NO312665B1 - Sulfonerte aminosyrederivater, preparater for inhibering av metalloproteinase inneholdende slike forbindelser, samt anvendelseav slike forbindelser til fremstilling av farmasöytiske preparater - Google Patents
Sulfonerte aminosyrederivater, preparater for inhibering av metalloproteinase inneholdende slike forbindelser, samt anvendelseav slike forbindelser til fremstilling av farmasöytiske preparater Download PDFInfo
- Publication number
- NO312665B1 NO312665B1 NO19983376A NO983376A NO312665B1 NO 312665 B1 NO312665 B1 NO 312665B1 NO 19983376 A NO19983376 A NO 19983376A NO 983376 A NO983376 A NO 983376A NO 312665 B1 NO312665 B1 NO 312665B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- optionally substituted
- alkyl
- alkoxy
- groups
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 210
- 230000002401 inhibitory effect Effects 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 22
- 102000005741 Metalloproteases Human genes 0.000 title claims description 16
- 108010006035 Metalloproteases Proteins 0.000 title claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 12
- 150000003862 amino acid derivatives Chemical class 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 245
- -1 biphenylyl Chemical group 0.000 claims description 141
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 89
- 125000003545 alkoxy group Chemical group 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 125000001624 naphthyl group Chemical group 0.000 claims description 72
- 125000004076 pyridyl group Chemical group 0.000 claims description 72
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 62
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
- 125000001589 carboacyl group Chemical group 0.000 claims description 58
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 52
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 52
- 125000001544 thienyl group Chemical group 0.000 claims description 52
- 239000013543 active substance Substances 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 43
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 42
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 42
- 125000002757 morpholinyl group Chemical group 0.000 claims description 42
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 37
- 125000003282 alkyl amino group Chemical group 0.000 claims description 34
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
- 125000004414 alkyl thio group Chemical group 0.000 claims description 26
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000000335 thiazolyl group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 16
- 102000029816 Collagenase Human genes 0.000 claims description 16
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- 229960002424 collagenase Drugs 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
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- 229940088598 enzyme Drugs 0.000 claims description 12
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 11
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 11
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- 230000000694 effects Effects 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 9
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- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010027476 Metastases Diseases 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 230000009401 metastasis Effects 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
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- 239000003814 drug Substances 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
