JP2020520358A5 - - Google Patents
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- Publication number
- JP2020520358A5 JP2020520358A5 JP2019563493A JP2019563493A JP2020520358A5 JP 2020520358 A5 JP2020520358 A5 JP 2020520358A5 JP 2019563493 A JP2019563493 A JP 2019563493A JP 2019563493 A JP2019563493 A JP 2019563493A JP 2020520358 A5 JP2020520358 A5 JP 2020520358A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- ethylamino
- benzo
- ethoxy
- thiophene
- 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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- -1 (C 1-3 ) Fluoralkoxy Chemical group 0.000 claims 161
- 125000000217 alkyl group Chemical group 0.000 claims 83
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- 239000001257 hydrogen Substances 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 18
- 206010028980 Neoplasm Diseases 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 201000011510 cancer Diseases 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 7
- 239000012634 fragment Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- BOWYQHCFTNADQJ-UHFFFAOYSA-N OC1=CN=NO1 Chemical compound OC1=CN=NO1 BOWYQHCFTNADQJ-UHFFFAOYSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 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
- 125000005842 heteroatom Chemical group 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
- 229910052717 sulfur Chemical group 0.000 claims 3
- 238000002626 targeted therapy Methods 0.000 claims 3
- DRZPPOHRKRYJNO-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]-4H-1,2,4-oxadiazol-5-one Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)C1=NOC(N1)=O DRZPPOHRKRYJNO-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
- ZLWFDOKXWKWTQU-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC)C1=NOC(N1)=O ZLWFDOKXWKWTQU-UHFFFAOYSA-N 0.000 claims 2
- ZZBXEAKSGATTQW-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1)C1=NOC(N1)=O ZZBXEAKSGATTQW-UHFFFAOYSA-N 0.000 claims 2
- SJBCVOFICHXQFN-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=C2C=CC=NC2=CC=1F)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=C2C=CC=NC2=CC=1F)C1=NOC(N1)=O SJBCVOFICHXQFN-UHFFFAOYSA-N 0.000 claims 2
- AHVBCTXWALXLQJ-UHFFFAOYSA-N C(C)OC=1N=C(SC=1C1=NOC(N1)=O)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C Chemical compound C(C)OC=1N=C(SC=1C1=NOC(N1)=O)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C AHVBCTXWALXLQJ-UHFFFAOYSA-N 0.000 claims 2
- MGRKHQCOOKRBFT-UHFFFAOYSA-N CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc3OCOc3c2)ncn1 Chemical compound CCOc1cc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc3OCOc3c2)ncn1 MGRKHQCOOKRBFT-UHFFFAOYSA-N 0.000 claims 2
- NRRZENWPIWMAKM-UHFFFAOYSA-N CCc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc3ccccc3c2C)ncn1 Chemical compound CCc1nc(sc1-c1nc(=O)o[nH]1)-c1cc(NCCc2ccc3ccccc3c2C)ncn1 NRRZENWPIWMAKM-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
- PMXJZZCLJHTWBP-UHFFFAOYSA-N S1C2=C(C=C1)C=C(C=C2)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC Chemical compound S1C2=C(C=C1)C=C(C=C2)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(N1)=O)OCC PMXJZZCLJHTWBP-UHFFFAOYSA-N 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
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 208000022185 autosomal dominant polycystic kidney disease Diseases 0.000 claims 2
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- FUOSTELFLYZQCW-UHFFFAOYSA-N 1,2-oxazol-3-one Chemical compound OC=1C=CON=1 FUOSTELFLYZQCW-UHFFFAOYSA-N 0.000 claims 1
- RKKFNFCRPPQVHO-UHFFFAOYSA-N 2-(difluoromethoxy)-4-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound FC(OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)F RKKFNFCRPPQVHO-UHFFFAOYSA-N 0.000 claims 1
- KIONIRQNHYPKSU-UHFFFAOYSA-N 2-[2-(difluoromethoxy)-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound FC(OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)CC(=O)O)F KIONIRQNHYPKSU-UHFFFAOYSA-N 0.000 claims 1
- JHNSYBZXMAMJST-UHFFFAOYSA-N 2-[2-chloro-6-ethyl-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound ClC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)CC)CC(=O)O JHNSYBZXMAMJST-UHFFFAOYSA-N 0.000 claims 1
- XNFXHUOQAYYYFT-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(1-fluoro-3-methoxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)F)CC(=O)O XNFXHUOQAYYYFT-UHFFFAOYSA-N 0.000 claims 1
- OQFWFTXONUXMOZ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-ethoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OCC)C)CC(=O)O OQFWFTXONUXMOZ-UHFFFAOYSA-N 0.000 claims 1
- PONUIMWKJAGNFL-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-ethoxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1OCC PONUIMWKJAGNFL-UHFFFAOYSA-N 0.000 claims 1
- JRRDXBVIIGOMRM-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-ethynylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1C#C JRRDXBVIIGOMRM-UHFFFAOYSA-N 0.000 claims 1
- QRYFVGLKTZCVQR-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)CC(=O)O QRYFVGLKTZCVQR-UHFFFAOYSA-N 0.000 claims 1
- UWYGTGUPSLOZHY-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-methoxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1OC UWYGTGUPSLOZHY-UHFFFAOYSA-N 0.000 claims 1
- ZJMMPAHNHBAYNZ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(3-propan-2-yloxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1OC(C)C ZJMMPAHNHBAYNZ-UHFFFAOYSA-N 0.000 claims 1
- KMOJTRYMLJKSSI-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)F)CC(=O)O KMOJTRYMLJKSSI-UHFFFAOYSA-N 0.000 claims 1
- FVVHAHYELUPKFH-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-methoxy-1-benzofuran-6-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(C=CO2)C=C1OC FVVHAHYELUPKFH-UHFFFAOYSA-N 0.000 claims 1
- QMRJLRSVGOEGRG-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-ethoxy-2,3-dihydro-1,4-benzodioxin-7-yl)ethylamino]pyrimidin-4-yl]-6-fluorophenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(OCCO2)C=C1OCC)F)CC(=O)O QMRJLRSVGOEGRG-UHFFFAOYSA-N 0.000 claims 1
- LVIPPUGQNCDWQZ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-fluoro-1-benzofuran-5-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=1C(=CC2=C(C=CO2)C=1)F LVIPPUGQNCDWQZ-UHFFFAOYSA-N 0.000 claims 1
- YKZVZANWVARNFS-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-1-benzofuran-5-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=1C(=CC2=C(C=CO2)C=1)OC YKZVZANWVARNFS-UHFFFAOYSA-N 0.000 claims 1
- HTDYKLXJWRAUQH-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]phenoxy]propanoic acid Chemical compound C(C)OC1=C(OC(C(=O)O)C)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1)OC HTDYKLXJWRAUQH-UHFFFAOYSA-N 0.000 claims 1
- ZQKFQOGMUHUXAK-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1)OC)CC(=O)O ZQKFQOGMUHUXAK-UHFFFAOYSA-N 0.000 claims 1
- WEYBQOJYNCNXJT-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC WEYBQOJYNCNXJT-UHFFFAOYSA-N 0.000 claims 1
- ORRFZNBFGHTUCT-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC)CC(=O)O ORRFZNBFGHTUCT-UHFFFAOYSA-N 0.000 claims 1
- CKHMZTVLUNYGEK-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-4-methyl-1-benzofuran-5-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=1C(=CC2=C(C=CO2)C=1C)OC CKHMZTVLUNYGEK-UHFFFAOYSA-N 0.000 claims 1
- LMNCNHSINKGPRZ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methoxy-4-methyl-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1C)OC)CC(=O)O LMNCNHSINKGPRZ-UHFFFAOYSA-N 0.000 claims 1
- QBEWNACGCZOAAT-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]-2-oxoacetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)C(C(=O)O)=O QBEWNACGCZOAAT-UHFFFAOYSA-N 0.000 claims 1
- CTZJOCZOIMHDJU-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)CC(=O)O CTZJOCZOIMHDJU-UHFFFAOYSA-N 0.000 claims 1
- LURFEAJTFZWXSW-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1OC)F)CC(=O)O LURFEAJTFZWXSW-UHFFFAOYSA-N 0.000 claims 1
- HNIMEFSRGAFFIQ-UHFFFAOYSA-N 2-[2-ethoxy-6-fluoro-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)F)CC(=O)O HNIMEFSRGAFFIQ-UHFFFAOYSA-N 0.000 claims 1
- XVTBFBOMKTZQGG-UHFFFAOYSA-N 2-[2-ethoxy-6-fluoro-4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)F)F)CC(=O)O XVTBFBOMKTZQGG-UHFFFAOYSA-N 0.000 claims 1
- PYOHDHMORFMFPU-UHFFFAOYSA-N 2-[2-ethoxy-6-fluoro-4-[6-[2-(4-methyl-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)C)F)CC(=O)O PYOHDHMORFMFPU-UHFFFAOYSA-N 0.000 claims 1
- IMCMITYHYCMPFG-UHFFFAOYSA-N 2-[2-ethoxy-6-fluoro-4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC)F)CC(=O)O IMCMITYHYCMPFG-UHFFFAOYSA-N 0.000 claims 1
- KXBLIBGCVULMOP-UHFFFAOYSA-N 2-[2-ethoxy-6-fluoro-4-[6-[2-(7-methoxy-5-methyl-2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(OCCO2)C=C1OC)C)F)CC(=O)O KXBLIBGCVULMOP-UHFFFAOYSA-N 0.000 claims 1
- LPHVFYUNSCQVRE-UHFFFAOYSA-N 2-[2-ethyl-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)C1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)CC(=O)O LPHVFYUNSCQVRE-UHFFFAOYSA-N 0.000 claims 1
- FVRNKSRNLIBYBK-UHFFFAOYSA-N 2-[2-ethyl-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-6-methylphenyl]acetic acid Chemical compound C(C)C1=C(C(=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)C)CC(=O)O FVRNKSRNLIBYBK-UHFFFAOYSA-N 0.000 claims 1
- ZHKMHWWTRNNRRJ-UHFFFAOYSA-N 2-[2-methoxy-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound COC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)CC(=O)O ZHKMHWWTRNNRRJ-UHFFFAOYSA-N 0.000 claims 1
- NZBWZSWTIRJIDK-UHFFFAOYSA-N 2-[2-methoxy-4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound COC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC)CC(=O)O NZBWZSWTIRJIDK-UHFFFAOYSA-N 0.000 claims 1
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- LCOPXFSCLUHKIK-UHFFFAOYSA-N 2-[3-ethoxy-5-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]acetic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)CC(=O)O LCOPXFSCLUHKIK-UHFFFAOYSA-N 0.000 claims 1
- LTRAWVGAFMVZJA-UHFFFAOYSA-N 2-[3-ethyl-5-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]acetic acid Chemical compound C(C)C1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F)CC(=O)O LTRAWVGAFMVZJA-UHFFFAOYSA-N 0.000 claims 1
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- CWYWFLNZTJOBSJ-UHFFFAOYSA-N 2-[4-[6-[2-(3-chloro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-(trifluoromethoxy)phenyl]acetic acid Chemical compound ClC=1C2=C(SC=1)C=CC(=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC(F)(F)F CWYWFLNZTJOBSJ-UHFFFAOYSA-N 0.000 claims 1
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- DETVNRSUMJMDJM-UHFFFAOYSA-N 2-[4-[6-[2-(3-chloro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound ClC=1C2=C(SC=1)C=CC(=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC DETVNRSUMJMDJM-UHFFFAOYSA-N 0.000 claims 1
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- AWYAHNDCVXJZCW-UHFFFAOYSA-N 2-[4-[6-[2-(3-cyanonaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]acetic acid Chemical compound C(#N)C=1C(=CC2=CC=CC=C2C=1)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OCC AWYAHNDCVXJZCW-UHFFFAOYSA-N 0.000 claims 1
- BTRHEFWWSJRNDO-UHFFFAOYSA-N 2-[4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-2-(trifluoromethoxy)phenyl]acetic acid Chemical compound COC=1C(=C(C2=CC=CC=C2C=1)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC(F)(F)F BTRHEFWWSJRNDO-UHFFFAOYSA-N 0.000 claims 1
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- QGZGABCPDXOEFG-UHFFFAOYSA-N 2-[4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound COC=1C(=C(C2=CC=CC=C2C=1)C)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC QGZGABCPDXOEFG-UHFFFAOYSA-N 0.000 claims 1
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- JSKVKOYQKFWJQR-UHFFFAOYSA-N 2-[4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-propan-2-yloxyphenyl]acetic acid Chemical compound FC1=C(C=CC=2SC=CC=21)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC(C)C JSKVKOYQKFWJQR-UHFFFAOYSA-N 0.000 claims 1
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- QHYJKLDAUACQES-UHFFFAOYSA-N 2-[4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound FC1=C(C=CC=2SC=CC=21)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC QHYJKLDAUACQES-UHFFFAOYSA-N 0.000 claims 1
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- QMIDAUZYIQILJU-UHFFFAOYSA-N 2-[4-[6-[2-(5-methyl-2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound CC1=C(C=CC=2OCCOC=21)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC QMIDAUZYIQILJU-UHFFFAOYSA-N 0.000 claims 1
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- FTNCYRRIOOXEHH-UHFFFAOYSA-N 2-[4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound COC=1C(=CC2=C(SC=C2)C=1)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC FTNCYRRIOOXEHH-UHFFFAOYSA-N 0.000 claims 1
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- DJKYWLCSVDTOSU-UHFFFAOYSA-N 2-[4-[6-[2-(7-fluoro-6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-(2-methylpropyl)phenyl]acetic acid Chemical compound FC1=C(C(=CC2=C1SC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CC(C)C)OC DJKYWLCSVDTOSU-UHFFFAOYSA-N 0.000 claims 1
- RCQLSZKOPNUTHA-UHFFFAOYSA-N 2-[4-[6-[2-(7-fluoro-6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenyl]acetic acid Chemical compound FC1=C(C(=CC2=C1SC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)OC)OC RCQLSZKOPNUTHA-UHFFFAOYSA-N 0.000 claims 1
- BMHLCVJKWYONCC-UHFFFAOYSA-N 2-[4-[6-[2-(7-fluoro-6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-propylphenyl]acetic acid Chemical compound FC1=C(C(=CC2=C1SC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CC(=O)O)CCC)OC BMHLCVJKWYONCC-UHFFFAOYSA-N 0.000 claims 1
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- DERDQFJUHHJXQD-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(4-methyl-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)C DERDQFJUHHJXQD-UHFFFAOYSA-N 0.000 claims 1
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- LLSZBAJHHYLNRH-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(6-methoxy-4-methyl-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1C)OC LLSZBAJHHYLNRH-UHFFFAOYSA-N 0.000 claims 1
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- ABHZOEHNABPFDK-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(7-methoxy-5-methyl-2,3-dihydro-1,4-benzodioxin-6-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(OCCO2)C=C1OC)C ABHZOEHNABPFDK-UHFFFAOYSA-N 0.000 claims 1
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- FKHWTMXAEWFULH-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(1-methylnaphthalen-2-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(C2=CC=CC=C2C=C1)C FKHWTMXAEWFULH-UHFFFAOYSA-N 0.000 claims 1
- WRKGVSOPOQILRX-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(3-ethoxy-1-fluoronaphthalen-2-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(C2=CC=CC=C2C=C1OCC)F WRKGVSOPOQILRX-UHFFFAOYSA-N 0.000 claims 1
- KCIIZFRKZIOIJE-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(3-ethoxy-1-methylnaphthalen-2-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(C2=CC=CC=C2C=C1OCC)C KCIIZFRKZIOIJE-UHFFFAOYSA-N 0.000 claims 1
- GCTUHBBRFXBEML-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(3-ethynylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1C#C GCTUHBBRFXBEML-UHFFFAOYSA-N 0.000 claims 1
- JTMJYENFSAFDLD-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-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(C2=CC=CC=C2C=C1OC)C JTMJYENFSAFDLD-UHFFFAOYSA-N 0.000 claims 1
- QNZZPZOPTCRVLV-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(4-fluoro-1-benzothiophen-5-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(C2=C(SC=C2)C=C1)F QNZZPZOPTCRVLV-UHFFFAOYSA-N 0.000 claims 1
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- COSRONUEIINCOD-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(4-methyl-1-benzothiophen-5-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(C2=C(SC=C2)C=C1)C COSRONUEIINCOD-UHFFFAOYSA-N 0.000 claims 1
- SYXYQCPUVDHUOA-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-ethoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OCC SYXYQCPUVDHUOA-UHFFFAOYSA-N 0.000 claims 1
- WEECDNMGAKMXEP-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-ethoxy-2,3-dihydro-1,4-benzodioxin-7-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(OCCO2)C=C1OCC WEECDNMGAKMXEP-UHFFFAOYSA-N 0.000 claims 1
- NNNAFIKSZZKLBH-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-fluoro-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1)F NNNAFIKSZZKLBH-UHFFFAOYSA-N 0.000 claims 1
- FQPRBKFSHGIFNI-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-methoxy-1,3-benzodioxol-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(OCO2)C=C1OC FQPRBKFSHGIFNI-UHFFFAOYSA-N 0.000 claims 1
- NIPRXIDXHSFUAA-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-methoxy-1-benzofuran-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(C=CO2)C=1)OC NIPRXIDXHSFUAA-UHFFFAOYSA-N 0.000 claims 1
- AXKXISNPOIGAIU-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1OC AXKXISNPOIGAIU-UHFFFAOYSA-N 0.000 claims 1
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- VNXYLVCARUDCIC-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(6-methyl-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C=C1C VNXYLVCARUDCIC-UHFFFAOYSA-N 0.000 claims 1
- QISYYUXNJPDLLW-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-N-(2-hydroxyethyl)benzamide Chemical compound C(C)OC1=C(C(=O)NCCO)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F QISYYUXNJPDLLW-UHFFFAOYSA-N 0.000 claims 1
- YHMSTNLGNNTAES-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F YHMSTNLGNNTAES-UHFFFAOYSA-N 0.000 claims 1
- ZIUCFTPLIQYRSS-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(7-fluoro-6-methoxy-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1OC)F ZIUCFTPLIQYRSS-UHFFFAOYSA-N 0.000 claims 1
- UVKXTESVTFELMF-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(7-methoxy-5-methyl-2,3-dihydro-1,4-benzodioxin-6-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(C2=C(OCCO2)C=C1OC)C UVKXTESVTFELMF-UHFFFAOYSA-N 0.000 claims 1
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- BXYDWWULQCGATC-UHFFFAOYSA-N 2-ethyl-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)C1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F BXYDWWULQCGATC-UHFFFAOYSA-N 0.000 claims 1
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- STMIAYFDVBKIMI-UHFFFAOYSA-N 2-ethylsulfanyl-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)SC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F STMIAYFDVBKIMI-UHFFFAOYSA-N 0.000 claims 1
- JYQSPWXBVLOMHZ-UHFFFAOYSA-N 2-fluoro-4-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-6-propylbenzoic acid Chemical compound FC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)CCC JYQSPWXBVLOMHZ-UHFFFAOYSA-N 0.000 claims 1
- RZHVLCNTOJOZCG-UHFFFAOYSA-N 3-(2-hydroxyethoxy)-5-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound OCCOC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)C(=O)O RZHVLCNTOJOZCG-UHFFFAOYSA-N 0.000 claims 1
- HBUDCDIHGSCFJA-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]phenoxy]propanoic acid Chemical compound C(C)OC1=C(OCCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C HBUDCDIHGSCFJA-UHFFFAOYSA-N 0.000 claims 1
- MLSFULIDTYJAPK-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenoxy]propanoic acid Chemical compound C(C)OC1=C(OCCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)F MLSFULIDTYJAPK-UHFFFAOYSA-N 0.000 claims 1
- WFKWPAJAHUQKBJ-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]phenoxy]propanoic acid Chemical compound C(C)OC1=C(OCCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2)C(=C1)F WFKWPAJAHUQKBJ-UHFFFAOYSA-N 0.000 claims 1
- XZKQEYLRWNFALU-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]propanoic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)CCC(=O)O XZKQEYLRWNFALU-UHFFFAOYSA-N 0.000 claims 1
- KTQOLHDXXKWHCJ-UHFFFAOYSA-N 3-[4-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenoxy]propanoic acid Chemical compound FC1=C(C=CC=2SC=CC=21)CCNC1=CC(=NC=N1)C1=CC(=C(OCCC(=O)O)C=C1)OC KTQOLHDXXKWHCJ-UHFFFAOYSA-N 0.000 claims 1
- ZUCUZISYQXJTNG-UHFFFAOYSA-N 3-[4-[6-[2-(7-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenoxy]propanoic acid Chemical compound FC1=CC(=CC2=C1SC=C2)CCNC1=CC(=NC=N1)C1=CC(=C(OCCC(=O)O)C=C1)OC ZUCUZISYQXJTNG-UHFFFAOYSA-N 0.000 claims 1
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- KZNWYIRFLTWFAK-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1-fluoro-3-methoxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)F)C(=O)O KZNWYIRFLTWFAK-UHFFFAOYSA-N 0.000 claims 1
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- KQGKCBAKUSXYLS-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-N-methylsulfonylthiophene-2-carboxamide Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)C(=O)NS(=O)(=O)C KQGKCBAKUSXYLS-UHFFFAOYSA-N 0.000 claims 1
- GBIVLBIVINFOEE-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]-N-sulfamoylthiophene-2-carboxamide Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)C(=O)NS(N)(=O)=O GBIVLBIVINFOEE-UHFFFAOYSA-N 0.000 claims 1
- KYJGUOFPWNZANJ-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1)C)C(=O)O KYJGUOFPWNZANJ-UHFFFAOYSA-N 0.000 claims 1
- FQVUYUAYLHTQEO-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1H-indol-5-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=C2C=CNC2=CC=1)C(=O)O FQVUYUAYLHTQEO-UHFFFAOYSA-N 0.000 claims 1
- NNPGDNSFSJVMDO-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(1H-indol-6-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC=C2C=CNC2=C1)C(=O)O NNPGDNSFSJVMDO-UHFFFAOYSA-N 0.000 claims 1
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- LLVHCXCMJZLBAP-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-methoxy-1-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=CC=CC=C2C=C1OC)C)C(=O)O LLVHCXCMJZLBAP-UHFFFAOYSA-N 0.000 claims 1
- CUAYUQNCBCQDHC-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC=2CCCCC=2C=C1OC)C(=O)O CUAYUQNCBCQDHC-UHFFFAOYSA-N 0.000 claims 1
- GWEIYCPSANDHOA-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-methoxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1OC)C(=O)O GWEIYCPSANDHOA-UHFFFAOYSA-N 0.000 claims 1
- AEEZGBRAUTZKJH-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-methyl-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=C(SC=C2C)C=C1)C(=O)O AEEZGBRAUTZKJH-UHFFFAOYSA-N 0.000 claims 1
- VQGROINTIJGVQZ-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-methylnaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1C)C(=O)O VQGROINTIJGVQZ-UHFFFAOYSA-N 0.000 claims 1
- MDKTVSWFYZEBSP-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(3-propan-2-yloxynaphthalen-2-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC2=CC=CC=C2C=C1OC(C)C)C(=O)O MDKTVSWFYZEBSP-UHFFFAOYSA-N 0.000 claims 1
- KYKZPBGOBWSCOS-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(4-fluoro-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound CCOc1cc(sc1C(O)=O)-c1cc(NCCc2ccc3sccc3c2F)ncn1 KYKZPBGOBWSCOS-UHFFFAOYSA-N 0.000 claims 1
- XLBYBDNACPCWJS-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(4-fluoro-7-methoxy-2-methyl-1-benzothiophen-6-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=C(C2=C(SC(=C2)C)C=1OC)F)C(=O)O XLBYBDNACPCWJS-UHFFFAOYSA-N 0.000 claims 1
- ITWCVWZTYHAOAM-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(4-methyl-1-benzothiophen-5-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C2=C(SC=C2)C=C1)C)C(=O)O ITWCVWZTYHAOAM-UHFFFAOYSA-N 0.000 claims 1
- AONJJKBADCIWHY-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-fluoroquinolin-6-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C(=C2C=CC=NC2=CC=1)F)C(=O)O AONJJKBADCIWHY-UHFFFAOYSA-N 0.000 claims 1
- LYDZXEASJPKRPO-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(5-methoxy-1-benzothiophen-6-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C(=CC2=C(SC=C2)C=1)OC)C(=O)O LYDZXEASJPKRPO-UHFFFAOYSA-N 0.000 claims 1
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- 2018-05-17 LT LTEPPCT/EP2018/062844T patent/LT3625228T/lt unknown
- 2018-05-17 EA EA201992677A patent/EA201992677A1/ru unknown
- 2018-05-17 DK DK18725498.2T patent/DK3625228T3/da active
- 2018-05-17 WO PCT/EP2018/062844 patent/WO2018210988A1/en not_active Ceased
- 2018-05-17 PT PT187254982T patent/PT3625228T/pt unknown
- 2018-05-17 CA CA3060394A patent/CA3060394A1/en active Pending
- 2018-05-17 RS RS20211222A patent/RS62398B1/sr unknown
- 2018-05-17 ES ES18725498T patent/ES2887041T3/es active Active
- 2018-05-17 US US16/614,209 patent/US11839613B2/en active Active
- 2018-05-17 PL PL18725498T patent/PL3625228T3/pl unknown
- 2018-05-17 SG SG11201908097Y patent/SG11201908097YA/en unknown
- 2018-05-17 KR KR1020197037039A patent/KR102626982B1/ko active Active
- 2018-05-17 BR BR112019024105-1A patent/BR112019024105A2/pt not_active IP Right Cessation
- 2018-05-17 MA MA049128A patent/MA49128A/fr unknown
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2019
- 2019-09-26 CO CONC2019/0010505A patent/CO2019010505A2/es unknown
- 2019-11-13 IL IL270620A patent/IL270620B2/en unknown
- 2019-11-14 CL CL2019003274A patent/CL2019003274A1/es unknown
- 2019-11-15 PH PH12019502564A patent/PH12019502564A1/en unknown
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2021
- 2021-10-06 CY CY20211100870T patent/CY1124799T1/el unknown
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