HRP20000543A2 - N-hydroxy-2-(alkyl, aryl or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors - Google Patents
N-hydroxy-2-(alkyl, aryl or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors Download PDFInfo
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- HRP20000543A2 HRP20000543A2 HR20000543A HRP20000543A HRP20000543A2 HR P20000543 A2 HRP20000543 A2 HR P20000543A2 HR 20000543 A HR20000543 A HR 20000543A HR P20000543 A HRP20000543 A HR P20000543A HR P20000543 A2 HRP20000543 A2 HR P20000543A2
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- HR
- Croatia
- Prior art keywords
- independently selected
- optionally substituted
- benzenesulfonyl
- methoxy
- groups independently
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- 125000003118 aryl group Chemical group 0.000 title claims description 81
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 title claims description 39
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title claims description 3
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title claims description 3
- 238000000034 method Methods 0.000 claims description 379
- 125000004432 carbon atom Chemical group C* 0.000 claims description 146
- -1 cyano, amino Chemical group 0.000 claims description 128
- 125000001072 heteroaryl group Chemical group 0.000 claims description 91
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229910052760 oxygen Inorganic materials 0.000 claims description 81
- 229910052717 sulfur Inorganic materials 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 78
- 125000005842 heteroatom Chemical group 0.000 claims description 73
- 239000002253 acid Substances 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 49
- 125000001624 naphthyl group Chemical group 0.000 claims description 48
- ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims description 42
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 29
- 125000002619 bicyclic group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 125000002950 monocyclic group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 102000002274 Matrix Metalloproteinases Human genes 0.000 claims description 15
- 108010000684 Matrix Metalloproteinases Proteins 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 102100031111 Disintegrin and metalloproteinase domain-containing protein 17 Human genes 0.000 claims description 10
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 9
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- NZSGHPOSLLMCJS-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 NZSGHPOSLLMCJS-UHFFFAOYSA-N 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- PRBMKJZQAUSBQV-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 PRBMKJZQAUSBQV-UHFFFAOYSA-N 0.000 claims description 5
- IMKDKHQDFFLOKK-UHFFFAOYSA-N 1-benzyl-4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical group C1CC(C(=O)NO)(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CCN1CC1=CC=CC=C1 IMKDKHQDFFLOKK-UHFFFAOYSA-N 0.000 claims description 4
- CXFQYPXLXLPGNM-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxamide Chemical group C1=CC(OCCC(C)C)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 CXFQYPXLXLPGNM-UHFFFAOYSA-N 0.000 claims description 4
- UZVVYDVVOHQVFV-UHFFFAOYSA-N 1-butyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 UZVVYDVVOHQVFV-UHFFFAOYSA-N 0.000 claims description 4
- WUEIXXXLLWDJHC-UHFFFAOYSA-N 1-butyl-n-hydroxy-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxamide Chemical group C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 WUEIXXXLLWDJHC-UHFFFAOYSA-N 0.000 claims description 4
- GJICTISPMDMSQH-UHFFFAOYSA-N 1-cyclooctyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C2CCCCCCC2)CC1 GJICTISPMDMSQH-UHFFFAOYSA-N 0.000 claims description 4
- MWFBMGWABXFCCK-UHFFFAOYSA-N 1-ethyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1CN(CC)CCC1(C(=O)NO)S(=O)(=O)C1=CC=C(OC)C=C1 MWFBMGWABXFCCK-UHFFFAOYSA-N 0.000 claims description 4
- MLJSRWALBCZDCB-UHFFFAOYSA-N 1-tert-butyl-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C(C)(C)C)CC1 MLJSRWALBCZDCB-UHFFFAOYSA-N 0.000 claims description 4
- HFGTXSVDSMTFIN-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-n-hydroxy-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical group C1=CC(C)=CC=C1CN1C(S(=O)(=O)C=2C=CC(OCC=3C=CC(Cl)=CC=3)=CC=2)CC(C(=O)NO)CC1 HFGTXSVDSMTFIN-UHFFFAOYSA-N 0.000 claims description 4
