JP2020520354A5 - - Google Patents
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- Publication number
- JP2020520354A5 JP2020520354A5 JP2019563368A JP2019563368A JP2020520354A5 JP 2020520354 A5 JP2020520354 A5 JP 2020520354A5 JP 2019563368 A JP2019563368 A JP 2019563368A JP 2019563368 A JP2019563368 A JP 2019563368A JP 2020520354 A5 JP2020520354 A5 JP 2020520354A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- ethylamino
- naphthalene
- ethoxy
- alkyl
- 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 3-oxo-2,3-dihydro- [1,2,4] oxadiazole-5-yl Chemical group 0.000 claims 145
- 125000000217 alkyl group Chemical group 0.000 claims 79
- 125000000753 cycloalkyl group Chemical group 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 19
- 125000002947 alkylene group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 206010028980 Neoplasm Diseases 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 13
- 201000011510 cancer Diseases 0.000 claims 12
- 239000012634 fragment Substances 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 239000001301 oxygen Substances 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 239000004480 active ingredient Substances 0.000 claims 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims 5
- 229940079593 drug Drugs 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 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
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 230000028993 immune response Effects 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
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- XEVOMDSRWWQOFS-UHFFFAOYSA-N 4-[6-[2-(1,5-dimethylindol-4-yl)ethylamino]pyrimidin-4-yl]-2-methylsulfanylbenzoic acid Chemical compound CN1C=CC2=C(C(=CC=C12)C)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)SC XEVOMDSRWWQOFS-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
- FJVAGFQJAVIAJM-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)C1=NOC(=N1)O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)C1=NOC(=N1)O FJVAGFQJAVIAJM-UHFFFAOYSA-N 0.000 claims 2
- CWDQVZBCJXQWDE-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CC=NC2=CC=C1OC)C1=NOC(=N1)O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CC=NC2=CC=C1OC)C1=NOC(=N1)O CWDQVZBCJXQWDE-UHFFFAOYSA-N 0.000 claims 2
- VUEONTPMDHNVHR-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CNC2=CC=C1)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CNC2=CC=C1)C1=NOC(N1)=O VUEONTPMDHNVHR-UHFFFAOYSA-N 0.000 claims 2
- ZVGWIVKKFFFOOT-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC=C(C2=CC=CC=C12)OC)C1=NOC(=N1)O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC=C(C2=CC=CC=C12)OC)C1=NOC(=N1)O ZVGWIVKKFFFOOT-UHFFFAOYSA-N 0.000 claims 2
- DTXKOLKFOCYAPU-UHFFFAOYSA-N C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=CC=C2C=CN=CC=12)C1=NOC(N1)=O Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC=1C=CC=C2C=CN=CC=12)C1=NOC(N1)=O DTXKOLKFOCYAPU-UHFFFAOYSA-N 0.000 claims 2
- LZDUJKANULCQMR-UHFFFAOYSA-N C(C)OC=1N=C(SC=1C1=NOC(N1)=O)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC Chemical compound C(C)OC=1N=C(SC=1C1=NOC(N1)=O)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC LZDUJKANULCQMR-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
- YZZPXLJBWJDUCV-UHFFFAOYSA-N N1C=CC2=CC=CC(=C12)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(=N1)O)OCC Chemical compound N1C=CC2=CC=CC(=C12)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C1=NOC(=N1)O)OCC YZZPXLJBWJDUCV-UHFFFAOYSA-N 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
- 208000022185 autosomal dominant polycystic kidney disease Diseases 0.000 claims 2
