TWI719078B - 做為pge2受體調節劑之n-取代吲哚衍生物 - Google Patents
做為pge2受體調節劑之n-取代吲哚衍生物 Download PDFInfo
- Publication number
- TWI719078B TWI719078B TW105137938A TW105137938A TWI719078B TW I719078 B TWI719078 B TW I719078B TW 105137938 A TW105137938 A TW 105137938A TW 105137938 A TW105137938 A TW 105137938A TW I719078 B TWI719078 B TW I719078B
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- Prior art keywords
- pyrimidin
- indol
- fluoro
- methoxy
- methyl
- Prior art date
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- -1 N-substituted indole Chemical class 0.000 title claims description 1115
- 102000008866 Prostaglandin E receptors Human genes 0.000 title description 4
- 108010088540 Prostaglandin E receptors Proteins 0.000 title description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 434
- 229910052739 hydrogen Inorganic materials 0.000 claims description 314
- 239000001257 hydrogen Substances 0.000 claims description 314
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 312
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 171
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 164
- 229910052731 fluorine Inorganic materials 0.000 claims description 137
- 239000011737 fluorine Substances 0.000 claims description 137
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 133
- 125000001424 substituent group Chemical group 0.000 claims description 125
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 97
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 97
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 93
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 86
- 239000000460 chlorine Substances 0.000 claims description 86
- 229910052801 chlorine Inorganic materials 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 150000002431 hydrogen Chemical class 0.000 claims description 66
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 239000004593 Epoxy Substances 0.000 claims description 63
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 52
- 125000002947 alkylene group Chemical group 0.000 claims description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 125000004429 atom Chemical group 0.000 claims description 46
- 125000001072 heteroaryl group Chemical group 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000004434 sulfur atom Chemical group 0.000 claims description 36
- 125000002619 bicyclic group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 32
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 30
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 125000000335 thiazolyl group Chemical group 0.000 claims description 19
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000001041 indolyl group Chemical group 0.000 claims description 16
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 15
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
- 229960004365 benzoic acid Drugs 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000002883 imidazolyl group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 14
- 239000005711 Benzoic acid Substances 0.000 claims description 13
- 125000002971 oxazolyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 5
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- UIRRBSPUIYGBOF-UHFFFAOYSA-N 5-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylic acid Chemical compound C(#N)C=1N(C2=C(C=CC(=C2C=1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(S1)C(=O)O)OCC UIRRBSPUIYGBOF-UHFFFAOYSA-N 0.000 claims description 4
