JP2010530847A5 - - Google Patents
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- Publication number
- JP2010530847A5 JP2010530847A5 JP2010511290A JP2010511290A JP2010530847A5 JP 2010530847 A5 JP2010530847 A5 JP 2010530847A5 JP 2010511290 A JP2010511290 A JP 2010511290A JP 2010511290 A JP2010511290 A JP 2010511290A JP 2010530847 A5 JP2010530847 A5 JP 2010530847A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- methyl
- indan
- benzoylamino
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 9
- -1 ( C 1 -C 10) - alkyl carbonyl - Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 230000004962 physiological condition Effects 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims 2
- MSOVLVYBZYSIEE-UHFFFAOYSA-N 5-fluoro-2-[[3-methyl-2-(2-methylpropyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=CC=C2C1 MSOVLVYBZYSIEE-UHFFFAOYSA-N 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- CGVUCVLXGMIVEB-UHFFFAOYSA-N 1,3-dimethyl-5-(5,6,7,8-tetrahydronaphthalene-1-carbonylamino)-4,6-dihydrocyclopenta[c]thiophene-5-carboxylic acid Chemical compound C1CCCC2=C1C=CC=C2C(=O)NC1(C(O)=O)CC2=C(C)SC(C)=C2C1 CGVUCVLXGMIVEB-UHFFFAOYSA-N 0.000 claims 1
- QFAHOVXWUGTKOF-UHFFFAOYSA-N 1,3-dimethyl-5-[(3-methyl-2-propan-2-yloxybenzoyl)amino]-4,6-dihydrocyclopenta[c]thiophene-5-carboxylic acid Chemical compound CC(C)OC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=C(C)SC(C)=C2C1 QFAHOVXWUGTKOF-UHFFFAOYSA-N 0.000 claims 1
- GCFWKDAGJGTYAJ-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydronaphthalen-1-ylcarbamoyl)-1,3-dihydroindene-2-carboxylic acid Chemical compound C1CCCC2=C1C=CC=C2NC(=O)C1(C(=O)O)CC2=CC=CC=C2C1 GCFWKDAGJGTYAJ-UHFFFAOYSA-N 0.000 claims 1
- YAJDKGWZDVHDQJ-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydronaphthalene-1-carbonylamino)-1,3-dihydroindene-2-carboxylic acid Chemical compound C1CCCC2=C1C=CC=C2C(=O)NC1(C(=O)O)CC2=CC=CC=C2C1 YAJDKGWZDVHDQJ-UHFFFAOYSA-N 0.000 claims 1
- CZNADOCLOBYGRP-UHFFFAOYSA-N 2-[(2,3-dimethylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1C CZNADOCLOBYGRP-UHFFFAOYSA-N 0.000 claims 1
- VEICCNMVJHBRAF-UHFFFAOYSA-N 2-[(2-butan-2-yloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCC(C)OC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 VEICCNMVJHBRAF-UHFFFAOYSA-N 0.000 claims 1
- PSJYLQUBGXKMQM-UHFFFAOYSA-N 2-[(2-chloro-6-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(Cl)=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 PSJYLQUBGXKMQM-UHFFFAOYSA-N 0.000 claims 1
- OGIZPFDDOBNJOF-UHFFFAOYSA-N 2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1OC1CCC1 OGIZPFDDOBNJOF-UHFFFAOYSA-N 0.000 claims 1
- SOUFZMAJMOXZDL-UHFFFAOYSA-N 2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-4-fluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=C(F)C=CC=C3C2)C(O)=O)=C1OC1CCC1 SOUFZMAJMOXZDL-UHFFFAOYSA-N 0.000 claims 1
- VTTYTIRVPPJERI-UHFFFAOYSA-N 2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-5,6-difluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC(F)=C(F)C=C3C2)C(O)=O)=C1OC1CCC1 VTTYTIRVPPJERI-UHFFFAOYSA-N 0.000 claims 1
- JXBIPVFXGOBYMB-UHFFFAOYSA-N 2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-n-(trifluoromethylsulfonyl)-1,3-dihydroindene-2-carboxamide Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(=O)NS(=O)(=O)C(F)(F)F)=C1OC1CCC1 JXBIPVFXGOBYMB-UHFFFAOYSA-N 0.000 claims 1
- NIIGEKNBVCDNHH-UHFFFAOYSA-N 2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-n-methylsulfonyl-1,3-dihydroindene-2-carboxamide Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(=O)NS(C)(=O)=O)=C1OC1CCC1 NIIGEKNBVCDNHH-UHFFFAOYSA-N 0.000 claims 1
- DOPQJZLIDGRTTR-UHFFFAOYSA-N 2-[(2-cyclopentyl-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1C1CCCC1 DOPQJZLIDGRTTR-UHFFFAOYSA-N 0.000 claims 1
- HYDZAARUIWGUGM-UHFFFAOYSA-N 2-[(2-hex-3-en-3-yl-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCC=C(CC)C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 HYDZAARUIWGUGM-UHFFFAOYSA-N 0.000 claims 1
- RXQPOEOJKHCXBJ-UHFFFAOYSA-N 2-[(2-hexan-3-yl-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCCC(CC)C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 RXQPOEOJKHCXBJ-UHFFFAOYSA-N 0.000 claims 1
- MOZHMAHPPVDMSW-UHFFFAOYSA-N 2-[(2-phenylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C1C2=CC=CC=C2CC1(C(=O)O)NC(=O)C1=CC=CC=C1C1=CC=CC=C1 MOZHMAHPPVDMSW-UHFFFAOYSA-N 0.000 claims 1
- AXWYMDVKFCTCSX-UHFFFAOYSA-N 2-[(2-propan-2-ylsulfanylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)SC1=CC=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 AXWYMDVKFCTCSX-UHFFFAOYSA-N 0.000 claims 1
- KXMYCMOTDIYDMS-UHFFFAOYSA-N 2-[(3,5-dichloro-2-cyclobutyloxybenzoyl)amino]-5-fluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound C1C2=CC=C(F)C=C2CC1(C(=O)O)NC(=O)C1=CC(Cl)=CC(Cl)=C1OC1CCC1 KXMYCMOTDIYDMS-UHFFFAOYSA-N 0.000 claims 1
- YIJFSXUJEOMRLN-UHFFFAOYSA-N 2-[(3,5-dichloro-2-prop-2-enoxyphenyl)sulfonylamino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C1C2=CC=CC=C2CC1(C(=O)O)NS(=O)(=O)C1=CC(Cl)=CC(Cl)=C1OCC=C YIJFSXUJEOMRLN-UHFFFAOYSA-N 0.000 claims 1
- UDQBYOINRNOXIK-UHFFFAOYSA-N 2-[(3,5-dichloro-2-propan-2-yloxyphenyl)sulfonylamino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)OC1=C(Cl)C=C(Cl)C=C1S(=O)(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 UDQBYOINRNOXIK-UHFFFAOYSA-N 0.000 claims 1
- SIDVYXCWNASQAI-UHFFFAOYSA-N 2-[(3-bromo-2-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=C(Br)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 SIDVYXCWNASQAI-UHFFFAOYSA-N 0.000 claims 1
- KBANFOAVVPTUAL-UHFFFAOYSA-N 2-[(3-chloro-2-prop-2-enoxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C1C2=CC=CC=C2CC1(C(=O)O)NC(=O)C1=CC=CC(Cl)=C1OCC=C KBANFOAVVPTUAL-UHFFFAOYSA-N 0.000 claims 1
