JP2017519772A5 - - Google Patents
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- Publication number
- JP2017519772A5 JP2017519772A5 JP2016574242A JP2016574242A JP2017519772A5 JP 2017519772 A5 JP2017519772 A5 JP 2017519772A5 JP 2016574242 A JP2016574242 A JP 2016574242A JP 2016574242 A JP2016574242 A JP 2016574242A JP 2017519772 A5 JP2017519772 A5 JP 2017519772A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- piperidin
- quinazolin
- cyclopropyl
- phenyl
- 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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- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000002431 hydrogen Chemical class 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 23
- 239000000651 prodrug Substances 0.000 claims 23
- 229940002612 prodrug Drugs 0.000 claims 23
- 239000012453 solvate Substances 0.000 claims 23
- 150000001204 N-oxides Chemical class 0.000 claims 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
- -1 2-Dimethylamino-phenyl Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- SQSASMLYFCBHPV-OAQYLSRUSA-N (3R)-1-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@@H](CC1)O SQSASMLYFCBHPV-OAQYLSRUSA-N 0.000 claims 3
- 125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims 3
- JPWQBXUIRBWWIL-JOCHJYFZSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-6-[(3R)-3-methoxypyrrolidin-1-yl]quinazoline Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@@H](CC1)OC JPWQBXUIRBWWIL-JOCHJYFZSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- SQSASMLYFCBHPV-NRFANRHFSA-N (3S)-1-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@H](CC1)O SQSASMLYFCBHPV-NRFANRHFSA-N 0.000 claims 2
- ZIZNYROAMFIPDX-FQEVSTJZSA-N (3S)-1-[8-chloro-2-(1-fluorocyclobutyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=C(Cl)C=C(C=C12)N1CC[C@H](O)C1)C1(F)CCC1 ZIZNYROAMFIPDX-FQEVSTJZSA-N 0.000 claims 2
- FMFRQMRIYSDVQZ-UHFFFAOYSA-N 1-[2-(1-fluorocyclobutyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]pyrido[3,4-d]pyrimidin-6-yl]pyrrolidin-3-ol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=C2C=C(N=CC2=NC(=N1)C1(F)CCC1)N1CCC(O)C1 FMFRQMRIYSDVQZ-UHFFFAOYSA-N 0.000 claims 2
- FDWXBJUKEDKWII-UHFFFAOYSA-N 1-[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]pyrido[3,4-d]pyrimidin-6-yl]pyrrolidin-3-ol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=C2C=C(N=CC2=NC(=N1)C1(F)CC1)N1CCC(O)C1 FDWXBJUKEDKWII-UHFFFAOYSA-N 0.000 claims 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 2
- MMDSVKYAQRIDEA-UHFFFAOYSA-N 2-[[2-(1-fluorocyclobutyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CCC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C MMDSVKYAQRIDEA-UHFFFAOYSA-N 0.000 claims 2
- YOJPYKIAGMVMSR-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]pyrido[3,4-d]pyrimidin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C=1N=C(C2=C(N=1)C=NC(=C2)N(CCO)C)N1CCC(CC1)C1=C(C=CC=C1)OC YOJPYKIAGMVMSR-UHFFFAOYSA-N 0.000 claims 2
- BLWXTJQMEBQCIZ-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C BLWXTJQMEBQCIZ-UHFFFAOYSA-N 0.000 claims 2
- VDPVHNVRGBBVTG-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(3-methoxythiophen-2-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C=1SC=CC=1OC)N(CCO)C VDPVHNVRGBBVTG-UHFFFAOYSA-N 0.000 claims 2
- HAYILJUSPUGKGI-UHFFFAOYSA-N 2-[[2-cyclopropyl-8-fluoro-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CC1)C1=NC2=C(C=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C)F HAYILJUSPUGKGI-UHFFFAOYSA-N 0.000 claims 2
