JP5575799B2 - ７−フェノキシクロマンカルボン酸誘導体 - Google Patents

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Publication number

JP5575799B2

JP5575799B2 JP2011542470A JP2011542470A JP5575799B2 JP 5575799 B2 JP5575799 B2 JP 5575799B2 JP 2011542470 A JP2011542470 A JP 2011542470A JP 2011542470 A JP2011542470 A JP 2011542470A JP 5575799 B2 JP5575799 B2 JP 5575799B2

Authority

JP

Japan

Prior art keywords

phenoxy

carboxylic acid

chroman

ylcarbamoyl

chloro

Prior art date

2008-12-22

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.)

Expired - Fee Related

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• 239000002253 acid Substances 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims description 309
• 238000000034 method Methods 0.000 claims description 134
• 125000000217 alkyl group Chemical group 0.000 claims description 128
• -1 2-oxopyridin-1 (2H) -yl Chemical group 0.000 claims description 100
• 125000001424 substituent group Chemical group 0.000 claims description 89
• 239000000203 mixture Substances 0.000 claims description 74
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 68
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 150000002367 halogens Chemical class 0.000 claims description 48
• 150000003839 salts Chemical class 0.000 claims description 46
• 125000005842 heteroatom Chemical group 0.000 claims description 43
• 229910052801 chlorine Inorganic materials 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 125000004429 atom Chemical group 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 239000003054 catalyst Substances 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 230000008569 process Effects 0.000 claims description 26
• 239000003446 ligand Substances 0.000 claims description 25
• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• GWDVHHFYMYWYNA-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 GWDVHHFYMYWYNA-UHFFFAOYSA-N 0.000 claims description 20
• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• RGWHTTALQBHDGZ-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)CCOC2=C1 RGWHTTALQBHDGZ-UHFFFAOYSA-N 0.000 claims description 16
• YYASZOUWMTWJBY-UHFFFAOYSA-N 6-chloro-7-[4-[(6-chloroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(Cl)C=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 YYASZOUWMTWJBY-UHFFFAOYSA-N 0.000 claims description 16
• 229910052763 palladium Inorganic materials 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 208000026278 immune system disease Diseases 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 10
• DZQHRTYQJRHWQE-UHFFFAOYSA-N 6-cyano-7-[4-[[6-(3,4-dimethylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)C#N)=CC=2)=N1 DZQHRTYQJRHWQE-UHFFFAOYSA-N 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• FZHBLVWFBLYBRU-UHFFFAOYSA-N 6-chloro-7-[4-[(6-phenylpyrazin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CN=CC=1C1=CC=CC=C1 FZHBLVWFBLYBRU-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• SJHMZSZLEVAPPS-UHFFFAOYSA-N 6-chloro-7-[4-[(4-methylquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=C2C(C)=CC(NC(=O)C=3C=CC(OC=4C(=CC=5C(C(O)=O)CCOC=5C=4)Cl)=CC=3)=NC2=C1 SJHMZSZLEVAPPS-UHFFFAOYSA-N 0.000 claims description 6
• XNYIKJKWMIPXIC-UHFFFAOYSA-N 6-chloro-7-[4-[(5-chloroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC1=CC=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 XNYIKJKWMIPXIC-UHFFFAOYSA-N 0.000 claims description 6
• BZSIIAXZXXYBNG-UHFFFAOYSA-N 6-cyano-7-[4-(quinolin-3-ylcarbamoyl)phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=CC2=CC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3C#N)C(=O)O)=CN=C21 BZSIIAXZXXYBNG-UHFFFAOYSA-N 0.000 claims description 6
• 150000001879 copper Chemical class 0.000 claims description 6
• 229910052751 metal Inorganic materials 0.000 claims description 6