- FXQJUIQGXOEANG-UHFFFAOYSA-N 7-fluoro-4-methoxy-1-[2-[[6-(2-oxo-1,3-dihydrobenzimidazol-5-yl)pyrimidin-4-yl]amino]ethyl]indole-2-carbonitrile Chemical compound FC=1C=CC(=C2C=C(N(C=12)CCNC1=NC=NC(=C1)C1=CC2=C(NC(N2)=O)C=C1)C#N)OC FXQJUIQGXOEANG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 claims description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 3
- WZANTBKSCXLPER-UHFFFAOYSA-N 4-[6-[2-(2-chloro-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound ClC=1N(C2=C(C=CC(=C2C=1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC WZANTBKSCXLPER-UHFFFAOYSA-N 0.000 claims description 3
- HMDSDLURRRRLGX-UHFFFAOYSA-N 4-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxybenzoic acid Chemical compound C(#N)C=1N(C2=C(C=CC(=C2C=1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(C(=O)O)C=C1)OCC HMDSDLURRRRLGX-UHFFFAOYSA-N 0.000 claims description 3
- SARJDGXCJNUNIP-UHFFFAOYSA-N N-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethyl]-6-quinolin-6-ylpyrimidin-4-amine Chemical compound FC=1C=CC(=C2C=C(N(C=12)CCNC1=NC=NC(=C1)C=1C=C2C=CC=NC2=CC=1)C)OC SARJDGXCJNUNIP-UHFFFAOYSA-N 0.000 claims description 3
- MHBANBFOAQZFHJ-BQYQJAHWSA-N (E)-3-[3-ethoxy-5-[6-[2-(7-fluoro-4-methoxy-2-methylindol-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)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)/C=C/C(=O)O MHBANBFOAQZFHJ-BQYQJAHWSA-N 0.000 claims description 2
- GWEYPKZLUHKSPZ-UHFFFAOYSA-N 1-[2-[[6-(2-cyclopropylpyridin-4-yl)pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound C1(CC1)C1=NC=CC(=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N GWEYPKZLUHKSPZ-UHFFFAOYSA-N 0.000 claims description 2
- YWJZIFFJGSSQDG-UHFFFAOYSA-N 1-[2-[[6-(2H-benzotriazol-5-yl)pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound N1=NNC2=C1C=CC(=C2)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N YWJZIFFJGSSQDG-UHFFFAOYSA-N 0.000 claims description 2
- OAROFKKXHCFVDX-UHFFFAOYSA-N 1-[2-[[6-[2-(azetidin-1-yl)pyridin-4-yl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound N1(CCC1)C1=NC=CC(=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N OAROFKKXHCFVDX-UHFFFAOYSA-N 0.000 claims description 2
- WHZJEJUQSXFCDU-UHFFFAOYSA-N 1-[2-[[6-[3-ethoxy-4-(2H-triazol-4-yl)phenyl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound C(C)OC=1C=C(C=CC=1C=1NN=NC=1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N WHZJEJUQSXFCDU-UHFFFAOYSA-N 0.000 claims description 2
- MPOKAISNMMUNOF-UHFFFAOYSA-N 1-[2-[[6-[4-(1,5-dimethylimidazol-4-yl)phenyl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound CN1C=NC(=C1C)C1=CC=C(C=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N MPOKAISNMMUNOF-UHFFFAOYSA-N 0.000 claims description 2
- YKYHNQLCVJDXGG-UHFFFAOYSA-N 1-[2-[[6-[4-(2,5-dimethyl-1H-imidazol-4-yl)phenyl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound CC=1NC(=C(N=1)C1=CC=C(C=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N)C YKYHNQLCVJDXGG-UHFFFAOYSA-N 0.000 claims description 2
- DBEXLCRZYVLXIQ-UHFFFAOYSA-N 1-[2-[[6-[4-(2-cyclopropyl-1-methylimidazol-4-yl)phenyl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound C1(CC1)C=1N(C=C(N=1)C1=CC=C(C=C1)C1=CC(=NC=N1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N)C DBEXLCRZYVLXIQ-UHFFFAOYSA-N 0.000 claims description 2
- ICVOGTLXRFNRCI-UHFFFAOYSA-N 1-[2-[[6-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]pyrimidin-4-yl]amino]ethyl]-7-fluoro-4-methoxyindole-2-carbonitrile Chemical compound COc1ccc(F)c2n(CCNc3cc(ncn3)-c3ccc(cc3)-c3cnc([nH]3)C3CC3)c(cc12)C#N ICVOGTLXRFNRCI-UHFFFAOYSA-N 0.000 claims description 2