- 201000010881 cervical cancer Diseases 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 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
- 210000000987 immune system Anatomy 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
- 239000008177 pharmaceutical agent Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 230000000069 prophylactic effect 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
- YELLUWAGQVKCEQ-ZHACJKMWSA-N (E)-3-[3-ethoxy-5-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]prop-2-enoic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)/C=C/C(=O)O YELLUWAGQVKCEQ-ZHACJKMWSA-N 0.000 claims 1
- MVCFDHLQJVJMDE-UHFFFAOYSA-N 1-methyl-3,4-dihydroquinazolin-2-one Chemical group C1=CC=C2N(C)C(=O)NCC2=C1 MVCFDHLQJVJMDE-UHFFFAOYSA-N 0.000 claims 1
- LGPAAAVNLKVZLA-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound OCCOC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC LGPAAAVNLKVZLA-UHFFFAOYSA-N 0.000 claims 1
- NKYVKUVRUYQSNA-UHFFFAOYSA-N 2-(difluoromethoxy)-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound FC(OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)F NKYVKUVRUYQSNA-UHFFFAOYSA-N 0.000 claims 1
- YVBVAXYJWJSXLQ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]anilino]-2-oxoacetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)NC(C(=O)O)=O YVBVAXYJWJSXLQ-UHFFFAOYSA-N 0.000 claims 1
- LBJPNTLBHDXUGV-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)CC(=O)O LBJPNTLBHDXUGV-UHFFFAOYSA-N 0.000 claims 1
- MSOOEGZULITGAO-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-fluoronaphthalen-1-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=C(C=CC=C12)F)CC(=O)O MSOOEGZULITGAO-UHFFFAOYSA-N 0.000 claims 1
- QULBLXOBUFTFGY-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-methoxy-1-benzothiophen-4-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC=2SC=CC=21)OC)CC(=O)O QULBLXOBUFTFGY-UHFFFAOYSA-N 0.000 claims 1
- LSAPIVLONBDMJJ-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-methoxy-1-methylindol-4-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CN(C2=CC=C1OC)C)CC(=O)O LSAPIVLONBDMJJ-UHFFFAOYSA-N 0.000 claims 1
- GEKANDQYTKFKRR-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(5-methylnaphthalen-1-yl)ethylamino]pyrimidin-4-yl]phenyl]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=C(C=CC=C12)C)CC(=O)O GEKANDQYTKFKRR-UHFFFAOYSA-N 0.000 claims 1
- NWLPAUQNSPXWCT-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-methylisoquinolin-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=C2C=CN=CC2=CC=C1C NWLPAUQNSPXWCT-UHFFFAOYSA-N 0.000 claims 1
- AGTHGFJXPNXZFV-UHFFFAOYSA-N 2-[3-ethoxy-5-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]acetic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)CC(=O)O AGTHGFJXPNXZFV-UHFFFAOYSA-N 0.000 claims 1
- BCMUZUWYJVPNHI-UHFFFAOYSA-N 2-butoxy-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(CCC)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC BCMUZUWYJVPNHI-UHFFFAOYSA-N 0.000 claims 1
- FJSYNQADNPNRDP-UHFFFAOYSA-N 2-butoxy-6-fluoro-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(CCC)OC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)F FJSYNQADNPNRDP-UHFFFAOYSA-N 0.000 claims 1
- HLCCSAMCKPNYDS-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(1-methylindol-4-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C1(CCC1)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CN(C2=CC=C1)C HLCCSAMCKPNYDS-UHFFFAOYSA-N 0.000 claims 1
- RNQHJLHFYFKDHR-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(2-ethoxynaphthalen-1-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(C=CC2=CC=CC=C12)OCC RNQHJLHFYFKDHR-UHFFFAOYSA-N 0.000 claims 1
- UTAHKVCSFFTZRX-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(2-fluoronaphthalen-1-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(C=CC2=CC=CC=C12)F UTAHKVCSFFTZRX-UHFFFAOYSA-N 0.000 claims 1
- HONGSMWWUADXNX-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(2-methoxynaphthalen-1-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(C=CC2=CC=CC=C12)OC HONGSMWWUADXNX-UHFFFAOYSA-N 0.000 claims 1
- VBOATZJDTYSZFC-UHFFFAOYSA-N 2-cyclobutyloxy-4-[6-[2-(6-methoxyquinolin-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=C2C=CC=NC2=CC=C1OC VBOATZJDTYSZFC-UHFFFAOYSA-N 0.000 claims 1
- ROIVISKTRQIUSL-UHFFFAOYSA-N 2-ethoxy-4-[6-(2-naphthalen-1-ylethylamino)pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=CC=CC=C12 ROIVISKTRQIUSL-UHFFFAOYSA-N 0.000 claims 1
- MNBJSMFQNPTKBK-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(2-ethoxynaphthalen-1-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(C=CC2=CC=CC=C12)OCC MNBJSMFQNPTKBK-UHFFFAOYSA-N 0.000 claims 1
- PNXLIMSFSSKCDO-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(2-fluoronaphthalen-1-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(C=CC2=CC=CC=C12)F PNXLIMSFSSKCDO-UHFFFAOYSA-N 0.000 claims 1
- DUVRDYGFJRKPBT-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(2-methoxynaphthalen-1-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(C=CC2=CC=CC=C12)OC DUVRDYGFJRKPBT-UHFFFAOYSA-N 0.000 claims 1
- ILQRVBBBFCVXEZ-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(4-fluoronaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=C(C2=CC=CC=C12)F ILQRVBBBFCVXEZ-UHFFFAOYSA-N 0.000 claims 1
- NQCQTAIJUGKBBP-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-ethoxy-1-benzothiophen-4-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(C=CC=2SC=CC=21)OCC NQCQTAIJUGKBBP-UHFFFAOYSA-N 0.000 claims 1
- FUPVSZQXWQQSMJ-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-fluoronaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=C(C=CC=C12)F FUPVSZQXWQQSMJ-UHFFFAOYSA-N 0.000 claims 1
- DFURTOXHJRTLLB-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-methoxy-1-benzothiophen-4-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(C=CC=2SC=CC=21)OC DFURTOXHJRTLLB-UHFFFAOYSA-N 0.000 claims 1
- GHKDPVZDNVYMIO-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-methoxy-1-methylindol-4-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=C2C=CN(C2=CC=C1OC)C GHKDPVZDNVYMIO-UHFFFAOYSA-N 0.000 claims 1
- LUQYWVDQSWLMKV-UHFFFAOYSA-N 2-ethoxy-4-[6-[2-(5-methylnaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)OC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=C(C=CC=C12)C LUQYWVDQSWLMKV-UHFFFAOYSA-N 0.000 claims 1
- HYWOJAFGCKEDNG-UHFFFAOYSA-N 2-ethylsulfanyl-4-[6-[2-(4-methylnaphthalen-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)SC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCC1=CC=C(C2=CC=CC=C12)C HYWOJAFGCKEDNG-UHFFFAOYSA-N 0.000 claims 1
- YGTPBBJTFZKRQW-UHFFFAOYSA-N 2-fluoro-4-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-6-propylbenzoic acid Chemical compound FC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)CCC YGTPBBJTFZKRQW-UHFFFAOYSA-N 0.000 claims 1
- SILSNVVREOXZHF-UHFFFAOYSA-N 3-(2-hydroxyethoxy)-5-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound OCCOC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)C(=O)O SILSNVVREOXZHF-UHFFFAOYSA-N 0.000 claims 1
- RCAFKJJOITZWSR-UHFFFAOYSA-N 3-[2-ethoxy-4-[6-[2-(2-methoxynaphthalen-1-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(C=CC2=CC=CC=C12)OC RCAFKJJOITZWSR-UHFFFAOYSA-N 0.000 claims 1
- HYGFYVIPXZPNOK-UHFFFAOYSA-N 3-[3-ethoxy-5-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]propanoic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)CCC(=O)O HYGFYVIPXZPNOK-UHFFFAOYSA-N 0.000 claims 1
- ZUQABPPYELXLDD-UHFFFAOYSA-N 3-ethoxy-5-[6-(2-naphthalen-1-ylethylamino)pyrimidin-4-yl]thiophene-2-carboxylic acid Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=CC=CC2=CC=CC=C12)C(=O)O ZUQABPPYELXLDD-UHFFFAOYSA-N 0.000 claims 1
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- CLZFKCUEKMVYPW-UHFFFAOYSA-N 3-ethoxy-5-[6-[2-(2-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-N-methylsulfonylthiophene-2-carboxamide Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCC1=C(C=CC2=CC=CC=C12)OC)C(=O)NS(=O)(=O)C CLZFKCUEKMVYPW-UHFFFAOYSA-N 0.000 claims 1
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- XDQSKBNMZJVGCA-UHFFFAOYSA-N 5-[6-[2-(1-benzothiophen-7-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound S1C2=C(C=C1)C=CC=C2CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC XDQSKBNMZJVGCA-UHFFFAOYSA-N 0.000 claims 1
- NMRGOCVSRAFKHL-UHFFFAOYSA-N 5-[6-[2-(2,3-dimethoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound COC1=C(C2=CC=CC=C2C=C1OC)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC NMRGOCVSRAFKHL-UHFFFAOYSA-N 0.000 claims 1
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- MNVQXGLUPCHWDO-UHFFFAOYSA-N 5-[6-[2-(2,5-dimethoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound COC1=C(C2=CC=CC(=C2C=C1)OC)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC MNVQXGLUPCHWDO-UHFFFAOYSA-N 0.000 claims 1
- WKOBOVDFXBAZHH-UHFFFAOYSA-N 5-[6-[2-(2-bromonaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound BrC1=C(C2=CC=CC=C2C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC WKOBOVDFXBAZHH-UHFFFAOYSA-N 0.000 claims 1
- KNMCKLMWFYDLBY-UHFFFAOYSA-N 5-[6-[2-(2-cyano-8-fluoro-5-methoxynaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound C(#N)C1=C(C2=C(C=CC(=C2C=C1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC KNMCKLMWFYDLBY-UHFFFAOYSA-N 0.000 claims 1
- VTYCMWGQRNABBQ-UHFFFAOYSA-N 5-[6-[2-(2-cyanonaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound C(#N)C1=C(C2=CC=CC=C2C=C1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC VTYCMWGQRNABBQ-UHFFFAOYSA-N 0.000 claims 1
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- BJXHJCQVQMALDH-UHFFFAOYSA-N 5-[6-[2-(4-cyanonaphthalen-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound C(#N)C1=CC=C(C2=CC=CC=C12)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC BJXHJCQVQMALDH-UHFFFAOYSA-N 0.000 claims 1
- PBMVEMRTKWZVIP-UHFFFAOYSA-N 5-[6-[2-(6-methoxy-1-methyl-3,4-dihydro-2H-quinolin-5-yl)ethylamino]pyrimidin-4-yl]-3-(trifluoromethyl)thiophene-2-carboxylic acid Chemical compound COC=1C(=C2CCCN(C2=CC=1)C)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)C(F)(F)F PBMVEMRTKWZVIP-UHFFFAOYSA-N 0.000 claims 1
- SGZSEOHQPAWAMJ-UHFFFAOYSA-N 5-[6-[2-(6-methoxyquinolin-5-yl)ethylamino]pyrimidin-4-yl]-3-(trifluoromethyl)thiophene-2-carboxylic acid Chemical compound COC=1C(=C2C=CC=NC2=CC=1)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)C(F)(F)F SGZSEOHQPAWAMJ-UHFFFAOYSA-N 0.000 claims 1
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| CN110621671A (zh) | 2017-05-18 | 2019-12-27 | 爱杜西亚药品有限公司 | 作为pge2受体调节剂的苯并呋喃及苯并噻吩衍生物 |
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| US20220048987A1 (en) * | 2020-08-13 | 2022-02-17 | The Board Of Trustees Of The Leland Stanford Junior University | Method of treatment to prevent or reverse age-associated inflammation, cognitive decline, and neurodegeneration |
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- 2018-05-17 WO PCT/EP2018/062858 patent/WO2018210992A1/en not_active Ceased
- 2018-05-17 JP JP2019563368A patent/JP7253500B2/ja active Active
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