- DIBVWAWXUHMLDF-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical group CN1CCC(C(=O)NO)CC1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 DIBVWAWXUHMLDF-UHFFFAOYSA-N 0.000 claims description 4
- NYBGUTIMRHCTPX-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-[(3,4-dichlorophenyl)methyl]-n-hydroxypiperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 NYBGUTIMRHCTPX-UHFFFAOYSA-N 0.000 claims description 4
- WRYYVCSFLUPFIQ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-ethyl-n-hydroxypiperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC)CC1 WRYYVCSFLUPFIQ-UHFFFAOYSA-N 0.000 claims description 4
- GMRJGTBNERTZIB-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-(2-phenoxyethyl)piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCOC=2C=CC=CC=2)CC1 GMRJGTBNERTZIB-UHFFFAOYSA-N 0.000 claims description 4
- WYISEDIVNLCBRU-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-(pyridin-4-ylmethyl)piperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CN=CC=2)CC1 WYISEDIVNLCBRU-UHFFFAOYSA-N 0.000 claims description 4
- NAXMTMYDSBOGMZ-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OC)=CC=2)CC1 NAXMTMYDSBOGMZ-UHFFFAOYSA-N 0.000 claims description 4
- DZBQEKPCHHIFND-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[(4-methylphenyl)methyl]piperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(C)=CC=2)CC1 DZBQEKPCHHIFND-UHFFFAOYSA-N 0.000 claims description 4
- GQEYBNSJJQDDLY-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 GQEYBNSJJQDDLY-UHFFFAOYSA-N 0.000 claims description 4
- NLPICQLAIKGJBE-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical group C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C)CC1 NLPICQLAIKGJBE-UHFFFAOYSA-N 0.000 claims description 4
- AUWOIDNULNLPBA-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-ethyl-n-hydroxypiperidine-4-carboxamide Chemical group C1CN(CC)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 AUWOIDNULNLPBA-UHFFFAOYSA-N 0.000 claims description 4
- WUWBMHSDQYCLTI-UHFFFAOYSA-N 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxy-1-methylpiperidine-4-carboxamide Chemical group C1CN(C)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 WUWBMHSDQYCLTI-UHFFFAOYSA-N 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 210000000845 cartilage Anatomy 0.000 claims description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
- KLYIBVBIKFMTRO-UHFFFAOYSA-N n-hydroxy-1-[(4-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(=O)NO)CC1 KLYIBVBIKFMTRO-UHFFFAOYSA-N 0.000 claims description 4
- KASLMAICRUMQME-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(2-phenylethyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCC=2C=CC=CC=2)CC1 KASLMAICRUMQME-UHFFFAOYSA-N 0.000 claims description 4
- FJXZBLKBEVSCAB-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(3-methylbut-2-enyl)piperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=C(C)C)CC1 FJXZBLKBEVSCAB-UHFFFAOYSA-N 0.000 claims description 4
- FBLQAKOTTHGGBJ-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCCOC=2C=CC=CC=2)CC1 FBLQAKOTTHGGBJ-UHFFFAOYSA-N 0.000 claims description 4
- UTDYWIPXAVCYCE-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 UTDYWIPXAVCYCE-UHFFFAOYSA-N 0.000 claims description 4
- UYOSMJLYSRXRLI-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-pyridin-2-ylphenyl)methyl]piperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2N=CC=CC=2)CC1 UYOSMJLYSRXRLI-UHFFFAOYSA-N 0.000 claims description 4
- RHTOEITZKIINCY-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-[(4-thiophen-2-ylphenyl)methyl]piperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(=CC=2)C=2SC=CC=2)CC1 RHTOEITZKIINCY-UHFFFAOYSA-N 0.000 claims description 4
- RBRSAOMOZVVQSQ-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C)CC1 RBRSAOMOZVVQSQ-UHFFFAOYSA-N 0.000 claims description 4
- IEGOFALJZJPJJD-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-propan-2-ylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(C(C)C)CC1 IEGOFALJZJPJJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 claims description 4
- NPFGSGCFKYSLPI-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(Cl)C(Cl)=CC=2)CC1 NPFGSGCFKYSLPI-UHFFFAOYSA-N 0.000 claims description 3
- HYZDHISHDZBYBQ-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-n-hydroxy-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC(F)=CC=2)CC1 HYZDHISHDZBYBQ-UHFFFAOYSA-N 0.000 claims description 3
- BZJNHCZGKWQZOC-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CCN1CCC(S(=O)(=O)C=2C=CC(OC)=CC=2)(C(O)=O)CC1 BZJNHCZGKWQZOC-UHFFFAOYSA-N 0.000 claims description 3
- SRPXVKQVZQEPFT-UHFFFAOYSA-N 1-benzyl-4-(4-butoxyphenyl)sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 SRPXVKQVZQEPFT-UHFFFAOYSA-N 0.000 claims description 3
- VAMOVZICEXQQGW-UHFFFAOYSA-N 1-benzyl-4-[4-(2-ethylbutoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical group C1=CC(OCC(CC)CC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=CC=CC=2)CC1 VAMOVZICEXQQGW-UHFFFAOYSA-N 0.000 claims description 3
- ATFPFLNWBZIBTJ-UHFFFAOYSA-N 1-benzyl-n-hydroxy-4-(4-phenylmethoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical group C1CC(C(=O)NO)(S(=O)(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCN1CC1=CC=CC=C1 ATFPFLNWBZIBTJ-UHFFFAOYSA-N 0.000 claims description 3
- DTPBPOWGEIFZGM-UHFFFAOYSA-N 1-butyl-4-[4-(4-chlorophenoxy)phenyl]sulfonyl-n-hydroxypiperidine-4-carboxamide Chemical group C1CN(CCCC)CCC1(C(=O)NO)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 DTPBPOWGEIFZGM-UHFFFAOYSA-N 0.000 claims description 3
- AIZQGRMSEBXCNI-UHFFFAOYSA-N 4-(4-butoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylic acid Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(O)=O)CCN(CCCOC=2C=CC=CC=2)CC1 AIZQGRMSEBXCNI-UHFFFAOYSA-N 0.000 claims description 3
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- LCQNQVIUMDNDJS-UHFFFAOYSA-N n-hydroxy-1-[(3-methoxyphenyl)methyl]-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxamide Chemical group C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CC=2C=C(OC)C=CC=2)CC1 LCQNQVIUMDNDJS-UHFFFAOYSA-N 0.000 claims description 3
- YJOSMOCGEMCNLK-UHFFFAOYSA-N n-hydroxy-4-(4-methoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1(C(=O)NO)CCN(CCOC=2C=CC=CC=2)CC1 YJOSMOCGEMCNLK-UHFFFAOYSA-N 0.000 claims description 3
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
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- 239000011230 binding agent Substances 0.000 description 2
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- TXQUFLGNWCZQMN-UHFFFAOYSA-N ethyl 1-benzyl-4-(4-phenylmethoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CCN1CC1=CC=CC=C1 TXQUFLGNWCZQMN-UHFFFAOYSA-N 0.000 description 2
- RWOMYWIVLFLSRW-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(2-ethylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCC(CC)CC)=CC=2)CCN1CC1=CC=CC=C1 RWOMYWIVLFLSRW-UHFFFAOYSA-N 0.000 description 2
- FLHXAGJEFNGPIJ-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OCCC(C)C)=CC=2)CCN1CC1=CC=CC=C1 FLHXAGJEFNGPIJ-UHFFFAOYSA-N 0.000 description 2
- ZHXQPJIOBXPJAI-UHFFFAOYSA-N ethyl 1-benzyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CCN1CC1=CC=CC=C1 ZHXQPJIOBXPJAI-UHFFFAOYSA-N 0.000 description 2
- FVNQRHTZLGYVPB-UHFFFAOYSA-N ethyl 1-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 FVNQRHTZLGYVPB-UHFFFAOYSA-N 0.000 description 2
- MJTSJHUOKOJUMA-UHFFFAOYSA-N ethyl 1-butyl-4-[4-(3-methylbutoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C1=CC=C(OCCC(C)C)C=C1 MJTSJHUOKOJUMA-UHFFFAOYSA-N 0.000 description 2
- YGXWWBWXUAITAS-UHFFFAOYSA-N ethyl 1-butyl-4-[4-(4-chlorophenoxy)phenyl]sulfonylpiperidine-4-carboxylate Chemical compound C1CN(CCCC)CCC1(C(=O)OCC)S(=O)(=O)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 YGXWWBWXUAITAS-UHFFFAOYSA-N 0.000 description 2
- NUXWDBFBHPVLBS-UHFFFAOYSA-N ethyl 1-cyclooctyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1C1CCCCCCC1 NUXWDBFBHPVLBS-UHFFFAOYSA-N 0.000 description 2
- YJKSGYFKCIWOGH-UHFFFAOYSA-N ethyl 1-ethyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 YJKSGYFKCIWOGH-UHFFFAOYSA-N 0.000 description 2
- MSZXFLPUTGBOCD-UHFFFAOYSA-N ethyl 1-tert-butyl-4-(4-methoxyphenyl)sulfonylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C(C)(C)C)CC1 MSZXFLPUTGBOCD-UHFFFAOYSA-N 0.000 description 2
- RXARYKXIADEHEH-UHFFFAOYSA-N ethyl 2-(1-methylimidazol-2-yl)sulfanyloctanoate Chemical compound CCCCCCC(C(=O)OCC)SC1=NC=CN1C RXARYKXIADEHEH-UHFFFAOYSA-N 0.000 description 2
- DVTWAYDUKSKNND-UHFFFAOYSA-N ethyl 2-(4-bromophenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(Br)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 DVTWAYDUKSKNND-UHFFFAOYSA-N 0.000 description 2
- XGGLBNSAOMPWEP-UHFFFAOYSA-N ethyl 2-(4-butoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 XGGLBNSAOMPWEP-UHFFFAOYSA-N 0.000 description 2
- PFPUODQZTDRKHA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyl-2,5-dimethylhex-4-enoate Chemical compound CCOC(=O)C(C)(CC=C(C)C)SC1=CC=C(OC)C=C1 PFPUODQZTDRKHA-UHFFFAOYSA-N 0.000 description 2
- ORJYHHCCMHGXMH-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyl-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1SC(C)(C(=O)OCC)CC1=CC=CC=C1 ORJYHHCCMHGXMH-UHFFFAOYSA-N 0.000 description 2
- PYQGMWISPUMMGX-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylbutanoate Chemical compound CCOC(=O)C(CC)SC1=CC=C(OC)C=C1 PYQGMWISPUMMGX-UHFFFAOYSA-N 0.000 description 2
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- ZXEMOHZODGJZRR-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanylpentanoate Chemical compound CCOC(=O)C(CCC)SC1=CC=C(OC)C=C1 ZXEMOHZODGJZRR-UHFFFAOYSA-N 0.000 description 2
- HKBAKJPOGVGKQT-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfanyltetradecanoate Chemical compound CCCCCCCCCCCCC(C(=O)OCC)SC1=CC=C(OC)C=C1 HKBAKJPOGVGKQT-UHFFFAOYSA-N 0.000 description 2
- TVEDWNPEBHXGTP-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2,5,9-trimethyldeca-4,8-dienoate Chemical compound CC(C)=CCCC(C)=CCC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 TVEDWNPEBHXGTP-UHFFFAOYSA-N 0.000 description 2
- HSOHVBFCNPZNTB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2,5-dimethylhex-4-enoate Chemical compound CCOC(=O)C(C)(CC=C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 HSOHVBFCNPZNTB-UHFFFAOYSA-N 0.000 description 2
- DSYJMXBZORREPG-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-(pyridin-3-ylmethyl)decanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCCCC)(C(=O)OCC)CC1=CC=CN=C1 DSYJMXBZORREPG-UHFFFAOYSA-N 0.000 description 2
- VGCXAPCFWLAJSG-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]butanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 VGCXAPCFWLAJSG-UHFFFAOYSA-N 0.000 description 2
- SWIDUBMDSRKUOF-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[3-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=1)=CC=CC=1OCCN1CCCCC1 SWIDUBMDSRKUOF-UHFFFAOYSA-N 0.000 description 2
- CWAFAZWMPYPCLU-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 CWAFAZWMPYPCLU-UHFFFAOYSA-N 0.000 description 2
- VAILMDDBHWCDBB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-naphthalen-2-ylpropanoate Chemical compound C=1C=C2C=CC=CC2=CC=1CC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 VAILMDDBHWCDBB-UHFFFAOYSA-N 0.000 description 2
- HRBLYZSWZKHYRS-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 HRBLYZSWZKHYRS-UHFFFAOYSA-N 0.000 description 2
- DVQKRPPWXYFHKP-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-pyridin-3-ylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CN=C1 DVQKRPPWXYFHKP-UHFFFAOYSA-N 0.000 description 2
- KPLAHYNVDLMTEM-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-3-quinolin-6-ylpropanoate Chemical compound C=1C=C2N=CC=CC2=CC=1CC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 KPLAHYNVDLMTEM-UHFFFAOYSA-N 0.000 description 2
- LGIKDVVXIPXGCQ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-2-methyl-5-phenylpent-4-enoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC=CC1=CC=CC=C1 LGIKDVVXIPXGCQ-UHFFFAOYSA-N 0.000 description 2
- YKKSGDSVVLJFRV-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-3-naphthalen-2-ylpropanoate Chemical compound C=1C=C2C=CC=CC2=CC=1CC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 YKKSGDSVVLJFRV-UHFFFAOYSA-N 0.000 description 2
- FHBZHQBXIAQDPX-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-4-methyl-2-(pyridin-3-ylmethyl)pentanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC(C)C)(C(=O)OCC)CC1=CC=CN=C1 FHBZHQBXIAQDPX-UHFFFAOYSA-N 0.000 description 2
- GJIDIAMNHVTXST-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5,9-dimethyl-2-[[4-(2-morpholin-4-ylethoxy)phenyl]methyl]deca-4,8-dienoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC=C(C)CCC=C(C)C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCOCC1 GJIDIAMNHVTXST-UHFFFAOYSA-N 0.000 description 2
- GZEXMJCTLYCWDA-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5,9-dimethyldeca-4,8-dienoate Chemical compound CC(C)=CCCC(C)=CCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 GZEXMJCTLYCWDA-UHFFFAOYSA-N 0.000 description 2
- JOMQHYMCOSSKMB-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(3-methylbut-2-enyl)hex-4-enoate Chemical compound CCOC(=O)C(CC=C(C)C)(CC=C(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 JOMQHYMCOSSKMB-UHFFFAOYSA-N 0.000 description 2
- KISAIXBGYVAYSS-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hex-4-enoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CC=C(C)C)(C(=O)OCC)CC1=CC=CN=C1 KISAIXBGYVAYSS-UHFFFAOYSA-N 0.000 description 2
- QFTQYBHPTTWRHL-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methyl-2-(pyridin-3-ylmethyl)hexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC(C)C)(C(=O)OCC)CC1=CC=CN=C1 QFTQYBHPTTWRHL-UHFFFAOYSA-N 0.000 description 2
- GOSIRUVUSZAKHO-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-5-methylhexanoate Chemical compound CCOC(=O)C(CCC(C)C)S(=O)(=O)C1=CC=C(OC)C=C1 GOSIRUVUSZAKHO-UHFFFAOYSA-N 0.000 description 2
- BWLSVHPFJJBRND-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-6-phenoxy-2-(pyridin-3-ylmethyl)hexanoate Chemical compound C=1C=CN=CC=1CC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CCCCOC1=CC=CC=C1 BWLSVHPFJJBRND-UHFFFAOYSA-N 0.000 description 2
- UKTUZPXOLAKKJJ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyl-6-phenoxyhexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C(=O)OCC)CCCCOC1=CC=CC=C1 UKTUZPXOLAKKJJ-UHFFFAOYSA-N 0.000 description 2
- QHHSTBCZKQFZRZ-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyldecanoate Chemical compound CCCCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 QHHSTBCZKQFZRZ-UHFFFAOYSA-N 0.000 description 2
- RYUMOQZQWYMLME-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)sulfonyloctanoate Chemical compound CCCCCCC(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 RYUMOQZQWYMLME-UHFFFAOYSA-N 0.000 description 2
- UJSPUGKQHPIXDV-UHFFFAOYSA-N ethyl 2-(4-phenylmethoxyphenyl)sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OCC)=CC=C1OCC1=CC=CC=C1 UJSPUGKQHPIXDV-UHFFFAOYSA-N 0.000 description 2
- UXJFKHKHUREURW-UHFFFAOYSA-N ethyl 2-(cyclohexylmethyl)-2-(4-methoxyphenyl)sulfonyl-3-pyridin-3-ylpropanoate Chemical compound C=1C=CN=CC=1CC(S(=O)(=O)C=1C=CC(OC)=CC=1)(C(=O)OCC)CC1CCCCC1 UXJFKHKHUREURW-UHFFFAOYSA-N 0.000 description 2
- OGCZFGRUVNFOFU-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methylsulfonyl]-2-methyl-3-phenylpropanoate Chemical compound C=1C=C(OC)C=CC=1CS(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1 OGCZFGRUVNFOFU-UHFFFAOYSA-N 0.000 description 2
- ZTIGBUWNNZCRJQ-UHFFFAOYSA-N ethyl 2-[2-(4-methoxyphenyl)sulfanylphenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC=C1SC1=CC=C(OC)C=C1 ZTIGBUWNNZCRJQ-UHFFFAOYSA-N 0.000 description 2
- CMLJYJOADGIECP-UHFFFAOYSA-N ethyl 2-[4-(2-ethylbutoxy)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(OCC(CC)CC)C=C1 CMLJYJOADGIECP-UHFFFAOYSA-N 0.000 description 2
- YPSKGXCMXOMOLG-UHFFFAOYSA-N ethyl 2-[4-(3-methylbutoxy)phenyl]sulfanylacetate Chemical compound CCOC(=O)CSC1=CC=C(OCCC(C)C)C=C1 YPSKGXCMXOMOLG-UHFFFAOYSA-N 0.000 description 2
- LAKFTOVKYBHAHH-UHFFFAOYSA-N ethyl 2-[4-(4-chlorophenoxy)phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OCC)=CC=C1OC1=CC=C(Cl)C=C1 LAKFTOVKYBHAHH-UHFFFAOYSA-N 0.000 description 2
- QKVULLBGMGCRRD-UHFFFAOYSA-N ethyl 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-[(4-methylphenyl)methyl]piperidine-4-carboxylate Chemical compound C=1C=C(OCC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1CC(C(=O)OCC)CCN1CC1=CC=C(C)C=C1 QKVULLBGMGCRRD-UHFFFAOYSA-N 0.000 description 2
- HGOADIBTJSEIAQ-UHFFFAOYSA-N ethyl 2-[4-[(4-chlorophenyl)methoxy]phenyl]sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C1C(C(=O)OCC)CCN(C)C1S(=O)(=O)C(C=C1)=CC=C1OCC1=CC=C(Cl)C=C1 HGOADIBTJSEIAQ-UHFFFAOYSA-N 0.000 description 2
- VBYHDMCZQKMCFS-UHFFFAOYSA-N ethyl 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonyloctanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCCCC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 VBYHDMCZQKMCFS-UHFFFAOYSA-N 0.000 description 2
- XWEJKPRYBSCRRP-UHFFFAOYSA-N ethyl 2-[[4-[2-(azepan-1-yl)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylpentanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCC)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 XWEJKPRYBSCRRP-UHFFFAOYSA-N 0.000 description 2
- DFDQUBGZZSOJCX-UHFFFAOYSA-N ethyl 2-[[4-[2-(diethylamino)ethoxy]phenyl]methyl]-2-(4-methoxyphenyl)sulfonylhexanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCCC)(C(=O)OCC)CC1=CC=C(OCCN(CC)CC)C=C1 DFDQUBGZZSOJCX-UHFFFAOYSA-N 0.000 description 2
- OWFFBQYWNMOPCF-UHFFFAOYSA-N ethyl 2-benzyl-4-[di(propan-2-yl)amino]-2-(4-methoxyphenyl)sulfonylbutanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(CCN(C(C)C)C(C)C)(C(=O)OCC)CC1=CC=CC=C1 OWFFBQYWNMOPCF-UHFFFAOYSA-N 0.000 description 2
- WNFUWONOILPKNX-UHFFFAOYSA-N ethyl 2-bromo-3-methylbutanoate Chemical compound CCOC(=O)C(Br)C(C)C WNFUWONOILPKNX-UHFFFAOYSA-N 0.000 description 2
- QGTKTXXIQKTTAO-UHFFFAOYSA-N ethyl 2-methyl-2-(1-methylimidazol-2-yl)sulfonyl-3-(4-phenylphenyl)propanoate Chemical compound N=1C=CN(C)C=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1C1=CC=CC=C1 QGTKTXXIQKTTAO-UHFFFAOYSA-N 0.000 description 2
- ARXUZBQWANCFJB-UHFFFAOYSA-N ethyl 2-methyl-2-(2-methylfuran-3-yl)sulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=COC(C)=C1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 ARXUZBQWANCFJB-UHFFFAOYSA-N 0.000 description 2
- GHWNVKMMFLFGET-UHFFFAOYSA-N ethyl 2-methyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]-2-thiophen-2-ylsulfonylpropanoate Chemical compound C=1C=CSC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCC1 GHWNVKMMFLFGET-UHFFFAOYSA-N 0.000 description 2
- JTSIFOFUGUMYKR-UHFFFAOYSA-N ethyl 2-octylsulfonyl-3-[4-(2-piperidin-1-ylethoxy)phenyl]propanoate Chemical compound C1=CC(CC(S(=O)(=O)CCCCCCCC)C(=O)OCC)=CC=C1OCCN1CCCCC1 JTSIFOFUGUMYKR-UHFFFAOYSA-N 0.000 description 2
- VJGPENBRHUYYBS-UHFFFAOYSA-N ethyl 2-thiophen-2-ylsulfonylpropanoate Chemical compound CCOC(=O)C(C)S(=O)(=O)C1=CC=CS1 VJGPENBRHUYYBS-UHFFFAOYSA-N 0.000 description 2
- ZRFSFNRGMBEKDH-UHFFFAOYSA-N ethyl 3-(2-bromophenyl)-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=CC=C1Br ZRFSFNRGMBEKDH-UHFFFAOYSA-N 0.000 description 2
- KVZUGUQIGQCTCH-UHFFFAOYSA-N ethyl 3-(4-bromophenyl)-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1=CC=C(Br)C=C1 KVZUGUQIGQCTCH-UHFFFAOYSA-N 0.000 description 2
- WNLFBMUVOBRWNX-UHFFFAOYSA-N ethyl 3-[4-[2-(azepan-1-yl)ethoxy]phenyl]-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCN1CCCCCC1 WNLFBMUVOBRWNX-UHFFFAOYSA-N 0.000 description 2
- CDQJTGRQQLBDSY-UHFFFAOYSA-N ethyl 3-cyclohexyl-2-(4-methoxyphenyl)sulfonyl-2-methylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C)(C(=O)OCC)CC1CCCCC1 CDQJTGRQQLBDSY-UHFFFAOYSA-N 0.000 description 2
- GXRFWWPEFWDKPA-UHFFFAOYSA-N ethyl 3-cyclohexyl-2-(4-methoxyphenyl)sulfonylpropanoate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C(C(=O)OCC)CC1CCCCC1 GXRFWWPEFWDKPA-UHFFFAOYSA-N 0.000 description 2
- KHHADIVHVMPMRM-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CCOC=2C=CC=CC=2)CC1 KHHADIVHVMPMRM-UHFFFAOYSA-N 0.000 description 2
- QQUKJPDPCXYTIS-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CCCOC=2C=CC=CC=2)CC1 QQUKJPDPCXYTIS-UHFFFAOYSA-N 0.000 description 2
- UOMOHRMEQBUFJM-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(3-methoxyphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=C(OC)C=CC=2)CC1 UOMOHRMEQBUFJM-UHFFFAOYSA-N 0.000 description 2
- NPVGYDOJJJMTIL-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(3-phenoxyphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=C(OC=3C=CC=CC=3)C=CC=2)CC1 NPVGYDOJJJMTIL-UHFFFAOYSA-N 0.000 description 2
- BOZRNWRFPVETEO-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-cyanophenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(=CC=2)C#N)CC1 BOZRNWRFPVETEO-UHFFFAOYSA-N 0.000 description 2
- CGTUSHQZZDHNDJ-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-fluorophenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(F)=CC=2)CC1 CGTUSHQZZDHNDJ-UHFFFAOYSA-N 0.000 description 2
- HSTSPDIMHZEZDT-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[(4-methoxyphenyl)methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(OC)=CC=2)CC1 HSTSPDIMHZEZDT-UHFFFAOYSA-N 0.000 description 2
- KPDIQWMNLROMAP-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC=2C=CC(OCCN3CCCCC3)=CC=2)CC1 KPDIQWMNLROMAP-UHFFFAOYSA-N 0.000 description 2
- GZBSOQZXQQQEHJ-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-ethylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 GZBSOQZXQQQEHJ-UHFFFAOYSA-N 0.000 description 2
- JPLKAYSUFIYVRB-UHFFFAOYSA-N ethyl 4-(4-butoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 JPLKAYSUFIYVRB-UHFFFAOYSA-N 0.000 description 2
- RKGXYKXFAZIFTJ-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(2-phenoxyethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCOC1=CC=CC=C1 RKGXYKXFAZIFTJ-UHFFFAOYSA-N 0.000 description 2
- ILOBLRACMDRJCE-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(2-phenylethyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCC1=CC=CC=C1 ILOBLRACMDRJCE-UHFFFAOYSA-N 0.000 description 2
- OBLAEDSPDBRSER-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-methylbut-2-enyl)piperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC=C(C)C)CC1 OBLAEDSPDBRSER-UHFFFAOYSA-N 0.000 description 2
