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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| 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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| EP4359399A4 (en) | 2021-06-24 | 2025-04-23 | Reservoir Neuroscience, Inc. | EP2 antagonist compounds |
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Family Cites Families (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5948786A (en) | 1996-04-12 | 1999-09-07 | Sumitomo Pharmaceuticals Company, Limited | Piperidinylpyrimidine derivatives |
| JP2003528144A (ja) | 2000-03-24 | 2003-09-24 | ファーマジーン ラボラトリーズ リミテッド | 頭痛治療のためのプロスタノイドｅｐ４受容体アンタゴニストの使用およびそのアンタゴニストについてのアッセイ |
| HN2001000224A (es) | 2000-10-19 | 2002-06-13 | Pfizer | Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos. |
| GB0031302D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Napthalene derivatives |
| GB0031295D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Naphthalene derivatives |
| GB0103269D0 (en) | 2001-02-09 | 2001-03-28 | Glaxo Group Ltd | Napthalene derivatives |
| EP1495005A1 (en) | 2002-04-12 | 2005-01-12 | Pfizer Japan Inc. | Pyrazole compounds as anti-inflammatory and analgesic agents |
| EP1494667A1 (en) | 2002-04-12 | 2005-01-12 | Pfizer Japan Inc. | Imidazole compounds as anti-inflammatory and analgesic agents |
| JP2006506327A (ja) | 2002-05-23 | 2006-02-23 | セラテクノロジーズ インコーポレイティド | プロスタグランジンｅ２の受容体サブタイプｅｐ４のアンタゴニスト・ポリペプチド |
| CN100408570C (zh) | 2003-01-29 | 2008-08-06 | 阿斯特兰德英国有限公司 | Ep4受体拮抗剂 |
| TW200519116A (en) | 2003-08-26 | 2005-06-16 | Teijin Pharma Ltd | Pyrrolopyrimidine derivatives |
| AP2006003534A0 (en) | 2003-09-03 | 2006-04-30 | Pfizer | Phenyl or pyridyl amide compounds as prostaglandin E2 antagonists. |
| EP1678147B1 (en) | 2003-09-15 | 2012-08-08 | Lead Discovery Center GmbH | Pharmaceutically active 4,6-disubstituted aminopyrimidine derivatives as modulators of protein kinases |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| BRPI0510666A (pt) | 2004-05-04 | 2007-12-04 | Pfizer | compostos de amida de arila ou heteroarila de metila substituìda, composições farmacêuticas compreendendo os mesmos, uso e combinação |
| JP4054369B2 (ja) | 2004-05-04 | 2008-02-27 | ファイザー株式会社 | オルト置換アリールまたはヘテロアリールアミド化合物 |
| HN2005000795A (es) | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| AU2006246930C1 (en) | 2005-05-19 | 2012-01-19 | Merck Canada Inc. | Quinoline derivatives as EP4 antagonists |
| WO2006128129A2 (en) | 2005-05-26 | 2006-11-30 | Synta Pharmaceuticals Corp. | Method for treating cancer |
| AR060403A1 (es) | 2006-04-12 | 2008-06-11 | Sanofi Aventis | Compuestos de amino- pirimidina 2,6- sustituidos -4- monosustituidos como antagonistas del receptor de prostaglandina d2 |
| JP5244091B2 (ja) | 2006-04-24 | 2013-07-24 | メルク カナダ インコーポレイテッド | Ｅｐ４受容体アンタゴニストとしてのインドールアミド誘導体 |
| EP2035376B1 (en) | 2006-06-12 | 2014-08-27 | Merck Canada Inc. | Indoline amide derivatives as ep4 receptor ligands |
| US20080280891A1 (en) | 2006-06-27 | 2008-11-13 | Locus Pharmaceuticals, Inc. | Anti-cancer agents and uses thereof |
| WO2008008059A1 (en) | 2006-07-12 | 2008-01-17 | Locus Pharmaceuticals, Inc. | Anti-cancer agents ans uses thereof |
| CA2657227A1 (en) | 2006-07-14 | 2008-01-17 | Novartis Ag | Pyrimidine derivatives as alk-5 inhibitors |
| EP2054401B1 (en) | 2006-08-11 | 2013-05-01 | Merck Canada Inc. | Thiophenecarboxamide derivatives as ep4 receptor ligands |
| WO2008039882A1 (en) | 2006-09-30 | 2008-04-03 | Sanofi-Aventis U.S. Llc | A combination of niacin and a prostaglandin d2 receptor antagonist |
