AP733A - Arylsulfonylamino hydroxamic acid derivatives. - Google Patents
Arylsulfonylamino hydroxamic acid derivatives. Download PDFInfo
- Publication number
- AP733A AP733A APAP/P/1997/001078A AP9701078A AP733A AP 733 A AP733 A AP 733A AP 9701078 A AP9701078 A AP 9701078A AP 733 A AP733 A AP 733A
- Authority
- AP
- ARIPO
- Prior art keywords
- alkyl
- aryl
- amino
- methoxybenzenesulfonyl
- heteroaryl
- Prior art date
Links
- -1 Arylsulfonylamino hydroxamic Chemical compound 0.000 title claims abstract description 77
- 239000002253 acid Substances 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 230000000694 effects Effects 0.000 claims abstract description 11
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 208000025865 Ulcer Diseases 0.000 claims abstract description 8
- 206010003246 arthritis Diseases 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 8
- 230000036269 ulceration Effects 0.000 claims abstract description 8
- 206010040047 Sepsis Diseases 0.000 claims abstract description 7
- 206010040070 Septic Shock Diseases 0.000 claims abstract description 7
- 208000028169 periodontal disease Diseases 0.000 claims abstract description 7
- 230000036303 septic shock Effects 0.000 claims abstract description 7
- 208000030507 AIDS Diseases 0.000 claims abstract description 6
- 206010014989 Epidermolysis bullosa Diseases 0.000 claims abstract description 6
- 206010039705 Scleritis Diseases 0.000 claims abstract description 6
- 229940035676 analgesics Drugs 0.000 claims abstract description 6
- 239000000730 antalgic agent Substances 0.000 claims abstract description 6
- 231100000433 cytotoxic Toxicity 0.000 claims abstract description 6
- 230000001472 cytotoxic effect Effects 0.000 claims abstract description 6
- 208000037803 restenosis Diseases 0.000 claims abstract description 6
- 208000002780 macular degeneration Diseases 0.000 claims abstract description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 27
- 102000003390 tumor necrosis factor Human genes 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 230000005764 inhibitory process Effects 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 12
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 12
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 4
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 150000008575 L-amino acids Chemical class 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- RDPDVZHMIQZOOF-UHFFFAOYSA-N 1-[3-[[1-cyclohexyl-2-(hydroxyamino)-2-oxoethyl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C1CCCCC1)C(=O)NO)CCC(=O)N1CCC(C(O)=O)CC1 RDPDVZHMIQZOOF-UHFFFAOYSA-N 0.000 claims description 2
- VJHJDEUUCPMADI-UHFFFAOYSA-N 2,3-dihydro-1h-inden-5-yl 3-[[1-cyclohexyl-2-(hydroxyamino)-2-oxoethyl]-(4-methoxyphenyl)sulfonylamino]propanoate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C1CCCCC1)C(=O)NO)CCC(=O)OC1=CC=C(CCC2)C2=C1 VJHJDEUUCPMADI-UHFFFAOYSA-N 0.000 claims description 2
- IIVQAZHUVWRZHJ-UHFFFAOYSA-N 2-cyclohexyl-n-hydroxy-2-[[3-(4-hydroxypiperidin-1-yl)-3-oxopropyl]-(4-methoxyphenyl)sulfonylamino]acetamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C1CCCCC1)C(=O)NO)CCC(=O)N1CCC(O)CC1 IIVQAZHUVWRZHJ-UHFFFAOYSA-N 0.000 claims description 2
- NXVDNEFRXVHBBN-UHFFFAOYSA-N 3-cyclohexyl-n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-[3-[4-(methylamino)piperidin-1-yl]-3-oxopropyl]amino]propanamide Chemical compound C1CC(NC)CCN1C(=O)CCN(S(=O)(=O)C=1C=CC(OC)=CC=1)C(C(=O)NO)CC1CCCCC1 NXVDNEFRXVHBBN-UHFFFAOYSA-N 0.000 claims description 2
- 229960001171 acetohydroxamic acid Drugs 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- YGWRGHCWEAPMJM-UHFFFAOYSA-N ethoxycarbonyloxymethyl 3-[[4-(4-fluorophenoxy)phenyl]sulfonyl-[1-(hydroxyamino)-3-methyl-1-oxobutan-2-yl]amino]propanoate Chemical compound C1=CC(S(=O)(=O)N(C(C(C)C)C(=O)NO)CCC(=O)OCOC(=O)OCC)=CC=C1OC1=CC=C(F)C=C1 YGWRGHCWEAPMJM-UHFFFAOYSA-N 0.000 claims description 2
- YYGXSXMKOALHSY-UHFFFAOYSA-N ethyl 1-[3-[[1-cyclohexyl-2-(hydroxyamino)-2-oxoethyl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)CCN(S(=O)(=O)C=1C=CC(OC)=CC=1)C(C(=O)NO)C1CCCCC1 YYGXSXMKOALHSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- FGEAIMWSTJVRJE-UHFFFAOYSA-N n-hydroxy-2-[[3-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-3-oxopropyl]-(4-methoxyphenyl)sulfonylamino]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C(C)C)C(=O)NO)CCC(=O)N1CCN(CC(C)(C)O)CC1 FGEAIMWSTJVRJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 229940080818 propionamide Drugs 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims 1
- ICUPWPPAYPPYQN-UHFFFAOYSA-N 2-cyclohexyl-n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-[3-[4-(methylamino)piperidin-1-yl]-3-oxopropyl]amino]acetamide Chemical compound C1CC(NC)CCN1C(=O)CCN(S(=O)(=O)C=1C=CC(OC)=CC=1)C(C(=O)NO)C1CCCCC1 ICUPWPPAYPPYQN-UHFFFAOYSA-N 0.000 claims 1
- 229910003844 NSO2 Inorganic materials 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- OTXRGOWUZRTWRY-UHFFFAOYSA-N ethoxycarbonyloxymethyl 3-[[1-cyclohexyl-2-(hydroxyamino)-2-oxoethyl]-(4-methoxyphenyl)sulfonylamino]propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)N(CCC(=O)OCOC(=O)OCC)C(C(=O)NO)C1CCCCC1 OTXRGOWUZRTWRY-UHFFFAOYSA-N 0.000 claims 1
- FDDVYQSFBLLBLU-UHFFFAOYSA-N n-hydroxy-2-[[3-(4-hydroxypiperidin-1-yl)-3-oxopropyl]-(4-methoxyphenyl)sulfonylamino]-3-methylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C(C)C)C(=O)NO)CCC(=O)N1CCC(O)CC1 FDDVYQSFBLLBLU-UHFFFAOYSA-N 0.000 claims 1
- PELDTXBSNDSZOG-UHFFFAOYSA-N n-hydroxy-2-[[3-(4-hydroxypiperidin-1-yl)-3-oxopropyl]-(4-phenylmethoxyphenyl)sulfonylamino]-3-methylbutanamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1S(=O)(=O)N(C(C(C)C)C(=O)NO)CCC(=O)N1CCC(O)CC1 PELDTXBSNDSZOG-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 abstract description 6
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- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 abstract description 2
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- 238000004458 analytical method Methods 0.000 description 16
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229960005190 phenylalanine Drugs 0.000 description 1
- XCOWFHRNGJAHDO-UHFFFAOYSA-N piperidin-4-yl acetate Chemical compound CC(=O)OC1CCNCC1 XCOWFHRNGJAHDO-UHFFFAOYSA-N 0.000 description 1
- YNHMMVMSCFNCJS-UHFFFAOYSA-N piperidin-4-yl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCNCC1 YNHMMVMSCFNCJS-UHFFFAOYSA-N 0.000 description 1
- FNCPWWQBPOBMIQ-UHFFFAOYSA-N piperidin-4-yl butanoate Chemical compound CCCC(=O)OC1CCNCC1 FNCPWWQBPOBMIQ-UHFFFAOYSA-N 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- 108010052605 prostromelysin Proteins 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium 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
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- ZFWTZYHCRVDAMC-UHFFFAOYSA-N tert-butyl N-[[1-[3-[(1-amino-2-hydroxy-4,4-dimethyl-1-oxopentan-2-yl)-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C(C)(C)(C)OC(NCC1CCN(CC1)C(CCN(S(=O)(=O)C1=CC=C(C=C1)OC)C(CC(C)(C)C)(O)C(N)=O)=O)=O ZFWTZYHCRVDAMC-UHFFFAOYSA-N 0.000 description 1
- TWTYDVMFTUTDDD-UHFFFAOYSA-N tert-butyl n-[[1-[3-[(3-amino-1-hydroxy-2-naphthalen-1-yl-3-oxopropyl)-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(O)C(C(N)=O)C=1C2=CC=CC=C2C=CC=1)CCC(=O)N1CCC(CNC(=O)OC(C)(C)C)CC1 TWTYDVMFTUTDDD-UHFFFAOYSA-N 0.000 description 1
- CZCPDXYAIURWOM-UHFFFAOYSA-N tert-butyl n-[[1-[3-[[1-(hydroxyamino)-1-oxo-4-phenylbutan-2-yl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CCC=1C=CC=CC=1)C(=O)NO)CCC(=O)N1CCC(CNC(=O)OC(C)(C)C)CC1 CZCPDXYAIURWOM-UHFFFAOYSA-N 0.000 description 1
- QHWVASUHXPOWQV-UHFFFAOYSA-N tert-butyl n-[[1-[3-[[1-(hydroxyamino)-1-oxohexan-2-yl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)N(C(CCCC)C(=O)NO)CCC(=O)N1CCC(CNC(=O)OC(C)(C)C)CC1 QHWVASUHXPOWQV-UHFFFAOYSA-N 0.000 description 1
- NXFJYRUCPDHCSA-UHFFFAOYSA-N tert-butyl n-[[1-[3-[[1-cyclohexyl-2-oxo-2-(phenylmethoxyamino)ethyl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(C1CCCCC1)C(=O)NOCC=1C=CC=CC=1)CCC(=O)N1CCC(CNC(=O)OC(C)(C)C)CC1 NXFJYRUCPDHCSA-UHFFFAOYSA-N 0.000 description 1
- HSYPVXMFPNQEIT-UHFFFAOYSA-N tert-butyl n-[[1-[3-[[3-cyclohexyl-1-(hydroxyamino)-1-oxopropan-2-yl]-(4-methoxyphenyl)sulfonylamino]propanoyl]piperidin-4-yl]methyl]carbamate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC1CCCCC1)C(=O)NO)CCC(=O)N1CCC(CNC(=O)OC(C)(C)C)CC1 HSYPVXMFPNQEIT-UHFFFAOYSA-N 0.000 description 1
- KTJOZDBANQOLHP-UHFFFAOYSA-N tert-butyl-(3-iodopropoxy)-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCCI KTJOZDBANQOLHP-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- FKPIQXKEFGLMNA-UHFFFAOYSA-N trimethyl-[2-(2-trimethylsilylethoxy)ethyl]silane Chemical compound C[Si](C)(C)CCOCC[Si](C)(C)C FKPIQXKEFGLMNA-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 230000006433 tumor necrosis factor production Effects 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
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- 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
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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
- A61P1/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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
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- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2467596P | 1996-08-23 | 1996-08-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9701078A0 AP9701078A0 (en) | 1997-10-31 |
| AP733A true AP733A (en) | 1999-02-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1997/001078A AP733A (en) | 1996-08-23 | 1997-08-21 | Arylsulfonylamino hydroxamic acid derivatives. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6153609A (is) |
| EP (1) | EP0922030A1 (is) |
| JP (1) | JP2000501423A (is) |
| KR (1) | KR20000068248A (is) |
| CN (1) | CN1228083A (is) |
| AP (1) | AP733A (is) |
| AR (1) | AR009292A1 (is) |
| AU (1) | AU711585B2 (is) |
| BG (1) | BG103191A (is) |
| BR (1) | BR9711223A (is) |
| CA (1) | CA2264284A1 (is) |
| CO (1) | CO4600003A1 (is) |
| EA (1) | EA199900139A1 (is) |
| GT (1) | GT199700094A (is) |
| HN (1) | HN1997000110A (is) |
| HR (1) | HRP970453A2 (is) |
| ID (1) | ID18063A (is) |
| IL (1) | IL128189A0 (is) |
| IS (1) | IS4958A (is) |
| MA (1) | MA24307A1 (is) |
| NO (1) | NO990821L (is) |
| OA (1) | OA10978A (is) |
| PA (1) | PA8435301A1 (is) |
| PE (1) | PE99698A1 (is) |
| PL (1) | PL331895A1 (is) |
| SK (1) | SK21499A3 (is) |
| TN (1) | TNSN97139A1 (is) |
| TR (1) | TR199900387T2 (is) |
| TW (1) | TW397823B (is) |
| WO (1) | WO1998007697A1 (is) |
| ZA (1) | ZA977561B (is) |
Families Citing this family (317)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6500948B1 (en) | 1995-12-08 | 2002-12-31 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors-compositions, uses preparation and intermediates thereof |
| IL124559A (en) * | 1995-12-08 | 2004-07-25 | Agouron Pharma | Inhibitors of metalloproteinases, pharmaceutical preparations containing them and their use |
| 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 |
| US5985900A (en) * | 1997-04-01 | 1999-11-16 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| WO1998050348A1 (en) * | 1997-05-09 | 1998-11-12 | Agouron Pharmaceuticals, Inc. | Metalloproteinase inhibitors, pharmaceutical compositions containing them and their pharmaceutical uses |
| AUPO721997A0 (en) * | 1997-06-06 | 1997-07-03 | Queensland Institute Of Medical Research, The | Anticancer compounds |
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| EP0606046A1 (en) * | 1993-01-06 | 1994-07-13 | Ciba-Geigy Ag | Arylsulfonamido-substituted hydroxamic acids |
| WO1996000214A1 (en) * | 1994-06-24 | 1996-01-04 | Ciba-Geigy Ag | Arylsulfonamido-substituted hydroxamic acids as matrix metalloproteinase inhibitors |
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| GB8827305D0 (en) * | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| ES2133785T3 (es) * | 1994-06-22 | 1999-09-16 | British Biotech Pharm | Inhibidores de metaloproteinasas. |
| US5863949A (en) * | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| CN1198096A (zh) * | 1995-08-08 | 1998-11-04 | 菲布洛根有限公司 | 用于治疗与胶原蛋白过量产生有关的疾病的c-蛋白酶抑制剂 |
| US5994351A (en) * | 1998-07-27 | 1999-11-30 | Pfizer Inc. | Arylsulfonylamino hydroxamic acid derivatives |
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1997
- 1997-07-25 PL PL97331895A patent/PL331895A1/xx unknown
- 1997-07-25 IL IL12818997A patent/IL128189A0/xx unknown
- 1997-07-25 TR TR1999/00387T patent/TR199900387T2/xx unknown
- 1997-07-25 KR KR1019997001383A patent/KR20000068248A/ko not_active Ceased
- 1997-07-25 CN CN97197354A patent/CN1228083A/zh active Pending
- 1997-07-25 WO PCT/IB1997/000924 patent/WO1998007697A1/en not_active Ceased
- 1997-07-25 US US09/242,504 patent/US6153609A/en not_active Expired - Fee Related
- 1997-07-25 AU AU34563/97A patent/AU711585B2/en not_active Ceased
- 1997-07-25 BR BR9711223A patent/BR9711223A/pt unknown
- 1997-07-25 EA EA199900139A patent/EA199900139A1/ru unknown
- 1997-07-25 JP JP10510535A patent/JP2000501423A/ja active Pending
- 1997-07-25 EP EP97930699A patent/EP0922030A1/en not_active Withdrawn
- 1997-07-25 CA CA002264284A patent/CA2264284A1/en not_active Abandoned
- 1997-07-25 SK SK214-99A patent/SK21499A3/sk unknown
- 1997-08-06 PA PA19978435301A patent/PA8435301A1/es unknown
- 1997-08-18 PE PE1997000727A patent/PE99698A1/es not_active Application Discontinuation
- 1997-08-19 GT GT199700094A patent/GT199700094A/es unknown
- 1997-08-20 TN TNTNSN97139A patent/TNSN97139A1/fr unknown
- 1997-08-20 TW TW086112058A patent/TW397823B/zh active
- 1997-08-21 MA MA24774A patent/MA24307A1/fr unknown
- 1997-08-21 AP APAP/P/1997/001078A patent/AP733A/en active
- 1997-08-21 ID IDP972918A patent/ID18063A/id unknown
- 1997-08-21 CO CO97048269A patent/CO4600003A1/es unknown
- 1997-08-21 AR ARP970103803A patent/AR009292A1/es unknown
- 1997-08-22 ZA ZA977561A patent/ZA977561B/xx unknown
- 1997-08-22 HR HR60/024,675A patent/HRP970453A2/hr not_active Application Discontinuation
- 1997-08-30 HN HN1997000110A patent/HN1997000110A/es unknown
-
1999
- 1999-01-26 IS IS4958A patent/IS4958A/is unknown
- 1999-02-19 OA OA9900036A patent/OA10978A/en unknown
- 1999-02-22 NO NO990821A patent/NO990821L/no not_active Application Discontinuation
- 1999-02-22 BG BG103191A patent/BG103191A/xx unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0606046A1 (en) * | 1993-01-06 | 1994-07-13 | Ciba-Geigy Ag | Arylsulfonamido-substituted hydroxamic acids |
| 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 |
|---|---|
| EP0922030A1 (en) | 1999-06-16 |
| MA24307A1 (fr) | 1998-04-01 |
| AP9701078A0 (en) | 1997-10-31 |
| GT199700094A (es) | 1999-02-10 |
| NO990821D0 (no) | 1999-02-22 |
| TR199900387T2 (xx) | 1999-04-21 |
| BG103191A (en) | 1999-11-30 |
| HN1997000110A (es) | 1998-02-26 |
| EA199900139A1 (ru) | 1999-08-26 |
| US6153609A (en) | 2000-11-28 |
| AR009292A1 (es) | 2000-04-12 |
| CO4600003A1 (es) | 1998-05-08 |
| OA10978A (en) | 2001-11-05 |
| PE99698A1 (es) | 1998-12-26 |
| SK21499A3 (en) | 2000-05-16 |
| HRP970453A2 (en) | 1998-08-31 |
| KR20000068248A (ko) | 2000-11-25 |
| PA8435301A1 (es) | 1999-12-27 |
| JP2000501423A (ja) | 2000-02-08 |
| AU3456397A (en) | 1998-03-06 |
| AU711585B2 (en) | 1999-10-14 |
| IS4958A (is) | 1999-01-26 |
| IL128189A0 (en) | 1999-11-30 |
| CN1228083A (zh) | 1999-09-08 |
| WO1998007697A1 (en) | 1998-02-26 |
| ZA977561B (en) | 1999-02-22 |
| TW397823B (en) | 2000-07-11 |
| ID18063A (id) | 1998-02-26 |
| PL331895A1 (en) | 1999-08-16 |
| BR9711223A (pt) | 1999-08-17 |
| TNSN97139A1 (fr) | 2005-03-15 |
| CA2264284A1 (en) | 1998-02-26 |
| NO990821L (no) | 1999-02-23 |
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