IE49914B1 - Inhibitors of mammalian collagenase - Google Patents
Inhibitors of mammalian collagenaseInfo
- Publication number
- IE49914B1 IE49914B1 IE1251/80A IE125180A IE49914B1 IE 49914 B1 IE49914 B1 IE 49914B1 IE 1251/80 A IE1251/80 A IE 1251/80A IE 125180 A IE125180 A IE 125180A IE 49914 B1 IE49914 B1 IE 49914B1
- Authority
- IE
- Ireland
- Prior art keywords
- methyl
- oxopentyl
- accordance
- compound
- product
- Prior art date
Links
- 102000029816 Collagenase Human genes 0.000 title claims abstract description 11
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- 239000003112 inhibitor Substances 0.000 title description 2
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 33
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- 150000003839 salts Chemical class 0.000 claims abstract description 12
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- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical group C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 7
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical group OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims abstract description 7
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- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical group CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
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- UVYHDQCPQHQXPP-BYPYZUCNSA-N (2S)-2-[amino(hydroxy)amino]-5-(diaminomethylideneamino)pentanoic acid Chemical group NN(O)[C@H](C(O)=O)CCCNC(N)=N UVYHDQCPQHQXPP-BYPYZUCNSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
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- 238000000034 method Methods 0.000 claims description 5
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- GCTDRFXPPSVRRP-UHFFFAOYSA-N 4-methyl-2-(sulfanylmethyl)pentanoic acid Chemical compound CC(C)CC(CS)C(O)=O GCTDRFXPPSVRRP-UHFFFAOYSA-N 0.000 claims description 3
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- JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000001304 sample melting Methods 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/051,915 US4235885A (en) | 1979-06-25 | 1979-06-25 | Inhibitors of mammalian collagenase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE801251L IE801251L (en) | 1980-12-25 |
| IE49914B1 true IE49914B1 (en) | 1986-01-08 |
Family
ID=21974174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1251/80A IE49914B1 (en) | 1979-06-25 | 1980-06-17 | Inhibitors of mammalian collagenase |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4235885A (en:Method) |
| EP (1) | EP0021766B1 (en:Method) |
| JP (1) | JPS5612353A (en:Method) |
| AU (1) | AU539714B2 (en:Method) |
| CA (1) | CA1180324A (en:Method) |
| DE (1) | DE3061889D1 (en:Method) |
| IE (1) | IE49914B1 (en:Method) |
| ZA (1) | ZA803198B (en:Method) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4611002A (en) * | 1977-07-14 | 1986-09-09 | E. R. Squibb And Sons, Inc. | Carboxymethyl esters of mercaptopropanoic acids as enkephalinase inhibitors |
| ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
| US4692458A (en) * | 1980-03-05 | 1987-09-08 | University Of Miami | Anti-hypertensive agents |
| GB2076809B (en) * | 1980-05-30 | 1984-03-14 | Squibb & Sons Inc | N-substituted mercapto propionamides |
| US4382081A (en) * | 1981-06-12 | 1983-05-03 | E. R. Squibb & Sons, Inc. | Inhibitors of mammalian collagenase |
| US4424354A (en) | 1981-06-12 | 1984-01-03 | E. R. Squibb & Sons, Inc. | Inhibitors of mammalian collagenase |
| US4371465A (en) * | 1981-10-07 | 1983-02-01 | American Home Products Corporation | Mammalian collagenase inhibitors |
| US4374765A (en) * | 1981-10-07 | 1983-02-22 | American Home Products Corporation | Mammalian collagenase inhibitors |
| US4371466A (en) * | 1981-10-07 | 1983-02-01 | American Home Products Corporation | Mammalian collagenase inhibitors |
| US4401677A (en) * | 1981-10-09 | 1983-08-30 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
| US4474795A (en) * | 1981-10-09 | 1984-10-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
