-05-06 |
| AU727648B2 (en) | 2000-12-21 |
| SV1997000034A (en) | 1999-07-05 |
| HRP970246A2 (en) | 1998-04-30 |
| AU3121997A (en) | 1997-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |