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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- 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
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| CL2008001632A1 (es) | 2007-06-05 | 2009-10-16 | Sanofi Aventis | Compuestos derivados de acidos benzoilamino-indan-2-carboxilicos sustituidos, inhibidores del receptor cxcr5; composicion farmaceutica; y su uso en el tratamiento de efecciones fisiologicas inflamatorias, tales como artritis reumatoidea y asma. |
| RU2529484C2 (ru) * | 2008-05-05 | 2014-09-27 | Санофи-Авентис | Ациламино-замещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств |
| 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 |
| JP5746334B2 (ja) * | 2010-06-16 | 2015-07-08 | シマベイ セラピューティクス， インコーポレーテッド | Ｇｐｒ１２０受容体作動薬及びその使用 |
| CA2852160A1 (en) | 2011-10-28 | 2013-05-02 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
| CN104870012A (zh) * | 2012-06-27 | 2015-08-26 | 吉安特科技公司 | 用于炎性疾病的抗-cxcl9、抗-cxcl10、抗-cxcl11、抗-cxcl13、抗-cxcr3和抗-cxcr5试剂 |
| LT3319959T (lt) | 2015-07-06 | 2021-12-27 | Alkermes, Inc. | Histono deacetilazės hetero-halogeno inhibitoriai |
| 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 |
| RS62959B1 (sr) | 2017-01-11 | 2022-03-31 | Alkermes Inc | Biciklični inhibitori histon-deacetilaze |
| GB201704476D0 (en) | 2017-03-21 | 2017-05-03 | Antabio Sas | Chemical compounds |
| US11225475B2 (en) | 2017-08-07 | 2022-01-18 | Alkermes, Inc. | Substituted pyridines as inhibitors of histone deacetylase |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| BR112021005532A2 (pt) | 2018-09-25 | 2021-06-29 | Antabio Sas | composto, composição farmacêutica e combinação |
| EP3628672A1 (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 |
| EP3628666A1 (en) | 2018-09-25 | 2020-04-01 | Antabio SAS | Indane derivatives for use in the treatment of bacterial infection |
| MA53188A1 (fr) * | 2018-10-11 | 2021-12-31 | Basf As | Composés aromatiques et leurs utilisations pharmaceutiques |
| 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 |
| US20240016941A1 (en) | 2020-03-24 | 2024-01-18 | 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 |
| CN115915941B (zh) | 2020-05-06 | 2025-07-15 | 拜耳公司 | 作为杀真菌化合物的吡啶（硫代）酰胺 |
| JP7840878B2 (ja) | 2020-06-04 | 2026-04-06 | バイエル、アクチエンゲゼルシャフト | 新規殺真菌剤としてのヘテロシクリルピリジン |
| 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. |
| EP0977733B1 (en) * | 1997-02-03 | 2003-09-03 | Pfizer Products Inc. | Arylsulfonylamino hydroxamic acid derivatives |
| US5932765A (en) * | 1997-05-23 | 1999-08-03 | Merck Patent Gesellschaft Mit | Nitromethyl ketones, process for preparing them and compositions containing them |
| CA2291708A1 (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 |
| ATE502025T1 (de) * | 2004-10-19 | 2011-04-15 | Compass Pharmaceuticals Llc | Arylcarboxamide und ihre verwendung als antitumormittel |
| 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 |
| EP1849465A4 (en) * | 2005-02-18 | 2008-12-24 | Takeda Pharmaceutical | AGENS TO CONTROL THE FUNCTION OF THE GPR34 RECEPTOR |
| KR20090023645A (ko) * | 2006-06-28 | 2009-03-05 | 사노피-아벤티스 | 신규한 ｃｘｃｒ2 억제제 |
| JP5232144B2 (ja) * | 2006-06-28 | 2013-07-10 | サノフイ | Ｃｘｃｒ２阻害剤 |
| WO2008036967A2 (en) * | 2006-09-22 | 2008-03-27 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds as lasy activators |
| CL2008001632A1 (es) | 2007-06-05 | 2009-10-16 | Sanofi Aventis | Compuestos derivados de acidos benzoilamino-indan-2-carboxilicos sustituidos, inhibidores del receptor cxcr5; composicion farmaceutica; y su uso en el tratamiento de efecciones fisiologicas inflamatorias, tales como artritis reumatoidea y asma. |
| RU2529484C2 (ru) * | 2008-05-05 | 2014-09-27 | Санофи-Авентис | Ациламино-замещенные производные конденсированных циклопентанкарбоновых кислот и их применение в качестве фармацевтических средств |
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2010
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