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- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- UPTYCYWTFGTCCG-UHFFFAOYSA-N 5-(1-piperazinylsulfonyl)isoquinoline Chemical compound C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCNCC1 UPTYCYWTFGTCCG-UHFFFAOYSA-N 0.000 claims 1
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- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000006032 tissue transformation Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
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- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- 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
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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- 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
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- 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
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- 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
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- C07C311/46—Y being a hydrogen or a carbon atom
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- C07C311/47—Y being a hetero atom
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3008296 | 1996-01-23 | ||
| JP21355596 | 1996-08-13 | ||
| PCT/JP1997/000126 WO1997027174A1 (en) | 1996-01-23 | 1997-01-22 | Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO983376D0 NO983376D0 (no) | 1998-07-22 |
| NO983376L NO983376L (no) | 1998-09-14 |
| NO312665B1 true NO312665B1 (no) | 2002-06-17 |
Family
ID=26368369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19983376A NO312665B1 (no) | 1996-01-23 | 1998-07-22 | Sulfonerte aminosyrederivater, preparater for inhibering av metalloproteinase inneholdende slike forbindelser, samt anvendelseav slike forbindelser til fremstilling av farmasöytiske preparater |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US6207698B1 (cs) |
| EP (2) | EP0950656B1 (cs) |
| JP (1) | JP3628335B2 (cs) |
| KR (2) | KR100338861B1 (cs) |
| CN (1) | CN100413859C (cs) |
| AT (1) | ATE359264T1 (cs) |
| AU (1) | AU715764B2 (cs) |
| BR (1) | BR9707010B1 (cs) |
| CZ (1) | CZ298814B6 (cs) |
| DE (1) | DE69737605T2 (cs) |
| ES (1) | ES2284180T3 (cs) |
| HU (1) | HU226006B1 (cs) |
| IL (1) | IL125378A0 (cs) |
| NO (1) | NO312665B1 (cs) |
| NZ (1) | NZ325939A (cs) |
| PL (2) | PL198905B1 (cs) |
| RU (1) | RU2198656C2 (cs) |
| SK (1) | SK282995B6 (cs) |
| TR (1) | TR199801419T2 (cs) |
| TW (3) | TWI244474B (cs) |
| WO (1) | WO1997027174A1 (cs) |
Families Citing this family (103)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2195034T3 (es) * | 1995-12-08 | 2003-12-01 | Agouron Pharma | Inhibidor de metaloproteinasas, composicion farmaceutica que contiene este inhibidor y su utilizacion farmaceutica, y procedimientos que sirven para su preparacion. |
| US6500948B1 (en) | 1995-12-08 | 2002-12-31 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors-compositions, uses preparation and intermediates thereof |
| NZ325939A (en) | 1996-01-23 | 2000-06-23 | Shionogi & Co | Sulphonated amino acid derivatives and matrix metalloproteinase inhibitors (MMP) containing these derivatives |
| US6919375B1 (en) | 1996-01-23 | 2005-07-19 | Shionogi & Co., Ltd. | Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same |
| EP0915086A4 (en) * | 1996-05-24 | 2001-01-17 | Ono Pharmaceutical Co | PHENYLSULFONAMIDE DERIVATIVES |
| US6624177B1 (en) | 1996-09-04 | 2003-09-23 | Warner-Lambert Company | Matrix metalloproteinase inhibitors and their therapeutic uses |
| AU736347B2 (en) * | 1996-09-04 | 2001-07-26 | Warner-Lambert Company | Compounds for and a method of inhibiting matrix metalloproteinases |
| CA2256716A1 (en) * | 1996-09-04 | 1998-03-12 | Warner-Lambert Company | Matrix metalloproteinase inhibitors and their therapeutic uses |