- VXGZSCGHSSMMRH-UHFFFAOYSA-N 2-[(3-chloro-2-propan-2-yloxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)OC1=C(Cl)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 VXGZSCGHSSMMRH-UHFFFAOYSA-N 0.000 claims 1
- ZHZVTFBAVDBLOC-UHFFFAOYSA-N 2-[(3-cyano-2-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=C(C#N)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 ZHZVTFBAVDBLOC-UHFFFAOYSA-N 0.000 claims 1
- XTSVCKSIAZUPIW-UHFFFAOYSA-N 2-[(3-methyl-2-pentylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCCCCC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 XTSVCKSIAZUPIW-UHFFFAOYSA-N 0.000 claims 1
- YTFNGIWSLSXQTE-UHFFFAOYSA-N 2-[(3-methyl-2-prop-1-enylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC=CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 YTFNGIWSLSXQTE-UHFFFAOYSA-N 0.000 claims 1
- BGHPCLFHLVTPQG-UHFFFAOYSA-N 2-[(3-methyl-2-prop-2-enoxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1OCC=C BGHPCLFHLVTPQG-UHFFFAOYSA-N 0.000 claims 1
- FDPUDIAMESRREB-UHFFFAOYSA-N 2-[(3-methyl-2-propan-2-yloxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)OC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 FDPUDIAMESRREB-UHFFFAOYSA-N 0.000 claims 1
- PMGMYYQMBLQSCM-UHFFFAOYSA-N 2-[(3-methyl-2-propan-2-yloxybenzoyl)amino]-5-(trifluoromethyl)-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)OC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(C(F)(F)F)=CC=C2C1 PMGMYYQMBLQSCM-UHFFFAOYSA-N 0.000 claims 1
- PFESIXUWYFDMJH-UHFFFAOYSA-N 2-[(3-methyl-2-propylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCCC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 PFESIXUWYFDMJH-UHFFFAOYSA-N 0.000 claims 1
- YDGJSBIBYHQXFD-UHFFFAOYSA-N 2-[(5-bromo-2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC(Br)=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1OC1CCC1 YDGJSBIBYHQXFD-UHFFFAOYSA-N 0.000 claims 1
- DMZUYHOTMLQCOU-UHFFFAOYSA-N 2-[(5-chloro-2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC(Cl)=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1OC1CCC1 DMZUYHOTMLQCOU-UHFFFAOYSA-N 0.000 claims 1
- ALMZBDOLVFFLJZ-UHFFFAOYSA-N 2-[(5-chloro-2-cyclobutyloxy-3-methylbenzoyl)amino]-5-fluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC(Cl)=CC(C(=O)NC2(CC3=CC(F)=CC=C3C2)C(O)=O)=C1OC1CCC1 ALMZBDOLVFFLJZ-UHFFFAOYSA-N 0.000 claims 1
- FVCATFOILDZAGK-UHFFFAOYSA-N 2-[2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroinden-2-yl]acetic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC(O)=O)CC3=CC=CC=C3C2)=C1OC1CCC1 FVCATFOILDZAGK-UHFFFAOYSA-N 0.000 claims 1
- MCKNHMQFPZQZNR-UHFFFAOYSA-N 2-[[2-(2-cyclopropylethenyl)-3-methylbenzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1C=CC1CC1 MCKNHMQFPZQZNR-UHFFFAOYSA-N 0.000 claims 1
- LIZLWUTUDPLXHS-UHFFFAOYSA-N 2-[[2-(2-cyclopropylethyl)-3-methylbenzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1CCC1CC1 LIZLWUTUDPLXHS-UHFFFAOYSA-N 0.000 claims 1