- XVOZQUFANNBYBM-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-phenoxypropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCCOC1=CC=CC=C1 XVOZQUFANNBYBM-UHFFFAOYSA-N 0.000 description 2
- QJEGYSPYCYGEQL-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-(3-phenylpropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CCCC1=CC=CC=C1 QJEGYSPYCYGEQL-UHFFFAOYSA-N 0.000 description 2
- MFMDAOMSCGOFGX-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[(4-phenylphenyl)methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 MFMDAOMSCGOFGX-UHFFFAOYSA-N 0.000 description 2
- VERVFCODAACEKU-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)(S(=O)(=O)C=2C=CC(OC)=CC=2)CCN1CC(C=C1)=CC=C1OCCN1CCCCC1 VERVFCODAACEKU-UHFFFAOYSA-N 0.000 description 2
- ZOCIWLKGUFBEST-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 ZOCIWLKGUFBEST-UHFFFAOYSA-N 0.000 description 2
- URNMBYWPWHBBHU-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)sulfonyl-1-propan-2-ylpiperidine-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C(C)C)CC1 URNMBYWPWHBBHU-UHFFFAOYSA-N 0.000 description 2
- FXKFEHRDNSCQFF-UHFFFAOYSA-N ethyl 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-ethylpiperidine-4-carboxylate Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(CC)CC1 FXKFEHRDNSCQFF-UHFFFAOYSA-N 0.000 description 2
- RGZDGUMYXHVEJX-UHFFFAOYSA-N ethyl 4-[4-(4-chlorophenoxy)phenyl]sulfonyl-1-methylpiperidine-4-carboxylate Chemical compound C=1C=C(OC=2C=CC(Cl)=CC=2)C=CC=1S(=O)(=O)C1(C(=O)OCC)CCN(C)CC1 RGZDGUMYXHVEJX-UHFFFAOYSA-N 0.000 description 2
- VIKWZSNGLQSSJM-UHFFFAOYSA-N ethyl 5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enoate Chemical compound CCOC(=O)C(CC=C(C)C)(CC=C(C)C)S(=O)(=O)C1=CC=C(C)C=C1 VIKWZSNGLQSSJM-UHFFFAOYSA-N 0.000 description 2
- MHLHXNFBOSJAFV-UHFFFAOYSA-N ethyl 6-(1,3-dioxoisoindol-2-yl)-2-(4-methoxyphenyl)sulfonyl-2-methylhexanoate Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCC(C)(C(=O)OCC)S(=O)(=O)C1=CC=C(OC)C=C1 MHLHXNFBOSJAFV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 2
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 2
- BSXSSXPCEVBUSF-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-methylpropan-2-amine Chemical compound ClCCN(C(C)(C)C)CCCl BSXSSXPCEVBUSF-UHFFFAOYSA-N 0.000 description 2
- NSYROPDQXYIHMF-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-phenylethanamine Chemical compound ClCCN(CCCl)CCC1=CC=CC=C1 NSYROPDQXYIHMF-UHFFFAOYSA-N 0.000 description 2
- JZLVPSUROKRFMZ-UHFFFAOYSA-N n,n-bis(2-chloroethyl)cyclooctanamine Chemical compound ClCCN(CCCl)C1CCCCCCC1 JZLVPSUROKRFMZ-UHFFFAOYSA-N 0.000 description 2
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- UTPMYNWNHFDADN-UHFFFAOYSA-N n-hydroxy-3-methyl-2-naphthalen-2-ylsulfinylbutanamide Chemical compound C1=CC=CC2=CC(S(=O)C(C(=O)NO)C(C)C)=CC=C21 UTPMYNWNHFDADN-UHFFFAOYSA-N 0.000 description 1
- BNGKTXONUSUSAM-UHFFFAOYSA-N n-hydroxy-3-methyl-2-naphthalen-2-ylsulfonylbutanamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)C(C(=O)NO)C(C)C)=CC=C21 BNGKTXONUSUSAM-UHFFFAOYSA-N 0.000 description 1
- PPTJZFSGDMWVFF-UHFFFAOYSA-N n-hydroxy-5-methyl-2-(3-methylbut-2-enyl)-2-(4-methylphenyl)sulfonylhex-4-enamide Chemical compound CC(C)=CCC(CC=C(C)C)(C(=O)NO)S(=O)(=O)C1=CC=C(C)C=C1 PPTJZFSGDMWVFF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 108091007196 stromelysin Proteins 0.000 description 1
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- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- RXZKGZVHEPIEQB-UHFFFAOYSA-N tert-butyl 2-[2-(4-methoxyphenyl)sulfonylpyridin-3-yl]propanoate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=NC=CC=C1C(C)C(=O)OC(C)(C)C RXZKGZVHEPIEQB-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- STKLWCKTSXLYGY-UHFFFAOYSA-N thiadiazole-4-sulfonic acid Chemical compound OS(=O)(=O)C1=CSN=N1 STKLWCKTSXLYGY-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Reproductive Health (AREA)
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- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
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- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2637298A | 1998-02-19 | 1998-02-19 | |
PCT/US1998/017633 WO1999042436A1 (en) | 1998-02-19 | 1998-08-26 | N-hydroxy-2-(alkyl, aryl, or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000543A2 true HRP20000543A2 (en) | 2001-08-31 |
Family
