CA2253796A1 - Inhibition of matrix metalloproteases by acetylene containing compounds - Google Patents
Inhibition of matrix metalloproteases by acetylene containing compoundsInfo
- Publication number
- CA2253796A1 CA2253796A1 CA002253796A CA2253796A CA2253796A1 CA 2253796 A1 CA2253796 A1 CA 2253796A1 CA 002253796 A CA002253796 A CA 002253796A CA 2253796 A CA2253796 A CA 2253796A CA 2253796 A1 CA2253796 A1 CA 2253796A1
- Authority
- CA
- Canada
- Prior art keywords
- compounds
- disease
- conditions
- pharmaceutical compositions
- matrix metalloproteases
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 102000005741 Metalloproteases Human genes 0.000 title abstract 3
- 108010006035 Metalloproteases Proteins 0.000 title abstract 3
- 239000011159 matrix material Substances 0.000 title abstract 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- 102000002274 Matrix Metalloproteinases Human genes 0.000 abstract 2
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 208000025494 Aortic disease Diseases 0.000 abstract 1
- 206010053555 Arthritis bacterial Diseases 0.000 abstract 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 abstract 1
- 206010053177 Epidermolysis Diseases 0.000 abstract 1
- 208000004575 Infectious Arthritis Diseases 0.000 abstract 1
- 208000012659 Joint disease Diseases 0.000 abstract 1
- 206010060820 Joint injury Diseases 0.000 abstract 1
- 208000029725 Metabolic bone disease Diseases 0.000 abstract 1
- 206010027476 Metastases Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 206010064996 Ulcerative keratitis Diseases 0.000 abstract 1
- 210000000845 cartilage Anatomy 0.000 abstract 1
- 208000002528 coronary thrombosis Diseases 0.000 abstract 1
- 230000003412 degenerative effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000028709 inflammatory response Effects 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 230000009401 metastasis Effects 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 210000000653 nervous system Anatomy 0.000 abstract 1
- 208000028169 periodontal disease Diseases 0.000 abstract 1
- 201000001474 proteinuria Diseases 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
- 201000001223 septic arthritis Diseases 0.000 abstract 1
- 230000000472 traumatic effect Effects 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
- 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
- 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
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Matrix metalloprotease inhibiting compounds, pharmaceutical compositions thereof and a method of disease treatment using such compounds are presented. The compounds of the invention have the generalized formula:
(see formula I) where R15 is selected from the group comprising: HOCH2, (n-Pr)2NCH2, CH3CO2CH2, EtOCO2CH2, HO(CH2)2, CH3CO2(CH2)2, HO2C(CH2)2, OHC(CH2)3, HO(CH2)4, 3-HO-Ph, and PhCH2OCH2; and R16 is (see formula II or III) These compounds are useful for inhibiting matrix metalloproteases and, therefore, combating conditions to which MMP's contribute, such asosteoarthritis, rheumatoid arthritis, septic arthritis, periodontal disease, corneal ulceration, proteinuria, aneurysmal aortic disease, dystrophobic epidermolysis, bullosa conditions leading to inflammatory responses, osteopenias mediated by MMP activity, tempera mandibular joint disease, demyelating diseases of the nervous system, tumor metastasis or degenerative cartilage loss following traumatic joint injury, and coronary thrombosis from athrosclerotic plaque rupture. The present invention also provides pharmaceutical compositions and methods for treating such conditions.
(see formula I) where R15 is selected from the group comprising: HOCH2, (n-Pr)2NCH2, CH3CO2CH2, EtOCO2CH2, HO(CH2)2, CH3CO2(CH2)2, HO2C(CH2)2, OHC(CH2)3, HO(CH2)4, 3-HO-Ph, and PhCH2OCH2; and R16 is (see formula II or III) These compounds are useful for inhibiting matrix metalloproteases and, therefore, combating conditions to which MMP's contribute, such asosteoarthritis, rheumatoid arthritis, septic arthritis, periodontal disease, corneal ulceration, proteinuria, aneurysmal aortic disease, dystrophobic epidermolysis, bullosa conditions leading to inflammatory responses, osteopenias mediated by MMP activity, tempera mandibular joint disease, demyelating diseases of the nervous system, tumor metastasis or degenerative cartilage loss following traumatic joint injury, and coronary thrombosis from athrosclerotic plaque rupture. The present invention also provides pharmaceutical compositions and methods for treating such conditions.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64502896A | 1996-05-15 | 1996-05-15 | |
| US08/645,028 | 1996-05-15 | ||
| PCT/US1997/007921 WO1997043245A1 (en) | 1996-05-15 | 1997-05-12 | Inhibition of matrix metalloproteases by acetylene containing compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2253796A1 true CA2253796A1 (en) | 1997-11-20 |