- SIEJNOWZIDTSQJ-UHFFFAOYSA-N 2-[[4-(4-cyclohexylpiperidin-1-yl)-2-(1-fluorocyclopropyl)quinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CCCCC1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N(CCO)C)C1(CC1)F SIEJNOWZIDTSQJ-UHFFFAOYSA-N 0.000 claims 2
- TVMPWGASZCIMMZ-UHFFFAOYSA-N 2-[[4-[4-(2-methoxyphenyl)piperidin-1-yl]-2-(1-methylcyclopropyl)quinazolin-6-yl]-methylamino]ethanol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N(CCO)C)C1(CC1)C TVMPWGASZCIMMZ-UHFFFAOYSA-N 0.000 claims 2
- RFRDMPKLPBPXEU-UHFFFAOYSA-N 2-[[4-[4-(2-methoxyphenyl)piperidin-1-yl]-2-[1-(trifluoromethyl)cyclopropyl]quinazolin-6-yl]-methylamino]ethanol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N(C)CCO)C1(CC1)C(F)(F)F RFRDMPKLPBPXEU-UHFFFAOYSA-N 0.000 claims 2
- NEPBYKGTAIVOFI-UHFFFAOYSA-N 2-[[4-[4-[2-(dimethylamino)phenyl]piperidin-1-yl]-2-(1-fluorocyclobutyl)quinazolin-6-yl]-methylamino]ethanol Chemical compound CN(C1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N(CCO)C)C1(CCC1)F)C NEPBYKGTAIVOFI-UHFFFAOYSA-N 0.000 claims 2
- HHAPARWQHIFMKW-UHFFFAOYSA-N 2-[[7-fluoro-2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound COC1=CC=CC=C1C1CCN(CC1)C1=NC(=NC2=CC(F)=C(C=C12)N(C)CCO)C1(F)CC1 HHAPARWQHIFMKW-UHFFFAOYSA-N 0.000 claims 2
- JPWQBXUIRBWWIL-QFIPXVFZSA-N 2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-6-[(3S)-3-methoxypyrrolidin-1-yl]quinazoline Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@H](CC1)OC JPWQBXUIRBWWIL-QFIPXVFZSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000009032 substance abuse Diseases 0.000 claims 2
- 231100000736 substance abuse Toxicity 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- UNFCWKXOAHNNHK-HXUWFJFHSA-N (3R)-1-[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@@H](CC1)O UNFCWKXOAHNNHK-HXUWFJFHSA-N 0.000 claims 1
- UNFCWKXOAHNNHK-FQEVSTJZSA-N (3S)-1-[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1C[C@H](CC1)O UNFCWKXOAHNNHK-FQEVSTJZSA-N 0.000 claims 1
- INRBANSDBRGLRS-UHFFFAOYSA-N 1-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-N,N-dimethylpiperidin-4-amine Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N1CCC(CC1)N(C)C INRBANSDBRGLRS-UHFFFAOYSA-N 0.000 claims 1
- KQOJNRJDNGMXQW-UHFFFAOYSA-N 1-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]piperidin-4-ol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N1CCC(O)CC1)C1CC1 KQOJNRJDNGMXQW-UHFFFAOYSA-N 0.000 claims 1
- SQSASMLYFCBHPV-UHFFFAOYSA-N 1-[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound COC1=C(C=CC=C1)C1CCN(CC1)C1=NC(=NC2=CC=C(C=C12)N1CCC(O)C1)C1CC1 SQSASMLYFCBHPV-UHFFFAOYSA-N 0.000 claims 1
- PUCQMUWGJKWMRI-UHFFFAOYSA-N 1-[8-chloro-2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]pyrrolidin-3-ol Chemical compound ClC=1C=C(C=C2C(=NC(=NC=12)C1(CC1)F)N1CCC(CC1)C1=C(C=CC=C1)OC)N1CC(CC1)O PUCQMUWGJKWMRI-UHFFFAOYSA-N 0.000 claims 1
- MOJVGLAQYJKYQK-UHFFFAOYSA-N 2-(1-fluorocyclobutyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]-N-methyl-N-(2-morpholin-4-ylethyl)quinazolin-6-amine Chemical compound FC1(CCC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCN1CCOCC1)C MOJVGLAQYJKYQK-UHFFFAOYSA-N 0.000 claims 1
- VBZMXFCLNPYXGH-UHFFFAOYSA-N 2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]-N-methyl-N-propylquinazolin-6-amine Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCC)C VBZMXFCLNPYXGH-UHFFFAOYSA-N 0.000 claims 1