ID=21831431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000543A HRP20000543A2 (en) | 1998-02-19 | 2000-08-18 | N-hydroxy-2-(alkyl, aryl or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1054858A1 (xx) |
JP (1) | JP2002503717A (xx) |
KR (1) | KR20010041089A (xx) |
CN (1) | CN1213021C (xx) |
AU (1) | AU757719B2 (xx) |
BG (1) | BG104782A (xx) |
BR (1) | BR9815781A (xx) |
CA (1) | CA2320469A1 (xx) |
EA (1) | EA003283B1 (xx) |
EE (1) | EE200000471A (xx) |
GE (1) | GEP20022797B (xx) |
HR (1) | HRP20000543A2 (xx) |
HU (1) | HUP0101837A3 (xx) |
ID (1) | ID25639A (xx) |
IL (1) | IL137566A0 (xx) |
NO (1) | NO20004093L (xx) |
NZ (1) | NZ506184A (xx) |
PL (1) | PL342548A1 (xx) |
SK (1) | SK12332000A3 (xx) |
TR (1) | TR200002423T2 (xx) |
WO (1) | WO1999042436A1 (xx) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL341379A1 (en) | 1997-11-14 | 2001-04-09 | Searle & Co | Aromatic sulphone substituted hydroxamic acid as inhibitor of metalloprotease |
US6750228B1 (en) * | 1997-11-14 | 2004-06-15 | Pharmacia Corporation | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
US20010039287A1 (en) * | 1997-11-14 | 2001-11-08 | Thomas E Barta | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
AR035312A1 (es) * | 1999-01-27 | 2004-05-12 | Wyeth Corp | Compuestos de acido hidroxamico que contienen alquinilo como inhibidores de metaloproteinasa de matriz/tace, composicion farmaceutica que los comprenden y el uso de los mismos para la manufactura de un medicamento |
US6358980B1 (en) * | 1999-01-27 | 2002-03-19 | American Cyanamid Company | Alkynyl containing hydroxamic acid compounds as matrix metalloproteinase/tace inhibitors |
US6800646B1 (en) | 1999-02-08 | 2004-10-05 | Pharmacia Corporation | Sulfamato hydroxamic acid metalloprotease inhibitor |
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CN1400968A (zh) * | 2000-01-27 | 2003-03-05 | 美国氰胺公司 | 制备α-磺酰基异羟肟酸衍生物的方法 |
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FR2947268B1 (fr) | 2009-06-30 | 2011-08-26 | Galderma Res & Dev | Nouveaux composes benzene-sulfonamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique |
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-
1998
- 1998-08-26 IL IL13756698A patent/IL137566A0/xx unknown
- 1998-08-26 HU HU0101837A patent/HUP0101837A3/hu unknown
- 1998-08-26 EE EEP200000471A patent/EE200000471A/xx unknown
- 1998-08-26 KR KR1020007009128A patent/KR20010041089A/ko not_active Application Discontinuation
- 1998-08-26 CN CNB988139669A patent/CN1213021C/zh not_active Expired - Fee Related
- 1998-08-26 WO PCT/US1998/017633 patent/WO1999042436A1/en not_active Application Discontinuation
- 1998-08-26 ID IDW20001549A patent/ID25639A/id unknown
- 1998-08-26 EP EP98943392A patent/EP1054858A1/en not_active Withdrawn
- 1998-08-26 EA EA200000849A patent/EA003283B1/ru not_active IP Right Cessation
- 1998-08-26 NZ NZ506184A patent/NZ506184A/en unknown
- 1998-08-26 SK SK1233-2000A patent/SK12332000A3/sk unknown
- 1998-08-26 BR BR9815781-7A patent/BR9815781A/pt not_active Application Discontinuation
- 1998-08-26 TR TR2000/02423T patent/TR200002423T2/xx unknown
- 1998-08-26 CA CA002320469A patent/CA2320469A1/en not_active Abandoned
- 1998-08-26 JP JP2000532389A patent/JP2002503717A/ja active Pending
- 1998-08-26 AU AU91201/98A patent/AU757719B2/en not_active Ceased
- 1998-08-26 GE GEAP19985554A patent/GEP20022797B/en unknown
- 1998-08-26 PL PL98342548A patent/PL342548A1/xx unknown
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2000
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- 2000-08-18 HR HR20000543A patent/HRP20000543A2/hr not_active Application Discontinuation
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CN1213021C (zh) | 2005-08-03 |
HUP0101837A3 (en) | 2001-11-28 |
SK12332000A3 (sk) | 2001-02-12 |
BR9815781A (pt) | 2000-11-07 |
IL137566A0 (en) | 2001-07-24 |
GEP20022797B (en) | 2002-09-25 |
CN1291183A (zh) | 2001-04-11 |
KR20010041089A (ko) | 2001-05-15 |
NO20004093L (no) | 2000-10-03 |
JP2002503717A (ja) | 2002-02-05 |
PL342548A1 (en) | 2001-06-18 |
AU9120198A (en) | 1999-09-06 |
EA003283B1 (ru) | 2003-04-24 |
EP1054858A1 (en) | 2000-11-29 |
NO20004093D0 (no) | 2000-08-16 |
ID25639A (id) | 2000-10-19 |
EE200000471A (et) | 2002-02-15 |
NZ506184A (en) | 2003-05-30 |
HUP0101837A2 (hu) | 2001-10-28 |
TR200002423T2 (tr) | 2001-01-22 |
AU757719B2 (en) | 2003-03-06 |
BG104782A (bg) | 2001-08-31 |
WO1999042436A1 (en) | 1999-08-26 |
EA200000849A1 (ru) | 2001-04-23 |
CA2320469A1 (en) | 1999-08-26 |
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