JP2012513398A5 - - Google Patents
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- Publication number
- JP2012513398A5 JP2012513398A5 JP2011542470A JP2011542470A JP2012513398A5 JP 2012513398 A5 JP2012513398 A5 JP 2012513398A5 JP 2011542470 A JP2011542470 A JP 2011542470A JP 2011542470 A JP2011542470 A JP 2011542470A JP 2012513398 A5 JP2012513398 A5 JP 2012513398A5
- Authority
- JP
- Japan
- Prior art keywords
- phenoxy
- carboxylic acid
- chroman
- ylcarbamoyl
- chloro
- 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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- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- -1 2-oxopyridin-1 (2H) -yl Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 7
- 238000010168 coupling process Methods 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 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 4
- 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 4
- 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 3
- 239000000203 mixture Substances 0.000 claims 3
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 2
- 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 1
- YWORZDACRJYCNN-SFHVURJKSA-N (4s)-6,8-dichloro-7-[4-[[1-(3-chlorophenyl)pyrazol-3-yl]carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C([C@@H](C1=CC=2Cl)C(=O)O)COC1=C(Cl)C=2OC(C=C1)=CC=C1C(=O)NC(=N1)C=CN1C1=CC=CC(Cl)=C1 YWORZDACRJYCNN-SFHVURJKSA-N 0.000 claims 1
- 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 1
- IZVBLYPICXBAAW-UHFFFAOYSA-N 6,8-dichloro-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=C(Cl)C=1OC(C=C1)=CC=C1C(=O)NC(=C1)C=NN1C1=CC=CC(Cl)=C1 IZVBLYPICXBAAW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- PKNWQLDJFIQYJP-UHFFFAOYSA-N 6-chloro-7-[4-[(1-phenylpyrazol-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=C1 PKNWQLDJFIQYJP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SPZDSHAVHIXALS-UHFFFAOYSA-N 6-chloro-7-[4-[(3-phenyl-1,2,4-thiadiazol-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(SN=1)=NC=1C1=CC=CC=C1 SPZDSHAVHIXALS-UHFFFAOYSA-N 0.000 claims 1
- JPGKQYVKSXRIAI-UHFFFAOYSA-N 6-chloro-7-[4-[(3-propan-2-yl-1,2,4-thiadiazol-5-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)C1=NSC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 JPGKQYVKSXRIAI-UHFFFAOYSA-N 0.000 claims 1
- YJXQQNJWJBTDKA-UHFFFAOYSA-N 6-chloro-7-[4-[(4-propan-2-yl-1,3-thiazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)C1=CSC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 YJXQQNJWJBTDKA-UHFFFAOYSA-N 0.000 claims 1
- RZUGJKOLWNCXEU-UHFFFAOYSA-N 6-chloro-7-[4-[(5-chloro-1,3-benzoxazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound ClC1=CC=C2OC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=NC2=C1 RZUGJKOLWNCXEU-UHFFFAOYSA-N 0.000 claims 1
- UYFCDGODSUGZPJ-UHFFFAOYSA-N 6-chloro-7-[4-[(5-ethyl-4-phenyl-1,3-oxazol-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CCC=1OC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=NC=1C1=CC=CC=C1 UYFCDGODSUGZPJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- NOAMKWYWPPRBAY-UHFFFAOYSA-N 6-chloro-7-[4-[(6-fluoroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C(F)C=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 NOAMKWYWPPRBAY-UHFFFAOYSA-N 0.000 claims 1
- IZTVLPXYKZPJKT-UHFFFAOYSA-N 6-chloro-7-[4-[(6-methoxyquinolin-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=C(OC)C=C2C=C1 IZTVLPXYKZPJKT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- NBXVNDXQTKQYCG-UHFFFAOYSA-N 6-chloro-7-[4-[(7-chloroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(Cl)=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 NBXVNDXQTKQYCG-UHFFFAOYSA-N 0.000 claims 1
- SLWTWMSGXZMDED-UHFFFAOYSA-N 6-chloro-7-[4-[(7-chloroquinoxalin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(Cl)=CC2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CN=C21 SLWTWMSGXZMDED-UHFFFAOYSA-N 0.000 claims 1
- ZQAGTJFUODZGCW-UHFFFAOYSA-N 6-chloro-7-[4-[(8-chloroquinolin-2-yl)carbamoyl]phenoxy]-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=C(Cl)C2=NC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3Cl)C(=O)O)=CC=C21 ZQAGTJFUODZGCW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- SMSOZCVDRYOVOO-UHFFFAOYSA-N 7-[4-(1,3-benzoxazol-6-ylcarbamoyl)phenoxy]-6-cyano-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=C2N=COC2=CC(NC(=O)C2=CC=C(C=C2)OC=2C=C3OCCC(C3=CC=2C#N)C(=O)O)=C1 SMSOZCVDRYOVOO-UHFFFAOYSA-N 0.000 claims 1
- HULCBZHIDYHYDR-UHFFFAOYSA-N 7-[4-[(3-tert-butyl-1,2-oxazol-5-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1N=C(C(C)(C)C)C=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 HULCBZHIDYHYDR-UHFFFAOYSA-N 0.000 claims 1
- ACPVOWWHUFROEW-UHFFFAOYSA-N 7-[4-[(4-chloro-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-6-cyano-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC=C2SC(NC(=O)C3=CC=C(C=C3)OC=3C=C4OCCC(C4=CC=3C#N)C(=O)O)=NC2=C1Cl ACPVOWWHUFROEW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VDICMSCXSUUOBR-UHFFFAOYSA-N 7-[4-[(5-chloropyridin-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)NC1=CC=C(Cl)C=N1 VDICMSCXSUUOBR-UHFFFAOYSA-N 0.000 claims 1
- CCEODENKBYKHIU-UHFFFAOYSA-N 7-[4-[(5-tert-butyl-1,2-oxazol-3-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound O1C(C(C)(C)C)=CC(NC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 CCEODENKBYKHIU-UHFFFAOYSA-N 0.000 claims 1
- GRUSKGUHRZZJNT-UHFFFAOYSA-N 7-[4-[(5-tert-butyl-2-methylpyrazol-3-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 GRUSKGUHRZZJNT-UHFFFAOYSA-N 0.000 claims 1
- ZXTWIPZFTCEENJ-UHFFFAOYSA-N 7-[4-[(5-tert-butyl-4-methyl-1,3-thiazol-2-yl)carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound S1C(C(C)(C)C)=C(C)N=C1NC(=O)C(C=C1)=CC=C1OC(C(=C1)Cl)=CC2=C1C(C(O)=O)CCO2 ZXTWIPZFTCEENJ-UHFFFAOYSA-N 0.000 claims 1
- JVAZQDRGXSYFKL-UHFFFAOYSA-N 7-[4-[(6-chloro-1,3-benzothiazol-2-yl)carbamoyl]phenoxy]-6-cyano-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=3C#N)C(=O)O)=NC2=C1 JVAZQDRGXSYFKL-UHFFFAOYSA-N 0.000 claims 1
- SQZBBUWZFUXUGI-UHFFFAOYSA-N 7-[4-[(6-chloroquinazolin-2-yl)carbamoyl]phenoxy]-6-cyano-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=3C#N)C(=O)O)=NC=C21 SQZBBUWZFUXUGI-UHFFFAOYSA-N 0.000 claims 1
- MMIVYKQCJSPUGM-UHFFFAOYSA-N 7-[4-[(6-chloroquinolin-2-yl)carbamoyl]phenoxy]-6-cyano-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=3C#N)C(=O)O)=CC=C21 MMIVYKQCJSPUGM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WTSBOTWVLOADFP-UHFFFAOYSA-N 7-[4-[2-(4-tert-butyl-1,3-thiazol-2-yl)ethylcarbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound CC(C)(C)C1=CSC(CCNC(=O)C=2C=CC(OC=3C(=CC=4C(C(O)=O)CCOC=4C=3)Cl)=CC=2)=N1 WTSBOTWVLOADFP-UHFFFAOYSA-N 0.000 claims 1
- FAJGGAXMHIEXNO-UHFFFAOYSA-N 7-[4-[[6-(3-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=CC(Cl)=C1 FAJGGAXMHIEXNO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- ULXNLGDWIOEWMI-UHFFFAOYSA-N 7-[4-[[6-(4-tert-butylphenyl)pyridin-2-yl]carbamoyl]phenoxy]-6-chloro-3,4-dihydro-2h-chromene-4-carboxylic acid Chemical compound C1=CC(C(C)(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 ULXNLGDWIOEWMI-UHFFFAOYSA-N 0.000 claims 1
- GNANBGHBUUAASU-UHFFFAOYSA-N 8-bromo-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=C(Br)C=1OC(C=C1)=CC=C1C(=O)NC(N=1)=CC=CC=1C1=CC=C(Cl)C=C1 GNANBGHBUUAASU-UHFFFAOYSA-N 0.000 claims 1
- PHWJUOGUJZYWSW-UHFFFAOYSA-N C1CC1C2=CC(=C3C(=C2)C(CC(O3)OC4=CC=C(C=C4)C(=O)NC5=CC=CC(=N5)C6=CC=C(C=C6)Cl)C(=O)O)C7CC7 Chemical compound C1CC1C2=CC(=C3C(=C2)C(CC(O3)OC4=CC=C(C=C4)C(=O)NC5=CC=CC(=N5)C6=CC=C(C=C6)Cl)C(=O)O)C7CC7 PHWJUOGUJZYWSW-UHFFFAOYSA-N 0.000 claims 1
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| RS53665B1 (sr) * | 2008-06-25 | 2015-04-30 | Array Biopharma Inc. | Derivati 6-supstituisane fenoksihroman karboksilne kiseline |
| ES2921576T3 (es) | 2008-12-19 | 2022-08-29 | Vertex Pharma | Compuestos útiles como inhibidores de la quinasa ATR |
| EP2569313A1 (en) | 2010-05-12 | 2013-03-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| EP3878851A1 (en) | 2011-09-30 | 2021-09-15 | Vertex Pharmaceuticals Incorporated | Process for making compounds useful as inhibitors of atr kinase |
| RU2018108589A (ru) | 2011-09-30 | 2019-02-25 | Вертекс Фармасьютикалз Инкорпорейтед | Лечение рака поджелудочной железы и немелкоклеточного рака легкого ингибиторами atr |
| PT2833973T (pt) | 2012-04-05 | 2017-12-21 | Vertex Pharma | Compostos úteis como inibidores da cinase atr e terapias de combinação dos mesmos |
| CN104583194A (zh) | 2012-05-11 | 2015-04-29 | 艾伯维公司 | 作为nampt抑制剂的哒嗪和吡啶衍生物 |
| TWI654180B (zh) | 2012-06-29 | 2019-03-21 | 美商艾佛艾姆希公司 | 殺真菌之雜環羧醯胺 |
| WO2014055756A1 (en) | 2012-10-04 | 2014-04-10 | Vertex Pharmaceuticals Incorporated | Method for measuring atr inhibition mediated increases in dna damage |
| ES2991300T3 (es) * | 2015-02-13 | 2024-12-03 | Inserm Institut Nat De La Sante Et De Larecherche Medicale | Antagonistas de PTGDR-1 y/o PTGDR-2 para prevenir y/o tratar lupus eritematoso sistémico |
| EP3355926B1 (en) | 2015-09-30 | 2025-12-24 | Vertex Pharmaceuticals Inc. | Combination of dna damaging agents and atr inhibitors for use in a method for treating cancer using |
| WO2021063735A1 (en) | 2019-10-02 | 2021-04-08 | Basf Se | New bicyclic pyridine derivatives |
| CN111228247B (zh) * | 2019-12-05 | 2023-01-31 | 青海大学 | 一种用于治疗包虫病的含苯亚甲基丙酮药物及其制备方法 |
| CA3249692A1 (en) * | 2022-04-19 | 2023-10-26 | Gilgamesh Pharmaceuticals, Inc. | PYRIDINE DERIVATIVES FOR THE TREATMENT OF PSYCHIATRIC DISORDERS |
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| AU2003297398B2 (en) * | 2002-12-20 | 2009-09-24 | Amgen Inc. | Asthma and allergic inflammation modulators |
| GB0611781D0 (en) | 2006-06-14 | 2006-07-26 | Argenta Discovery Ltd | 2-Oxo-2H-Chromene Compounds |
| AU2007286829B2 (en) * | 2006-08-21 | 2013-05-02 | Array Biopharma, Inc. | 4-substituted phenoxyphenylacetic acid derivatives |
| US8039484B2 (en) | 2006-10-31 | 2011-10-18 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| US7960567B2 (en) * | 2007-05-02 | 2011-06-14 | Amgen Inc. | Compounds and methods useful for treating asthma and allergic inflammation |
| WO2009061730A2 (en) | 2007-11-05 | 2009-05-14 | Array Biopharma Inc. | 4-heteroaryl-substituted phenoxyphenylacetic acid |
| RS53665B1 (sr) * | 2008-06-25 | 2015-04-30 | Array Biopharma Inc. | Derivati 6-supstituisane fenoksihroman karboksilne kiseline |
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