- PUOWKWPAXWOGIH-UHFFFAOYSA-N 2-(1-fluorocyclopropyl)-N-(2-methoxyethyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]-N-methylquinazolin-6-amine Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(C)CCOC PUOWKWPAXWOGIH-UHFFFAOYSA-N 0.000 claims 1
- GNSJVEIUKZFLII-UHFFFAOYSA-N 2-(1-fluorocyclopropyl)-N-[2-(2-fluoroethoxy)ethyl]-4-[4-(2-methoxyphenyl)piperidin-1-yl]-N-methylquinazolin-6-amine Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(C)CCOCCF GNSJVEIUKZFLII-UHFFFAOYSA-N 0.000 claims 1
- RYUBYUHKYQBTMP-UHFFFAOYSA-N 2-N-cyclobutyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-6-N-methyl-6-N-propylquinazoline-2,6-diamine Chemical compound C1(CCC1)NC1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCC)C RYUBYUHKYQBTMP-UHFFFAOYSA-N 0.000 claims 1
- ZSRGRQMMDDLRSB-UHFFFAOYSA-N 2-[4-[2-cyclopropyl-6-[methyl(2-morpholin-4-ylethyl)amino]quinazolin-4-yl]piperazin-1-yl]cyclopentan-1-ol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCN(CC1)C1C(CCC1)O)N(CCN1CCOCC1)C ZSRGRQMMDDLRSB-UHFFFAOYSA-N 0.000 claims 1
- ZAPCFZAGTOOGFP-UHFFFAOYSA-N 2-[4-[2-cyclopropyl-6-[methyl(propyl)amino]quinazolin-4-yl]piperazin-1-yl]cyclopentan-1-ol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCN(CC1)C1C(CCC1)O)N(CCC)C ZAPCFZAGTOOGFP-UHFFFAOYSA-N 0.000 claims 1
- DCSMIYHPFWSTAI-UHFFFAOYSA-N 2-[[2-(1-fluorocyclobutyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]pyrido[3,4-d]pyrimidin-6-yl]-methylamino]ethanol Chemical compound FC1(CCC1)C=1N=C(C2=C(N=1)C=NC(=C2)N(CCO)C)N1CCC(CC1)C1=C(C=CC=C1)OC DCSMIYHPFWSTAI-UHFFFAOYSA-N 0.000 claims 1
- PTGZYCCNOLGXNW-UHFFFAOYSA-N 2-[[2-(1-fluorocyclobutyl)-4-[4-(3-methoxypyrazin-2-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CCC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=NC=CN=C1OC)N(CCO)C PTGZYCCNOLGXNW-UHFFFAOYSA-N 0.000 claims 1
- VHBZAXNDJDJDBT-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopentyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CCCC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C VHBZAXNDJDJDBT-UHFFFAOYSA-N 0.000 claims 1
- STCVZTQULCNRFV-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(2-methoxycyclohexyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1C(CCCC1)OC)N(CCO)C STCVZTQULCNRFV-UHFFFAOYSA-N 0.000 claims 1
- CGYAGEFRHONHQE-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]acetic acid Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CC(=O)O)C CGYAGEFRHONHQE-UHFFFAOYSA-N 0.000 claims 1
- IPBWPASLBVYBRX-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(2-methoxypyridin-3-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C=1C(=NC=CC=1)OC)N(CCO)C IPBWPASLBVYBRX-UHFFFAOYSA-N 0.000 claims 1
- MDXLNHPYSRIMBX-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(3-methoxypyrazin-2-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=NC=CN=C1OC)N(CCO)C MDXLNHPYSRIMBX-UHFFFAOYSA-N 0.000 claims 1
- RNTYDOJPGNZLAB-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(3-methoxypyridin-2-yl)piperazin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCN(CC1)C1=NC=CC=C1OC)N(CCO)C RNTYDOJPGNZLAB-UHFFFAOYSA-N 0.000 claims 1
- DWRNVKJPTZELIW-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(3-methoxypyridin-2-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=NC=CC=C1OC)N(CCO)C DWRNVKJPTZELIW-UHFFFAOYSA-N 0.000 claims 1
- AIJZUMVUKYYUQD-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(3-methoxypyridin-4-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=NC=C1)OC)N(CCO)C AIJZUMVUKYYUQD-UHFFFAOYSA-N 0.000 claims 1
- ITVDMACUSARXLN-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(4-iodo-2-methoxyphenyl)piperazin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCN(CC1)C1=C(C=C(C=C1)I)OC)N(CCO)C ITVDMACUSARXLN-UHFFFAOYSA-N 0.000 claims 1
- FWLPWNPXPAWKDY-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(4-methoxypyridin-3-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C=1C=NC=CC=1OC)N(CCO)C FWLPWNPXPAWKDY-UHFFFAOYSA-N 0.000 claims 1
- OXVOXIXQMSZKQM-UHFFFAOYSA-N 2-[[2-(1-fluorocyclopropyl)-4-[4-(5-methoxypyrimidin-4-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=NC=NC=C1OC)N(CCO)C OXVOXIXQMSZKQM-UHFFFAOYSA-N 0.000 claims 1
- QWZQBLFVZCIFRK-UHFFFAOYSA-N 2-[[2-(cyclobutylamino)-4-[4-(2-methoxyphenyl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CCC1)NC1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C QWZQBLFVZCIFRK-UHFFFAOYSA-N 0.000 claims 1
- PNDBFIFSSFFOIT-UHFFFAOYSA-N 2-[[2-[1-(fluoromethyl)cyclopropyl]-4-[4-(3-methoxypyrazin-2-yl)piperidin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound FCC1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCC(CC1)C1=NC=CN=C1OC)N(CCO)C PNDBFIFSSFFOIT-UHFFFAOYSA-N 0.000 claims 1
- HODWJSJMXZRVHQ-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxycyclopentyl)piperazin-1-yl]quinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CC1)C1=NC2=CC=C(C=C2C(=N1)N1CCN(CC1)C1C(CCC1)OC)N(CCO)C HODWJSJMXZRVHQ-UHFFFAOYSA-N 0.000 claims 1
- MBJDJOWCPZTZGV-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-7-methylquinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CC1)C1=NC2=CC(=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C)C MBJDJOWCPZTZGV-UHFFFAOYSA-N 0.000 claims 1
- KJRIJBVRTOLCQH-UHFFFAOYSA-N 2-[[2-cyclopropyl-4-[4-(2-methoxyphenyl)piperidin-1-yl]-8-methylquinazolin-6-yl]-methylamino]ethanol Chemical compound C1(CC1)C1=NC2=C(C=C(C=C2C(=N1)N1CCC(CC1)C1=C(C=CC=C1)OC)N(CCO)C)C KJRIJBVRTOLCQH-UHFFFAOYSA-N 0.000 claims 1
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| CN102786483B (zh) | 2011-05-19 | 2016-03-30 | 复旦大学 | 4-（4-苯基哌嗪基）喹唑啉类衍生物的药用用途 |
| US9914730B2 (en) | 2012-09-28 | 2018-03-13 | Cancer Research Technology Limited | Azaquinazoline inhibitors of Atypical protein Kinase C |
| WO2014100501A1 (en) * | 2012-12-20 | 2014-06-26 | Sanford-Burnham Medical Research Institute | Small molecule agonists of neurotensin receptor 1 |
| JP6599908B2 (ja) | 2014-06-25 | 2019-10-30 | サンフォード−バーンハム メディカル リサーチ インスティテュート | ニューロテンシン受容体１の小分子アゴニスト |
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2015
- 2015-06-24 JP JP2016574242A patent/JP6599908B2/ja active Active
- 2015-06-24 CA CA2952732A patent/CA2952732C/en active Active
- 2015-06-24 EP EP15811366.2A patent/EP3160961B1/en active Active
- 2015-06-24 US US15/319,329 patent/US10118902B2/en active Active
- 2015-06-24 WO PCT/US2015/037515 patent/WO2015200534A2/en not_active Ceased
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2018
- 2018-09-24 US US16/140,363 patent/US10584103B2/en active Active
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2020
- 2020-01-14 US US16/742,431 patent/US11261164B2/en active Active
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