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

Info

Publication number

NO314452B1

NO314452B1 NO19990543A NO990543A NO314452B1 NO 314452 B1 NO314452 B1 NO 314452B1 NO 19990543 A NO19990543 A NO 19990543A NO 990543 A NO990543 A NO 990543A NO 314452 B1 NO314452 B1 NO 314452B1

Authority

NO

Norway

Prior art keywords

acid

hydroxyamide

alkyl

phenyl

phenylpentanoic

Prior art date

1996-08-07

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• 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
• 206010048998 Acute phase reaction Diseases 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
• 208000023275 Autoimmune disease Diseases 0.000 claims description 2
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• 201000009273 Endometriosis Diseases 0.000 claims description 2
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• 208000031886 HIV Infections Diseases 0.000 claims description 2
• 206010019280 Heart failures Diseases 0.000 claims description 2
• 206010061218 Inflammation Diseases 0.000 claims description 2
• 102000010781 Interleukin-6 Receptors Human genes 0.000 claims description 2
• 108010038501 Interleukin-6 Receptors Proteins 0.000 claims description 2
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• 208000017442 Retinal disease Diseases 0.000 claims description 2
• 206010038923 Retinopathy Diseases 0.000 claims description 2
• 208000006011 Stroke Diseases 0.000 claims description 2
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• 206010047115 Vasculitis Diseases 0.000 claims description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
• 230000001154 acute effect Effects 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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• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• KCFJQJBCBNSJPA-UHFFFAOYSA-N n-hydroxy-2-(2-methylpropylsulfonylmethyl)-5-phenylpentanamide Chemical compound CC(C)CS(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 KCFJQJBCBNSJPA-UHFFFAOYSA-N 0.000 claims description 2
• 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
• XNRJUTGTRAWAEA-UHFFFAOYSA-N n-hydroxy-2-[(4-hydroxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound C=1C=C(O)C=CC=1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 XNRJUTGTRAWAEA-UHFFFAOYSA-N 0.000 claims description 2
• RSOTXVOGGIMXHW-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]-5-phenylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)CC(C(=O)NO)CCCC1=CC=CC=C1 RSOTXVOGGIMXHW-UHFFFAOYSA-N 0.000 claims description 2
• URQUSFCKSGRQNP-UHFFFAOYSA-N n-hydroxy-2-[(4-methoxyphenyl)sulfonylmethyl]pentanamide Chemical compound CCCC(C(=O)NO)CS(=O)(=O)C1=CC=C(OC)C=C1 URQUSFCKSGRQNP-UHFFFAOYSA-N 0.000 claims description 2
• SCDTVKKBOXTTSJ-UHFFFAOYSA-N n-hydroxy-2-[[4-[hydroxy(phenyl)methyl]phenyl]sulfonylmethyl]-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 SCDTVKKBOXTTSJ-UHFFFAOYSA-N 0.000 claims description 2
• 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
• AFJPLWPNTPTDED-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfonyl-4-phenylbutanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(CC(=O)NO)CC1=CC=CC=C1 AFJPLWPNTPTDED-UHFFFAOYSA-N 0.000 claims description 2
• QFCZCAQONLOMIR-UHFFFAOYSA-N n-hydroxy-3-(4-methoxyphenyl)sulfonylpropanamide Chemical compound COC1=CC=C(S(=O)(=O)CCC(=O)NO)C=C1 QFCZCAQONLOMIR-UHFFFAOYSA-N 0.000 claims description 2
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