| CA2253796C CA2253796C (en) | 2003-10-28 |
Family
ID=24587368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253796A Expired - Fee Related CA2253796C (en) | 1996-05-15 | 1997-05-12 | Inhibition of matrix metalloproteases by acetylene containing compounds |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0912496A1 (en) |
| JP (1) | JP3090957B2 (en) |
| CN (1) | CN1139570C (en) |
| AR (1) | AR007097A1 (en) |
| AU (1) | AU710759B2 (en) |
| BR (1) | BR9709077A (en) |
| CA (1) | CA2253796C (en) |
| CO (1) | CO5080759A1 (en) |
| HN (1) | HN1997000088A (en) |
| HR (1) | HRP970245B1 (en) |
| ID (1) | ID16910A (en) |
| PA (1) | PA8429301A1 (en) |
| SV (1) | SV1997000035A (en) |
| TN (1) | TNSN97084A1 (en) |
| TW (1) | TW381079B (en) |
| WO (1) | WO1997043245A1 (en) |
| YU (1) | YU18697A (en) |
| ZA (1) | ZA974031B (en) |
Families Citing this family (9)
| 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 |
| AR035478A1 (en) * | 1999-01-27 | 2004-06-02 | Wyeth Corp | AMIDA-HYDROXAMIC ACID, ACETYLLENE, BETA-SULPHONAMIDE AND PHOSPHINIC ACID AS INHIBITORS OF TACE, USE OF THE SAME FOR THE MANUFACTURE OF A MEDICINAL PRODUCT AND PHARMACEUTICAL COMPOSITION CONTAINING THEM |
| US6326516B1 (en) | 1999-01-27 | 2001-12-04 | American Cyanamid Company | Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors |
| EP1031349A1 (en) * | 1999-02-25 | 2000-08-30 | Bayer Aktiengesellschaft | Use of substituted 4-biarylbutyric and 5-biarylpentanoic acid derivatives for the treatment of cerebral diseases |
| US7141607B1 (en) | 2000-03-10 | 2006-11-28 | Insite Vision Incorporated | Methods and compositions for treating and inhibiting retinal neovascularization |
| ES2592154T3 (en) | 2010-07-08 | 2016-11-28 | Kaken Pharmaceutical Co., Ltd. | N-Hydroxyformamide derivative and medicine containing the same |
| WO2015150363A1 (en) | 2014-04-03 | 2015-10-08 | Bayer Pharma Aktiengesellschaft | 2,5-disubstituted cyclopentane carboxylic acids and use thereof |
| CN106661008A (en) | 2014-04-03 | 2017-05-10 | 拜耳制药股份公司 | 2,5-disubstituted cyclopentane carboxylic acids for the treatment of respiratoy tract diseases |
| US20170119776A1 (en) | 2014-04-03 | 2017-05-04 | Bayer Pharma Aktiengesellschaft | Chiral 2,5-disubstituted cyclopentanecarboxylic acid derivatives and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3784701A (en) * | 1970-09-21 | 1974-01-08 | American Cyanamid Co | Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain |
| DE2112716A1 (en) * | 1971-03-17 | 1972-10-05 | Thomae Gmbh Dr K | Biphenylyl-butyric acid derivs. - anti phlogistics |
| US5789434A (en) * | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
-
1997
- 1997-05-09 ZA ZA9704031A patent/ZA974031B/en unknown
- 1997-05-09 HR HR970245A patent/HRP970245B1/en not_active IP Right Cessation
- 1997-05-09 TN TNTNSN97084A patent/TNSN97084A1/en unknown
- 1997-05-09 CO CO97025172A patent/CO5080759A1/en unknown
- 1997-05-12 PA PA19978429301A patent/PA8429301A1/en unknown
- 1997-05-12 JP JP09540980A patent/JP3090957B2/en not_active Expired - Fee Related
- 1997-05-12 WO PCT/US1997/007921 patent/WO1997043245A1/en not_active Application Discontinuation
- 1997-05-12 AR ARP970101977A patent/AR007097A1/en unknown
- 1997-05-12 YU YU18697A patent/YU18697A/en unknown
- 1997-05-12 CN CNB971964564A patent/CN1139570C/en not_active Expired - Fee Related
- 1997-05-12 BR BR9709077A patent/BR9709077A/en not_active Application Discontinuation
- 1997-05-12 AU AU29386/97A patent/AU710759B2/en not_active Ceased
- 1997-05-12 CA CA002253796A patent/CA2253796C/en not_active Expired - Fee Related
- 1997-05-12 EP EP97923622A patent/EP0912496A1/en not_active Withdrawn
- 1997-05-12 SV SV1997000035A patent/SV1997000035A/en unknown
- 1997-05-12 TW TW086106283A patent/TW381079B/en not_active IP Right Cessation
- 1997-05-12 HN HN1997000088A patent/HN1997000088A/en unknown
- 1997-05-14 ID IDP971606A patent/ID16910A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HN1997000088A (en) | 1997-06-18 |
| ID16910A (en) | 1997-11-20 |
| TW381079B (en) | 2000-02-01 |
| JP3090957B2 (en) | 2000-09-25 |
| EP0912496A1 (en) | 1999-05-06 |
| AR007097A1 (en) | 1999-10-13 |
| HRP970245A2 (en) | 1998-04-30 |
| CA2253796C (en) | 2003-10-28 |
| CO5080759A1 (en) | 2001-09-25 |
| YU18697A (en) | 1999-11-22 |
| BR9709077A (en) | 1999-08-03 |
| AU2938697A (en) | 1997-12-05 |
| WO1997043245A1 (en) | 1997-11-20 |
| SV1997000035A (en) | 1999-01-14 |
| CN1225623A (en) | 1999-08-11 |
| AU710759B2 (en) | 1999-09-30 |
| TNSN97084A1 (en) | 2005-03-15 |
| PA8429301A1 (en) | 2000-05-24 |
| JPH11511179A (en) | 1999-09-28 |
| HRP970245B1 (en) | 2002-06-30 |
| ZA974031B (en) | 1998-02-19 |
| CN1139570C (en) | 2004-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |