CA2748099C - 7-phenoxychroman carboxylic acid derivatives - Google Patents

Info

Publication number

CA2748099C

CA2748099C CA2748099A CA2748099A CA2748099C CA 2748099 C CA2748099 C CA 2748099C CA 2748099 A CA2748099 A CA 2748099A CA 2748099 A CA2748099 A CA 2748099A CA 2748099 C CA2748099 C CA 2748099C

Authority

CA

Canada

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

Links

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• XLFDDXZOBBEBLN-UHFFFAOYSA-N 7-phenoxy-3,4-dihydro-2h-chromene-2-carboxylic acid Chemical class C1=C2OC(C(=O)O)CCC2=CC=C1OC1=CC=CC=C1 XLFDDXZOBBEBLN-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 270
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 238000004519 manufacturing process Methods 0.000 claims abstract description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 115
• -1 2-oxopyridin-1(2H)-yl Chemical group 0.000 claims description 106
• 125000000217 alkyl group Chemical group 0.000 claims description 86
• 125000001424 substituent group Chemical group 0.000 claims description 68
• 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 64
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 60
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 159000000000 sodium salts Chemical group 0.000 claims description 33
• 125000005842 heteroatom Chemical group 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
• 125000004429 atom Chemical group 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 22
• 239000003446 ligand Substances 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 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 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 20
• 239000003054 catalyst Substances 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 17
• 230000008878 coupling Effects 0.000 claims description 17
• 238000010168 coupling process Methods 0.000 claims description 17
• 238000005859 coupling reaction Methods 0.000 claims description 17
• 125000006575 electron-withdrawing group Chemical group 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 12
• 229910052763 palladium Inorganic materials 0.000 claims description 12
• 125000006239 protecting group Chemical group 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 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 7
• OWMWSDWNPGDQAO-UHFFFAOYSA-N 6-chloro-7-[4-[2-[6-cyclopropyl-2-(dimethylamino)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C=1C=C(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)C(N(C)C)=NC=1C1CC1 OWMWSDWNPGDQAO-UHFFFAOYSA-N 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
• 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 6
• 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 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• NYLDFERJNDCQBO-UHFFFAOYSA-N 6-chloro-7-[4-[2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C=1C=C(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)C(OC)=NC=1C1CC1 NYLDFERJNDCQBO-UHFFFAOYSA-N 0.000 claims description 5
• YNHGPRVRAXSUMU-UHFFFAOYSA-N 6-chloro-7-[4-[2-[2-cyclopropyl-6-(trifluoromethyl)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=C(C(F)(F)F)N=C1C1CC1 YNHGPRVRAXSUMU-UHFFFAOYSA-N 0.000 claims description 5
• 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 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
• 150000001879 copper Chemical class 0.000 claims description 5
• 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
• 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 4
• 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 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
• 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 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
• 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 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
• 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
• JHGPUDIYXDMHKJ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(3-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=CC(Cl)=C1 JHGPUDIYXDMHKJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• NPQGSVSVVBMWIH-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[2-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=C1Cl NPQGSVSVVBMWIH-UHFFFAOYSA-N 0.000 claims description 4
• JRTKPZRXXAFERK-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[2-fluoro-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=C1F JRTKPZRXXAFERK-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
• OTCZFDOCIXJFBU-UHFFFAOYSA-N 6-cyano-7-[4-[2-[5-(trifluoromethyl)pyridin-2-yl]ethylcarbamoyl]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)NCCC1=CC=C(C(F)(F)F)C=N1 OTCZFDOCIXJFBU-UHFFFAOYSA-N 0.000 claims description 4
• GZXFDSKBZKZYTR-UHFFFAOYSA-N 6-cyano-7-[4-[[5-(trifluoromethyl)pyridin-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)NC1=CC=C(C(F)(F)F)C=N1 GZXFDSKBZKZYTR-UHFFFAOYSA-N 0.000 claims description 4
• 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 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
• 230000001900 immune effect Effects 0.000 claims description 4
• 229910052751 metal Inorganic materials 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 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
• 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
• INWQZPNIGBKAIH-UHFFFAOYSA-N 6-chloro-7-[4-[(3-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=NC2=CC=CC=C2C=C1C INWQZPNIGBKAIH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
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• DGYBAGDSEIAVDH-UHFFFAOYSA-N 6-chloro-7-[4-[(6-cyclopropylpyridin-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=1C1CC1 DGYBAGDSEIAVDH-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
• 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
• 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
• GKIKXBMROJUWKX-UHFFFAOYSA-N 6-chloro-7-[4-[2-[2-(dimethylamino)-6-(trifluoromethyl)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CN(C)C1=NC(C(F)(F)F)=CC=C1CCNC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 GKIKXBMROJUWKX-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
• 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
• PRTKFYVSDMZVMY-UHFFFAOYSA-N 6-chloro-7-[4-[[1-(3,4-dichlorophenyl)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(Cl)=C1 PRTKFYVSDMZVMY-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
• 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
• 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
• 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
• 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
• 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
• ZZZSTWBQTXCFHG-UHFFFAOYSA-N 6-chloro-7-[4-[[5-(3-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=CC(Cl)=C1 ZZZSTWBQTXCFHG-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
• 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
• 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 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
• 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
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• UGXYUMKQULHZHQ-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(4-chloro-2-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=C1F UGXYUMKQULHZHQ-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
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• 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
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• 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
• PVWKKIYDXWUOGR-UHFFFAOYSA-N 6-chloro-7-[4-[[6-(trifluoromethyl)quinolin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(C(F)(F)F)C=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 PVWKKIYDXWUOGR-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
• CIRDMOUXXVIZGO-UHFFFAOYSA-N 6-chloro-7-[4-[[6-[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=1)=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 CIRDMOUXXVIZGO-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
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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
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• 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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• BZPBEMRLNVMIST-UHFFFAOYSA-N 6-cyano-7-[4-[2-[6-(trifluoromethyl)pyridin-3-yl]ethylcarbamoyl]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)NCCC1=CC=C(C(F)(F)F)N=C1 BZPBEMRLNVMIST-UHFFFAOYSA-N 0.000 claims description 2
• HBHOVRHWHRJYBF-UHFFFAOYSA-N 6-cyano-7-[4-[[2-(trifluoromethyl)-3h-benzimidazol-5-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C2N=C(C(F)(F)F)NC2=CC(NC(=O)C2=CC=C(C=C2)OC=2C=C3OCCC(C3=CC=2C#N)C(=O)O)=C1 HBHOVRHWHRJYBF-UHFFFAOYSA-N 0.000 claims description 2
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• KRQSYTFABPZBFK-UHFFFAOYSA-N 6-cyano-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=3C#N)C(=O)O)=NC2=C1 KRQSYTFABPZBFK-UHFFFAOYSA-N 0.000 claims description 2
• PJFVEJKMZOKLRJ-UHFFFAOYSA-N 6-cyano-7-[4-[[6-[3-(trifluoromethyl)phenyl]pyridin-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(N=1)=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 PJFVEJKMZOKLRJ-UHFFFAOYSA-N 0.000 claims description 2
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• LVNKSUDQTKKEDM-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[(8-methylquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound C1=CC=C(C)C2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)OCC)=CC=C21 LVNKSUDQTKKEDM-UHFFFAOYSA-N 0.000 description 2
• LTFUXRSTUTUVTP-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[2-(3,5-dichloropyridin-2-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=NC=C(Cl)C=C1Cl LTFUXRSTUTUVTP-UHFFFAOYSA-N 0.000 description 2
• CSUMLNHLSOWOTE-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[2-(6-cyclopropyl-2-methoxypyridin-3-yl)ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC(C(=N1)OC)=CC=C1C1CC1 CSUMLNHLSOWOTE-UHFFFAOYSA-N 0.000 description 2
• BATOHPOIKKMNIV-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[2-[2-cyclopropyl-6-(trifluoromethyl)pyridin-3-yl]ethylcarbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NCCC1=CC=C(C(F)(F)F)N=C1C1CC1 BATOHPOIKKMNIV-UHFFFAOYSA-N 0.000 description 2
• AJOFALWRCRPVCY-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[1-(3,4-difluorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=C(F)C(F)=C1 AJOFALWRCRPVCY-UHFFFAOYSA-N 0.000 description 2
• NSSIJDOUTMXLIS-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[1-(3-chlorophenyl)pyrazol-4-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(=C1)C=NN1C1=CC=CC(Cl)=C1 NSSIJDOUTMXLIS-UHFFFAOYSA-N 0.000 description 2
• HUFWAVPPJNQBLX-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[2-(3-chlorophenyl)pyrimidin-5-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(C=N1)=CN=C1C1=CC=CC(Cl)=C1 HUFWAVPPJNQBLX-UHFFFAOYSA-N 0.000 description 2
• FYORGWUAJLPTTA-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[5-(4-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=C1)=CC=C1C1=CC=C(Cl)C=C1 FYORGWUAJLPTTA-UHFFFAOYSA-N 0.000 description 2
• JLALFJRABWUXBZ-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-(2,4-difluorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(F)C=C1F JLALFJRABWUXBZ-UHFFFAOYSA-N 0.000 description 2
• LWSBCTXCBVPDIY-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-(2-chlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=CC=C1Cl LWSBCTXCBVPDIY-UHFFFAOYSA-N 0.000 description 2
• MNCRHQGPOBLDBL-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-(3,4-dichlorophenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C(Cl)=C1 MNCRHQGPOBLDBL-UHFFFAOYSA-N 0.000 description 2
• LVMZLUSTGDQOOE-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-(4-methylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(C)C=C1 LVMZLUSTGDQOOE-UHFFFAOYSA-N 0.000 description 2
• XFXBLQOJIPPICC-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-(trifluoromethyl)-1,3-benzothiazol-2-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate 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)OCC)=NC2=C1 XFXBLQOJIPPICC-UHFFFAOYSA-N 0.000 description 2
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• WXFKAXRCOAPQHG-UHFFFAOYSA-N ethyl 6-chloro-7-[4-[[6-[4-(trifluoromethyl)phenyl]pyridazin-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC(N=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 WXFKAXRCOAPQHG-UHFFFAOYSA-N 0.000 description 2
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• LZWAZYQUKNTGCU-UHFFFAOYSA-N ethyl 7-[4-[(5-bromopyrazin-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC1=CN=C(Br)C=N1 LZWAZYQUKNTGCU-UHFFFAOYSA-N 0.000 description 2
• MZJLUKUEFMVQTN-UHFFFAOYSA-N ethyl 7-[4-[(5-bromopyridin-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound ClC=1C=C2C(C(=O)OCC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC1=CC=C(Br)C=N1 MZJLUKUEFMVQTN-UHFFFAOYSA-N 0.000 description 2
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• HBTATTZHQOSGOX-UHFFFAOYSA-N methyl 7-[4-[(6-bromopyridin-2-yl)carbamoyl]phenoxy]-6-cyano-3,4-dihydro-2h-chromene-4-carboxylate Chemical compound N#CC=1C=C2C(C(=O)OC)CCOC2=CC=1OC(C=C1)=CC=C1C(=O)NC1=CC=CC(Br)=N1 HBTATTZHQOSGOX-UHFFFAOYSA-N 0.000 description 2
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