- UTBBRYWZBCVFOA-UHFFFAOYSA-N 1-[3-ethoxy-5-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]ethanol Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)C(C)O UTBBRYWZBCVFOA-UHFFFAOYSA-N 0.000 claims description 2
- OHZPFROBINOYRT-UHFFFAOYSA-N 1-ethyl-3-[2-methoxy-4-[6-[2-(4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]phenyl]urea Chemical compound C(C)NC(=O)NC1=C(C=C(C=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC=C12)OC)C)OC OHZPFROBINOYRT-UHFFFAOYSA-N 0.000 claims description 2
- MNFUKETUVVWJQQ-UHFFFAOYSA-N 1-ethyl-3-[4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenyl]urea Chemical compound C(C)NC(=O)NC1=C(C=C(C=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)OC MNFUKETUVVWJQQ-UHFFFAOYSA-N 0.000 claims description 2
- FQEFOSLMGSULTO-UHFFFAOYSA-N 2-(dimethylamino)ethyl 5-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-3-ethoxythiophene-2-carboxylate Chemical compound CN(CCOC(=O)C=1SC(=CC=1OCC)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N)C FQEFOSLMGSULTO-UHFFFAOYSA-N 0.000 claims description 2
- AVNYRMJDLYCTGA-UHFFFAOYSA-N 2-(ethylamino)-4-[6-[2-(4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC=C12)OC)C AVNYRMJDLYCTGA-UHFFFAOYSA-N 0.000 claims description 2
- MOMJSYQKXSMPEF-UHFFFAOYSA-N 2-(ethylamino)-4-[6-[2-(6-fluoro-2,4-dimethylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=C(C=C12)F)C)C MOMJSYQKXSMPEF-UHFFFAOYSA-N 0.000 claims description 2
- JBTCPYYWIDGVRH-UHFFFAOYSA-N 2-(ethylamino)-4-[6-[2-(7-fluoro-2,4-dimethylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)C)C JBTCPYYWIDGVRH-UHFFFAOYSA-N 0.000 claims description 2
- IPUVTHYKQMTNQK-UHFFFAOYSA-N 2-(ethylamino)-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C IPUVTHYKQMTNQK-UHFFFAOYSA-N 0.000 claims description 2
- FBKPTLLSKZOTAK-UHFFFAOYSA-N 2-(ethylamino)-6-fluoro-4-[6-[2-(7-fluoro-2,4-dimethylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)C)C)F FBKPTLLSKZOTAK-UHFFFAOYSA-N 0.000 claims description 2
- DMISQJXWQXSQQJ-UHFFFAOYSA-N 2-(ethylamino)-6-fluoro-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]benzoic acid Chemical compound C(C)NC1=C(C(=O)O)C(=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)F DMISQJXWQXSQQJ-UHFFFAOYSA-N 0.000 claims description 2
- QFZUUNHBQHGZGS-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(6-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]anilino]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=C(C=C12)F)OC)C)NCC(=O)O QFZUUNHBQHGZGS-UHFFFAOYSA-N 0.000 claims description 2
- MARYMFUPCQSHEU-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-2,4-dimethylindol-1-yl)ethylamino]pyrimidin-4-yl]anilino]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)C)C)NCC(=O)O MARYMFUPCQSHEU-UHFFFAOYSA-N 0.000 claims description 2
- UFJLPGHTGJNULB-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]anilino]acetic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)NCC(=O)O UFJLPGHTGJNULB-UHFFFAOYSA-N 0.000 claims description 2
- HDIZQAQMLAOQHL-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]anilino]propanoic acid Chemical compound C(C)OC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)NC(C(=O)O)C HDIZQAQMLAOQHL-UHFFFAOYSA-N 0.000 claims description 2
- TYGGMCSFGYLJQN-UHFFFAOYSA-N 2-[2-ethoxy-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]phenoxy]acetic acid Chemical compound C(C)OC1=C(OCC(=O)O)C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C TYGGMCSFGYLJQN-UHFFFAOYSA-N 0.000 claims description 2
