KR20000068415A - 매트릭스 메탈로프로테이나제 억제용 화합물 및 방법 - Google Patents
매트릭스 메탈로프로테이나제 억제용 화합물 및 방법 Download PDFInfo
- Publication number
- KR20000068415A KR20000068415A KR1019997001757A KR19997001757A KR20000068415A KR 20000068415 A KR20000068415 A KR 20000068415A KR 1019997001757 A KR1019997001757 A KR 1019997001757A KR 19997001757 A KR19997001757 A KR 19997001757A KR 20000068415 A KR20000068415 A KR 20000068415A
- Authority
- KR
- South Korea
- Prior art keywords
- dibenzofuran
- sulfonylamino
- acid
- phenyl
- hexanoic 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 115
- 238000000034 method Methods 0.000 title claims abstract description 52
- 102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 38
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 38
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 5
- 150000001413 amino acids Chemical class 0.000 claims abstract description 18
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 15
- 201000011510 cancer Diseases 0.000 claims abstract description 14
- 208000037260 Atherosclerotic Plaque Diseases 0.000 claims abstract description 12
- 206010019280 Heart failures Diseases 0.000 claims abstract description 12
- 206010052428 Wound Diseases 0.000 claims abstract description 10
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 10
- 206010003246 arthritis Diseases 0.000 claims abstract description 10
- 230000001684 chronic effect Effects 0.000 claims abstract description 10
- 208000025865 Ulcer Diseases 0.000 claims abstract description 9
- 208000007474 aortic aneurysm Diseases 0.000 claims abstract description 9
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
- 210000000265 leukocyte Anatomy 0.000 claims abstract description 9
- 230000005747 tumor angiogenesis Effects 0.000 claims abstract description 9
- 231100000397 ulcer Toxicity 0.000 claims abstract description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 8
- 206010027476 Metastases Diseases 0.000 claims abstract description 8
- 208000004210 Pressure Ulcer Diseases 0.000 claims abstract description 8
- 230000001363 autoimmune Effects 0.000 claims abstract description 8
- 201000007717 corneal ulcer Diseases 0.000 claims abstract description 8
- 230000009545 invasion Effects 0.000 claims abstract description 8
- 230000009401 metastasis Effects 0.000 claims abstract description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 8
- 208000028169 periodontal disease Diseases 0.000 claims abstract description 8
- 208000037803 restenosis Diseases 0.000 claims abstract description 8
- 206010064996 Ulcerative keratitis Diseases 0.000 claims abstract description 6
- 206010011985 Decubitus ulcer Diseases 0.000 claims abstract description 4
- -1 6- (2-cyclopent-1-enyl-acetylamino) -2- (dibenzofuran-2-sulfonylamino) -hexanoic acid Chemical compound 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229940024606 amino acid Drugs 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YPOJAHGDLHWILP-IBGZPJMESA-N (2s)-2-(dibenzofuran-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C([C@@H](C(=O)O)NS(=O)(=O)C=1C=C2C3=CC=CC=C3OC2=CC=1)CC1=CC=CC=C1 YPOJAHGDLHWILP-IBGZPJMESA-N 0.000 claims description 3
- XDLSSXYTUMNOHY-AWEZNQCLSA-N (3s)-3-[(dibenzofuran-2-ylsulfonylamino)methyl]-5-methylhexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC[C@@H](CC(C)C)CC(O)=O)=CC=C3OC2=C1 XDLSSXYTUMNOHY-AWEZNQCLSA-N 0.000 claims description 3
- JENZVHXFRQGOFL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-2-phenylacetic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)C1=CC=CC=C1 JENZVHXFRQGOFL-UHFFFAOYSA-N 0.000 claims description 3
- SJPXJSANXSAHSU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-(4-fluorophenyl)propanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CC1=CC=C(F)C=C1 SJPXJSANXSAHSU-UHFFFAOYSA-N 0.000 claims description 3
- COJSFTGHLOFDLF-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid Chemical compound C1=CC(OC(C)(C)C)=CC=C1CC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 COJSFTGHLOFDLF-UHFFFAOYSA-N 0.000 claims description 3
- SDUOASNEYVEUJP-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-3-phenylmethoxypropanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)COCC1=CC=CC=C1 SDUOASNEYVEUJP-UHFFFAOYSA-N 0.000 claims description 3
- CHJPBQOZZLPRAI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-oxo-4-(4-propylphenyl)butanoic acid Chemical compound C1=CC(CCC)=CC=C1C(=O)CC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 CHJPBQOZZLPRAI-UHFFFAOYSA-N 0.000 claims description 3
- YPOJAHGDLHWILP-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-4-phenylbutanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC1=CC=CC=C1 YPOJAHGDLHWILP-UHFFFAOYSA-N 0.000 claims description 3
- SRZSAFSUWTXQMW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(2,2-diphenylethylamino)-5-oxopentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCC(C=1C=CC=CC=1)C1=CC=CC=C1 SRZSAFSUWTXQMW-UHFFFAOYSA-N 0.000 claims description 3
- LRTMILMJYXVICS-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(2-hydroxypropylamino)-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NCC(O)C)C(O)=O)=CC=C3OC2=C1 LRTMILMJYXVICS-UHFFFAOYSA-N 0.000 claims description 3
- AKGOCXPAZXSPOW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(2-methylbutylamino)-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NCC(C)CC)C(O)=O)=CC=C3OC2=C1 AKGOCXPAZXSPOW-UHFFFAOYSA-N 0.000 claims description 3
- MTRHSROQRITLBQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(4-methylpentan-2-ylamino)-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NC(C)CC(C)C)C(O)=O)=CC=C3OC2=C1 MTRHSROQRITLBQ-UHFFFAOYSA-N 0.000 claims description 3
- DMQDCKWVHYQISX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCNC(=O)OCC1=CC=CC=C1 DMQDCKWVHYQISX-UHFFFAOYSA-N 0.000 claims description 3
- WGWURNSXKJRMJU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[(2-methoxyphenyl)methylamino]-5-oxopentanoic acid Chemical compound COC1=CC=CC=C1CNC(=O)CCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 WGWURNSXKJRMJU-UHFFFAOYSA-N 0.000 claims description 3
- PUWFHONXMCBSPN-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[(4-methylphenyl)sulfonylamino]pentanoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 PUWFHONXMCBSPN-UHFFFAOYSA-N 0.000 claims description 3
- RKWQDCZIHNOUDQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[2-(1-methylpyrrol-2-yl)ethylamino]-5-oxopentanoic acid Chemical compound CN1C=CC=C1CCNC(=O)CCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 RKWQDCZIHNOUDQ-UHFFFAOYSA-N 0.000 claims description 3
- HDXHPZRRHOAZES-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-[2-(dimethylamino)ethylamino]-5-oxopentanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCC(=O)NCCN(C)C)C(O)=O)=CC=C3OC2=C1 HDXHPZRRHOAZES-UHFFFAOYSA-N 0.000 claims description 3
- HDHGKKSSTJLVPS-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(2-phenylethylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCCC1=CC=CC=C1 HDHGKKSSTJLVPS-UHFFFAOYSA-N 0.000 claims description 3
- OGJYDFVQYYKOEE-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(2-pyridin-4-ylethylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCCC1=CC=NC=C1 OGJYDFVQYYKOEE-UHFFFAOYSA-N 0.000 claims description 3
- ZLNOARBTWFZMLC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(2-thiophen-2-ylethylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCCC1=CC=CS1 ZLNOARBTWFZMLC-UHFFFAOYSA-N 0.000 claims description 3
- ZWEPYHCGARNIDW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(4-phenylbutylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCCCCC1=CC=CC=C1 ZWEPYHCGARNIDW-UHFFFAOYSA-N 0.000 claims description 3
- CQOICWRPIYBULF-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(4-propylanilino)pentanoic acid Chemical compound C1=CC(CCC)=CC=C1NC(=O)CCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 CQOICWRPIYBULF-UHFFFAOYSA-N 0.000 claims description 3
- IEZZTTCMBWIYEC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-5-oxo-5-(thiophen-2-ylmethylamino)pentanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCC(=O)NCC1=CC=CS1 IEZZTTCMBWIYEC-UHFFFAOYSA-N 0.000 claims description 3
- KTBUWUJBOXSXNR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-methylpropoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)OCC(C)C)C(O)=O)=CC=C3OC2=C1 KTBUWUJBOXSXNR-UHFFFAOYSA-N 0.000 claims description 3
- YEPAWRGTEBVAEZ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenoxybutanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(O)=O)CCCCNC(=O)C(CC)OC1=CC=CC=C1 YEPAWRGTEBVAEZ-UHFFFAOYSA-N 0.000 claims description 3
- NRXAXCZPWVAPDR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenylbutanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(O)=O)CCCCNC(=O)C(CC)C1=CC=CC=C1 NRXAXCZPWVAPDR-UHFFFAOYSA-N 0.000 claims description 3
- KJFFSAMWNSAFLX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(2-phenylethenylsulfonylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C=CC1=CC=CC=C1 KJFFSAMWNSAFLX-UHFFFAOYSA-N 0.000 claims description 3
- VMMQXFIQQBCZEK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3,3,3-triphenylpropanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VMMQXFIQQBCZEK-UHFFFAOYSA-N 0.000 claims description 3
- YXCUPVJSRBXQQZ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-phenylprop-2-enoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)C=CC1=CC=CC=C1 YXCUPVJSRBXQQZ-UHFFFAOYSA-N 0.000 claims description 3
- GPSMOFOMKBFFPD-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-phenylpropanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCC1=CC=CC=C1 GPSMOFOMKBFFPD-UHFFFAOYSA-N 0.000 claims description 3
- OOWMSOXRLQBHJU-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(3-pyridin-4-ylpropanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCC1=CC=NC=C1 OOWMSOXRLQBHJU-UHFFFAOYSA-N 0.000 claims description 3
- UUJPYVXIRFHAFR-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(4-thiophen-2-ylbutanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCC1=CC=CS1 UUJPYVXIRFHAFR-UHFFFAOYSA-N 0.000 claims description 3
- WMSIPIBCOFPIEL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(6-phenylhexanoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCCCC1=CC=CC=C1 WMSIPIBCOFPIEL-UHFFFAOYSA-N 0.000 claims description 3
- MKGITNAOWOTDLE-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(9h-fluoren-9-ylmethoxycarbonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)OCC4C5=CC=CC=C5C5=CC=CC=C54)C(=O)O)=CC=C3OC2=C1 MKGITNAOWOTDLE-UHFFFAOYSA-N 0.000 claims description 3
- LUGWBOODZQKESV-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(naphthalen-1-ylsulfonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)C(=O)O)=CC=C3OC2=C1 LUGWBOODZQKESV-UHFFFAOYSA-N 0.000 claims description 3
- JQMYQNYDESVNOP-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(naphthalen-2-ylcarbamothioylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=S)NC=4C=C5C=CC=CC5=CC=4)C(=O)O)=CC=C3OC2=C1 JQMYQNYDESVNOP-UHFFFAOYSA-N 0.000 claims description 3
- RNSICHYXRFBCKS-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(naphthalen-2-ylsulfonylamino)hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNS(=O)(=O)C=4C=C5C=CC=CC5=CC=4)C(=O)O)=CC=C3OC2=C1 RNSICHYXRFBCKS-UHFFFAOYSA-N 0.000 claims description 3
- MVDDWKMEAQHMRK-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(phenylcarbamoylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)NC1=CC=CC=C1 MVDDWKMEAQHMRK-UHFFFAOYSA-N 0.000 claims description 3
- CPAXWZYVQBSDOD-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)OCC1=CC=CC=C1 CPAXWZYVQBSDOD-UHFFFAOYSA-N 0.000 claims description 3
- ALMQENWFOJJCQE-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-(pyridin-3-ylcarbamothioylamino)hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=S)NC1=CC=CN=C1 ALMQENWFOJJCQE-UHFFFAOYSA-N 0.000 claims description 3
- IKAUYSNMEWLNGX-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(1-phenylcyclopropanecarbonyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)C1(C=2C=CC=CC=2)CC1 IKAUYSNMEWLNGX-UHFFFAOYSA-N 0.000 claims description 3
- FZOUYLLHFHPZDI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-naphthalen-1-yloxyacetyl)amino]hexanoic acid Chemical compound C1=CC=C2C3=CC(S(=O)(=O)NC(CCCCNC(=O)COC=4C5=CC=CC=C5C=CC=4)C(=O)O)=CC=C3OC2=C1 FZOUYLLHFHPZDI-UHFFFAOYSA-N 0.000 claims description 3
- HOSXXBOASBEGAM-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-phenoxyacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)COC1=CC=CC=C1 HOSXXBOASBEGAM-UHFFFAOYSA-N 0.000 claims description 3
- HMHKHUNQFYTFFA-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-phenylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=C1 HMHKHUNQFYTFFA-UHFFFAOYSA-N 0.000 claims description 3
- SNDIGWWLXHMQSH-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-2-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=N1 SNDIGWWLXHMQSH-UHFFFAOYSA-N 0.000 claims description 3
- ATAVAGZOGOKAAC-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-3-ylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CN=C1 ATAVAGZOGOKAAC-UHFFFAOYSA-N 0.000 claims description 3
- JKSGPZSPMJSVPL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(2-pyridin-4-ylsulfanylacetyl)amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CSC1=CC=NC=C1 JKSGPZSPMJSVPL-UHFFFAOYSA-N 0.000 claims description 3
- NRJXEHVDVCJWFL-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(3,4-dichlorophenyl)carbamoylamino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)NC1=CC=C(Cl)C(Cl)=C1 NRJXEHVDVCJWFL-UHFFFAOYSA-N 0.000 claims description 3
- RXOISJMDLIMNAM-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(4-fluorophenyl)sulfonylamino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNS(=O)(=O)C1=CC=C(F)C=C1 RXOISJMDLIMNAM-UHFFFAOYSA-N 0.000 claims description 3
- CLAMRBVWUQQDAY-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(4-methoxyphenyl)carbamoylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1NC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 CLAMRBVWUQQDAY-UHFFFAOYSA-N 0.000 claims description 3
- NNIRCQIXFDXRIO-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[(4-methoxyphenyl)sulfonylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 NNIRCQIXFDXRIO-UHFFFAOYSA-N 0.000 claims description 3
- DWHWANYQSULZPQ-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(2-methoxyphenyl)propanoylamino]hexanoic acid Chemical compound COC1=CC=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 DWHWANYQSULZPQ-UHFFFAOYSA-N 0.000 claims description 3
- JAVKOMHYDZLWAO-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[3-(3,4-dimethoxyphenyl)propanoylamino]hexanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CCC(=O)NCCCCC(C(O)=O)NS(=O)(=O)C1=CC=C(OC=2C3=CC=CC=2)C3=C1 JAVKOMHYDZLWAO-UHFFFAOYSA-N 0.000 claims description 3
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- ISYGRERUFBRMRI-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[4-(4-nitrophenyl)butanoylamino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CCCC1=CC=C([N+]([O-])=O)C=C1 ISYGRERUFBRMRI-UHFFFAOYSA-N 0.000 claims description 3
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- CQPZMQSGTMCLLW-UHFFFAOYSA-N 2-(dibenzofuran-2-ylsulfonylamino)-6-[[2-(2-phenylmethoxyphenyl)acetyl]amino]hexanoic acid Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1S(=O)(=O)NC(C(=O)O)CCCCNC(=O)CC1=CC=CC=C1OCC1=CC=CC=C1 CQPZMQSGTMCLLW-UHFFFAOYSA-N 0.000 claims description 3
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- 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
- 239000004317 sodium nitrate Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 210000001215 vagina Anatomy 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 238000007805 zymography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2506396P | 1996-09-04 | 1996-09-04 | |
| US60/025,063 | 1996-09-04 | ||
| US5571497P | 1997-08-07 | 1997-08-07 | |
| US60/055,714 | 1997-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20000068415A true KR20000068415A (ko) | 2000-11-25 |
Family
ID=26699217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997001757A Abandoned KR20000068415A (ko) | 1996-09-04 | 1997-09-02 | 매트릭스 메탈로프로테이나제 억제용 화합물 및 방법 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6294674B1 (enExample) |
| EP (1) | EP0929542A1 (enExample) |
| JP (1) | JP2002514180A (enExample) |
| KR (1) | KR20000068415A (enExample) |
| AU (1) | AU736347B2 (enExample) |
| BR (1) | BR9712794A (enExample) |
| CA (1) | CA2256631A1 (enExample) |
| HR (1) | HRP970474B1 (enExample) |
| NZ (1) | NZ333064A (enExample) |
| WO (1) | WO1998009957A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU226006B1 (en) * | 1996-01-23 | 2008-02-28 | Shionogi & Co | Thiophene-sulfonylamino carboxylic and hidroxamic acid derivatives and pharmaceutical compositions with metalloproteinase inhibitory activity containing the same |
| US6919375B1 (en) | 1996-01-23 | 2005-07-19 | Shionogi & Co., Ltd. | Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same |
| NZ334897A (en) * | 1996-12-09 | 2001-02-23 | Warner Lambert Co | Medicaments for treating and preventing heart failure and ventricular dilatation |
| WO2000006560A1 (en) * | 1998-07-30 | 2000-02-10 | Warner-Lambert Company | Tricyclic heteroaromatics and their derivatives as inhibitors of matrix metalloproteinases |
| SK1192001A3 (en) * | 1998-07-30 | 2002-02-05 | Warner Lambert Co | Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases |
| AU5647099A (en) * | 1998-09-11 | 2000-04-03 | Shionogi & Co., Ltd. | Remedal or preventive agent for congestive heart failure |
| SK14852002A3 (sk) * | 2000-03-27 | 2003-06-03 | The Scripps Research Institute | Spôsoby inhibície angiogenézy a rastu tumoru |
| GB2365425A (en) * | 2000-08-01 | 2002-02-20 | Parke Davis & Co Ltd | Alkyl amino acid derivatives useful as pharmaceutical agents |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US20030129672A1 (en) * | 2001-08-29 | 2003-07-10 | Dyer Richard Dennis | Method for identifying metalloenzyme inhibitors |
| PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| JP2006516548A (ja) | 2002-12-30 | 2006-07-06 | アンジオテック インターナショナル アクツィエン ゲゼルシャフト | 迅速ゲル化ポリマー組成物からの薬物送達法 |
| CN1318411C (zh) * | 2005-03-21 | 2007-05-30 | 中国海洋大学 | 氢化轮枝霉酮类化合物及其制备方法和用途 |
| WO2007079199A2 (en) * | 2005-12-30 | 2007-07-12 | Alantos Pharmaceuticals, Holding, Inc. | Substituted bis-amide metalloprotease inhibitors |
| JP2010507674A (ja) * | 2006-10-27 | 2010-03-11 | ワイス エルエルシー | マトリクスメタロプロテアーゼ阻害剤としての三環式化合物 |
| GB0621973D0 (en) * | 2006-11-03 | 2006-12-13 | Philogen Spa | Binding molecules and uses thereof |
| AR066412A1 (es) * | 2007-05-04 | 2009-08-19 | Wyeth Corp | Derivados de dibenzofurano y dibenzotiofeno, composiciones farmaceuticas que los contienen y usos en patologias tales como trastornos oseos, crecimiento de tumores, diabetes y obesidad. |
| AU2008302667B2 (en) * | 2007-06-15 | 2014-07-10 | Board Of Regents, The University Of Texas System | Methods and compositions to inhibit edema factor and adenylyl cyclase |
| JP2012051804A (ja) * | 2008-12-26 | 2012-03-15 | Kyoto Univ | Eg5阻害剤 |
| TWI854164B (zh) | 2016-02-01 | 2024-09-01 | 美商百歐克斯製藥公司 | 苯并吡唑化合物及其類似物 |
| WO2021147882A1 (zh) * | 2020-01-21 | 2021-07-29 | 深圳信立泰药业股份有限公司 | 一种二苯并呋喃类衍生物组织蛋白酶k抑制剂及其制备方法和医药用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2065966C3 (de) | 1969-09-06 | 1978-11-16 | Ajinomoto Co., Inc., Tokio | N-Fluorenyl-sulfonyl-aminocarbonsäuren sowie diese enthaltende Mittel |
| US3845097A (en) | 1969-09-06 | 1974-10-29 | Ajinomoto Kk | N-substituted amino acids and novel ester |
| US4097472A (en) | 1974-11-08 | 1978-06-27 | Mitsubishi Chemical Industries Limited | N2 -arylsulfonyl-l-argininamides and the pharmaceutically acceptable salts thereof |
| DE2236876C3 (de) * | 1971-08-19 | 1981-02-12 | Ajinomoto Co., Inc., Tokio | N-Substituierte Aminocarbonsäuren und diese Verbindungen enthaltende Arzneimittel |
| EP0183271B1 (en) * | 1984-11-30 | 1990-05-16 | Shosuke Okamoto | Lysin derivative and proteinase inhibitor |
| PH31294A (en) * | 1992-02-13 | 1998-07-06 | Thomae Gmbh Dr K | Benzimidazolyl derivatives, pharmaceutical compositions containing these compounds and process for preparing them. |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5665764A (en) | 1995-06-02 | 1997-09-09 | Warner-Lambert Company | Tricyclic inhibitors of matrix metalloproteinases |
| US5627206A (en) | 1995-06-02 | 1997-05-06 | Warner-Lambert Company | Tricyclic inhibitor of matrix metalloproteinases |
| DE69615680T2 (de) | 1995-06-02 | 2002-07-11 | Warner-Lambert Co., Morris Plains | Trizyklische verbindungen als matrix-metalloproteinase inhibitoren |
| NZ321293A (en) | 1995-11-17 | 2001-04-27 | Warner Lambert Co | Sulfonamide inhibitors of matrix metalloproteinases |
| HU226006B1 (en) * | 1996-01-23 | 2008-02-28 | Shionogi & Co | Thiophene-sulfonylamino carboxylic and hidroxamic acid derivatives and pharmaceutical compositions with metalloproteinase inhibitory activity containing the same |
| EP0931045A1 (en) | 1996-09-04 | 1999-07-28 | Warner-Lambert Company | Matrix metalloproteinase inhibitors and their therapeutic uses |
-
1997
- 1997-09-02 KR KR1019997001757A patent/KR20000068415A/ko not_active Abandoned
- 1997-09-02 AU AU41770/97A patent/AU736347B2/en not_active Ceased
- 1997-09-02 JP JP51281898A patent/JP2002514180A/ja not_active Abandoned
- 1997-09-02 NZ NZ333064A patent/NZ333064A/xx unknown
- 1997-09-02 WO PCT/US1997/015444 patent/WO1998009957A1/en not_active Ceased
- 1997-09-02 EP EP97939751A patent/EP0929542A1/en not_active Withdrawn
- 1997-09-02 US US09/254,403 patent/US6294674B1/en not_active Expired - Fee Related
- 1997-09-02 CA CA002256631A patent/CA2256631A1/en not_active Abandoned
- 1997-09-02 BR BR9712794-9A patent/BR9712794A/pt not_active Application Discontinuation
- 1997-09-04 HR HR970474A patent/HRP970474B1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2256631A1 (en) | 1998-03-12 |
| AU4177097A (en) | 1998-03-26 |
| AU736347B2 (en) | 2001-07-26 |
| EP0929542A1 (en) | 1999-07-21 |
| HRP970474B1 (en) | 2002-10-31 |
| JP2002514180A (ja) | 2002-05-14 |
| BR9712794A (pt) | 1999-12-14 |
| US6294674B1 (en) | 2001-09-25 |
| WO1998009957A1 (en) | 1998-03-12 |
| NZ333064A (en) | 2000-11-24 |
| HRP970474A2 (en) | 1998-12-31 |
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