- YYQWWUQBLCCMJM-UHFFFAOYSA-N 2-[[2-(2-methylbutan-2-yl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCC(C)(C)C1=CC=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 YYQWWUQBLCCMJM-UHFFFAOYSA-N 0.000 claims 1
- QQQZWHUERYOCHQ-UHFFFAOYSA-N 2-[[2-(cyclohexen-1-yl)-3-methylbenzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1C1=CCCCC1 QQQZWHUERYOCHQ-UHFFFAOYSA-N 0.000 claims 1
- JMXZJWLQQXRYCF-UHFFFAOYSA-N 2-[[2-(cyclopenten-1-yl)-3-methylbenzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1C1=CCCC1 JMXZJWLQQXRYCF-UHFFFAOYSA-N 0.000 claims 1
- SSCNSRFCMRTGIA-UHFFFAOYSA-N 2-[[2-(cyclopenten-1-yl)-3-methylbenzoyl]amino]-5-fluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC(F)=CC=C3C2)C(O)=O)=C1C1=CCCC1 SSCNSRFCMRTGIA-UHFFFAOYSA-N 0.000 claims 1
- HCKMCGDTQYQUSD-UHFFFAOYSA-N 2-[[2-(cyclopenten-1-yl)-3-methylbenzoyl]amino]-n-(trifluoromethylsulfonyl)-1,3-dihydroindene-2-carboxamide Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(=O)NS(=O)(=O)C(F)(F)F)=C1C1=CCCC1 HCKMCGDTQYQUSD-UHFFFAOYSA-N 0.000 claims 1
- LQYWUXJBHFXOOE-UHFFFAOYSA-N 2-[[2-(cyclopropylmethoxy)-3-methylbenzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC=CC=C3C2)C(O)=O)=C1OCC1CC1 LQYWUXJBHFXOOE-UHFFFAOYSA-N 0.000 claims 1
- ZAFOXUZNHBJXET-UHFFFAOYSA-N 2-[[2-[ethyl(methyl)amino]pyridine-3-carbonyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCN(C)C1=NC=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 ZAFOXUZNHBJXET-UHFFFAOYSA-N 0.000 claims 1
- BGXUVTNSAMGSBX-UHFFFAOYSA-N 2-[[2-[methyl(propan-2-yl)amino]pyridine-3-carbonyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)N(C)C1=NC=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 BGXUVTNSAMGSBX-UHFFFAOYSA-N 0.000 claims 1
- FQSVUDYSMORLMZ-UHFFFAOYSA-N 2-[[3-methyl-2-(2-methylprop-1-enyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)=CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 FQSVUDYSMORLMZ-UHFFFAOYSA-N 0.000 claims 1
- RDEPYTOUBFCJKH-UHFFFAOYSA-N 2-[[3-methyl-2-(2-methylpropanoyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)C(=O)C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 RDEPYTOUBFCJKH-UHFFFAOYSA-N 0.000 claims 1
- CVZZXXPJPJIHNE-UHFFFAOYSA-N 2-[[3-methyl-2-(2-methylpropyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 CVZZXXPJPJIHNE-UHFFFAOYSA-N 0.000 claims 1
- MXEZMFDQDAPMOI-LFYBBSHMSA-N 2-[[3-methyl-2-[(e)-pent-1-enyl]benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCC\C=C\C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 MXEZMFDQDAPMOI-LFYBBSHMSA-N 0.000 claims 1
- MXEZMFDQDAPMOI-XGICHPGQSA-N 2-[[3-methyl-2-[(z)-pent-1-enyl]benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCC\C=C/C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 MXEZMFDQDAPMOI-XGICHPGQSA-N 0.000 claims 1
- VGAHKLJXSCXITG-UHFFFAOYSA-N 2-[[5-chloro-2-[methyl(propan-2-yl)amino]pyridine-3-carbonyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)N(C)C1=NC=C(Cl)C=C1C(=O)NC1(C(O)=O)CC2=CC=CC=C2C1 VGAHKLJXSCXITG-UHFFFAOYSA-N 0.000 claims 1
- OQBZNYNXTIFJRU-UHFFFAOYSA-N 2-cyclobutyloxy-3-methyl-n-[2-(2h-tetrazol-5-yl)-1,3-dihydroinden-2-yl]benzamide Chemical compound C1CCC1OC=1C(C)=CC=CC=1C(=O)NC1(CC2=CC=CC=C2C1)C1=NN=NN1 OQBZNYNXTIFJRU-UHFFFAOYSA-N 0.000 claims 1
- IJBOCWVIWAISBD-UHFFFAOYSA-N 4,5-dichloro-2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=C(Cl)C(Cl)=CC=C3C2)C(O)=O)=C1OC1CCC1 IJBOCWVIWAISBD-UHFFFAOYSA-N 0.000 claims 1
- BMBSLTRHUKLFAS-UHFFFAOYSA-N 4,5-difluoro-2-[[3-methyl-2-(2-methylprop-1-enyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)=CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=C(F)C(F)=CC=C2C1 BMBSLTRHUKLFAS-UHFFFAOYSA-N 0.000 claims 1
- FSIHSVMSLLMCQD-UHFFFAOYSA-N 4,7-difluoro-2-[[3-methyl-2-(2-methylpropyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC(C(F)=CC=C2F)=C2C1 FSIHSVMSLLMCQD-UHFFFAOYSA-N 0.000 claims 1
- UHRGPFIPUHZRNO-UHFFFAOYSA-N 5,6-difluoro-2-[(3-methyl-2-prop-1-enylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC=CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=C(F)C=C2C1 UHRGPFIPUHZRNO-UHFFFAOYSA-N 0.000 claims 1
- HCLWVZVGWADYDV-UHFFFAOYSA-N 5,6-difluoro-2-[(3-methyl-2-propylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CCCC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=C(F)C=C2C1 HCLWVZVGWADYDV-UHFFFAOYSA-N 0.000 claims 1
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- ZHYHJVGTMITYTB-UHFFFAOYSA-N 5-bromo-2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid;2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-5-fluoro-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC(F)=CC=C3C2)C(O)=O)=C1OC1CCC1.CC1=CC=CC(C(=O)NC2(CC3=CC(Br)=CC=C3C2)C(O)=O)=C1OC1CCC1 ZHYHJVGTMITYTB-UHFFFAOYSA-N 0.000 claims 1
- BSNIHAUVELATMP-HWKANZROSA-N 5-bromo-2-[[3-methyl-2-[(e)-prop-1-enyl]benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C\C=C\C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(Br)=CC=C2C1 BSNIHAUVELATMP-HWKANZROSA-N 0.000 claims 1
- RREJNSHSDBPJIE-UHFFFAOYSA-N 5-chloro-2-[(2-cyclobutyloxy-3-methylbenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2(CC3=CC(Cl)=CC=C3C2)C(O)=O)=C1OC1CCC1 RREJNSHSDBPJIE-UHFFFAOYSA-N 0.000 claims 1
- JJAGIHLMZAAAQP-UHFFFAOYSA-N 5-fluoro-2-[(3-methyl-2-propan-2-yloxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)OC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=CC=C2C1 JJAGIHLMZAAAQP-UHFFFAOYSA-N 0.000 claims 1
- MCAZANBPBDWLKT-UHFFFAOYSA-N 5-fluoro-2-[[3-methyl-2-(2-methylprop-1-enyl)benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound CC(C)=CC1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=CC=C2C1 MCAZANBPBDWLKT-UHFFFAOYSA-N 0.000 claims 1
- RCKNFKFXUYXQGD-HWKANZROSA-N 5-fluoro-2-[[3-methyl-2-[(e)-prop-1-enyl]benzoyl]amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C\C=C\C1=C(C)C=CC=C1C(=O)NC1(C(O)=O)CC2=CC(F)=CC=C2C1 RCKNFKFXUYXQGD-HWKANZROSA-N 0.000 claims 1
- ZEZCZUQIVHQJHW-UHFFFAOYSA-N 5-methoxy-2-(5,6,7,8-tetrahydronaphthalene-1-carbonylamino)-1,3-dihydroindene-2-carboxylic acid Chemical compound C1CCCC2=C1C=CC=C2C(=O)NC1(C(O)=O)CC2=CC=C(OC)C=C2C1 ZEZCZUQIVHQJHW-UHFFFAOYSA-N 0.000 claims 1
- ZFNNJCNJQGPLHU-UHFFFAOYSA-N 5-methoxy-2-[(3-methyl-2-propan-2-yloxybenzoyl)amino]-1,3-dihydroindene-2-carboxylic acid Chemical compound C1C2=CC(OC)=CC=C2CC1(C(O)=O)NC(=O)C1=CC=CC(C)=C1OC(C)C ZFNNJCNJQGPLHU-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
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- NAWVGYMUSFGIFN-UHFFFAOYSA-N ClC=1C=C2CC(CC2=CC1)(C(=O)O)NC(C1=C(C(=CC=C1)C)C=C(C)C)=O.ClC=1C=C2CC(CC2=CC1)(C(=O)O)NC(C1=C(C(=CC=C1)C)CC(C)C)=O Chemical compound ClC=1C=C2CC(CC2=CC1)(C(=O)O)NC(C1=C(C(=CC=C1)C)C=C(C)C)=O.ClC=1C=C2CC(CC2=CC1)(C(=O)O)NC(C1=C(C(=CC=C1)C)CC(C)C)=O NAWVGYMUSFGIFN-UHFFFAOYSA-N 0.000 claims 1
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| CN101679346B (zh) | 2007-06-05 | 2014-10-22 | 塞诺菲-安万特股份有限公司 | 取代的苯甲酰氨基茚满-2-羧酸及相关化合物 |
| CN102083432B (zh) * | 2008-05-05 | 2016-02-17 | 赛诺菲-安万特 | 酰基氨基取代的稠合环戊烷羧酸衍生物及它们作为药物的用途 |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| EP2316818A1 (en) * | 2009-11-03 | 2011-05-04 | Active Biotech AB | Method for the preparation of 2-amino-6-ethylbenzoic acid |
| CN101735041B (zh) * | 2009-12-17 | 2013-06-12 | 太仓市运通化工厂 | 一种邻羧基苯甲醛的制备方法 |
| US8299117B2 (en) | 2010-06-16 | 2012-10-30 | Metabolex Inc. | GPR120 receptor agonists and uses thereof |
| CA2801182A1 (en) * | 2010-06-16 | 2011-12-22 | Metabolex, Inc. | Gpr120 receptor agonists and uses thereof |
| EP2771484A1 (en) | 2011-10-28 | 2014-09-03 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
| WO2014003744A1 (en) * | 2012-06-27 | 2014-01-03 | Morehouse School Of Medicine | Anti-cxcl9, anti-cxcl 10, anti-cxcl 11, anti-cxcl 13, anti-cxcr3 and anti-cxcr5 agents for inflammatory disorder |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
| EP3319968A1 (en) | 2015-07-06 | 2018-05-16 | Rodin Therapeutics, Inc. | Heterobicyclic n-aminophenyl-amides as inhibitors of histone deacetylase |
| GB201615191D0 (en) * | 2016-09-07 | 2016-10-19 | Takeda Pharmaceuticals Co | Novel compounds |
| AU2018207402B2 (en) | 2017-01-11 | 2023-09-28 | Alkermes, Inc. | Bicyclic inhibitors of histone deacetylase |
| GB201704476D0 (en) | 2017-03-21 | 2017-05-03 | Antabio Sas | Chemical compounds |
| EA039417B1 (ru) | 2017-08-07 | 2022-01-25 | Родин Терапеутикс, Инк. | Бициклические ингибиторы гистондеацетилазы |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| EP3628666A1 (en) | 2018-09-25 | 2020-04-01 | Antabio SAS | Indane derivatives for use in the treatment of bacterial infection |
| WO2020064175A1 (en) | 2018-09-25 | 2020-04-02 | Antabio Sas | Indane derivatives for use in the treatment of bacterial infection |
| EP3628672A1 (en) | 2018-09-25 | 2020-04-01 | Antabio SAS | Indane derivatives for use in the treatment of bacterial infection |
| MA53706A (fr) | 2018-09-25 | 2021-12-29 | Antabio Sas | Dérivés d'indane destinés à être utilisés dans le traitement d'une infection bactérienne |
| SG11202103011YA (en) * | 2018-10-11 | 2021-04-29 | Basf As | Aromatic compounds and pharmaceutical uses thereof |
| CN110938015B (zh) * | 2019-12-06 | 2022-10-25 | 重庆工商大学 | 一种叠氮基取代的水杨酸衍生物的制备方法 |
| WO2021191240A1 (en) | 2020-03-24 | 2021-09-30 | Antabio Sas | Combination therapy |
| WO2021202553A1 (en) * | 2020-03-31 | 2021-10-07 | Yale University | Cxcr5 antagonists and methods of treating diseases or disorders using same |
| BR112022022595A2 (pt) | 2020-05-06 | 2022-12-20 | Bayer Ag | Piridina (tio)amidas como compostos fungicidas |
| CN116157397B (zh) | 2020-06-04 | 2025-07-15 | 拜耳公司 | 作为新杀真菌剂的杂环基吡啶 |
| WO2023042314A1 (ja) * | 2021-09-15 | 2023-03-23 | 和幸 吉崎 | 免疫異常性炎症性疾患を治療または予防するための組成物 |
| EP4441049A1 (en) | 2021-11-30 | 2024-10-09 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether oxadiazines as fungicidal compounds |
| CN116217415B (zh) * | 2023-02-13 | 2024-06-18 | 武汉大学 | 一种合成手性3-氨基-1-苯基丙醇和手性3-(甲氨基)-1-苯基丙醇的方法 |
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| FR2701480B1 (fr) * | 1993-02-15 | 1995-05-24 | Sanofi Elf | Composés à groupe sulfamoyle et amidino, leur procédé de préparation et les compositions pharmaceutiques les contenant. |
| TR199901849T2 (xx) * | 1997-02-03 | 2000-02-21 | Pfizer Products Inc. | Arils�lfonilamino hidroksamik asit t�revleri. |
| US5932765A (en) * | 1997-05-23 | 1999-08-03 | Merck Patent Gesellschaft Mit | Nitromethyl ketones, process for preparing them and compositions containing them |
| WO1998053818A1 (en) * | 1997-05-29 | 1998-12-03 | Merck & Co., Inc. | Sulfonamides as cell adhesion inhibitors |
| KR100352316B1 (ko) * | 1997-07-31 | 2002-09-12 | 더 프록터 앤드 갬블 캄파니 | 메탈로프로테아제억제제로서사용되는술포닐아미노치환히드록삼산유도체 |
| US6929928B2 (en) * | 2003-06-12 | 2005-08-16 | E. I. Du Pont De Nemours And Company | Genes encoding carotenoid compounds |
| JP2008516989A (ja) * | 2004-10-19 | 2008-05-22 | コンパス ファーマシューティカルズ リミティド ライアビリティ カンパニー | 組成物及び抗腫瘍剤としてのその使用 |
| EP1676834A1 (en) * | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| US20100130737A1 (en) * | 2005-02-18 | 2010-05-27 | Takeda Pharmaceutical Company Limited | Regulating Agent of GPR34 Receptor Function |
| WO2008000407A1 (en) * | 2006-06-28 | 2008-01-03 | Sanofi-Aventis | Inhibitors of cxcr2 |
| JP5237938B2 (ja) * | 2006-06-28 | 2013-07-17 | サノフイ | 新規なｃｘｃｒ２阻害剤 |
| WO2008036967A2 (en) * | 2006-09-22 | 2008-03-27 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds as lasy activators |
| CN101679346B (zh) | 2007-06-05 | 2014-10-22 | 塞诺菲-安万特股份有限公司 | 取代的苯甲酰氨基茚满-2-羧酸及相关化合物 |
| CN102083432B (zh) * | 2008-05-05 | 2016-02-17 | 赛诺菲-安万特 | 酰基氨基取代的稠合环戊烷羧酸衍生物及它们作为药物的用途 |
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