SK25099A3 - Substituted cyclic amine metalloprotease inhibitors - Google Patents
Substituted cyclic amine metalloprotease inhibitors Download PDFInfo
- Publication number
- SK25099A3 SK25099A3 SK250-99A SK25099A SK25099A3 SK 25099 A3 SK25099 A3 SK 25099A3 SK 25099 A SK25099 A SK 25099A SK 25099 A3 SK25099 A3 SK 25099A3
- Authority
- SK
- Slovakia
- Prior art keywords
- mmol
- hydroxycarboxamido
- methoxyphenylsulfonyl
- alkyl
- etoac
- Prior art date
Links
- -1 cyclic amine Chemical class 0.000 title claims description 71
- 239000003475 metalloproteinase inhibitor Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 102000005741 Metalloproteases Human genes 0.000 claims abstract description 75
- 108010006035 Metalloproteases Proteins 0.000 claims abstract description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 49
- 230000000694 effects Effects 0.000 claims abstract description 39
- 201000010099 disease Diseases 0.000 claims abstract description 35
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 150000002148 esters Chemical class 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
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- 125000003277 amino group Chemical group 0.000 claims description 8
- FUTBJBSRCVJYCQ-UHFFFAOYSA-N n-hexylpyrrolidin-1-amine Chemical compound CCCCCCNN1CCCC1 FUTBJBSRCVJYCQ-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 5
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- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 description 1
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- 201000010901 lateral sclerosis Diseases 0.000 description 1
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- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
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- XYDMJRNLTAJWKE-UHFFFAOYSA-N n-pyrrolidin-1-ylmethanesulfonamide Chemical compound CS(=O)(=O)NN1CCCC1 XYDMJRNLTAJWKE-UHFFFAOYSA-N 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- RVWMQSODNUSUBL-UHFFFAOYSA-N potassium;oxidoamine Chemical compound [K+].[O-]N RVWMQSODNUSUBL-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- ATHQLWIRLNAEKR-UHFFFAOYSA-M sodium;benzoic acid;hydroxide Chemical compound O.[Na+].[O-]C(=O)C1=CC=CC=C1 ATHQLWIRLNAEKR-UHFFFAOYSA-M 0.000 description 1
- ZBFCVKZIVHEDOE-UHFFFAOYSA-M sodium;propane-1,2,3-triol;fluoride Chemical compound [F-].[Na+].OCC(O)CO ZBFCVKZIVHEDOE-UHFFFAOYSA-M 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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- 150000007970 thio esters Chemical class 0.000 description 1
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- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
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Classifications
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- 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
- C07D207/42—Nitro radicals
-
- 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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- 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
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- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2484296P | 1996-08-28 | 1996-08-28 | |
| PCT/US1997/014555 WO1998008815A1 (en) | 1996-08-28 | 1997-08-22 | Substituted cyclic amine metalloprotease inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK25099A3 true SK25099A3 (en) | 2000-02-14 |
Family
ID=21822685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK250-99A SK25099A3 (en) | 1996-08-28 | 1997-08-22 | Substituted cyclic amine metalloprotease inhibitors |
Country Status (30)
| Country | Link |
|---|---|
| US (6) | US6417219B1 (ru) |
| EP (1) | EP0927161B1 (ru) |
| JP (2) | JP3541043B2 (ru) |
| KR (1) | KR100323272B1 (ru) |
| CN (1) | CN1232451A (ru) |
| AT (1) | ATE226193T1 (ru) |
| AU (1) | AU741893B2 (ru) |
| BR (1) | BR9713465A (ru) |
| CA (1) | CA2263928A1 (ru) |
| CO (1) | CO4900036A1 (ru) |
| CZ (1) | CZ63199A3 (ru) |
| DE (1) | DE69716449T2 (ru) |
| DK (1) | DK0927161T3 (ru) |
| ES (1) | ES2201318T3 (ru) |
| HK (1) | HK1020962A1 (ru) |
| HU (1) | HUP0000478A3 (ru) |
| ID (1) | ID18143A (ru) |
| IL (1) | IL128666A (ru) |
| MY (1) | MY116959A (ru) |
| NO (1) | NO315371B1 (ru) |
| NZ (1) | NZ334256A (ru) |
| PE (1) | PE109098A1 (ru) |
| PL (1) | PL331802A1 (ru) |
| PT (1) | PT927161E (ru) |
| RU (1) | RU2221782C2 (ru) |
| SK (1) | SK25099A3 (ru) |
| TR (1) | TR199900431T2 (ru) |
| TW (1) | TWI232218B (ru) |
| WO (1) | WO1998008815A1 (ru) |
| ZA (1) | ZA977698B (ru) |
Families Citing this family (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR199800990T2 (xx) * | 1995-12-08 | 1998-07-21 | Agouron Pharmaceuticals, Inc. | Metaloproteinaz inhibit�rleri, bunlar� i�eren farmas�tik bile�imler, bunlar�n farmas�tik kullan�mlar� ve bunlar�n �retiminde kullan�labilecek y�ntemler ve ara �r�nler. |
| US6500948B1 (en) | 1995-12-08 | 2002-12-31 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors-compositions, uses preparation and intermediates thereof |
| US20020128476A1 (en) * | 1996-08-08 | 2002-09-12 | Smithkline Beecham Corporation | Inhibitors of cysteine protease |
| ATE226193T1 (de) * | 1996-08-28 | 2002-11-15 | Procter & Gamble | Substituierte zyklische amine als metalloproteaseinhibitoren |
| US6872742B2 (en) * | 1996-08-28 | 2005-03-29 | The Procter & Gamble Company | Substituted cyclic amine metalloprotease inhibitors |
| US6174915B1 (en) | 1997-03-25 | 2001-01-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| US6008243A (en) * | 1996-10-24 | 1999-12-28 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use |
| ZA98376B (en) * | 1997-01-23 | 1998-07-23 | Hoffmann La Roche | Sulfamide-metalloprotease inhibitors |
| HUP0000657A3 (en) | 1997-02-11 | 2000-10-30 | Pfizer | N-arylsulfonyl-piperidine, -morpholine hydroxamic acid derivatives and pharmaceutical compositions containing them |
| US5985900A (en) * | 1997-04-01 | 1999-11-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| AU7294098A (en) * | 1997-05-09 | 1998-11-27 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| EP1009737A2 (en) | 1997-07-31 | 2000-06-21 | The Procter & Gamble Company | Sulfonylamino substituted hydroxamic acid derivatives as metalloprotease inhibitors |
| US6130220A (en) * | 1997-10-16 | 2000-10-10 | Syntex (Usa) Inc. | Sulfamide-metalloprotease inhibitors |
| US6410580B1 (en) | 1998-02-04 | 2002-06-25 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
| TR200002224T2 (tr) | 1998-02-04 | 2000-12-21 | Novartis Ag | Matris-bozucu metalloproteinasları inhibe eden sülfonilamino türevleri. |
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- 1997-08-22 WO PCT/US1997/014555 patent/WO1998008815A1/en active IP Right Grant
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- 1997-08-22 CA CA002263928A patent/CA2263928A1/en not_active Abandoned
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- 1997-08-22 ES ES97938412T patent/ES2201318T3/es not_active Expired - Lifetime
- 1997-08-22 EP EP97938412A patent/EP0927161B1/en not_active Expired - Lifetime
- 1997-08-22 DE DE69716449T patent/DE69716449T2/de not_active Expired - Fee Related
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