| WO2008104055A1 (en) | 2007-02-26 | 2008-09-04 | Merck Frosst Canada Ltd. | Indole and indoline cyclopropyl amide derivatives as ep4 receptor antagonists |
| EP2141147A1 (en) | 2007-03-26 | 2010-01-06 | Astellas Pharma Inc. | Ornithine derivative |
| CA2681146A1 (en) | 2007-03-26 | 2008-10-02 | Merck Frosst Canada Ltd. | Naphthalene and quinoline sulfonylurea derivatives as ep4 receptor antagonists |
| EP2014657A1 (de) | 2007-06-21 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Diaminopyrimidine als Modulatoren des EP2-Rezeptors |
| US20110028463A1 (en) | 2007-07-03 | 2011-02-03 | Astellas Pharma Inc. | Amide compounds |
| CN101889004B (zh) | 2007-10-12 | 2014-09-10 | 阿斯利康公司 | 蛋白激酶抑制剂 |
| CA2714743C (en) | 2008-02-19 | 2017-01-17 | Janssen Pharmaceutica N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| SI2565191T1 (sl) | 2008-05-14 | 2014-12-31 | Astellas Pharma Inc. | Derivati 4-(indol-7-ilkarbonilaminometil)cikloheksan karboksilne kisline kot EP4 receptorski antagonisti, uporabni za zdravljenje kronične ledvične odpovedi ali diabetične nefropatije |
| US20130225528A1 (en) | 2008-05-21 | 2013-08-29 | Ariad Pharmaceuticals, Inc. | Phosphorus Derivatives as Kinase Inhibitors |
| US8404736B2 (en) | 2008-08-14 | 2013-03-26 | Beta Pharma Canada Inc. | Heterocyclic amide derivatives as EP4 receptor antagonists |
| CN102164942B (zh) | 2008-09-19 | 2017-02-15 | 生物科技研究有限公司 | 三萜系化合物及其使用的方法 |
| JP2012503605A (ja) | 2008-09-25 | 2012-02-09 | メルク カナダ インコーポレイテッド | Ｅｐ４受容体アンタゴニストとしてのベータ−カルボリンスルホニルウレア誘導体 |
| WO2011022348A1 (en) | 2009-08-18 | 2011-02-24 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid amide hydrolase |
| WO2011063181A1 (en) | 2009-11-23 | 2011-05-26 | Lexicon Pharmaceuticals, Inc. | Methods and assays for the treatment of irritable bowel syndrome |
| JP5607241B2 (ja) | 2010-05-21 | 2014-10-15 | ケミリア・エービー | 新規ピリミジン誘導体 |
| PT2619182T (pt) | 2010-09-21 | 2017-01-17 | Eisai R&D Man Co Ltd | Composição farmacêutica |
| KR101857310B1 (ko) | 2010-09-29 | 2018-05-11 | 가부시키가이샤 에누비 켄코우겡큐쇼 | 인간 프로스타글란딘 e2 수용체 ep4 에 대한 항체 |
| WO2012066065A1 (en) | 2010-11-17 | 2012-05-24 | Novartis Ag | Phenyl-heteroaryl amine compounds and their uses |
| BR112013012380A2 (pt) | 2010-11-17 | 2016-08-30 | Novartis Ag | compostos 3-(aminoaril)-piridina |
| WO2012076063A1 (en) * | 2010-12-10 | 2012-06-14 | Rottapharm S.P.A. | Pyridine amide derivatives as ep4 receptor antagonists |
| WO2012103071A2 (en) | 2011-01-25 | 2012-08-02 | Eisai R&D Management Co., Ltd. | Compounds and compositions |
| EP2688883B1 (en) | 2011-03-24 | 2016-05-18 | Noviga Research AB | Pyrimidine derivatives |
| EP2702043A1 (en) | 2011-04-29 | 2014-03-05 | Exelixis, Inc. | Inhibitors of inducible form of 6-phosphofructose-2-kinase |
| US9518044B2 (en) | 2011-06-20 | 2016-12-13 | Emory University | Prostaglandin receptor EP2 antagonists, derivatives, compositions, and uses related thereto |
| US9181279B2 (en) | 2011-07-04 | 2015-11-10 | Rottapharm Biotech S.R.L. | Cyclic amine derivatives as EP4 receptor antagonists |
| EP2554662A1 (en) | 2011-08-05 | 2013-02-06 | M Maria Pia Cosma | Methods of treatment of retinal degeneration diseases |
| US20150004175A1 (en) | 2011-12-13 | 2015-01-01 | Yale University | Compositions and Methods for Reducing CTL Exhaustion |
| RS61664B1 (sr) * | 2012-04-24 | 2021-04-29 | Vertex Pharma | Inhibitori dna-pk |
| TWI572597B (zh) | 2012-06-29 | 2017-03-01 | 美國禮來大藥廠 | 二甲基－苯甲酸化合物 |
| JO3296B1 (ar) | 2012-06-29 | 2018-09-16 | Lilly Co Eli | مركبات فينوكسي إيثيل بيبريدين |
| EP2711364A1 (en) | 2012-09-21 | 2014-03-26 | Chemilia AB | 4-(Indolyl or benzimidazolyl)amino-2-(2-(indol-3-yl)ethyl)aminopyrimidines useful for the treatment of cancer |
| MY182386A (en) | 2012-11-27 | 2021-01-22 | Thomas Helledays Stiftelse For Medicinsk Forskning | Pyrimidine-2,4-diamine derivatives for treatment of cancer |
| UA115576C2 (uk) | 2012-12-06 | 2017-11-27 | Байєр Фарма Акцієнгезелльшафт | Похідні бензимідазолу як антагоністи ер4 |
| EP2765128A1 (en) | 2013-02-07 | 2014-08-13 | Almirall, S.A. | Substituted benzamides with activity towards EP4 receptors |
| TW201443004A (zh) | 2013-02-15 | 2014-11-16 | Lilly Co Eli | 苯氧基乙氧基化合物 |
| TWI636046B (zh) | 2013-05-17 | 2018-09-21 | 美國禮來大藥廠 | 苯氧基乙基二氫－１ｈ－異喹啉化合物 |
| SG11201510121RA (en) | 2013-06-12 | 2016-01-28 | Kaken Pharma Co Ltd | 4-alkynyl imidazole derivative and medicine comprising same as active ingredient |
| AU2014315457B2 (en) | 2013-09-04 | 2018-05-10 | Bristol-Myers Squibb Company | Compounds useful as immunomodulators |
| JP6521977B2 (ja) | 2013-09-06 | 2019-05-29 | オーリジーン ディスカバリー テクノロジーズ リミテッドＡｕｒｉｇｅｎｅ Ｄｉｓｃｏｖｅｒｙ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｌｉｍｉｔｅｄ | 免疫調節剤としての１，２，４−オキサジアゾール誘導体 |
| WO2015044900A1 (en) | 2013-09-27 | 2015-04-02 | Aurigene Discovery Technologies Limited | Therapeutic immunomodulating compounds |
| CN105636958B (zh) * | 2013-10-17 | 2018-01-05 | 沃泰克斯药物股份有限公司 | Dna‑pk抑制剂 |
| SI3424920T1 (sl) | 2013-10-17 | 2020-08-31 | Vertex Pharmaceuticals Incorporated | Kokristali (s)-n-metil-8-(1-((2'-metil-(4,5'-bipirimidin)-6-il)amino)propan-2-il) kinolin-4-karboksamida in devterirani derivati le-teh kot inhibitorji dna-pk |
| DK3083562T3 (da) | 2013-12-17 | 2017-11-13 | Lilly Co Eli | Cykliske phenoxyethylaminderivater og deres aktivitet som EP4-receptormodulatorer |
| SI3083554T1 (sl) | 2013-12-17 | 2019-04-30 | Eli Lilly & Company | Spojine dimetilbenzojske kisline |
| TW201607943A (zh) | 2013-12-19 | 2016-03-01 | 拜耳製藥公司 | 作為ｅｐ４配體之新穎苯并咪唑衍生物 |
| TW201623277A (zh) | 2014-03-26 | 2016-07-01 | 安斯泰來製藥股份有限公司 | 醯胺化合物 |
| US10052332B2 (en) | 2014-04-29 | 2018-08-21 | Emory University | Prostaglandin receptor EP2 antagonists, derivatives, compositions, and uses related thereto |
| CN106572993B (zh) | 2014-05-23 | 2019-07-16 | 卫材R&D管理有限公司 | Ep4拮抗剂在制备治疗癌症的药物中的应用 |
| SG11201609981RA (en) | 2014-06-04 | 2016-12-29 | Thomas Helledays Stiftelse För Medicinsk Forskning | Mth1 inhibitors for treatment of inflammatory and autoimmune conditions |
| WO2016021742A1 (en) | 2014-08-07 | 2016-02-11 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds as ep4 receptor antagonists |
| TWI712595B (zh) | 2015-01-09 | 2020-12-11 | 日商小野藥品工業股份有限公司 | 三環性螺化合物 |
| CN108368127B (zh) | 2015-07-23 | 2020-12-11 | 武田药品工业株式会社 | 化合物及其作为ep4受体拮抗剂的用途 |
| US10316040B2 (en) | 2015-10-16 | 2019-06-11 | Eisai R&D Management Co., Ltd. | EP4 antagonists |
| CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
| EP4219462A1 (en) | 2016-07-13 | 2023-08-02 | Vertex Pharmaceuticals Incorporated | Methods, compositions and kits for increasing genome editing efficiency |
| LT3625224T (lt) | 2017-05-18 | 2021-10-25 | Idorsia Pharmaceuticals Ltd | N-pakeistieji indolo dariniai |
| 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 |
| LT3625222T (lt) | 2017-05-18 | 2021-11-10 | Idorsia Pharmaceuticals Ltd | Fenilo dariniai, kaip pge2 receptoriaus moduliatoriai |
| PT3625228T (pt) | 2017-05-18 | 2021-09-16 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores dos recetores de pge2 |
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- 2018-05-17 ES ES18725219T patent/ES2896476T3/es active Active
- 2018-05-17 JP JP2019563368A patent/JP7253500B2/ja active Active
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