• 239000002184 metal Substances 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• HRBZUZZOAMLGEA-UHFFFAOYSA-N 6-chloro-7-[4-[(8-methylquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1CCC(C(O)=O)C(C=C2Cl)=C1C=C2OC(C=C1)=CC=C1C(=O)NC1=CC=C2C=CC=C(C)C2=N1 HRBZUZZOAMLGEA-UHFFFAOYSA-N 0.000 claims description 5
• SPINOQDNCUSTKB-UHFFFAOYSA-N 6-chloro-7-[4-[[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=NC=CC=1C1=CC=C(C(F)(F)F)C=C1 SPINOQDNCUSTKB-UHFFFAOYSA-N 0.000 claims description 5
• WIEFDEFRFUUWAB-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CN=CC=1C1=CC=C(Cl)C=C1 WIEFDEFRFUUWAB-UHFFFAOYSA-N 0.000 claims description 5
• TVECIIONJRJXNM-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(C(F)(F)F)C=C2SC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=NC2=C1 TVECIIONJRJXNM-UHFFFAOYSA-N 0.000 claims description 5
• AAMHDHWZSLVHKR-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[4-(trifluoromethyl)phenyl]pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 AAMHDHWZSLVHKR-UHFFFAOYSA-N 0.000 claims description 5
• RABQXOOGHHUVJW-UHFFFAOYSA-N 7-[4-[(6-tert-butylsulfanylpyridin-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)(C)SC1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 RABQXOOGHHUVJW-UHFFFAOYSA-N 0.000 claims description 5
• VKTOBDTYSOSXNN-UHFFFAOYSA-N 7-[4-[[5-(4-chlorophenyl)-1,3,4-thiadiazol-2-yl]carbamoyl]phenoxy]-6-cyano-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N#CC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(S1)=NN=C1C1=CC=C(Cl)C=C1 VKTOBDTYSOSXNN-UHFFFAOYSA-N 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 159000000000 sodium salts Chemical group 0.000 claims description 5
• OJKWSDCUYCFNGK-UHFFFAOYSA-N 6,8-dichloro-7-[4-[[2-(4-chlorophenyl)pyrimidin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=C(Cl)C=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=NC=1C1=CC=C(Cl)C=C1 OJKWSDCUYCFNGK-UHFFFAOYSA-N 0.000 claims description 4
• FQRDDNOFDCFIBV-UHFFFAOYSA-N 6-chloro-7-[4-[(5-phenyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 FQRDDNOFDCFIBV-UHFFFAOYSA-N 0.000 claims description 4
• OPGLODHIMZZHOF-UHFFFAOYSA-N 6-chloro-7-[4-[(6-ethoxypyridin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CCOC1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 OPGLODHIMZZHOF-UHFFFAOYSA-N 0.000 claims description 4
• ZYBBRMMZDJYIPW-UHFFFAOYSA-N 6-chloro-7-[4-[(6-phenylpyridin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=CC=C1 ZYBBRMMZDJYIPW-UHFFFAOYSA-N 0.000 claims description 4
• QMZNCJJCBUYPHV-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3,4-difluorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=C(F)C(F)=C1 QMZNCJJCBUYPHV-UHFFFAOYSA-N 0.000 claims description 4
• DIYOYANZNFBPIV-UHFFFAOYSA-N 6-chloro-7-[4-[[2-(3-chlorophenyl)pyrimidin-5-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=N1)=CN=C1C1=CC=CC(Cl)=C1 DIYOYANZNFBPIV-UHFFFAOYSA-N 0.000 claims description 4
• ZHDLHVSCMVNSPV-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=C(Cl)C=C1 ZHDLHVSCMVNSPV-UHFFFAOYSA-N 0.000 claims description 4
• OECZNJKOFOUYRR-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(6-methoxypyridin-3-yl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C(C=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 OECZNJKOFOUYRR-UHFFFAOYSA-N 0.000 claims description 4
• UHPIXACTSXFYIJ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,4-difluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(F)C=C1F UHPIXACTSXFYIJ-UHFFFAOYSA-N 0.000 claims description 4
• DZEPISVCRQTZFC-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3,4-dichlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C(Cl)=C1 DZEPISVCRQTZFC-UHFFFAOYSA-N 0.000 claims description 4
• FWLMIJBJQMPGQB-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3,4-difluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(F)C(F)=C1 FWLMIJBJQMPGQB-UHFFFAOYSA-N 0.000 claims description 4
• CTDVSHPTVFGJIW-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=CC(Cl)=C1 CTDVSHPTVFGJIW-UHFFFAOYSA-N 0.000 claims description 4
• MUXYSSSHCXLYSY-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-fluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(F)C=C1 MUXYSSSHCXLYSY-UHFFFAOYSA-N 0.000 claims description 4
• OQPQBEQBVTVBCQ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-methylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 OQPQBEQBVTVBCQ-UHFFFAOYSA-N 0.000 claims description 4
• VHBVQFRVFVYGGU-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(6-methoxypyridin-3-yl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 VHBVQFRVFVYGGU-UHFFFAOYSA-N 0.000 claims description 4
• HDWHDDUVTFWFTG-UHFFFAOYSA-N 6-cyano-7-[4-[(5-phenyl-1,3,4-thiadiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N#CC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(S1)=NN=C1C1=CC=CC=C1 HDWHDDUVTFWFTG-UHFFFAOYSA-N 0.000 claims description 4
• UILIDWGGEZGPAF-UHFFFAOYSA-N 6-cyano-7-[4-[(8-methoxyquinolin-3-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1CCC(C(O)=O)C(C=C2C#N)=C1C=C2OC(C=C1)=CC=C1C(=O)NC1=CN=C2C(OC)=CC=CC2=C1 UILIDWGGEZGPAF-UHFFFAOYSA-N 0.000 claims description 4
• YLYOKCKVFUCCCK-UHFFFAOYSA-N 6-cyano-7-[4-[[6-(trifluoromethyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N#CC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC1=CC=C(C(F)(F)F)N=C1 YLYOKCKVFUCCCK-UHFFFAOYSA-N 0.000 claims description 4
• VVVLCEWRMAEEIH-UHFFFAOYSA-N 7-[4-[(4-tert-butyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)(C)C1=CSC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 VVVLCEWRMAEEIH-UHFFFAOYSA-N 0.000 claims description 4
• ISVMYAIYXBBHRC-UHFFFAOYSA-N 7-[4-[(6-tert-butylpyridin-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)(C)C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 ISVMYAIYXBBHRC-UHFFFAOYSA-N 0.000 claims description 4
• RYMJOBFRSDYUCR-UHFFFAOYSA-N 7-[4-[[6-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-6-cyano-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N#CC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 RYMJOBFRSDYUCR-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• GWDVHHFYMYWYNA-HXUWFJFHSA-N (4r)-6-chloro-7-[4-[[6-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C([C@H](C1=CC=2Cl)C(=O)O)COC1=CC=2OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 GWDVHHFYMYWYNA-HXUWFJFHSA-N 0.000 claims description 3
• AUOQMJHEAQOWSL-UHFFFAOYSA-N 6,8-dichloro-7-[4-[(6-chloroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(Cl)C=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C(Cl)=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 AUOQMJHEAQOWSL-UHFFFAOYSA-N 0.000 claims description 3
• FCMCTZXRSOYHAJ-UHFFFAOYSA-N 6,8-dichloro-7-[4-[[6-(3-chlorophenyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=C(Cl)C=1OC(C=C1)=CC=C1C(=O)NC(C=N1)=CC=C1C1=CC=CC(Cl)=C1 FCMCTZXRSOYHAJ-UHFFFAOYSA-N 0.000 claims description 3
• GCSFTPXITUWVMA-UHFFFAOYSA-N 6,8-dichloro-7-[4-[[6-(4-chlorophenyl)pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=C(Cl)C=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CN=CC=1C1=CC=C(Cl)C=C1 GCSFTPXITUWVMA-UHFFFAOYSA-N 0.000 claims description 3
• ODEXLFJUFJNFGN-UHFFFAOYSA-N 6,8-dichloro-7-[4-[[6-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=C(Cl)C=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 ODEXLFJUFJNFGN-UHFFFAOYSA-N 0.000 claims description 3
• RFQWZVDCGCJUNL-UHFFFAOYSA-N 6-chloro-7-[4-(quinolin-2-ylcarbamoyl)phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 RFQWZVDCGCJUNL-UHFFFAOYSA-N 0.000 claims description 3
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• HLHGWLLNDDRPCD-UHFFFAOYSA-N 6-chloro-7-[4-[(6-chloro-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=NC2=C1 HLHGWLLNDDRPCD-UHFFFAOYSA-N 0.000 claims description 2
• IVTOKRFTFFBYSW-UHFFFAOYSA-N 6-chloro-7-[4-[(6-chloroquinoxalin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(Cl)C=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CN=C21 IVTOKRFTFFBYSW-UHFFFAOYSA-N 0.000 claims description 2
• YDTWIGFGPBOEHS-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2,4-dimethoxypyrimidin-5-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(OC)=NC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 YDTWIGFGPBOEHS-UHFFFAOYSA-N 0.000 claims description 2
• MNJIPDQQKLLOQJ-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2,6-dimethoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(OC)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 MNJIPDQQKLLOQJ-UHFFFAOYSA-N 0.000 claims description 2
• FPNNLPTWLTXDFP-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2-cyclopropylpyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=CC=CN=C1C1CC1 FPNNLPTWLTXDFP-UHFFFAOYSA-N 0.000 claims description 2
• BBLPUZNRFGBKCD-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2-ethoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CCOC1=NC=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 BBLPUZNRFGBKCD-UHFFFAOYSA-N 0.000 claims description 2
• ZAEJDCBIHHXOBU-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2-methoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 ZAEJDCBIHHXOBU-UHFFFAOYSA-N 0.000 claims description 2
• FXDFCCGWLSIFBF-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2-piperidin-1-ylpyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=CC=CN=C1N1CCCCC1 FXDFCCGWLSIFBF-UHFFFAOYSA-N 0.000 claims description 2
• BLNZFCFOYHUZHA-UHFFFAOYSA-N 6-chloro-7-[4-[2-(2-propan-2-yloxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)OC1=NC=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 BLNZFCFOYHUZHA-UHFFFAOYSA-N 0.000 claims description 2
• OUYSBENYJUSRMS-UHFFFAOYSA-N 6-chloro-7-[4-[2-(3,5-dichloropyridin-2-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=NC=C(Cl)C=C1Cl OUYSBENYJUSRMS-UHFFFAOYSA-N 0.000 claims description 2
• VDULVQCTLJTXJN-UHFFFAOYSA-N 6-chloro-7-[4-[2-(4-chloro-2-oxopyridin-1-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCN1C=CC(Cl)=CC1=O VDULVQCTLJTXJN-UHFFFAOYSA-N 0.000 claims description 2
• QFKMEADYERWQNI-UHFFFAOYSA-N 6-chloro-7-[4-[2-(6-methoxypyridin-2-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=CC=CC(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 QFKMEADYERWQNI-UHFFFAOYSA-N 0.000 claims description 2
• KOGQBRFSBDWDEO-UHFFFAOYSA-N 6-chloro-7-[4-[2-(6-methoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=NC(OC)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 KOGQBRFSBDWDEO-UHFFFAOYSA-N 0.000 claims description 2
• FNCWIPLMWZBXKN-UHFFFAOYSA-N 6-chloro-7-[4-[2-[1-[4-(trifluoromethyl)phenyl]pyrrol-2-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=CC=CN1C1=CC=C(C(F)(F)F)C=C1 FNCWIPLMWZBXKN-UHFFFAOYSA-N 0.000 claims description 2
• VOXHCSHXHCBBFH-UHFFFAOYSA-N 6-chloro-7-[4-[2-[2-(2-chlorophenyl)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=CC=CN=C1C1=CC=CC=C1Cl VOXHCSHXHCBBFH-UHFFFAOYSA-N 0.000 claims description 2
• SZLLIQYDICTOMW-UHFFFAOYSA-N 6-chloro-7-[4-[2-[2-(dimethylamino)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CN(C)C1=NC=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 SZLLIQYDICTOMW-UHFFFAOYSA-N 0.000 claims description 2
• ARYZFRWMNCQJDZ-UHFFFAOYSA-N 6-chloro-7-[4-[2-[2-methoxy-6-(trifluoromethyl)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(C(F)(F)F)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 ARYZFRWMNCQJDZ-UHFFFAOYSA-N 0.000 claims description 2
• YYLXBKJMSSFXTJ-UHFFFAOYSA-N 6-chloro-7-[4-[2-[3-(4-chlorophenyl)pyrazol-1-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCN(N=1)C=CC=1C1=CC=C(Cl)C=C1 YYLXBKJMSSFXTJ-UHFFFAOYSA-N 0.000 claims description 2
• NOMMAWFICBYJTI-UHFFFAOYSA-N 6-chloro-7-[4-[2-[6-(2-chlorophenyl)pyridin-2-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC(N=1)=CC=CC=1C1=CC=CC=C1Cl NOMMAWFICBYJTI-UHFFFAOYSA-N 0.000 claims description 2
• PCLNRTYEJUBBOL-UHFFFAOYSA-N 6-chloro-7-[4-[2-[6-(4-methoxyphenyl)pyridin-2-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 PCLNRTYEJUBBOL-UHFFFAOYSA-N 0.000 claims description 2
• TYQZGWUYEJRSRL-UHFFFAOYSA-N 6-chloro-7-[4-[2-[6-(6-methoxypyridin-3-yl)pyridin-2-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 TYQZGWUYEJRSRL-UHFFFAOYSA-N 0.000 claims description 2
• GUOWDEQMXUTURH-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(2,4-difluorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=C(F)C=C1F GUOWDEQMXUTURH-UHFFFAOYSA-N 0.000 claims description 2
• BCVKOZDLGJLESV-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(2-chlorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=CC=C1Cl BCVKOZDLGJLESV-UHFFFAOYSA-N 0.000 claims description 2
• OTFGKLMPCUTEKN-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3-chloro-2-fluorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=CC(Cl)=C1F OTFGKLMPCUTEKN-UHFFFAOYSA-N 0.000 claims description 2
• LCZBAERCTHXSSV-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3-chloro-4-fluorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=C(F)C(Cl)=C1 LCZBAERCTHXSSV-UHFFFAOYSA-N 0.000 claims description 2
• MYYRXMOGEKDEHB-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3-chlorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=CC(Cl)=C1 MYYRXMOGEKDEHB-UHFFFAOYSA-N 0.000 claims description 2
• FRRRYBLSANIYRN-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3-chlorophenyl)pyrazol-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=C1)C=NN1C1=CC=CC(Cl)=C1 FRRRYBLSANIYRN-UHFFFAOYSA-N 0.000 claims description 2
• WGEWXXGQUVPYJG-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(4-chlorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=C(Cl)C=C1 WGEWXXGQUVPYJG-UHFFFAOYSA-N 0.000 claims description 2
• JWXMKTLFZQTAQJ-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(4-methoxyphenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1N=C(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)C=C1 JWXMKTLFZQTAQJ-UHFFFAOYSA-N 0.000 claims description 2
• WYVOXTSVOBKWER-UHFFFAOYSA-N 6-chloro-7-[4-[[1-[6-(trifluoromethyl)pyridin-2-yl]piperidin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(CC1)CCN1C1=CC=CC(C(F)(F)F)=N1 WYVOXTSVOBKWER-UHFFFAOYSA-N 0.000 claims description 2
• GMXQACKKZRIQRO-UHFFFAOYSA-N 6-chloro-7-[4-[[2-(3-chlorophenyl)pyridin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=1)=CC=NC=1C1=CC=CC(Cl)=C1 GMXQACKKZRIQRO-UHFFFAOYSA-N 0.000 claims description 2
• JNUODVFSEPRKKX-UHFFFAOYSA-N 6-chloro-7-[4-[[2-(4-chlorophenyl)pyridin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=1)=CC=NC=1C1=CC=C(Cl)C=C1 JNUODVFSEPRKKX-UHFFFAOYSA-N 0.000 claims description 2
• NDJCYLXJRYGHAT-UHFFFAOYSA-N 6-chloro-7-[4-[[2-(4-chlorophenyl)pyrimidin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=NC=1C1=CC=C(Cl)C=C1 NDJCYLXJRYGHAT-UHFFFAOYSA-N 0.000 claims description 2
• PFDJEVWITFRSPJ-UHFFFAOYSA-N 6-chloro-7-[4-[[3-(4-chlorophenyl)-1,2-oxazol-5-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(ON=1)=CC=1C1=CC=C(Cl)C=C1 PFDJEVWITFRSPJ-UHFFFAOYSA-N 0.000 claims description 2
• BYKAWOPELOINPD-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(SC=1)=NC=1C1=CC=C(F)C=C1F BYKAWOPELOINPD-UHFFFAOYSA-N 0.000 claims description 2
• ACWDTZXYYGPMHY-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(2-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=CC=1)=CC=1C1=CC=CC=C1Cl ACWDTZXYYGPMHY-UHFFFAOYSA-N 0.000 claims description 2
• RWHPUTLFPZCIBK-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(SC=1)=NC=1C1=CC=C(F)C(F)=C1 RWHPUTLFPZCIBK-UHFFFAOYSA-N 0.000 claims description 2
• YRPZDYPSBVSFOZ-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(3-chlorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(SC=1)=NC=1C1=CC=CC(Cl)=C1 YRPZDYPSBVSFOZ-UHFFFAOYSA-N 0.000 claims description 2
• KRIGRIIKODHMES-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(3-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=CC=1)=CC=1C1=CC=CC(Cl)=C1 KRIGRIIKODHMES-UHFFFAOYSA-N 0.000 claims description 2
• FOHIZMPCZRBWJB-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(SC=1)=NC=1C1=CC=C(Cl)C=C1 FOHIZMPCZRBWJB-UHFFFAOYSA-N 0.000 claims description 2
• GIYRSINCDCLTQN-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=CC=1)=CC=1C1=CC=C(Cl)C=C1 GIYRSINCDCLTQN-UHFFFAOYSA-N 0.000 claims description 2
• OZOWFMMFYWHOFW-UHFFFAOYSA-N 6-chloro-7-[4-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(SC=1)=NC=1C1=CC=C(F)C=C1 OZOWFMMFYWHOFW-UHFFFAOYSA-N 0.000 claims description 2
• IDMAMFGDVJNXIB-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(2,6-dimethoxypyridin-3-yl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(OC)=CC=C1C(C=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 IDMAMFGDVJNXIB-UHFFFAOYSA-N 0.000 claims description 2
• HNLMKMLSHVUZGR-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(2-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=CC=C1Cl HNLMKMLSHVUZGR-UHFFFAOYSA-N 0.000 claims description 2
• VBWZFTOXATUDDX-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(3-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=CC(Cl)=C1 VBWZFTOXATUDDX-UHFFFAOYSA-N 0.000 claims description 2
• KTYDFICNCHRUMZ-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(3-chlorophenyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=1)=CN=CC=1C1=CC=CC(Cl)=C1 KTYDFICNCHRUMZ-UHFFFAOYSA-N 0.000 claims description 2
• PZXUTMUZARLUEH-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(4-chlorophenyl)pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CN=C1C1=CC=C(Cl)C=C1 PZXUTMUZARLUEH-UHFFFAOYSA-N 0.000 claims description 2
• HEBOWRBEGORLOY-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(4-chlorophenyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=1)=CN=CC=1C1=CC=C(Cl)C=C1 HEBOWRBEGORLOY-UHFFFAOYSA-N 0.000 claims description 2
• AHYHVKGPXRDNSS-UHFFFAOYSA-N 6-chloro-7-[4-[[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 AHYHVKGPXRDNSS-UHFFFAOYSA-N 0.000 claims description 2
• CMNWDFVVOUXMGM-UHFFFAOYSA-N 6-chloro-7-[4-[[5-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CN=C1C1=CC=C(C(F)(F)F)C=C1 CMNWDFVVOUXMGM-UHFFFAOYSA-N 0.000 claims description 2
• UGLOTMMCSKMRKI-UHFFFAOYSA-N 6-chloro-7-[4-[[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UGLOTMMCSKMRKI-UHFFFAOYSA-N 0.000 claims description 2
• PUHPEWQWAPQSMA-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,3-difluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=CC(F)=C1F PUHPEWQWAPQSMA-UHFFFAOYSA-N 0.000 claims description 2
• OYNWVRGLQQPXHY-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,4-dichlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1Cl OYNWVRGLQQPXHY-UHFFFAOYSA-N 0.000 claims description 2
• SXXRGUGYCBPBGU-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,4-difluorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(F)C=C1F SXXRGUGYCBPBGU-UHFFFAOYSA-N 0.000 claims description 2
• KQWZXCLEIBQDHT-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,6-dimethoxypyridin-3-yl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(OC)=CC=C1C(N=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 KQWZXCLEIBQDHT-UHFFFAOYSA-N 0.000 claims description 2
• DJGXFUXLDJMERI-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(2,6-dimethoxypyridin-3-yl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=NC(OC)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 DJGXFUXLDJMERI-UHFFFAOYSA-N 0.000 claims description 2
• BZNNZRYYZHWOIW-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3,4-dichlorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(Cl)C(Cl)=C1 BZNNZRYYZHWOIW-UHFFFAOYSA-N 0.000 claims description 2
• PQYZFWGXCIWJPW-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3,5-difluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC(F)=CC(F)=C1 PQYZFWGXCIWJPW-UHFFFAOYSA-N 0.000 claims description 2
• OXLCDEFFDBLGKB-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3-chlorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=CC(Cl)=C1 OXLCDEFFDBLGKB-UHFFFAOYSA-N 0.000 claims description 2
