JP2020520357A5 - - Google Patents
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- Publication number
- JP2020520357A5 JP2020520357A5 JP2019563492A JP2019563492A JP2020520357A5 JP 2020520357 A5 JP2020520357 A5 JP 2020520357A5 JP 2019563492 A JP2019563492 A JP 2019563492A JP 2019563492 A JP2019563492 A JP 2019563492A JP 2020520357 A5 JP2020520357 A5 JP 2020520357A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- thiophene
- ethylamino
- benzo
- fluoro
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 77
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims 28
- -1 3-oxo-2,3-dihydro- [1,2,4] oxadiazole-5-yl Chemical group 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 19
- 206010028980 Neoplasm Diseases 0.000 claims 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 201000011510 cancer Diseases 0.000 claims 13
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 239000012634 fragment Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical compound O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 claims 3
- BOWYQHCFTNADQJ-UHFFFAOYSA-N OC1=CN=NO1 Chemical compound OC1=CN=NO1 BOWYQHCFTNADQJ-UHFFFAOYSA-N 0.000 claims 3
- 239000002246 antineoplastic agent Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 230000028993 immune response Effects 0.000 claims 3
- 210000000987 immune system Anatomy 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000001959 radiotherapy Methods 0.000 claims 3
- 238000002626 targeted therapy Methods 0.000 claims 3
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical compound OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 claims 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- FJQPFVGROPWAOR-UHFFFAOYSA-N 5-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]-1,2,4-oxadiazol-3-one Chemical compound Cc1sc2c(C)cc(F)cc2c1CCNc1cc(ncn1)-c1ccc(cc1)-c1nc(=O)[nH]o1 FJQPFVGROPWAOR-UHFFFAOYSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000010061 Autosomal Dominant Polycystic Kidney Diseases 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- ADJNAWHYBDCIIM-UHFFFAOYSA-N C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C1=NOC(N1)=O Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C1=NOC(N1)=O ADJNAWHYBDCIIM-UHFFFAOYSA-N 0.000 claims 2
- WSEGYGCPKGZKII-UHFFFAOYSA-N Cc1sc2c(C)cc(F)cc2c1CCNc1cc(ncn1)-c1ccc(cc1)-c1nc(=O)o[nH]1 Chemical compound Cc1sc2c(C)cc(F)cc2c1CCNc1cc(ncn1)-c1ccc(cc1)-c1nc(=O)o[nH]1 WSEGYGCPKGZKII-UHFFFAOYSA-N 0.000 claims 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 2
- 206010029260 Neuroblastoma Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- 230000001154 acute effect Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 208000022185 autosomal dominant polycystic kidney disease Diseases 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000035558 fertility Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 201000005202 lung cancer Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000007420 reactivation Effects 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- IZGGFIMMCYZQHE-AATRIKPKSA-N (E)-3-[3-ethoxy-5-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]prop-2-enoic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)/C=C/C(=O)O IZGGFIMMCYZQHE-AATRIKPKSA-N 0.000 claims 1
- ZWCCRLHJWVDZPZ-UHFFFAOYSA-N 1-[2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C1(CC1)C(=O)O ZWCCRLHJWVDZPZ-UHFFFAOYSA-N 0.000 claims 1
- PLYSXBBKZIODQV-UHFFFAOYSA-N 1-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]cyclopropane-1-carboxylic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)C2(CC2)C(=O)O)CCC)C)C(=C1)C PLYSXBBKZIODQV-UHFFFAOYSA-N 0.000 claims 1
- HKDVRELJPNFGNO-UHFFFAOYSA-N 2-(difluoromethoxy)-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound FC(OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)F HKDVRELJPNFGNO-UHFFFAOYSA-N 0.000 claims 1
- FAANGLNVDUYAEA-UHFFFAOYSA-N 2-[2-chloro-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-6-methylphenyl]acetic acid Chemical compound ClC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C)CC(=O)O FAANGLNVDUYAEA-UHFFFAOYSA-N 0.000 claims 1
- KSVVERKSSXOUIP-UHFFFAOYSA-N 2-[2-cyclopropyloxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C1(CC1)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)CC(=O)O KSVVERKSSXOUIP-UHFFFAOYSA-N 0.000 claims 1
- TXDGMOVFEMTKOJ-UHFFFAOYSA-N 2-[2-ethoxy-3-fluoro-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1F)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)CC(=O)O TXDGMOVFEMTKOJ-UHFFFAOYSA-N 0.000 claims 1
- PKSJIJYHYYMQSH-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(4-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)C PKSJIJYHYYMQSH-UHFFFAOYSA-N 0.000 claims 1
- BGOZPRZLQKIBPC-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]anilino]-2-oxoacetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)NC(C(=O)O)=O BGOZPRZLQKIBPC-UHFFFAOYSA-N 0.000 claims 1
- LQSQHUPBDPTJTM-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]anilino]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)NCC(=O)O LQSQHUPBDPTJTM-UHFFFAOYSA-N 0.000 claims 1
- LFKXOXIJWOANCC-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]-2-oxoacetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C(C(=O)O)=O LFKXOXIJWOANCC-UHFFFAOYSA-N 0.000 claims 1
- KKJMFKFQWRVNEA-UHFFFAOYSA-N 2-[2-ethyl-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-6-methylphenyl]acetic acid Chemical compound C(C)C1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C)CC(=O)O KKJMFKFQWRVNEA-UHFFFAOYSA-N 0.000 claims 1
- WXECWAXGLOGIRH-UHFFFAOYSA-N 2-[2-ethyl-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)C1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)CC(=O)O WXECWAXGLOGIRH-UHFFFAOYSA-N 0.000 claims 1
- DEOGQRDRPSMMNK-UHFFFAOYSA-N 2-[4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]acetic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OCC DEOGQRDRPSMMNK-UHFFFAOYSA-N 0.000 claims 1
- FOZRTMOFRNKHBV-UHFFFAOYSA-N 2-[4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenyl]acetic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OCC FOZRTMOFRNKHBV-UHFFFAOYSA-N 0.000 claims 1
- OAUFAWQWKAQHSH-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C=CC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OCC OAUFAWQWKAQHSH-UHFFFAOYSA-N 0.000 claims 1
- ZYLLNXQJNITIOW-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxy-6-fluorophenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=C1)F)CC(=O)O)OCC ZYLLNXQJNITIOW-UHFFFAOYSA-N 0.000 claims 1
- LFWIHZAZBFZDDJ-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OCC LFWIHZAZBFZDDJ-UHFFFAOYSA-N 0.000 claims 1
- WRUDTBDDAQXEPA-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC WRUDTBDDAQXEPA-UHFFFAOYSA-N 0.000 claims 1
- JDNROMXJOGQZGN-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propan-2-yloxyphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC(C)C JDNROMXJOGQZGN-UHFFFAOYSA-N 0.000 claims 1
- TZVWDEMUCNXVAT-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propoxyphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OCCC TZVWDEMUCNXVAT-UHFFFAOYSA-N 0.000 claims 1
- IOVZXLMJKWTTMX-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC IOVZXLMJKWTTMX-UHFFFAOYSA-N 0.000 claims 1
- DXVWFDSBYFPSDM-UHFFFAOYSA-N 2-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-(2-methylpropyl)phenyl]acetic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)CC(=O)O)CC(C)C)C)C(=C1)C DXVWFDSBYFPSDM-UHFFFAOYSA-N 0.000 claims 1
- FZVPXKGBCZSFLI-UHFFFAOYSA-N 2-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-(trifluoromethoxy)phenyl]acetic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)CC(=O)O)OC(F)(F)F)C)C(=C1)C FZVPXKGBCZSFLI-UHFFFAOYSA-N 0.000 claims 1
- OUQRUMHDVSQSII-UHFFFAOYSA-N 2-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propan-2-yloxyphenyl]acetic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)CC(=O)O)OC(C)C)C)C(=C1)C OUQRUMHDVSQSII-UHFFFAOYSA-N 0.000 claims 1
- UVRRIUUENWNKMA-UHFFFAOYSA-N 2-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propoxyphenyl]acetic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)CC(=O)O)OCCC)C)C(=C1)C UVRRIUUENWNKMA-UHFFFAOYSA-N 0.000 claims 1
- YYKVNZYQVYCERX-UHFFFAOYSA-N 2-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC(=C(C=C2)CC(=O)O)CCC)C)C(=C1)C YYKVNZYQVYCERX-UHFFFAOYSA-N 0.000 claims 1
- UUHVRCACPJWQDJ-UHFFFAOYSA-N 2-[4-[6-[2-(7-chloro-2-methyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]acetic acid Chemical compound ClC1=CC=CC=2C(=C(OC=21)C)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OCC UUHVRCACPJWQDJ-UHFFFAOYSA-N 0.000 claims 1
- LZMSPWIMOLKVGO-UHFFFAOYSA-N 2-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-1-benzothiophene-7-carboxylic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC3=C(S2)C(=CC=C3)C(=O)O)C)C(=C1)C LZMSPWIMOLKVGO-UHFFFAOYSA-N 0.000 claims 1
- YJNALSIQPJSMNA-UHFFFAOYSA-N 2-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-1H-indole-4-carboxylic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C=2NC=3C=CC=C(C=3C=2)C(=O)O)C)C(=C1)C YJNALSIQPJSMNA-UHFFFAOYSA-N 0.000 claims 1
- FUDCJKZNCNLHKP-UHFFFAOYSA-N 2-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-1H-indole-6-carboxylic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C=2NC3=CC(=CC=C3C=2)C(=O)O)C)C(=C1)C FUDCJKZNCNLHKP-UHFFFAOYSA-N 0.000 claims 1
- OBWVZYKZTPSZAN-UHFFFAOYSA-N 2-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-1H-indole-7-carboxylic acid Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C=2NC3=C(C=CC=C3C=2)C(=O)O)C)C(=C1)C OBWVZYKZTPSZAN-UHFFFAOYSA-N 0.000 claims 1
- RXJYDUBKSIPICR-UHFFFAOYSA-N 2-butoxy-6-fluoro-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(CCC)OC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)F RXJYDUBKSIPICR-UHFFFAOYSA-N 0.000 claims 1
- AZLVMEUYFFPUNU-UHFFFAOYSA-N 2-chloro-4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-6-methylsulfanylbenzoic acid Chemical compound ClC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2)C)SC AZLVMEUYFFPUNU-UHFFFAOYSA-N 0.000 claims 1
- VBKKHMAAJAJSBE-UHFFFAOYSA-N 2-cyclobutyloxy-3-fluoro-4-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1F)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)OC VBKKHMAAJAJSBE-UHFFFAOYSA-N 0.000 claims 1
- JBYOXDBUZWKJIH-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(4,5-difluoro-7-methoxy-2-methyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]-6-fluorobenzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C(=C(C=C2OC)F)F)C)F JBYOXDBUZWKJIH-UHFFFAOYSA-N 0.000 claims 1
- MPAKDAYNNBOYOS-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(4-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)C MPAKDAYNNBOYOS-UHFFFAOYSA-N 0.000 claims 1
- RICVDURVPXQKLI-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)OC RICVDURVPXQKLI-UHFFFAOYSA-N 0.000 claims 1
- JWCFCSRVHNIUSZ-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C JWCFCSRVHNIUSZ-UHFFFAOYSA-N 0.000 claims 1
- KLKSSYKUIBGSFL-UHFFFAOYSA-N 2-cyclobutylsulfanyl-4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)SC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2)C KLKSSYKUIBGSFL-UHFFFAOYSA-N 0.000 claims 1
- VHOPRGNUIKTOSA-UHFFFAOYSA-N 2-cyclobutylsulfanyl-4-[6-[2-(2-methyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)SC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C=CC=C2)C VHOPRGNUIKTOSA-UHFFFAOYSA-N 0.000 claims 1
- RENBHHNRBRDVSN-UHFFFAOYSA-N 2-cyclopentyloxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C=C(C=C2C)F)C RENBHHNRBRDVSN-UHFFFAOYSA-N 0.000 claims 1
- SNVAOSWGTQNQLX-UHFFFAOYSA-N 2-cyclopentyloxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C SNVAOSWGTQNQLX-UHFFFAOYSA-N 0.000 claims 1
- POUSVCWQHHPNNZ-UHFFFAOYSA-N 2-cyclopropyloxy-4-[6-[2-(4,5-difluoro-7-methoxy-2-methyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C(=C(C=C2OC)F)F)C POUSVCWQHHPNNZ-UHFFFAOYSA-N 0.000 claims 1
- QSPVCUIIEVOWOR-UHFFFAOYSA-N 2-cyclopropyloxy-4-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)OC QSPVCUIIEVOWOR-UHFFFAOYSA-N 0.000 claims 1
- DUOVZJWWKMFHPZ-UHFFFAOYSA-N 2-cyclopropyloxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C DUOVZJWWKMFHPZ-UHFFFAOYSA-N 0.000 claims 1
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- QSBMHVHSAAUGAD-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(4-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)C QSBMHVHSAAUGAD-UHFFFAOYSA-N 0.000 claims 1
- VVKAASKBCOLQNT-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)OC VVKAASKBCOLQNT-UHFFFAOYSA-N 0.000 claims 1
- LZQKWNSADOFMOW-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C=C(C=C2C)F)C LZQKWNSADOFMOW-UHFFFAOYSA-N 0.000 claims 1
- KFPNIIPSRKFVHN-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-N-methylbenzamide Chemical compound C(C)OC1=C(C(=O)NC)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C KFPNIIPSRKFVHN-UHFFFAOYSA-N 0.000 claims 1
- XFJNMJVAJCQPLJ-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzamide Chemical compound C(C)OC1=C(C(=O)N)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C XFJNMJVAJCQPLJ-UHFFFAOYSA-N 0.000 claims 1
- GFYNKNXKOYPXIR-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C GFYNKNXKOYPXIR-UHFFFAOYSA-N 0.000 claims 1
- BDZKVENJXODLNQ-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=C(C=C2)F)C BDZKVENJXODLNQ-UHFFFAOYSA-N 0.000 claims 1
- LZUMITQFLYTHDE-UHFFFAOYSA-N 2-ethyl-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)C1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C LZUMITQFLYTHDE-UHFFFAOYSA-N 0.000 claims 1
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- IQZXWDFGKPFWBZ-UHFFFAOYSA-N 2-ethylsulfanyl-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)SC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C IQZXWDFGKPFWBZ-UHFFFAOYSA-N 0.000 claims 1
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- MAKPRCQLHOKRJY-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenoxy]propanoic acid Chemical compound C(C)OC1=C(OCCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C MAKPRCQLHOKRJY-UHFFFAOYSA-N 0.000 claims 1
- KSNOYLBHCUCGDQ-UHFFFAOYSA-N 3-[4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]propanoic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(OCCC(=O)O)C=C1)OCC KSNOYLBHCUCGDQ-UHFFFAOYSA-N 0.000 claims 1
- CAWLTNMDNFVUAU-UHFFFAOYSA-N 3-[4-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]phenyl]-4-hydroxycyclobut-3-ene-1,2-dione Chemical compound FC1=CC2=C(SC(=C2CCNC2=CC(=NC=N2)C2=CC=C(C=C2)C=2C(C(C=2O)=O)=O)C)C(=C1)C CAWLTNMDNFVUAU-UHFFFAOYSA-N 0.000 claims 1
- QUFZJAMOBSJHEM-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(2-ethyl-5-fluoro-7-methyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C=C(C=C2C)F)CC)C(=O)O QUFZJAMOBSJHEM-UHFFFAOYSA-N 0.000 claims 1
- XBYXCCYSVHWLEE-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(4-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)C)C(=O)O XBYXCCYSVHWLEE-UHFFFAOYSA-N 0.000 claims 1
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- QYSGTPYWHIWGDG-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC=C2F)OC)C(=O)O QYSGTPYWHIWGDG-UHFFFAOYSA-N 0.000 claims 1
- ZJGSLDVFRRRWFD-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-fluoro-2,7-dimethyl-1-benzofuran-3-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(OC2=C1C=C(C=C2C)F)C)C(=O)O ZJGSLDVFRRRWFD-UHFFFAOYSA-N 0.000 claims 1
- MTYSSWFAARWBII-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-N-methylsulfonylthiophene-2-carboxamide Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C(=O)NS(=O)(=O)C MTYSSWFAARWBII-UHFFFAOYSA-N 0.000 claims 1
- WFQKJIUNXSYRGT-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-N-sulfamoylthiophene-2-carboxamide Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C(=O)NS(N)(=O)=O WFQKJIUNXSYRGT-UHFFFAOYSA-N 0.000 claims 1
- HPLBCTVOLVNJJQ-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-fluoro-2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C2=C(SC=1C)C(=CC(=C2)F)C)C(=O)O HPLBCTVOLVNJJQ-UHFFFAOYSA-N 0.000 claims 1
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- BFRSEWMMESMKJF-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-(2-methylpropylsulfanyl)benzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SCC(C)C BFRSEWMMESMKJF-UHFFFAOYSA-N 0.000 claims 1
- YWWMYNXRMUZGNW-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-(oxetan-3-ylsulfanyl)benzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC1COC1 YWWMYNXRMUZGNW-UHFFFAOYSA-N 0.000 claims 1
- ASKSOXZMQAQWQI-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC ASKSOXZMQAQWQI-UHFFFAOYSA-N 0.000 claims 1
- KKNKBDLEMAOKKE-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethylsulfanylbenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SCC KKNKBDLEMAOKKE-UHFFFAOYSA-N 0.000 claims 1
- VCDUNLSOOGJOGF-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-fluoro-6-methylsulfanylbenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C(=C1)SC)F VCDUNLSOOGJOGF-UHFFFAOYSA-N 0.000 claims 1
- CHTIJBJGEWMROT-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-methylsulfanylbenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC CHTIJBJGEWMROT-UHFFFAOYSA-N 0.000 claims 1
- IGIISPLQKOROLC-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propan-2-ylsulfanylbenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC(C)C IGIISPLQKOROLC-UHFFFAOYSA-N 0.000 claims 1
- HHMZCICERMWQBS-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-propylsulfanylbenzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SCCC HHMZCICERMWQBS-UHFFFAOYSA-N 0.000 claims 1
- JPOKLFDITJTROH-UHFFFAOYSA-N 4-[6-[2-(2,7-dimethyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound CC1=C(C2=C(S1)C(=CC=C2)C)CCNC1=CC(=NC=N1)C1=CC=C(C(=O)O)C=C1 JPOKLFDITJTROH-UHFFFAOYSA-N 0.000 claims 1
- QMJSQODVPUJADH-UHFFFAOYSA-N 4-[6-[2-(2-bromo-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound BrC1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC QMJSQODVPUJADH-UHFFFAOYSA-N 0.000 claims 1
- GUXWJKNRIQMENH-UHFFFAOYSA-N 4-[6-[2-(2-chloro-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound ClC1=C(C2=C(S1)C=CC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC GUXWJKNRIQMENH-UHFFFAOYSA-N 0.000 claims 1
- UBPODOBTNWTANB-UHFFFAOYSA-N 4-[6-[2-(2-chloro-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound CCOC1=C(C=CC(=C1)C1=CC(NCCC2=C(Cl)SC3=C(C)C=C(F)C=C23)=NC=N1)C(O)=O UBPODOBTNWTANB-UHFFFAOYSA-N 0.000 claims 1
- BJZOQDXOHNZHIH-UHFFFAOYSA-N 4-[6-[2-(2-cyano-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-methylsulfanylbenzoic acid Chemical compound C(#N)C1=C(C2=C(S1)C=CC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC BJZOQDXOHNZHIH-UHFFFAOYSA-N 0.000 claims 1
- VVBPHSZJOKDZPO-UHFFFAOYSA-N 4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC VVBPHSZJOKDZPO-UHFFFAOYSA-N 0.000 claims 1
- WGCHUSSBCAHOFX-UHFFFAOYSA-N 4-[6-[2-(2-cyano-5-fluoro-7-methyl-1-benzothiophen-3-yl)ethylamino]pyrimidin-4-yl]-2-methylsulfanylbenzoic acid Chemical compound C(#N)C1=C(C2=C(S1)C(=CC(=C2)F)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC WGCHUSSBCAHOFX-UHFFFAOYSA-N 0.000 claims 1
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| KR102684436B1 (ko) | 2015-10-16 | 2024-07-15 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | Ep4 길항제 |
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| EP4219462A1 (en) | 2016-07-13 | 2023-08-02 | Vertex Pharmaceuticals Incorporated | Methods, compositions and kits for increasing genome editing efficiency |
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| PE20191811A1 (es) | 2017-05-18 | 2019-12-26 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| EP3625223B1 (en) | 2017-05-18 | 2021-08-11 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives |
-
2018
- 2018-05-17 CN CN201880031813.3A patent/CN110621671A/zh active Pending
- 2018-05-17 KR KR1020197037357A patent/KR102612649B1/ko active Active
- 2018-05-17 WO PCT/EP2018/062843 patent/WO2018210987A1/en not_active Ceased
- 2018-05-17 TW TW107116711A patent/TW201900179A/zh unknown
- 2018-05-17 AR ARP180101312A patent/AR111807A1/es unknown
- 2018-05-17 ES ES18725497T patent/ES2929309T3/es active Active
- 2018-05-17 US US16/614,211 patent/US11325899B2/en active Active
- 2018-05-17 EP EP18725497.4A patent/EP3625227B1/en active Active
- 2018-05-17 CA CA3063632A patent/CA3063632A1/en active Pending
- 2018-05-17 JP JP2019563492A patent/JP7093791B2/ja active Active
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