| US6548524B2 (en) | 1996-10-16 | 2003-04-15 | American Cyanamid Company | Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors |
| US5962481A (en) * | 1996-10-16 | 1999-10-05 | American Cyanamid Company | Preparation and use of ortho-sulfonamido heteroaryl hydroxamic acids as matrix metalloproteinase and tace inhibitors |
| US6228869B1 (en) | 1996-10-16 | 2001-05-08 | American Cyanamid Company | Ortho-sulfonamido bicyclic hydroxamic acids as matrix metalloproteinase and TACE inhibitors |
| US5977408A (en) * | 1996-10-16 | 1999-11-02 | American Cyanamid Company | Preparation and use of β-sulfonamido hydroxamic acids as matrix metalloproteinase and TACE inhibitors |
| US5929097A (en) * | 1996-10-16 | 1999-07-27 | American Cyanamid Company | Preparation and use of ortho-sulfonamido aryl hydroxamic acids as matrix metalloproteinase and tace inhibitors |
| US5804593A (en) * | 1996-10-22 | 1998-09-08 | Pharmacia & Upjohn Company | α-Amino sulfonyl hydroxamic acids as matrix metalloproteinase 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 |
| AU741768B2 (en) * | 1996-12-09 | 2001-12-06 | Warner-Lambert Company | Method for treating and preventing heart failure and ventricular dilatation |
| UA59384C2 (uk) | 1996-12-20 | 2003-09-15 | Пфайзер, Інк. | Похідні сульфонамідів та амідів як агоністи простагландину, фармацевтична композиція та способи лікування на їх основі |
| EP0983267B1 (en) | 1997-03-04 | 2005-01-26 | Pharmacia Corporation | Amidoaromatic ring sulfonamide hydroxamic acid compounds |
| BR9809062A (pt) * | 1997-04-01 | 2000-08-01 | Agouron Pharmaceuticlas Inc | Inibidores da metaloproteinase, composições farmacêuticas comtendo os mesmos e seus usos farmacêuticos |
| US5985900A (en) * | 1997-04-01 | 1999-11-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| US5756545A (en) * | 1997-04-21 | 1998-05-26 | Warner-Lambert Company | Biphenysulfonamide matrix metal alloproteinase inhibitors |
| WO1998050348A1 (en) * | 1997-05-09 | 1998-11-12 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| DE19719621A1 (de) | 1997-05-09 | 1998-11-12 | Hoechst Ag | Sulfonylaminocarbonsäuren |
| DE69833940T2 (de) | 1997-07-22 | 2006-12-14 | Shionogi & Co., Ltd. | Therapeutisches oder vorbeugendes mittel für glomerulopathie |
| JP2001513484A (ja) | 1997-07-31 | 2001-09-04 | ザ プロクター アンド ギャンブル カンパニー | 非環式メタロプロテアーゼ阻害剤 |
| RU2208609C2 (ru) * | 1998-02-04 | 2003-07-20 | Новартис Аг | Сульфониламинопроизводные, которые ингибируют разлагающие матрикс металлопротеиназы |
| US6410580B1 (en) | 1998-02-04 | 2002-06-25 | Novartis Ag | Sulfonylamino derivatives which inhibit matrix-degrading metalloproteinases |
| DE19814546A1 (de) * | 1998-04-01 | 1999-10-07 | Hoechst Marion Roussel De Gmbh | (S)-2-(Biphenyl-4-sulfonylamino)-3-(1H-indol-3-yl)-propionsäurederivate |
| CN1304402A (zh) | 1998-04-03 | 2001-07-18 | 三共株式会社 | 磺酰胺衍生物 |
| WO2000015213A1 (en) * | 1998-09-11 | 2000-03-23 | Shionogi & Co., Ltd. | Remedal or preventive agent for congestive heart failure |
| US6946473B2 (en) | 1999-01-27 | 2005-09-20 | Wyeth Holdings Corporation | Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors |
| US6340691B1 (en) | 1999-01-27 | 2002-01-22 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase and tace inhibitors |
| US6762178B2 (en) | 1999-01-27 | 2004-07-13 | Wyeth Holdings Corporation | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors |
| US6225311B1 (en) | 1999-01-27 | 2001-05-01 | American Cyanamid Company | Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors |
| CN1178915C (zh) | 1999-01-27 | 2004-12-08 | 惠氏控股有限公司 | 含有炔基的异羟肟酸衍生物、其制备及其作为基质金属蛋白酶抑制剂/TNF-α转变酶抑制剂的用途 |
| US6326516B1 (en) | 1999-01-27 | 2001-12-04 | American Cyanamid Company | Acetylenic β-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors |
| US6313123B1 (en) | 1999-01-27 | 2001-11-06 | American Cyanamid Company | Acetylenic sulfonamide thiol tace inhibitors |
| US6277885B1 (en) | 1999-01-27 | 2001-08-21 | American Cyanamid Company | Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors |
| US6753337B2 (en) | 1999-01-27 | 2004-06-22 | Wyeth Holdings Corporation | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
| US6200996B1 (en) | 1999-01-27 | 2001-03-13 | American Cyanamid Company | Heteroaryl acetylenic sulfonamide and phosphinic acid amide hydroxamic acid tace inhibitors |
| TR200102523T2 (tr) | 1999-03-03 | 2002-02-21 | The Procter & Gamble Company | Alkenil ve alkinil içeren metaloproteaz inhibitörleri |
| PL350452A1 (en) * | 1999-03-03 | 2002-12-16 | Procter & Gamble | Dihetero-substituted metalloprotease inhibitors |
| KR20010113820A (ko) * | 1999-04-19 | 2001-12-28 | 시오노 요시히코 | 옥사디아졸 고리를 갖는 술폰아미드 유도체 |
| GB9911071D0 (en) * | 1999-05-12 | 1999-07-14 | Darwin Discovery Ltd | Hydroxamic and carboxylic acid derivatives |
| US6541521B1 (en) | 1999-07-12 | 2003-04-01 | Warner-Lambert Company | Benzene butyric acids and their derivatives as inhibitors of matrix metalloproteinases |
| WO2001005389A2 (en) * | 1999-07-16 | 2001-01-25 | G.D. Searle & Co. | N-sulfonylaminiacid derivatives as inhibitors of metalloprteinase |
| US6869951B1 (en) | 1999-07-16 | 2005-03-22 | Pharmacia Corporation | Method of changing conformation of a matrix metalloproteinase |
| GB9918684D0 (en) | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
| WO2001023363A1 (en) * | 1999-09-29 | 2001-04-05 | Sankyo Company, Limited | Sulfonamide derivatives |
| BR0015843A (pt) | 1999-11-26 | 2002-08-27 | Shionogi & Co | Antagonista de y5 para npy |
| WO2001055133A1 (en) * | 2000-01-26 | 2001-08-02 | Shionogi & Co., Ltd. | Substituted tryptophan derivatives |
| JP2003523994A (ja) * | 2000-02-24 | 2003-08-12 | スミスクライン ビーチャム パブリック リミテッド カンパニー | 新規cd23インヒビター |
| US6465508B1 (en) | 2000-02-25 | 2002-10-15 | Wyeth | Preparation and use of ortho-sulfonamido aryl hydroxamic acids as matrix metalloproteinase inhibitors |
| JP2003528080A (ja) * | 2000-03-21 | 2003-09-24 | ザ プロクター アンド ギャンブル カンパニー | 複素環式側鎖を含有するn−置換型メタロプロテアーゼ阻害物質 |
| JP2003528082A (ja) | 2000-03-21 | 2003-09-24 | ザ プロクター アンド ギャンブル カンパニー | ニフッ化酪酸メタロプロテアーゼ阻害物質 |
| AU2001249269A1 (en) * | 2000-03-21 | 2001-10-03 | The Procter & Gamble Company | Carbocyclic side chain containing metalloprotease inhibitors |
| HUP0300368A3 (en) * | 2000-04-06 | 2004-07-28 | Ono Pharmaceutical Co | Pharmaceutical composition for diseases due to stenotic lesions of blood vessel |
| AU2001248766A1 (en) * | 2000-04-19 | 2001-10-30 | Shionogi And Co., Ltd. | Process for preparation of sulfonamide derivatives and crystals thereof |
| US6897237B2 (en) | 2000-04-28 | 2005-05-24 | Shionogi & Co. Ltd. | MMP-12 inhibitors |
| AU2000265100A1 (en) * | 2000-07-12 | 2002-01-21 | G.D. Searle And Co. | N sulfonyl aminoacid derivatives as inhibitors of metalloproteinase |
| CN1273456C (zh) | 2000-09-29 | 2006-09-06 | 盐野义制药株式会社 | 噻唑和噁唑衍生物 |
| FR2819253B1 (fr) * | 2001-01-11 | 2004-12-03 | Servier Lab | Nouveaux derives d'acide hydroxamique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0103303D0 (en) | 2001-02-09 | 2001-03-28 | Novartis Ag | Organic compounds |
| JP4294321B2 (ja) * | 2001-03-14 | 2009-07-08 | ノバルティス アクチエンゲゼルシャフト | Mmp阻害剤としての使用のためのアザシクロアルキル置換酢酸誘導体 |
| FR2822827B1 (fr) * | 2001-03-28 | 2003-05-16 | Sanofi Synthelabo | Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant |
| US20030105144A1 (en) | 2001-04-17 | 2003-06-05 | Ping Gao | Stabilized oral pharmaceutical composition |
| US7547716B2 (en) | 2001-06-08 | 2009-06-16 | Institute Of Medicinal Molecular Design, Inc. | Sulfonamide derivatives |
| US20030082618A1 (en) * | 2001-10-15 | 2003-05-01 | Guangshan Li | Methods for detecting genetic aberrations |
| JP2005507937A (ja) | 2001-11-01 | 2005-03-24 | ワイス・ホールディングズ・コーポレイション | マトリックスメタロプロテイナーゼおよびtace阻害剤としてのアレンアリールスルホンアミドヒドロキサム酸 |
| JP4632288B2 (ja) * | 2002-02-27 | 2011-02-16 | 塩野義製薬株式会社 | 難水溶性薬物の吸収性を改善した固形状製剤 |
| TW200406197A (en) * | 2002-04-25 | 2004-05-01 | Ono Pharmaceutical Co | Therapelitic agent for inflammatory bowel disease containing hydroxamic acid as effective component |
| US7504425B2 (en) | 2002-05-29 | 2009-03-17 | Merck & Co., Inc. | Compounds useful in the treatment of anthrax and inhibiting lethal factor |
| US7199155B2 (en) | 2002-12-23 | 2007-04-03 | Wyeth Holdings Corporation | Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors |
| WO2004080452A1 (ja) * | 2003-03-10 | 2004-09-23 | Shionogi & Co., Ltd. | 網膜疾患治療薬 |
| MXPA05010937A (es) * | 2003-04-14 | 2005-11-25 | Inst For Pharm Discovery Inc | Derivados de fenilalanina n-(1,3-tiazol-2-il)amino)carbonil)fenil)sulfonil) y compuestos relacionados para el tratamiento de diabetes. |
| AU2004236173B2 (en) | 2003-04-30 | 2008-07-03 | The Institutes For Pharmaceutical Discovery, Llc | Substituted carboxylic acids |
| US7365223B2 (en) * | 2003-06-18 | 2008-04-29 | Nst Neurosurvival Technologies Ltd | Method for selective targeting of apoptotic cells and small molecule ligands used thereof |
| WO2004113258A1 (ja) * | 2003-06-20 | 2004-12-29 | Shionogi & Co., Ltd. | 炭素−炭素結合生成反応 |
| EP1650199A4 (en) | 2003-07-30 | 2008-11-19 | Shionogi & Co | SULPHONAMIDE DERIVATIVE WITH ISOXAZOL RING |
| KR20060093735A (ko) | 2003-12-04 | 2006-08-25 | 와이어쓰 | Mmp 억제제로서의 비아릴 설폰아미드 |
| CA2548513A1 (en) * | 2003-12-04 | 2005-07-07 | Wyeth | Biaryl sulfonamides and methods for using same |
| ZA200605247B (en) * | 2003-12-15 | 2007-10-31 | Japan Tobacco Inc | N-substituted-n-sulfonylaminocyclopropane compounds and pharmaceutical use thereof |
| JP2007516982A (ja) | 2003-12-15 | 2007-06-28 | 日本たばこ産業株式会社 | シクロプロパン化合物及びその医薬用途 |
| CN1660811A (zh) * | 2004-02-27 | 2005-08-31 | 中国科学院上海药物研究所 | 1,4-二取代苯类化合物及其制备方法和用途 |
| EP1747212A4 (en) | 2004-05-11 | 2009-03-25 | Merck & Co Inc | PROCESS FOR THE PREPARATION OF N-SULFONATED AMINOIC DERIVATIVES |
| JP2006036691A (ja) * | 2004-07-27 | 2006-02-09 | Shionogi & Co Ltd | 腎炎の治療または予防剤 |
| ITFI20040174A1 (it) * | 2004-08-03 | 2004-11-03 | Protera S R L | Derivati arilsolfonammidici dell'acido idrossammico ad azione inibitoria di metalloproteinasi |
| JP2008518926A (ja) * | 2004-10-28 | 2008-06-05 | ジ インスティチューツ フォー ファーマシューティカル ディスカバリー、エルエルシー | 置換フェニルアルカン酸 |
| US20060112494A1 (en) * | 2004-12-01 | 2006-06-01 | David Oppong | Method of protecting an animal skin product from metalloproteinase activity |
| US7576222B2 (en) | 2004-12-28 | 2009-08-18 | Wyeth | Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase |
| EP1997804A1 (en) | 2006-03-03 | 2008-12-03 | Shionogi & Co., Ltd. | Mmp-13-selective inhibitor |
| US8153166B2 (en) * | 2006-06-08 | 2012-04-10 | Chih-Hsiung Lin | Composition for prophylaxis or treatment of urinary system infection and method thereof |
| US20100099676A1 (en) | 2006-11-02 | 2010-04-22 | Shionogi & Co., Ltd. | Sulfonylurea derivative capable of selectively inhibiting mmp-13 |
| JP2010520200A (ja) * | 2007-02-28 | 2010-06-10 | クオナトウス ファーマシューティカルズ,インコーポレイテッド | 特定のマトリックスメタロプロテイナーゼ(mmp)阻害剤を使用する肝疾患を治療する方法 |
| WO2008106167A1 (en) * | 2007-02-28 | 2008-09-04 | Conatus Pharmaceuticals, Inc. | Combination therapy comprising matrix metalloproteinase inhibitors and caspase inhibitors for the treatment of liver diseases |
| EP2147684A1 (en) * | 2008-07-22 | 2010-01-27 | Bracco Imaging S.p.A | Diagnostic Agents Selective Against Metalloproteases |