- BUYKSHPPRRBWCM-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyanilino]acetic acid Chemical compound C(#N)C=1N(C2=CC=CC(=C2C=1)OC)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)NCC(=O)O)OCC BUYKSHPPRRBWCM-UHFFFAOYSA-N 0.000 claims description 2
- QXNJMKMOKDUBBA-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]acetic acid Chemical compound C(#N)C=1N(C2=CC=CC(=C2C=1)OC)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OCC QXNJMKMOKDUBBA-UHFFFAOYSA-N 0.000 claims description 2
- OZHIVSCFIWYOBD-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-6,7-difluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyanilino]acetic acid Chemical compound C(#N)C=1N(C2=C(C(=CC(=C2C=1)OC)F)F)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)NCC(=O)O)OCC OZHIVSCFIWYOBD-UHFFFAOYSA-N 0.000 claims description 2
- DXSIUIIEYOECSW-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-6,7-difluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-ethoxyphenoxy]acetic acid Chemical compound C(#N)C=1N(C2=C(C(=CC(=C2C=1)OC)F)F)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OCC DXSIUIIEYOECSW-UHFFFAOYSA-N 0.000 claims description 2
- KBJYGIHEDKGFNG-UHFFFAOYSA-N 2-[4-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-(trifluoromethoxy)phenoxy]acetic acid Chemical compound C(#N)C=1N(C2=C(C=CC(=C2C=1)OC)F)CCNC1=CC(=NC=N1)C1=CC(=C(OCC(=O)O)C=C1)OC(F)(F)F KBJYGIHEDKGFNG-UHFFFAOYSA-N 0.000 claims description 2
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- JTCXVYOJYVAFPK-UHFFFAOYSA-N N-ethyl-N-[5-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]thiophen-3-yl]formamide Chemical compound C(C)N(C=O)C1=CSC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C JTCXVYOJYVAFPK-UHFFFAOYSA-N 0.000 claims description 2
- MQISUGZXFKYYSR-UHFFFAOYSA-N [2-chloro-4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]phenyl]methanol Chemical compound ClC1=C(C=CC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)CO MQISUGZXFKYYSR-UHFFFAOYSA-N 0.000 claims description 2
- YCNHYENVXZLBEQ-UHFFFAOYSA-N [3-ethoxy-5-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]methanol Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)CO YCNHYENVXZLBEQ-UHFFFAOYSA-N 0.000 claims description 2
- YVKKQEPGRVRFIF-UHFFFAOYSA-N [3-ethoxy-5-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]thiophen-2-yl]urea Chemical compound C(C)OC1=C(SC(=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C)NC(=O)N YVKKQEPGRVRFIF-UHFFFAOYSA-N 0.000 claims description 2
- AGJDTSSPPOLBTM-UHFFFAOYSA-N [4-[6-[2-(7-fluoro-4-methoxy-2-methylindol-1-yl)ethylamino]pyrimidin-4-yl]-2-methoxyphenyl]methanol Chemical compound FC=1C=CC(=C2C=C(N(C=12)CCNC1=CC(=NC=N1)C1=CC(=C(C=C1)CO)OC)C)OC AGJDTSSPPOLBTM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- VTQFDDSUXWQVSY-UHFFFAOYSA-N methyl 2-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-1H-indole-5-carboxylate Chemical compound COC(=O)C=1C=C2C=C(NC2=CC=1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N VTQFDDSUXWQVSY-UHFFFAOYSA-N 0.000 claims description 2
- PVKNTWHNCDCTIX-UHFFFAOYSA-N methyl 4-[6-[2-(2-cyano-7-fluoro-4-methoxyindol-1-yl)ethylamino]pyrimidin-4-yl]-2-fluorobenzoate Chemical compound COC(C1=C(C=C(C=C1)C1=NC=NC(=C1)NCCN1C(=CC2=C(C=CC(=C12)F)OC)C#N)F)=O PVKNTWHNCDCTIX-UHFFFAOYSA-N 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
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- Medicinal Chemistry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| JP7330894B2 (ja) | 2017-03-27 | 2023-08-22 | ハイドロ-ケベック | 電解質組成物中でまたは電極の添加剤として使用される塩 |