| US4474799A (en) * | 1981-10-09 | 1984-10-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
| US4774256A (en) * | 1983-10-03 | 1988-09-27 | E. R. Squibb & Sons, Inc. | Use of enkephalinase inhibitors as analgesic agents |
| US4798904A (en) * | 1983-10-03 | 1989-01-17 | E. R. Squibb & Sons, Inc. | Certain [(lower alkanoyl-thio)methyl-1-oxo-3-phenyl propyl amino]benzene lower alkanoic acid or ester derivatives which inhibit enkephalinase |
| US4722810A (en) * | 1984-08-16 | 1988-02-02 | E. R. Squibb & Sons, Inc. | Enkephalinase inhibitors |
| DE3467754D1 (de) * | 1983-10-03 | 1988-01-07 | Squibb & Sons Inc | Enkephalinase inhibitors |
| FR2556721B1 (fr) * | 1983-12-14 | 1986-05-16 | Roussel Uclaf | Nouveaux derives de o-mercaptopropanamide d'o amino-acides, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| US4595700A (en) * | 1984-12-21 | 1986-06-17 | G. D. Searle & Co. | Thiol based collagenase inhibitors |
| CA1337400C (en) * | 1987-06-08 | 1995-10-24 | Norma G. Delaney | Inhibitors of neutral endopeptidase |
| US4855315A (en) * | 1988-09-02 | 1989-08-08 | E. R. Squibb & Sons, Inc. | Use of zofenopril for the treatment of rheumatoid arthritis |
| CA2045621A1 (en) * | 1989-11-24 | 1991-05-25 | Akira Okuyama | Physiologically active substance be-16627 |
| AU2228292A (en) * | 1991-06-14 | 1993-01-12 | Research Corporation Technologies, Inc. | Peptide derivatives of collagenase inhibitor |
| US5641636A (en) * | 1994-05-20 | 1997-06-24 | University Of Pennsylvania | Method of predicting fetal membrane rupture based on matrix metalloproteinase-9 activity |
| US6140099A (en) * | 1994-05-20 | 2000-10-31 | The Trustees Of The University Of Pennsylvania | Method of delaying fetal membrane rupture by inhibiting matrix metalloproteinase-9 activity |
| ES2133807T3 (es) * | 1994-10-05 | 1999-09-16 | Darwin Discovery Ltd | Compuestos de peptidilo y su uso terapeutico como inhibidores de metaloproteasas. |
| US5831004A (en) | 1994-10-27 | 1998-11-03 | Affymax Technologies N.V. | Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use |
| US5840698A (en) * | 1994-10-27 | 1998-11-24 | Affymax Technologies N.V. | Inhibitors of collagenase-1 and stormelysin-I metalloproteases, pharmaceutical compositions comprising same and methods of their use |
| US6294694B1 (en) | 1999-06-04 | 2001-09-25 | Wisconsin Alumni Research Foundation | Matrix metalloproteinase inhibitors and method of using same |
| AR050552A1 (es) * | 2004-09-02 | 2006-11-01 | Osi Pharm Inc | Mercaptoamidas como inhibidores de histona desacetilasa |
| JP6507832B2 (ja) * | 2015-05-07 | 2019-05-08 | 日油株式会社 | Ｎ−アシルアミノ酸の製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4105776A (en) * | 1976-06-21 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
| US4053651A (en) * | 1976-05-10 | 1977-10-11 | E. R. Squibb & Sons, Inc. | Compounds and method for alleviating angiotensin related hypertension |
| US4179434A (en) * | 1977-01-17 | 1979-12-18 | E. R. Squibb & Sons, Inc. | Amino acid derivatives |
| CA1125783A (en) * | 1978-03-27 | 1982-06-15 | Michael E. Condon | Thioalkanoylalkanoic acid compounds |
-
1979
- 1979-06-25 US US06/051,915 patent/US4235885A/en not_active Expired - Lifetime
-
1980
- 1980-05-28 AU AU58850/80A patent/AU539714B2/en not_active Ceased
- 1980-05-28 ZA ZA00803198A patent/ZA803198B/xx unknown
- 1980-06-04 CA CA000353379A patent/CA1180324A/en not_active Expired
- 1980-06-16 DE DE8080302024T patent/DE3061889D1/de not_active Expired
- 1980-06-16 EP EP80302024A patent/EP0021766B1/en not_active Expired
- 1980-06-17 IE IE1251/80A patent/IE49914B1/en not_active IP Right Cessation
- 1980-06-25 JP JP8721180A patent/JPS5612353A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0021766B1 (en) | 1983-02-09 |
| AU539714B2 (en) | 1984-10-11 |
| EP0021766A2 (en) | 1981-01-07 |
| JPS5612353A (en) | 1981-02-06 |
| CA1180324A (en) | 1985-01-02 |
| US4235885A (en) | 1980-11-25 |
| ZA803198B (en) | 1981-05-27 |
| IE801251L (en) | 1980-12-25 |
| AU5885080A (en) | 1981-02-05 |
| EP0021766A3 (en) | 1981-05-13 |
| JPS6338024B2 (en:Method) | 1988-07-28 |
| DE3061889D1 (en) | 1983-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |