CA2233560C - Inhibiteurs de metalloprotineases matricielles a base de sulfamide - Google Patents
Inhibiteurs de metalloprotineases matricielles a base de sulfamide Download PDFInfo
- Publication number
- CA2233560C CA2233560C CA002233560A CA2233560A CA2233560C CA 2233560 C CA2233560 C CA 2233560C CA 002233560 A CA002233560 A CA 002233560A CA 2233560 A CA2233560 A CA 2233560A CA 2233560 C CA2233560 C CA 2233560C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- compound
- benzenesulfonylamino
- piperidin
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 28
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 28
- 229940124530 sulfonamide Drugs 0.000 title abstract description 21
- 239000003112 inhibitor Substances 0.000 title abstract description 11
- 150000003456 sulfonamides Chemical class 0.000 title description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- -1 Sulfonamide compounds Chemical class 0.000 claims abstract description 68
- 102000000422 Matrix Metalloproteinase 3 Human genes 0.000 claims abstract description 25
- 208000025865 Ulcer Diseases 0.000 claims abstract description 25
- 231100000397 ulcer Toxicity 0.000 claims abstract description 25
- 102000000424 Matrix Metalloproteinase 2 Human genes 0.000 claims abstract description 22
- 108010016165 Matrix Metalloproteinase 2 Proteins 0.000 claims abstract description 22
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 108010016160 Matrix Metalloproteinase 3 Proteins 0.000 claims abstract description 18
- 201000011510 cancer Diseases 0.000 claims abstract description 17
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 16
- 230000001419 dependent effect Effects 0.000 claims abstract description 15
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 14
- 206010052428 Wound Diseases 0.000 claims abstract description 14
- 206010003246 arthritis Diseases 0.000 claims abstract description 14
- 230000001363 autoimmune Effects 0.000 claims abstract description 14
- 230000001684 chronic effect Effects 0.000 claims abstract description 14
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 14
- 230000009545 invasion Effects 0.000 claims abstract description 14
- 210000000265 leukocyte Anatomy 0.000 claims abstract description 14
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 14
- 208000037803 restenosis Diseases 0.000 claims abstract description 13
- 208000028169 periodontal disease Diseases 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000011734 sodium Chemical class 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000002399 angioplasty Methods 0.000 claims description 7
- 238000002513 implantation Methods 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- ZQXYDSXOIXNPBN-RUZDIDTESA-N (2r)-3-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C1=CC=CC=C1 ZQXYDSXOIXNPBN-RUZDIDTESA-N 0.000 claims description 3
- HEABEIGWLYMIBY-JOCHJYFZSA-N (2r)-4-methyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@H](CC(C)C)C(O)=O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 HEABEIGWLYMIBY-JOCHJYFZSA-N 0.000 claims description 3
- WKLSCPMFMSEKHJ-VWLOTQADSA-N (2s)-2-[[4-[4-(3-methoxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(N2CCN(CC2)C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)=C1 WKLSCPMFMSEKHJ-VWLOTQADSA-N 0.000 claims description 3
- ULOTXPTWJAUGGE-MHZLTWQESA-N (2s)-3-(1h-indol-3-yl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)S(=O)(=O)C(C=C1)=CC=C1N(CC1)CCC1C1=CC=CC=C1 ULOTXPTWJAUGGE-MHZLTWQESA-N 0.000 claims description 3
- HEABEIGWLYMIBY-QFIPXVFZSA-N (2s)-4-methyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]pentanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CC(C)C)C(O)=O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 HEABEIGWLYMIBY-QFIPXVFZSA-N 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- GNSLACGSDSJAIQ-UHFFFAOYSA-N [4-(4-phenyl-piperidin-1-yl)-benzenesulfonylamino]-acetic acid Chemical group C1=CC(S(=O)(=O)NCC(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 GNSLACGSDSJAIQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- CCLNNAZFIAEPBM-IBGZPJMESA-N (2r)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]-3-sulfanylpropanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](CS)C(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 CCLNNAZFIAEPBM-IBGZPJMESA-N 0.000 claims description 2
- ULOTXPTWJAUGGE-HHHXNRCGSA-N (2r)-3-(1h-indol-3-yl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound N([C@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)S(=O)(=O)C(C=C1)=CC=C1N(CC1)CCC1C1=CC=CC=C1 ULOTXPTWJAUGGE-HHHXNRCGSA-N 0.000 claims description 2
- DIMHQAITVXMHMQ-SANMLTNESA-N (2s)-2-[[4-(4-benzylpiperidin-1-yl)phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC=2C=CC=CC=2)CC1)C1=CC=CC=C1 DIMHQAITVXMHMQ-SANMLTNESA-N 0.000 claims description 2
- ADRXVXDGDFNWTL-JIDHJSLPSA-N (2s)-2-[[4-[4-(3-hydroxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid;hydrobromide Chemical compound Br.C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=C(O)C=CC=1)C1=CC=CC=C1 ADRXVXDGDFNWTL-JIDHJSLPSA-N 0.000 claims description 2
- HTOYWGIWQZQPSR-DEOSSOPVSA-N (2s)-2-[[4-[4-(4-chlorophenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 HTOYWGIWQZQPSR-DEOSSOPVSA-N 0.000 claims description 2
- PNCLRHJDVNOKGF-DEOSSOPVSA-N (2s)-2-[[4-[4-(4-hydroxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=CC(O)=CC=1)C1=CC=CC=C1 PNCLRHJDVNOKGF-DEOSSOPVSA-N 0.000 claims description 2
- PGXLAZACGSXLAI-VWLOTQADSA-N (2s)-2-[[4-[4-(4-methoxyphenyl)piperazin-1-yl]phenyl]sulfonylamino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(=CC=2)S(=O)(=O)N[C@@H](CC=2C=CC=CC=2)C(O)=O)CC1 PGXLAZACGSXLAI-VWLOTQADSA-N 0.000 claims description 2
- NSACXBTYAXSYCE-VWLOTQADSA-N (2s)-3-(4-hydroxyphenyl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C1=CC=C(O)C=C1 NSACXBTYAXSYCE-VWLOTQADSA-N 0.000 claims description 2
- IPPBZBAQYUONQO-YTTGMZPUSA-N (2s)-3-(4-phenylmethoxyphenyl)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 IPPBZBAQYUONQO-YTTGMZPUSA-N 0.000 claims description 2
- UBSXVJZNZIPKCM-DEOSSOPVSA-N (2s)-3-phenyl-2-[[4-(4-phenylpiperazin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCN(CC1)C=1C=CC=CC=1)C1=CC=CC=C1 UBSXVJZNZIPKCM-DEOSSOPVSA-N 0.000 claims description 2
- ZQXYDSXOIXNPBN-VWLOTQADSA-N (2s)-3-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)C1=CC=CC=C1 ZQXYDSXOIXNPBN-VWLOTQADSA-N 0.000 claims description 2
- SMCUDZWBQOPQEA-SANMLTNESA-N (2s)-4-phenyl-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]butanoic acid Chemical class C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)CC1=CC=CC=C1 SMCUDZWBQOPQEA-SANMLTNESA-N 0.000 claims description 2
- UXRQPYBOLVQYQD-UHFFFAOYSA-N 2-[2-methylpropyl-[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]acetic acid Chemical class C1=CC(S(=O)(=O)N(CC(O)=O)CC(C)C)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 UXRQPYBOLVQYQD-UHFFFAOYSA-N 0.000 claims description 2
- SQTBYARBJNHGQJ-UHFFFAOYSA-N 2-[[4-(4-phenylpiperazin-1-yl)phenyl]sulfonylamino]acetic acid Chemical class C1=CC(S(=O)(=O)NCC(=O)O)=CC=C1N1CCN(C=2C=CC=CC=2)CC1 SQTBYARBJNHGQJ-UHFFFAOYSA-N 0.000 claims description 2
- RDUOXXVFDHHAPP-UHFFFAOYSA-N 3-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]propanoic acid Chemical compound C1=CC(S(=O)(=O)NCCC(=O)O)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 RDUOXXVFDHHAPP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004682 monohydrates Chemical class 0.000 claims description 2
- XTZSTNYJRISMQA-UHFFFAOYSA-N n-hydroxy-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]acetamide Chemical compound C1=CC(S(=O)(=O)NCC(=O)NO)=CC=C1N1CCC(C=2C=CC=CC=2)CC1 XTZSTNYJRISMQA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- XHTVHWPJPDRGQI-QNGWXLTQSA-N (2r)-2-[[4-(4-phenylpiperidin-1-yl)phenyl]sulfonylamino]-3-tritylsulfanylpropanoic acid Chemical class C([C@@H](C(=O)O)NS(=O)(=O)C=1C=CC(=CC=1)N1CCC(CC1)C=1C=CC=CC=1)SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XHTVHWPJPDRGQI-QNGWXLTQSA-N 0.000 claims 1
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 46
- 206010019280 Heart failures Diseases 0.000 abstract description 9
- 206010064996 Ulcerative keratitis Diseases 0.000 abstract description 5
- 102000013382 Gelatinases Human genes 0.000 abstract description 4
- 108010026132 Gelatinases Proteins 0.000 abstract description 4
- 206010027476 Metastases Diseases 0.000 abstract description 4
- 230000009401 metastasis Effects 0.000 abstract description 4
- 230000005747 tumor angiogenesis Effects 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 239000002253 acid Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 239000007787 solid Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 31
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 229910000029 sodium carbonate Inorganic materials 0.000 description 18
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- 239000000243 solution Substances 0.000 description 15
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- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
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- 239000002775 capsule Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 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
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 238000007805 zymography Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
L'invention a trait à des composés de sulfamide, inhibiteurs de métalloprotinéases matricielles, notamment la stromélysine-1 et la gélatinase A (gélatinase de 72 kD). Elle concerne également des méthodes faisant appel à ces composés pour le traitement de la sclérose en plaques, de la rupture de la plaque athéroscléreuse, de l'anévrisme aortique, de l'insuffisance cardiaque, de la resténose, de la parodontopathie, de l'ulcération cornéenne, des brûlures, des ulcères du décubitus, d'ulcères chroniques ou de lésions, de métastases cancéreuses, de l'angiogénèse tumorale, de l'arthrite ou d'autres affections auto-immunes ou inflammatoires liées à une invasion leucocytaire des tissus.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US737295P | 1995-11-17 | 1995-11-17 | |
| US60/007,372 | 1995-11-17 | ||
| PCT/US1996/016761 WO1997019068A1 (fr) | 1995-11-17 | 1996-10-18 | Inhibiteurs de metalloprotineases matricielles a base de sulfamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2233560A1 CA2233560A1 (fr) | 1997-05-29 |
| CA2233560C true CA2233560C (fr) | 2005-12-20 |
Family
ID=35645828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002233560A Expired - Fee Related CA2233560C (fr) | 1995-11-17 | 1996-10-18 | Inhibiteurs de metalloprotineases matricielles a base de sulfamide |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2233560C (fr) |
-
1996
- 1996-10-18 CA CA002233560A patent/CA2233560C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2233560A1 (fr) | 1997-05-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |