EA001561B1 - Бифенилсульфонамидные ингибиторы матричных металлопротеиназ - Google Patents
Бифенилсульфонамидные ингибиторы матричных металлопротеиназ Download PDFInfo
- Publication number
- EA001561B1 EA001561B1 EA199800988A EA199800988A EA001561B1 EA 001561 B1 EA001561 B1 EA 001561B1 EA 199800988 A EA199800988 A EA 199800988A EA 199800988 A EA199800988 A EA 199800988A EA 001561 B1 EA001561 B1 EA 001561B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- sulfonylamino
- carbon atoms
- alkyl
- methylbutanoic acid
- acid
- Prior art date
Links
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- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title 1
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 53
- -1 phenoxy- Chemical class 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
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- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
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- ZGWIOFHKEXLJPC-UHFFFAOYSA-N 2-[[4-(4-formylphenyl)phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(C=O)C=C1 ZGWIOFHKEXLJPC-UHFFFAOYSA-N 0.000 claims abstract description 3
- QTBORBZHZRFVQM-UHFFFAOYSA-N 2-[[4-[4-(aminomethyl)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)NC(C(C)C)C(O)=O)=CC=C1C1=CC=C(CN)C=C1 QTBORBZHZRFVQM-UHFFFAOYSA-N 0.000 claims abstract description 3
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VFMGXRFRRDTHNX-UHFFFAOYSA-N tert-butyl 2-[(4-bromophenyl)sulfonylamino]-3-methylbutanoate Chemical compound CC(C)(C)OC(=O)C(C(C)C)NS(=O)(=O)C1=CC=C(Br)C=C1 VFMGXRFRRDTHNX-UHFFFAOYSA-N 0.000 description 1
- IUNJJJTYPANBGD-UHFFFAOYSA-N tert-butyl 2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-3-methylbutanoate Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)NC(C(C)C)C(=O)OC(C)(C)C)C=C1 IUNJJJTYPANBGD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P19/08—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
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/42—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1746096P | 1996-05-17 | 1996-05-17 | |
| PCT/US1997/006801 WO1997044315A1 (en) | 1996-05-17 | 1997-04-24 | Biphenylsulfonamide matrix metalloproteinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199800988A1 EA199800988A1 (ru) | 1999-04-29 |
| EA001561B1 true EA001561B1 (ru) | 2001-04-23 |
Family
ID=21782716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199800988A EA001561B1 (ru) | 1996-05-17 | 1997-04-24 | Бифенилсульфонамидные ингибиторы матричных металлопротеиназ |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0901466B1 (https=) |
| JP (1) | JP2000511175A (https=) |
| KR (1) | KR20000011095A (https=) |
| CN (1) | CN1077885C (https=) |
| AT (1) | ATE207891T1 (https=) |
| BG (1) | BG63940B1 (https=) |
| BR (1) | BR9710841A (https=) |
| CA (1) | CA2253342A1 (https=) |
| CZ (1) | CZ294063B6 (https=) |
| DE (1) | DE69707865T2 (https=) |
| DK (1) | DK0901466T3 (https=) |
| EA (1) | EA001561B1 (https=) |
| EE (1) | EE03965B1 (https=) |
| ES (1) | ES2167733T3 (https=) |
| IL (1) | IL126832A0 (https=) |
| NO (1) | NO312510B1 (https=) |
| NZ (1) | NZ332711A (https=) |
| PL (1) | PL186416B1 (https=) |
| PT (1) | PT901466E (https=) |
| SK (1) | SK282863B6 (https=) |
| WO (1) | WO1997044315A1 (https=) |