| CN103012207B (zh) * | 2012-12-29 | 2015-05-27 | 吉首大学 | 二芳基丙酰-n-甲基氧肟酸类尿素酶抑制剂及其合成和用途 |
| CN102993052B (zh) * | 2012-12-29 | 2014-07-09 | 吉首大学 | 芳基丙酰氧肟酸类尿素酶抑制剂及其合成和用途 |
| RU2646752C2 (ru) * | 2016-02-25 | 2018-03-07 | Федеральное государственное бюджетное научное учреждение "Научно-исследовательский институт фармакологии имени В.В. Закусова" | Ингибиторы цинк-зависимых металлопротеиназ (ММП-2 и ММП-9) в ряду бензоиламино(фенилсульфонил)-замещенных циклических аминокислот как потенциальные лекарственные средства, препятствующие постинфарктному ремоделированию левого желудочка сердца |
| TW202227394A (zh) * | 2020-09-11 | 2022-07-16 | 美商工匠生物科技股份有限公司 | 細菌毒素之小分子抑制劑 |
| CN115141128B (zh) * | 2022-06-24 | 2024-09-13 | 沈阳药科大学 | 3-芳基-3-(磺胺苯甲酰胺基)丙(烯)酸衍生物及其制备方法及应用 |
| CN116283895A (zh) * | 2023-01-09 | 2023-06-23 | 怀化宝华生物科技有限公司 | 一种2-[2-(噻吩基)乙基]苯甲酸的制备方法 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA113A (en) * | 1869-10-28 | J. Munson | Improvements in beehives | |
| 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 |
| US4269775A (en) | 1978-09-01 | 1981-05-26 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4347372A (en) | 1978-09-01 | 1982-08-31 | Ciba-Geigy Corporation | Benzoxazolyl-glyoxylonitrile-2-oxime ether derivatives |
| JPS5759969A (en) * | 1980-09-29 | 1982-04-10 | Pentel Kk | Water-based ink |
| FR2508444A1 (fr) * | 1981-06-29 | 1982-12-31 | Irceba | Nouveaux derives sulfonyle du tryptophane utiles en tant que medicaments et leur procede de preparation |
| US4578381A (en) * | 1982-07-05 | 1986-03-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| CA1260947A (en) * | 1984-12-29 | 1989-09-26 | Yoshitaka Ohishi | Benzofuran derivative, process for preparing the same and pharmaceutical composition containing the same |
| US4599361A (en) | 1985-09-10 | 1986-07-08 | G. D. Searle & Co. | Hydroxamic acid based collagenase inhibitors |
| US4632931A (en) | 1985-09-25 | 1986-12-30 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted amide-sulfonamide prostaglandin analogs useful in the treatment of thrombotic disease |
| JP2764262B2 (ja) | 1987-08-28 | 1998-06-11 | 持田製薬株式会社 | ヒダントイン誘導体及びそれを有効成分とする医薬組成物 |
| TW201303B (cs) * | 1990-07-05 | 1993-03-01 | Hoffmann La Roche | |
| US5270326A (en) | 1990-11-21 | 1993-12-14 | University Of Florida | Treatment for tissue ulceration |
| JPH05255089A (ja) | 1991-12-18 | 1993-10-05 | Sanwa Kagaku Kenkyusho Co Ltd | 抗ウイルス剤 |
| GB9200209D0 (en) * | 1992-01-07 | 1992-02-26 | British Bio Technology | Compounds |
| AU675689B2 (en) | 1992-12-01 | 1997-02-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5506242A (en) * | 1993-01-06 | 1996-04-09 | Ciba-Geigy Corporation | Arylsufonamido-substituted hydroxamic acids |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| WO1995001332A1 (en) | 1993-07-01 | 1995-01-12 | Nkk Corporation | Arylsulfonamide derivative and pharmaceutical composition containing the same |
| UA48121C2 (uk) * | 1993-11-04 | 2002-08-15 | Сінтекс (С.Ш.А.) Інк. | Інгібітори матричних металопротеаз і фармацетична композиція на їх основі |
| GB9323165D0 (en) | 1993-11-10 | 1994-01-05 | Chiros Ltd | Compounds |
| GB9323162D0 (en) * | 1993-11-10 | 1994-01-05 | British Bio Technology | 4-(1h-2-methylimidazo(4,5-c)pyridinylmethyl)phenylsulphonamid e derivatives as antagonists of paf |
| US5445258A (en) | 1994-02-22 | 1995-08-29 | Warn Industries, Inc. | Pulse actuated hub locks and control arrangement |
| NZ288298A (en) | 1994-06-22 | 1998-12-23 | British Biotech Pharm | Hydroxamic acid and carboxylic acid derivatives; medicaments containing such derivatives that are metalloproteinase inhibitors |
| HUT77282A (hu) | 1994-10-05 | 1998-03-30 | Darwin Discovery Limited | Peptidvegyületek és gyógyászati alkalmazásuk metalloproteáz inhibitorokként |