| AR111807A1 (es) | 2017-05-18 | 2019-08-21 | Idorsia Pharmaceuticals Ltd | Derivados de benzofurano y benzotiofeno como moduladores del receptor pge2 |
| AR111941A1 (es) | 2017-05-18 | 2019-09-04 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
| TW201900180A (zh) | 2017-05-18 | 2019-01-01 | 瑞士商愛杜西亞製藥有限公司 | 嘧啶衍生物 |
| HRP20211380T1 (hr) | 2017-05-18 | 2021-11-26 | Idorsia Pharmaceuticals Ltd | Derivati pirimidina kao modulatori receptora pge2 |
| CN109678780A (zh) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | 一种制备3-烷基吲哚衍生物的方法 |
| AU2018368790A1 (en) | 2017-11-20 | 2020-06-25 | Ichan School Of Medicine At Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
| AU2019205944A1 (en) | 2018-01-05 | 2020-07-09 | Icahn School Of Medicine At Mount Sinai | Method of increasing proliferation of pancreatic beta cells, treatment method, and composition |
| EP3768267B1 (en) | 2018-03-20 | 2025-05-14 | Icahn School of Medicine at Mount Sinai | Beta-carboline derivatives as dyrk1a inhibitors for the treatment of e.g. diabetes |
| AU2019418800A1 (en) * | 2018-12-31 | 2021-07-01 | Icahn School Of Medicine At Mount Sinai | Kinase inhibitor compounds and compositions and methods of use |
| EP3693359A1 (en) * | 2019-02-08 | 2020-08-12 | Medibiofarma, S.L. | New n-benzyl-2-phenoxybenzamide derivatives as prostaglandin e2 (pge2) receptors modulators |
| WO2021060281A1 (ja) * | 2019-09-24 | 2021-04-01 | Agc株式会社 | プロスタグランジンe2レセプターep2/ep4デュアルアンタゴニスト |
| CA3159561A1 (en) | 2019-11-04 | 2021-05-14 | Revolution Medicines, Inc. | Ras inhibitors |
| IL301298A (en) | 2020-09-15 | 2023-05-01 | Revolution Medicines Inc | Indole derivatives as RAS inhibitors in cancer therapy |
| TW202228674A (zh) | 2020-11-13 | 2022-08-01 | 日商小野藥品工業股份有限公司 | 藉由併用ep4拮抗藥與免疫檢查點抑制物質而進行之癌症治療 |
| EP4359399A4 (en) | 2021-06-24 | 2025-04-23 | Reservoir Neuroscience, Inc. | EP2 antagonist compounds |
| WO2025229177A1 (en) | 2024-05-02 | 2025-11-06 | Idorsia Pharmaceuticals Ltd | Crystalline forms of an n-substituted indole derivative |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2014657A1 (de) * | 2007-06-21 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Diaminopyrimidine als Modulatoren des EP2-Rezeptors |
| 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 |
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. |
| GB0031295D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Naphthalene derivatives |
| GB0031302D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Napthalene derivatives |
| GB0103269D0 (en) | 2001-02-09 | 2001-03-28 | Glaxo Group Ltd | Napthalene derivatives |
| AU2003216581A1 (en) | 2002-04-12 | 2003-10-27 | Pfizer Inc. | Pyrazole compounds as anti-inflammatory and analgesic agents |
| BR0309305A (pt) | 2002-04-12 | 2005-02-15 | Pfizer | Compostos de imidazol como agentes antiinflamatórios e analgésicos |
| 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 |
| CA2514220C (en) | 2003-01-29 | 2012-02-28 | Pharmagene Laboratories Limited | Ep4 receptor antagonists |
| AR045507A1 (es) | 2003-08-26 | 2005-11-02 | Teijin Pharma Ltd | Derivados de pirrolo [3,2-d] pirimidina |
| ES2441206T3 (es) | 2003-09-03 | 2014-02-03 | Raqualia Pharma Inc. | Compuestos de fenil o piridilamida como antagonistas de la prostaglandina E2 |
| US8084457B2 (en) | 2003-09-15 | 2011-12-27 | 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 |
| US7326732B2 (en) * | 2004-02-12 | 2008-02-05 | Pharmagene Laboratories Limited | EP2 receptor agonists |
| ES2327760T3 (es) | 2004-05-04 | 2009-11-03 | Raqualia Pharma Inc | Compuestos de aril-heteroaril-amida ortosustituidos. |
| WO2005105732A1 (en) | 2004-05-04 | 2005-11-10 | Pfizer Japan Inc. | Substituted methyl aryl or heteroaryl amide compounds |
| HN2005000795A (es) | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| EP1885722B1 (en) | 2005-05-19 | 2011-11-16 | 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 |
| AR061974A1 (es) | 2006-07-14 | 2008-08-10 | Novartis Ag | Derivados de pirimidina como inhibidores de alk, composiciones farmaceuticas y procesos de obtencion |
| WO2008017164A1 (en) | 2006-08-11 | 2008-02-14 | Merck Frosst Canada Ltd. | 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 |
| JP5301469B2 (ja) | 2007-02-26 | 2013-09-25 | 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及びインドリンシクロプロピルアミド誘導体 |
| US8030489B2 (en) | 2007-03-26 | 2011-10-04 | Astellas Pharma Inc. | Ornithine derivative |
| CN101636385B (zh) | 2007-03-26 | 2012-09-05 | 默克弗罗斯特加拿大有限公司 | 作为ep4受体拮抗剂的萘和喹啉磺酰脲衍生物 |
| EP2460787A1 (en) | 2007-07-03 | 2012-06-06 | Astellas Pharma Inc. | Amide compounds and their use as PGE2 antagonists. |
| KR20100090772A (ko) | 2007-10-12 | 2010-08-17 | 인게니움 파르마코이티칼스 게엠베하 | 단백질 키나제 억제제 |
| CA2714743C (en) | 2008-02-19 | 2017-01-17 | Janssen Pharmaceutica N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| KR101612971B1 (ko) | 2008-05-14 | 2016-04-15 | 아스테라스 세이야쿠 가부시키가이샤 | 아미드 화합물 |
| US20130225528A1 (en) | 2008-05-21 | 2013-08-29 | Ariad Pharmaceuticals, Inc. | Phosphorus Derivatives as Kinase Inhibitors |
| CA2733247C (en) | 2008-08-14 | 2018-04-03 | Beta Pharma Canada Inc. | Heterocyclic amide derivatives as ep4 receptor antagonists |
| WO2010032123A1 (en) | 2008-09-19 | 2010-03-25 | Biotechnology Research Corporation Limited | Triterpenoid compounds and methods of use thereof |
| AU2009295308A1 (en) | 2008-09-25 | 2010-04-01 | Merck Canada Inc. | Beta-carboline sulphonylurea derivatives as EP4 receptor antagonists |
| WO2011022348A1 (en) | 2009-08-18 | 2011-02-24 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid amide hydrolase |
| AU2010321905A1 (en) | 2009-11-23 | 2012-05-24 | Lexicon Pharmaceuticals, Inc. | Methods and assays for the treatment of irritable bowel syndrome |
| CN103003264B (zh) | 2010-05-21 | 2014-08-06 | 切米利亚股份公司 | 嘧啶衍生物 |
| LT2619182T (lt) | 2010-09-21 | 2017-01-25 | Eisai R&D Management Co., Ltd. | Farmacinė kompozicija |
| WO2012043634A1 (ja) | 2010-09-29 | 2012-04-05 | 株式会社エヌビィー健康研究所 | ヒトプロスタグランジンe2受容体ep4に対する抗体 |
| WO2012066065A1 (en) | 2010-11-17 | 2012-05-24 | Novartis Ag | Phenyl-heteroaryl amine compounds and their uses |
| AU2011331161A1 (en) | 2010-11-17 | 2013-05-02 | Novartis Ag | 3-(aminoaryl)-pyridine compounds |
| EP2649061B1 (en) | 2010-12-10 | 2015-05-13 | Rottapharm Biotech S.r.l. | Pyridine amide derivatives as ep4 receptor antagonists |
| WO2012103071A2 (en) | 2011-01-25 | 2012-08-02 | Eisai R&D Management Co., Ltd. | Compounds and compositions |
| AU2012230229A1 (en) | 2011-03-24 | 2013-10-10 | Noviga Research Ab | Novel pyrimidine derivatives |
| WO2012149528A1 (en) | 2011-04-29 | 2012-11-01 | Exelixis, Inc. | Inhibitors of inducible form of 6-phosphofructose-2-kinase |
| CA2839956A1 (en) | 2011-06-20 | 2012-12-27 | Emory University | Prostaglandin receptor ep2 antagonists, derivatives, compositions, and uses related thereto |
| KR101760164B1 (ko) | 2011-07-04 | 2017-07-20 | 로타팜 바이오테크 에스.알.엘 | Ep4 수용체 길항제로서 사이클릭 아민 유도체 |
| 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 |
| IN2014KN02601A (OSRAM) | 2012-04-24 | 2015-05-08 | Vertex Pharma | |
| 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 |
| BR112015011497B1 (pt) | 2012-11-27 | 2023-01-10 | Thomas Helledays Stiftelse För Medicinsk Forskning | Composto, e, formulação farmacêutica |
| 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 |
| RS57406B1 (sr) | 2013-06-12 | 2018-09-28 | Kaken Pharmaceutical Co Ltd | Derivat 4-alkinil imidazola i lekovi koji ga sadrže kao aktivni sastojak |
| JP6417419B2 (ja) | 2013-09-04 | 2018-11-07 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | 免疫調節剤として有用な化合物 |
| EA030155B1 (ru) | 2013-09-06 | 2018-06-29 | Ауриген Дискавери Текнолоджиз Лимитед | Производные 1,2,4-оксадиазола в качестве иммуномодуляторов |
| WO2015044900A1 (en) | 2013-09-27 | 2015-04-02 | Aurigene Discovery Technologies Limited | Therapeutic immunomodulating compounds |
| RS57306B1 (sr) | 2013-10-17 | 2018-08-31 | Vertex Pharma | Inhibitori dnk-pk |
| PL3424920T3 (pl) | 2013-10-17 | 2020-11-16 | Vertex Pharmaceuticals Incorporated | Kokryształy (S)-N-metylo-8-(1-((2'-metylo-4’,6'-dideutero-[4,5'-bipirymidyn]-6-ylo)amino)propan-2-ylo)chinolino-4-karboksyamidu i ich deuterowane pochodne jako inhibitory DNA-PK |
| WO2015094902A1 (en) | 2013-12-17 | 2015-06-25 | Eli Lilly And Company | Phenoxyethyl cyclic amine derivatives and their activity as ep4 receptor modulators |
| HRP20190793T1 (hr) | 2013-12-17 | 2019-06-28 | Eli Lilly & Company | Spojevi dimetilbenzojeve kiseline |
| 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 |
| EP3137074B1 (en) | 2014-04-29 | 2020-08-05 | Emory University | Prostaglandin receptor ep2 antagonists, derivatives, compositions, and uses related thereto |
| SG11201609770TA (en) | 2014-05-23 | 2016-12-29 | Eisai R&D Man Co Ltd | Combination therapies for the treatment of cancer |
| EP3151833A4 (en) | 2014-06-04 | 2018-01-10 | 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 |
| TWI852872B (zh) | 2015-01-09 | 2024-08-11 | 日商小野藥品工業股份有限公司 | 三環性螺化合物之用途 |
| EP3325490B1 (en) | 2015-07-23 | 2019-12-18 | Takeda Pharmaceutical Company Limited | 1-substituted 1,2,3,4-tetrahydro-1,7-naphthyridin-8-amine derivatives and their use as ep4 receptor antagonists |
| AU2016338679B2 (en) | 2015-10-16 | 2021-05-06 | 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 |
| MA45670A (fr) | 2016-07-13 | 2019-05-22 | Vertex Pharma | Procédés, compositions et kits pour augmenter l'efficacité d'édition du génome |
| HRP20211380T1 (hr) | 2017-05-18 | 2021-11-26 | Idorsia Pharmaceuticals Ltd | Derivati pirimidina kao modulatori receptora pge2 |
| AR111807A1 (es) | 2017-05-18 | 2019-08-21 | Idorsia Pharmaceuticals Ltd | Derivados de benzofurano y benzotiofeno como moduladores del receptor pge2 |
| TW201900180A (zh) | 2017-05-18 | 2019-01-01 | 瑞士商愛杜西亞製藥有限公司 | 嘧啶衍生物 |
| SI3625224T1 (sl) | 2017-05-18 | 2021-11-30 | Idorsia Pharmaceuticals Ltd | N-substituirani indolni derivati |
| AR111941A1 (es) | 2017-05-18 | 2019-09-04 | Idorsia Pharmaceuticals Ltd | Derivados de pirimidina como moduladores del receptor de pge2 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2014657A1 (de) * | 2007-06-21 | 2009-01-14 | Bayer Schering Pharma Aktiengesellschaft | Diaminopyrimidine als Modulatoren des EP2-Rezeptors |
| 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI754397B (zh) * | 2015-11-20 | 2022-02-01 | 瑞士商愛杜西亞製藥有限公司 | 做為pge2受體調節劑之n-取代吲哚衍生物 |
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