• JCNQQBPPYQRUPE-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3-chlorophenyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=N1)=CC=C1C1=CC=CC(Cl)=C1 JCNQQBPPYQRUPE-UHFFFAOYSA-N 0.000 claims description 2
• SKYXBXLTDYWHMN-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3-fluoro-4-methylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(F)C(C)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 SKYXBXLTDYWHMN-UHFFFAOYSA-N 0.000 claims description 2
• DHMRNLLMTHEIDU-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chloro-2-fluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1F DHMRNLLMTHEIDU-UHFFFAOYSA-N 0.000 claims description 2
• KASBFQPCLHHHAL-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chloro-2-methoxyphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound COC1=CC(Cl)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 KASBFQPCLHHHAL-UHFFFAOYSA-N 0.000 claims description 2
• APCYFDATFHWSSU-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chloro-3-fluorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(Cl)C(F)=C1 APCYFDATFHWSSU-UHFFFAOYSA-N 0.000 claims description 2
• JJPFTWKVPFCNRK-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chloro-3-fluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C(F)=C1 JJPFTWKVPFCNRK-UHFFFAOYSA-N 0.000 claims description 2
• TXVQYNZUPQFNQO-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)-2-methylpyrimidin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N=1C(C)=NC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=CC=1C1=CC=C(Cl)C=C1 TXVQYNZUPQFNQO-UHFFFAOYSA-N 0.000 claims description 2
• HYHJMSJZZBYJBZ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)-5-fluoropyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=C(F)C=1C1=CC=C(Cl)C=C1 HYHJMSJZZBYJBZ-UHFFFAOYSA-N 0.000 claims description 2
• VPKKIETYXSJEMT-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(Cl)C=C1 VPKKIETYXSJEMT-UHFFFAOYSA-N 0.000 claims description 2
• UQQGJGXYBISBBX-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-8-cyclopropyl-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound OC(=O)C1CCOC(C=2C3CC3)=C1C=C(Cl)C=2OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 UQQGJGXYBISBBX-UHFFFAOYSA-N 0.000 claims description 2
• AIMILWAKBYJDGG-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chlorophenyl)pyridin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=N1)=CC=C1C1=CC=C(Cl)C=C1 AIMILWAKBYJDGG-UHFFFAOYSA-N 0.000 claims description 2
• MXCGPOPQJPFFRM-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-fluoro-3-methylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2N=C(NC(=O)C=3C=CC(OC=4C(=CC=5C(C(O)=O)CCOC=5C=4)Cl)=CC=3)C=CC=2)=C1 MXCGPOPQJPFFRM-UHFFFAOYSA-N 0.000 claims description 2
• ZGDPLDHSVOJLGB-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-fluorophenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(F)C=C1 ZGDPLDHSVOJLGB-UHFFFAOYSA-N 0.000 claims description 2
• OBKKTFHVNPMINI-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-methoxyphenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(N=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 OBKKTFHVNPMINI-UHFFFAOYSA-N 0.000 claims description 2
• XHQHEIOPLFUAGZ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-methylphenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(N=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 XHQHEIOPLFUAGZ-UHFFFAOYSA-N 0.000 claims description 2
• VFRDMDPFMFGRHI-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-methylsulfanylphenyl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(SC)=CC=C1C(N=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 VFRDMDPFMFGRHI-UHFFFAOYSA-N 0.000 claims description 2
• XTKAQAORXBLNSY-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-methylsulfanylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(SC)=CC=C1C1=CC=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 XTKAQAORXBLNSY-UHFFFAOYSA-N 0.000 claims description 2
• TZFOHYCPJGAGJI-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(6-methoxypyridin-3-yl)pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=NC(OC)=CC=C1C(N=N1)=CC=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 TZFOHYCPJGAGJI-UHFFFAOYSA-N 0.000 claims description 2
• MKXZOKYQHADAAC-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[3-(trifluoromethyl)phenyl]pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CN=CC=1C1=CC=CC(C(F)(F)F)=C1 MKXZOKYQHADAAC-UHFFFAOYSA-N 0.000 claims description 2
• DHSBECRZKGCPCQ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[3-(trifluoromethyl)phenyl]pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 DHSBECRZKGCPCQ-UHFFFAOYSA-N 0.000 claims description 2
• SMTPGBINCMBPQC-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[3-chloro-4-(trifluoromethyl)phenyl]pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(C(F)(F)F)C(Cl)=C1 SMTPGBINCMBPQC-UHFFFAOYSA-N 0.000 claims description 2
• IIGNZCGZSKCJNG-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[4-(trifluoromethyl)phenyl]pyrazin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC=1C=C2C(C(=O)O)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CN=CC=1C1=CC=C(C(F)(F)F)C=C1 IIGNZCGZSKCJNG-UHFFFAOYSA-N 0.000 claims description 2
• FIHLWFSARDMFHZ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-methyl-2-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound N=1C(C)=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=NC=1C1=CC=C(C(F)(F)F)C=C1 FIHLWFSARDMFHZ-UHFFFAOYSA-N 0.000 claims description 2
• QZRUAYAWYVTLHG-UHFFFAOYSA-N 6-cyano-7-[4-(1h-indazol-5-ylcarbamoyl)phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C2NN=CC2=CC(NC(=O)C2=CC=C(C=C2)OC=2C=C3OCCC(C3=CC=2C#N)C(=O)O)=C1 QZRUAYAWYVTLHG-UHFFFAOYSA-N 0.000 claims description 2
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• WVJMGOFBPSAEGR-UHFFFAOYSA-N 6-cyano-7-[4-(quinolin-2-ylcarbamoyl)phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3C#N)C(=O)O)=CC=C21 WVJMGOFBPSAEGR-UHFFFAOYSA-N 0.000 claims description 2
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• MRRYVEFUHNZCNJ-UHFFFAOYSA-N 6-cyano-7-[4-[(2-methyl-1,3-benzothiazol-6-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1CCC(C(O)=O)C(C=C2C#N)=C1C=C2OC(C=C1)=CC=C1C(=O)NC1=CC=C2N=C(C)SC2=C1 MRRYVEFUHNZCNJ-UHFFFAOYSA-N 0.000 claims description 2
• XWTLPPIHTDOLSM-UHFFFAOYSA-N 6-cyano-7-[4-[(3-methyl-1,2-benzothiazol-5-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1CCC(C(O)=O)C(C=C2C#N)=C1C=C2OC(C=C1)=CC=C1C(=O)NC1=CC=C2SN=C(C)C2=C1 XWTLPPIHTDOLSM-UHFFFAOYSA-N 0.000 claims description 2
• BDGKCQJYBPBARE-UHFFFAOYSA-N 6-cyano-7-[4-[(4,6-difluoro-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(F)C=C2SC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3C#N)C(=O)O)=NC2=C1F BDGKCQJYBPBARE-UHFFFAOYSA-N 0.000 claims description 2
• SXKLBBQLXAVPHH-UHFFFAOYSA-N 6-cyano-7-[4-[(4-methyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC1=CSC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)C#N)=CC=2)=N1 SXKLBBQLXAVPHH-UHFFFAOYSA-N 0.000 claims description 2
• QKSQYRYOXSOWHP-UHFFFAOYSA-N 6-cyano-7-[4-[(5,6-dimethyl-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1CCC(C(O)=O)C(C=C2C#N)=C1C=C2OC(C=C1)=CC=C1C(=O)NC1=NC(C=C(C(=C2)C)C)=C2S1 QKSQYRYOXSOWHP-UHFFFAOYSA-N 0.000 claims description 2
• IHOGFOOUBHMHRJ-UHFFFAOYSA-N 6-cyano-7-[4-[(5-methyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound S1C(C)=CN=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)C#N)=CC2=C1C(C(O)=O)CCO2 IHOGFOOUBHMHRJ-UHFFFAOYSA-N 0.000 claims description 2
• SLTCKXRPBFEZPN-UHFFFAOYSA-N 6-cyano-7-[4-[(6-fluoro-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(F)C=C2SC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3C#N)C(=O)O)=NC2=C1 SLTCKXRPBFEZPN-UHFFFAOYSA-N 0.000 claims description 2
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