| US5789434A (en) | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| KR980009238A (ko) * | 1995-07-28 | 1998-04-30 | 우에노 도시오 | 설포닐아미노산 유도체 |
| US6022893A (en) * | 1995-08-08 | 2000-02-08 | Ono Pharmaceutical Co., Ltd. | Hydroxamic acid derivatives |
| CA2242416C (en) * | 1996-01-23 | 2006-03-21 | Shionogi & Co., Ltd. | Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same |
| NZ325939A (en) | 1996-01-23 | 2000-06-23 | Shionogi & Co | Sulphonated amino acid derivatives and matrix metalloproteinase inhibitors (MMP) containing these derivatives |
| US5900427A (en) | 1996-05-03 | 1999-05-04 | Wisconsin Alumni Research Foundation | N-heteroarenesulfonyl-protected amino acid reagents for peptide synthesis |
| EP0915086A4 (en) | 1996-05-24 | 2001-01-17 | Ono Pharmaceutical Co | PHENYLSULFONAMIDE DERIVATIVES |
| AU736347B2 (en) * | 1996-09-04 | 2001-07-26 | Warner-Lambert Company | Compounds for and a method of inhibiting matrix metalloproteinases |
| AU741768B2 (en) * | 1996-12-09 | 2001-12-06 | Warner-Lambert Company | Method for treating and preventing heart failure and ventricular dilatation |
| US5985900A (en) * | 1997-04-01 | 1999-11-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| US5756545A (en) | 1997-04-21 | 1998-05-26 | Warner-Lambert Company | Biphenysulfonamide matrix metal alloproteinase inhibitors |
-
1997
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- 1997-01-22 JP JP52672897A patent/JP3628335B2/ja not_active Expired - Fee Related
- 1997-01-22 IL IL12537897A patent/IL125378A0/xx not_active IP Right Cessation
- 1997-01-22 ES ES97900747T patent/ES2284180T3/es not_active Expired - Lifetime
- 1997-01-22 KR KR10-1998-0705577A patent/KR100338861B1/ko not_active Expired - Fee Related
- 1997-01-22 PL PL328270A patent/PL198905B1/pl not_active IP Right Cessation
- 1997-01-22 EP EP97900747A patent/EP0950656B1/en not_active Expired - Lifetime
- 1997-01-22 WO PCT/JP1997/000126 patent/WO1997027174A1/ja not_active Ceased
- 1997-01-22 AU AU13195/97A patent/AU715764B2/en not_active Ceased
- 1997-01-22 EP EP04021556A patent/EP1486207A3/en not_active Withdrawn
- 1997-01-22 CZ CZ0225298A patent/CZ298814B6/cs not_active IP Right Cessation
- 1997-01-22 AT AT97900747T patent/ATE359264T1/de not_active IP Right Cessation
- 1997-01-22 CN CNB971932263A patent/CN100413859C/zh not_active Expired - Fee Related
- 1997-01-22 TR TR1998/01419T patent/TR199801419T2/xx unknown
- 1997-01-22 SK SK984-98A patent/SK282995B6/sk not_active IP Right Cessation
- 1997-01-22 HU HU9903687A patent/HU226006B1/hu not_active IP Right Cessation
- 1997-01-22 PL PL381859A patent/PL205341B1/pl not_active IP Right Cessation
- 1997-01-22 RU RU98115659/14A patent/RU2198656C2/ru not_active IP Right Cessation
- 1997-01-22 DE DE69737605T patent/DE69737605T2/de not_active Expired - Lifetime
- 1997-01-22 KR KR1020017014157A patent/KR100338857B1/ko not_active Expired - Fee Related
- 1997-01-22 BR BRPI9707010-6A patent/BR9707010B1/pt not_active IP Right Cessation
- 1997-01-27 TW TW092127003A patent/TWI244474B/zh not_active IP Right Cessation
- 1997-01-27 TW TW092128956A patent/TWI244475B/zh not_active IP Right Cessation
- 1997-01-27 TW TW086100862A patent/TW575547B/zh not_active IP Right Cessation
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1998
- 1998-07-22 US US09/120,197 patent/US6207698B1/en not_active Expired - Fee Related
- 1998-07-22 NO NO19983376A patent/NO312665B1/no not_active IP Right Cessation
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1999
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2000
- 2000-11-14 US US09/710,904 patent/US6441021B1/en not_active Expired - Fee Related
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2002
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