| ZA (1) | ZA974223B (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10501806A (ja) * | 1994-06-22 | 1998-02-17 | ブリティッシュ バイオテック ファーマシューティカルズ リミテッド | 金属タンパク質分解酵素阻害剤 |
| US6124333A (en) * | 1995-06-22 | 2000-09-26 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
| CA2263886A1 (en) * | 1996-12-09 | 1998-06-18 | Warner-Lambert Company | Method for treating and preventing heart failure and ventricular dilatation |
| CA2264692A1 (en) * | 1996-12-17 | 1998-06-25 | Warner-Lambert Company | Use of matrix metalloproteinase inhibitors for treating neurological disorders and promoting wound healing |
| SI0946166T1 (en) * | 1996-12-17 | 2004-06-30 | Warner-Lambert Company Llc | Use of matrix metalloproteinase inhibitors for promoting wound healing |
| GB9706255D0 (en) | 1997-03-26 | 1997-05-14 | Smithkline Beecham Plc | Novel compounds |
| DE19719621A1 (de) * | 1997-05-09 | 1998-11-12 | Hoechst Ag | Sulfonylaminocarbonsäuren |
| CA2297011C (en) * | 1997-07-22 | 2007-01-30 | Shionogi & Co., Ltd. | Sulfonamide derivatives as therapeutic or prophylactic agent for glomerulopathy |
| WO1999032150A1 (en) * | 1997-12-23 | 1999-07-01 | Warner-Lambert Company | Ace inhibitor-mmp inhibitor combinations |
| US6410580B1 (en) | 1998-02-04 | 2002-06-25 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
| RU2208609C2 (ru) * | 1998-02-04 | 2003-07-20 | Новартис Аг | Сульфониламинопроизводные, которые ингибируют разлагающие матрикс металлопротеиназы |
| BR9815745A (pt) * | 1998-03-17 | 2000-11-14 | Warner Lambert Co | Combinações de inibidor de metaloproteinase de matriz estatina |
| EP0967201A1 (en) * | 1998-05-20 | 1999-12-29 | Roche Diagnostics GmbH | Pharmaceutical agents containing sulfonamids as matrix metalloproteinase inhibitors |
| ATE227295T1 (de) * | 1998-07-16 | 2002-11-15 | Aventis Pharma Gmbh | Phosphin- und phosphonsäurederivate als arzneimittel |
| ID30030A (id) * | 1998-07-21 | 2001-11-01 | Warner Lambert Co | Pemberian serta penghambat acat dan mmp untuk pengobatan luka-luka aterosklerosis |
| DE19851184A1 (de) * | 1998-11-06 | 2000-05-11 | Aventis Pharma Gmbh | N-Arylsulfonyl-aminosäure-omega-amide |
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| CN1347411A (zh) * | 1999-04-19 | 2002-05-01 | 盐野义制药株式会社 | 含有噁二唑环的磺酰胺衍生物 |
| GB9918684D0 (en) | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
| CA2389681C (en) | 1999-11-26 | 2010-11-02 | Shionogi & Co., Ltd. | Npy y5 antagonist |
| EP1331224A4 (en) * | 2000-09-29 | 2004-03-17 | Shionogi & Co | THIAZOLE AND OXAZOLE DERIVATIVES |
| GB0103303D0 (en) | 2001-02-09 | 2001-03-28 | Novartis Ag | Organic compounds |
| MXPA01013326A (es) | 2001-02-14 | 2002-08-26 | Warner Lambert Co | Bifenil sulfonamidas utiles como inhibisdores de metaloproteinasa de matriz. |
| WO2003035610A1 (en) * | 2001-10-26 | 2003-05-01 | Shionogi & Co., Ltd. | Sulfonamide derivative having mmp inhibitory activity |
| GB0314488D0 (en) * | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Therapeutically useful compounds |
| WO2005061459A1 (en) * | 2003-12-04 | 2005-07-07 | Wyeth | Biaryl sulfonamides and methods for using same |
| MXPA06010974A (es) * | 2004-03-22 | 2007-04-23 | Southern Res Inst | Inhibidores nopeptidos de metaloproteinasas de matriz. |
| CN101279956B (zh) * | 2008-04-25 | 2011-06-15 | 南昌大学 | 一种基质金属蛋白酶抑制剂及合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995035276A1 (en) * | 1994-06-22 | 1995-12-28 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
| WO1996000214A1 (en) * | 1994-06-24 | 1996-01-04 | Ciba-Geigy Ag | Arylsulfonamido-substituted hydroxamic acids as matrix metalloproteinase inhibitors |
-
1997
- 1997-04-24 NZ NZ332711A patent/NZ332711A/en unknown
- 1997-04-24 IL IL12683297A patent/IL126832A0/xx unknown
- 1997-04-24 KR KR1019980709253A patent/KR20000011095A/ko not_active Ceased
- 1997-04-24 BR BR9710841A patent/BR9710841A/pt not_active IP Right Cessation
- 1997-04-24 WO PCT/US1997/006801 patent/WO1997044315A1/en not_active Ceased
- 1997-04-24 CZ CZ19983668A patent/CZ294063B6/cs not_active IP Right Cessation
- 1997-04-24 ES ES97918788T patent/ES2167733T3/es not_active Expired - Lifetime
- 1997-04-24 EE EE9800397A patent/EE03965B1/xx not_active IP Right Cessation
- 1997-04-24 CN CN97194719A patent/CN1077885C/zh not_active Expired - Fee Related
- 1997-04-24 DK DK97918788T patent/DK0901466T3/da active
- 1997-04-24 AT AT97918788T patent/ATE207891T1/de not_active IP Right Cessation
- 1997-04-24 SK SK1577-98A patent/SK282863B6/sk unknown
- 1997-04-24 CA CA002253342A patent/CA2253342A1/en not_active Abandoned
- 1997-04-24 EA EA199800988A patent/EA001561B1/ru not_active IP Right Cessation
- 1997-04-24 PL PL97329929A patent/PL186416B1/pl not_active IP Right Cessation
- 1997-04-24 JP JP09542377A patent/JP2000511175A/ja not_active Abandoned
- 1997-04-24 EP EP97918788A patent/EP0901466B1/en not_active Expired - Lifetime
- 1997-04-24 PT PT97918788T patent/PT901466E/pt unknown
- 1997-04-24 DE DE69707865T patent/DE69707865T2/de not_active Expired - Fee Related
- 1997-05-15 ZA ZA9704223A patent/ZA974223B/xx unknown
-
1998
- 1998-11-12 BG BG102918A patent/BG63940B1/bg unknown
- 1998-11-16 NO NO19985326A patent/NO312510B1/no not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995035276A1 (en) * | 1994-06-22 | 1995-12-28 | British Biotech Pharmaceuticals Limited | Metalloproteinase inhibitors |
| WO1996000214A1 (en) * | 1994-06-24 | 1996-01-04 | Ciba-Geigy Ag | Arylsulfonamido-substituted hydroxamic acids as matrix metalloproteinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| AU713286B2 (en) | 1999-11-25 |
| KR20000011095A (ko) | 2000-02-25 |
| CN1077885C (zh) | 2002-01-16 |
| SK157798A3 (en) | 1999-04-13 |
| NZ332711A (en) | 2000-06-23 |
| NO985326D0 (no) | 1998-11-16 |
| PT901466E (pt) | 2002-04-29 |
| EE03965B1 (et) | 2003-02-17 |
| PL329929A1 (en) | 1999-04-26 |
| DE69707865D1 (de) | 2001-12-06 |
| ZA974223B (en) | 1997-12-10 |
| DK0901466T3 (da) | 2002-02-18 |
| BR9710841A (pt) | 1999-08-17 |
| NO312510B1 (no) | 2002-05-21 |
| CZ366898A3 (cs) | 1999-02-17 |
| AU2680397A (en) | 1997-12-09 |
| WO1997044315A1 (en) | 1997-11-27 |
| EP0901466A1 (en) | 1999-03-17 |
| SK282863B6 (sk) | 2002-12-03 |
| CA2253342A1 (en) | 1997-11-27 |
| BG102918A (en) | 1999-09-30 |
| PL186416B1 (pl) | 2004-01-30 |
| DE69707865T2 (de) | 2002-05-02 |
| BG63940B1 (bg) | 2003-07-31 |
| ES2167733T3 (es) | 2002-05-16 |
| EP0901466B1 (en) | 2001-10-31 |
| EA199800988A1 (ru) | 1999-04-29 |
| NO985326L (no) | 1999-01-14 |
| HK1019585A1 (en) | 2000-02-18 |
| CN1219166A (zh) | 1999-06-09 |
| IL126832A0 (en) | 1999-08-17 |
| ATE207891T1 (de) | 2001-11-15 |
| CZ294063B6 (cs) | 2004-09-15 |
| EE9800397A (et) | 1999-06-15 |
| JP2000511175A (ja) | 2000-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |