NO314452B1 - Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater - Google Patents

Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater Download PDF

Info

Publication number: NO314452B1
Authority: NO; Norway
Prior art keywords: acid; hydroxyamide; alkyl; phenyl; phenylpentanoic
Prior art date: 1996-08-07

Application number

NO19990543A

Other languages

English (en)

Norwegian (no)

Other versions

NO990543L (no

NO990543D0 (no

Inventor

David Alan Owen

John Gary Montana

John Fraser Keily

Robert John Watson

Andrew Douglas Baxter

Original Assignee

Darwin Discovery Ltd

Priority date (The priority date 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 date listed.)

1996-08-07

Filing date

1999-02-05

Publication date

2003-03-24

1996-08-07 Priority claimed from GBGB9616599.8A external-priority patent/GB9616599D0/en

1997-04-11 Priority claimed from GBGB9707427.2A external-priority patent/GB9707427D0/en

1999-02-05 Application filed by Darwin Discovery Ltd filed Critical Darwin Discovery Ltd

1999-02-05 Publication of NO990543D0 publication Critical patent/NO990543D0/no

1999-04-06 Publication of NO990543L publication Critical patent/NO990543L/no

2003-03-24 Publication of NO314452B1 publication Critical patent/NO314452B1/no

Links

NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title claims abstract description 8
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 title abstract description 5
230000000694 effects Effects 0.000 title description 26
230000005764 inhibitory process Effects 0.000 title description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
201000010099 disease Diseases 0.000 claims abstract description 14
102000002274 Matrix Metalloproteinases Human genes 0.000 claims abstract description 12
108010000684 Matrix Metalloproteinases Proteins 0.000 claims abstract description 12
206010028980 Neoplasm Diseases 0.000 claims abstract description 9
230000001404 mediated effect Effects 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 144
-1 C1-6 alkyl-furyl Chemical group 0.000 claims description 43
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 30
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 29
125000000217 alkyl group Chemical group 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
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 18
102100040247 Tumor necrosis factor Human genes 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 17
125000005037 alkyl phenyl group Chemical group 0.000 claims description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
125000004076 pyridyl group Chemical group 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 14
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000006383 alkylpyridyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000005544 phthalimido group Chemical group 0.000 claims description 6
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims description 5
102000004190 Enzymes Human genes 0.000 claims description 5
108090000790 Enzymes Proteins 0.000 claims description 5
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
230000015556 catabolic process Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
201000006417 multiple sclerosis Diseases 0.000 claims description 3
LDHFAXJQJCDJMI-UHFFFAOYSA-N 2-(2-methylpropylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound CC(C)CS(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 LDHFAXJQJCDJMI-UHFFFAOYSA-N 0.000 claims description 2
XRDGJPMQIGBTKA-UHFFFAOYSA-N 2-(benzenesulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 XRDGJPMQIGBTKA-UHFFFAOYSA-N 0.000 claims description 2
QGTUQYNQWGAEBS-UHFFFAOYSA-N 2-(benzenesulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 QGTUQYNQWGAEBS-UHFFFAOYSA-N 0.000 claims description 2
WKJPRPPGHTXSOY-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 WKJPRPPGHTXSOY-UHFFFAOYSA-N 0.000 claims description 2
DGPNURFBITXCMQ-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1CS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 DGPNURFBITXCMQ-UHFFFAOYSA-N 0.000 claims description 2
TUWPGTXCEXYISO-UHFFFAOYSA-N 2-(cyclopentylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C1CCCC1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 TUWPGTXCEXYISO-UHFFFAOYSA-N 0.000 claims description 2
LEIHFCIHIPZCEU-UHFFFAOYSA-N 2-(furan-2-ylmethylsulfonylmethyl)-5-phenylpentanoic acid Chemical compound C=1C=COC=1CS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 LEIHFCIHIPZCEU-UHFFFAOYSA-N 0.000 claims description 2
DBSJXSQIQXSWQQ-UHFFFAOYSA-N 2-[(1-benzoylpiperidin-4-yl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 DBSJXSQIQXSWQQ-UHFFFAOYSA-N 0.000 claims description 2
LVDKTEQDJVFFDJ-UHFFFAOYSA-N 2-[(2-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound COC1=CC=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 LVDKTEQDJVFFDJ-UHFFFAOYSA-N 0.000 claims description 2
XGDKWIGZGLKQFC-UHFFFAOYSA-N 2-[(3-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound COC1=CC=CC(S(=O)(=O)CC(CCCC=2C=CC=CC=2)C(O)=O)=C1 XGDKWIGZGLKQFC-UHFFFAOYSA-N 0.000 claims description 2
VFHDJZZCEWOUOH-UHFFFAOYSA-N 2-[(4-acetylphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 VFHDJZZCEWOUOH-UHFFFAOYSA-N 0.000 claims description 2
ZIJFLRSKJUVAIL-UHFFFAOYSA-N 2-[(4-acetylphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 ZIJFLRSKJUVAIL-UHFFFAOYSA-N 0.000 claims description 2
CFIUSWWECGEZJW-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfinylmethyl]-5-phenylpentanoic acid Chemical group C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)CC(C(=O)O)CCCC1=CC=CC=C1 CFIUSWWECGEZJW-UHFFFAOYSA-N 0.000 claims description 2
BBRNTPFFJDHXMZ-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-3-phenylpropanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CC1=CC=CC=C1 BBRNTPFFJDHXMZ-UHFFFAOYSA-N 0.000 claims description 2
ZOZVXTYPDINXPB-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-(1,3-dioxoisoindol-2-yl)-n-hydroxypentanamide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)NO)CS(=O)(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 ZOZVXTYPDINXPB-UHFFFAOYSA-N 0.000 claims description 2
OKNZAHMIAUSTEH-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-(1,3-dioxoisoindol-2-yl)pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(C(=O)O)CS(=O)(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 OKNZAHMIAUSTEH-UHFFFAOYSA-N 0.000 claims description 2
CTGVDIGFCHCCJU-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 CTGVDIGFCHCCJU-UHFFFAOYSA-N 0.000 claims description 2
SYAAEFMNVNGONW-UHFFFAOYSA-N 2-[(4-benzoylphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 SYAAEFMNVNGONW-UHFFFAOYSA-N 0.000 claims description 2
RCFNAYUVPMRIJQ-UHFFFAOYSA-N 2-[(4-cyclopentyloxyphenyl)sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(OC2CCCC2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RCFNAYUVPMRIJQ-UHFFFAOYSA-N 0.000 claims description 2
IZKHDGYESOPDLB-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]-3-methylbutanoic acid Chemical compound COC1=CC=C(S(=O)(=O)CC(C(C)C)C(O)=O)C=C1 IZKHDGYESOPDLB-UHFFFAOYSA-N 0.000 claims description 2
MXWKCWSXBXIQGR-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]-5-phenylpentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCCC1=CC=CC=C1 MXWKCWSXBXIQGR-UHFFFAOYSA-N 0.000 claims description 2
ZVZUJPISSVKCNA-UHFFFAOYSA-N 2-[(4-methoxyphenyl)sulfonylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC)C=C1 ZVZUJPISSVKCNA-UHFFFAOYSA-N 0.000 claims description 2
VNHDFBIMLUHZNY-UHFFFAOYSA-N 2-[2,6-dimethyl-4-(3-methyl-4-oxophthalazin-1-yl)phenoxy]-n-hydroxyacetamide Chemical compound CC1=C(OCC(=O)NO)C(C)=CC(C=2C3=CC=CC=C3C(=O)N(C)N=2)=C1 VNHDFBIMLUHZNY-UHFFFAOYSA-N 0.000 claims description 2
GLODGHWUWHRQAJ-UHFFFAOYSA-N 2-[[1-[(4-cyanophenyl)methyl]piperidin-4-yl]sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C1CN(CC=2C=CC(=CC=2)C#N)CCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 GLODGHWUWHRQAJ-UHFFFAOYSA-N 0.000 claims description 2
ZJICAGPAXQZDCW-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)phenyl]sulfonylmethyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 ZJICAGPAXQZDCW-UHFFFAOYSA-N 0.000 claims description 2
PRVHDGXLSWBKHA-UHFFFAOYSA-N 2-[[4-(trifluoromethoxy)phenyl]sulfonylmethyl]pentanoic acid Chemical compound CCCC(C(O)=O)CS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 PRVHDGXLSWBKHA-UHFFFAOYSA-N 0.000 claims description 2
XZMNZXGPDIGCKW-UHFFFAOYSA-N 2-[benzenesulfonyl(butoxy)methyl]-n-hydroxy-5-phenylpentanamide Chemical compound C=1C=CC=CC=1S(=O)(=O)C(OCCCC)C(C(=O)NO)CCCC1=CC=CC=C1 XZMNZXGPDIGCKW-UHFFFAOYSA-N 0.000 claims description 2
BQZHEGRXEZTRGH-UHFFFAOYSA-N 2-benzyl-3-(4-methoxyphenyl)sulfonylpropanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CC1=CC=CC=C1 BQZHEGRXEZTRGH-UHFFFAOYSA-N 0.000 claims description 2
YEMUGQVDLSZREQ-UHFFFAOYSA-N 3-(4-benzoylphenyl)sulfonyl-n-hydroxypropanamide Chemical compound C1=CC(S(=O)(=O)CCC(=O)NO)=CC=C1C(=O)C1=CC=CC=C1 YEMUGQVDLSZREQ-UHFFFAOYSA-N 0.000 claims description 2
IJEXBTJECGSFQO-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-n-hydroxybutanamide Chemical compound ONC(=O)CC(C)S(=O)(=O)C1=CC=C(Cl)C=C1 IJEXBTJECGSFQO-UHFFFAOYSA-N 0.000 claims description 2
UFOFDNMTDJQVDY-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-4-phenylbutanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(O)=O)CC1=CC=CC=C1 UFOFDNMTDJQVDY-UHFFFAOYSA-N 0.000 claims description 2
NUSZCZOBSDRJEK-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-hydroxypropanamide Chemical compound ONC(=O)CCS(=O)(=O)C1=CC=CC=C1 NUSZCZOBSDRJEK-UHFFFAOYSA-N 0.000 claims description 2
ILICNRPUTUXICM-UHFFFAOYSA-N 3-[(4-methoxyphenyl)sulfonylmethyl]-6-phenylhexanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(CC(O)=O)CCCC1=CC=CC=C1 ILICNRPUTUXICM-UHFFFAOYSA-N 0.000 claims description 2
CJVYAUOPKFJDEP-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)phenyl]sulfonyl-n-hydroxypropanamide Chemical compound C1=CC(S(=O)(=O)CCC(=O)NO)=CC=C1C1=CC=CC=C1Cl CJVYAUOPKFJDEP-UHFFFAOYSA-N 0.000 claims description 2
WASRPYPSPNBQPC-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-2-[(4-methoxyphenyl)sulfonylmethyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(O)=O)CCCN1C(=O)C2=CC=CC=C2C1=O WASRPYPSPNBQPC-UHFFFAOYSA-N 0.000 claims description 2
WMMSPEDOSMFAPB-UHFFFAOYSA-N 5-(1,3-dioxoisoindol-2-yl)-n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]pentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCN1C(=O)C2=CC=CC=C2C1=O WMMSPEDOSMFAPB-UHFFFAOYSA-N 0.000 claims description 2
OGKSJKFVMBKIMZ-UHFFFAOYSA-N 5-phenyl-2-(2-phenylethylsulfonylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 OGKSJKFVMBKIMZ-UHFFFAOYSA-N 0.000 claims description 2
MDMAPYXYBJUPHR-UHFFFAOYSA-N 5-phenyl-2-(3-phenylpropylsulfonylmethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CCCS(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 MDMAPYXYBJUPHR-UHFFFAOYSA-N 0.000 claims description 2
KNUFDULYTJPULS-UHFFFAOYSA-N 5-phenyl-2-(pyridin-4-ylsulfonylmethyl)pentanoic acid Chemical compound C=1C=NC=CC=1S(=O)(=O)CC(C(=O)O)CCCC1=CC=CC=C1 KNUFDULYTJPULS-UHFFFAOYSA-N 0.000 claims description 2
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BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
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MQPLZZGXGXHGEL-UHFFFAOYSA-N methyl 6-(hydroxyamino)-5-[(4-methoxyphenyl)sulfonylmethyl]-6-oxohexanoate Chemical compound COC(=O)CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC)C=C1 MQPLZZGXGXHGEL-UHFFFAOYSA-N 0.000 claims description 2
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KNBDUWFRLKQEEC-UHFFFAOYSA-N n-hydroxy-2-[(2-methoxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound COC1=CC=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 KNBDUWFRLKQEEC-UHFFFAOYSA-N 0.000 claims description 2
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JWOWZVHABOQFLT-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfinylpropanamide Chemical compound COC1=CC=C(S(=O)CCC(=O)NO)C=C1 JWOWZVHABOQFLT-UHFFFAOYSA-N 0.000 claims description 2
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239000000417 fungicide Substances 0.000 description 1
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229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
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FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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150000003840 hydrochlorides Chemical class 0.000 description 1
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XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
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WLKKJDMRRBROBV-UHFFFAOYSA-M lithium;2-bromoacetate Chemical compound [Li+].[O-]C(=O)CBr WLKKJDMRRBROBV-UHFFFAOYSA-M 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
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FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
SQBDDCLTIMQETN-UHFFFAOYSA-N methyl 2-(acetylsulfanylmethyl)-5-phenylpentanoate Chemical compound CC(=O)SCC(C(=O)OC)CCCC1=CC=CC=C1 SQBDDCLTIMQETN-UHFFFAOYSA-N 0.000 description 1
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QDBLPEJNKICFEF-UHFFFAOYSA-N methyl 2-(chlorosulfonylmethyl)-5-phenylpentanoate Chemical compound COC(=O)C(CS(Cl)(=O)=O)CCCC1=CC=CC=C1 QDBLPEJNKICFEF-UHFFFAOYSA-N 0.000 description 1
LFPHSFCDHACAEG-UHFFFAOYSA-N methyl 2-[(4-bromophenyl)sulfanylmethyl]-5-phenylpentanoate Chemical compound C=1C=C(Br)C=CC=1SCC(C(=O)OC)CCCC1=CC=CC=C1 LFPHSFCDHACAEG-UHFFFAOYSA-N 0.000 description 1
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AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
KTDNLFILVOTVAX-UHFFFAOYSA-N n-[(2-methylpropan-2-yl)oxy]-5-phenyl-2-[(4-phenylmethoxyphenyl)sulfonylmethyl]pentanamide Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1S(=O)(=O)CC(C(=O)NOC(C)(C)C)CCCC1=CC=CC=C1 KTDNLFILVOTVAX-UHFFFAOYSA-N 0.000 description 1
JVLQTFWIBKTBDE-UHFFFAOYSA-N n-hydroxy-2-(oxan-4-ylsulfonylmethyl)-5-phenylpentanamide Chemical compound C1COCCC1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 JVLQTFWIBKTBDE-UHFFFAOYSA-N 0.000 description 1
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QXBZUANJYGJRHA-UHFFFAOYSA-N n-hydroxy-2-[[4-(trifluoromethoxy)phenyl]sulfonylmethyl]-5-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)pentanamide Chemical compound O=C1C(C)(C)N(C)C(=O)N1CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 QXBZUANJYGJRHA-UHFFFAOYSA-N 0.000 description 1
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XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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AMMGCGVWJMRTQI-UHFFFAOYSA-N prop-1-en-2-yl carbonochloridate Chemical compound CC(=C)OC(Cl)=O AMMGCGVWJMRTQI-UHFFFAOYSA-N 0.000 description 1
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239000012264 purified product Substances 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
CFIKPWOOXQYEJO-UHFFFAOYSA-N pyridin-4-yl-(4-sulfanylphenyl)methanone Chemical compound C1=CC(S)=CC=C1C(=O)C1=CC=NC=C1 CFIKPWOOXQYEJO-UHFFFAOYSA-N 0.000 description 1
MHTSJSRDFXZFHQ-UHFFFAOYSA-N quinoline-8-thiol Chemical compound C1=CN=C2C(S)=CC=CC2=C1 MHTSJSRDFXZFHQ-UHFFFAOYSA-N 0.000 description 1
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SDWFMPSNHFWVOV-UHFFFAOYSA-N s-(1-benzoylpiperidin-4-yl) ethanethioate Chemical compound C1CC(SC(=O)C)CCN1C(=O)C1=CC=CC=C1 SDWFMPSNHFWVOV-UHFFFAOYSA-N 0.000 description 1
BYUNVFSCFPTRBA-UHFFFAOYSA-N s-(oxan-4-yl) ethanethioate Chemical compound CC(=O)SC1CCOCC1 BYUNVFSCFPTRBA-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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238000013207 serial dilution Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
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239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
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239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
ZNKXTIAQRUWLRL-UHFFFAOYSA-M sodium;sulfane;hydroxide Chemical compound O.[Na+].[SH-] ZNKXTIAQRUWLRL-UHFFFAOYSA-M 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
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239000007921 spray Substances 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
239000012622 synthetic inhibitor Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
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150000003892 tartrate salts Chemical class 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
230000008354 tissue degradation Effects 0.000 description 1
108091007466 transmembrane glycoproteins Proteins 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
WNBQNJANYUENGZ-UHFFFAOYSA-N triethyl butane-1,1,4-tricarboxylate Chemical compound CCOC(=O)CCCC(C(=O)OCC)C(=O)OCC WNBQNJANYUENGZ-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
230000005748 tumor development Effects 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
230000004572 zinc-binding Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Physical Education & Sports Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Ophthalmology & Optometry (AREA)
Immunology (AREA)
Dermatology (AREA)
Biomedical Technology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pyridine Compounds (AREA)
Pyrane Compounds (AREA)
Quinoline Compounds (AREA)
Furan Compounds (AREA)
Hydrogenated Pyridines (AREA)
Indole Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

NO19990543A 1996-08-07 1999-02-05 Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater NO314452B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9616599.8A GB9616599D0 (en)	1996-08-07	1996-08-07	Compounds
GBGB9707427.2A GB9707427D0 (en)	1997-04-11	1997-04-11	Compounds having mmp and tnf inhibitory activity
PCT/GB1997/002129 WO1998005635A1 (en)	1996-08-07	1997-08-07	Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity

Publications (3)

Publication Number	Publication Date
NO990543D0 NO990543D0 (no)	1999-02-05
NO990543L NO990543L (no)	1999-04-06
NO314452B1 true NO314452B1 (no)	2003-03-24

Family

ID=26309836

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19990543A NO314452B1 (no)	1996-08-07	1999-02-05	Hydroksam- og karboksylsyre-derivater med MMP- og TNF- inhiberingsaktivitet,anvendelse derav og farmasöytiske preparater inneholdende dissederivater

Country Status (17)

Country	Link
US (1)	US6118001A (pl)
EP (1)	EP0968182B1 (pl)
JP (1)	JP2000517297A (pl)
KR (1)	KR20000029858A (pl)
CN (1)	CN1227540A (pl)
AT (1)	ATE266000T1 (pl)
AU (1)	AU730464B2 (pl)
BR (1)	BR9711027A (pl)
CA (1)	CA2263154A1 (pl)
CZ (1)	CZ297278B6 (pl)
DE (1)	DE69729007T2 (pl)
DK (1)	DK0968182T3 (pl)
ES (1)	ES2217425T3 (pl)
NO (1)	NO314452B1 (pl)
PL (1)	PL193829B1 (pl)
PT (1)	PT968182E (pl)
WO (1)	WO1998005635A1 (pl)

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- 1997-08-07 CZ CZ0036899A patent/CZ297278B6/cs not_active IP Right Cessation
- 1997-08-07 PL PL97331598A patent/PL193829B1/pl not_active IP Right Cessation
- 1997-08-07 AU AU38564/97A patent/AU730464B2/en not_active Ceased
- 1997-08-07 DE DE69729007T patent/DE69729007T2/de not_active Expired - Fee Related
- 1997-08-07 BR BR9711027A patent/BR9711027A/pt unknown
- 1997-08-07 AT AT97935666T patent/ATE266000T1/de not_active IP Right Cessation
- 1997-08-07 DK DK97935666T patent/DK0968182T3/da active
- 1997-08-07 KR KR1019997001020A patent/KR20000029858A/ko not_active Ceased
- 1997-08-07 PT PT97935666T patent/PT968182E/pt unknown
- 1997-08-07 CN CN97197048A patent/CN1227540A/zh active Pending
- 1997-08-07 EP EP97935666A patent/EP0968182B1/en not_active Expired - Lifetime
- 1997-08-07 US US08/908,397 patent/US6118001A/en not_active Expired - Fee Related
- 1997-08-07 ES ES97935666T patent/ES2217425T3/es not_active Expired - Lifetime
- 1997-08-07 CA CA002263154A patent/CA2263154A1/en not_active Abandoned
- 1997-08-07 JP JP10507741A patent/JP2000517297A/ja not_active Ceased
- 1997-08-07 WO PCT/GB1997/002129 patent/WO1998005635A1/en not_active Ceased
1999
- 1999-02-05 NO NO19990543A patent/NO314452B1/no unknown

Also Published As

Publication number	Publication date
WO1998005635A1 (en)	1998-02-12
DE69729007D1 (de)	2004-06-09
CN1227540A (zh)	1999-09-01
CZ36899A3 (cs)	1999-07-14
PT968182E (pt)	2004-08-31
DK0968182T3 (da)	2004-08-16
EP0968182A1 (en)	2000-01-05
US6118001A (en)	2000-09-12
ES2217425T3 (es)	2004-11-01
JP2000517297A (ja)	2000-12-26
AU730464B2 (en)	2001-03-08
DE69729007T2 (de)	2005-04-07
ATE266000T1 (de)	2004-05-15
BR9711027A (pt)	1999-08-17
AU3856497A (en)	1998-02-25
NO990543L (no)	1999-04-06
NO990543D0 (no)	1999-02-05
PL193829B1 (pl)	2007-03-30
KR20000029858A (ko)	2000-05-25
EP0968182B1 (en)	2004-05-06
CZ297278B6 (cs)	2006-10-11
CA2263154A1 (en)	1998-02-12
PL331598A1 (en)	1999-08-02

Publication	Publication Date	Title
US6118001A (en)	2000-09-12	Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity
US6566384B1 (en)	2003-05-20	Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity
EP0960108B1 (en)	2004-10-27	Matrix metalloproteinase inhibitors
RU2210567C2 (ru)	2003-08-20	Производные гидроксамовой и карбоновой кислоты, имеющие mmp ингибирующую активность, и фармацевтическая композиция на их основе
US5120718A (en)	1992-06-09	Candida acid protease inhibiting compounds
US5554767A (en)	1996-09-10	Alpha-mercaptoacrylic acid derivatives having calpain inhibitory activity
US6329418B1 (en)	2001-12-11	Substituted pyrrolidine hydroxamate metalloprotease inhibitors
US6465468B1 (en)	2002-10-15	Hydroxamic and carboxylic acid derivatives
WO2002085899A1 (en)	2002-10-31	Heterocyclyldicarbamides as caspase inhibitors
EA002810B1 (ru)	2002-10-31	Сульфамидные ингибиторы металлопротеаз
HU217344B1 (hu)	2002-02-28	Merkapto-acil-dipeptid-származékok és alkalmazásuk metalloproteináz inhibitor hatású gyógyszerkészítmények előállítására
DE69620639T2 (de)	2002-10-17	Mercaptoalkylpeptidylverbindungen mit einem imidazolsubstituenten und ihre verwendung als inhibitoren der matrix metalloproteinasen (mmp) und/oder des tumor necrosis faktors (tnf)
JP2002535392A (ja)	2002-10-22	マトリックスメタロプロテイナーゼ阻害剤としての２，３，４，５−テトラヒドロ−１ｈ−〔１，４〕ベンゾジアゼピン−３−ヒドロキサム酸
NO326266B1 (no)	2008-10-27	Hydroksam- og karboksylsyrederivater, farmasoytiske preparater inneholdende slike for anvendelse i terapi samt anvendelse av slike forbindelser for fremstilling av medikamenter for behandling eller forebygging av sykdommer
US6949545B2 (en)	2005-09-27	Heterocyclic side chain containing, n-substituted metalloprotease inhibitors
US6455531B1 (en)	2002-09-24	Hydroxamic acid derivatives
AU776171B2 (en)	2004-09-02	Alpha-amino-beta-sulfonyl hydroxamic acid compounds
EP1053233B1 (en)	2003-08-20	Hydroxamic and carboxylic acid derivatives
WO1997012861A1 (en)	1997-04-10	Mercaptoamide derivatives and their therapeutic use
US6680338B2 (en)	2004-01-20	Hydroxamic and carboxylic acid derivatives
MXPA99001298A (es)	1999-06-01	Derivados de acido hidroxamico y carboxilico que tienen actividad inhibitoria de mpm y fnt
JP2001522843A (ja)	2001-11-20	Ｍｍｐおよびｔｎｆ抑制作用を有するヒドロキサム酸およびカルボン酸誘導体
US7015234B2 (en)	2006-03-21	Hydroxamic acid derivatives
MXPA00007570A (en)	2002-02-26	Hydroxamic and carboxylic acid derivatives
MXPA00004747A (en)	2001-09-07	Hydroxamic and carboxylic acid derivatives having mmp and tnf inhibitory activity