JP4436892B2 - ピリジン［３，４−ｂ］ピラジノン - Google Patents

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Publication number

JP4436892B2

JP4436892B2 JP2009505983A JP2009505983A JP4436892B2 JP 4436892 B2 JP4436892 B2 JP 4436892B2 JP 2009505983 A JP2009505983 A JP 2009505983A JP 2009505983 A JP2009505983 A JP 2009505983A JP 4436892 B2 JP4436892 B2 JP 4436892B2

Authority

JP

Japan

Prior art keywords

group

propoxyethyl

alkyl

pyrido

substituted

Prior art date

2006-04-21

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.)

Expired - Fee Related

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• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 title claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 5
• -1 cyano, hydroxy, carboxy Chemical group 0.000 claims description 350
• 150000001875 compounds Chemical class 0.000 claims description 185
• 125000001424 substituent group Chemical group 0.000 claims description 174
• 125000000217 alkyl group Chemical group 0.000 claims description 172
• 125000004193 piperazinyl group Chemical group 0.000 claims description 124
• 229910052736 halogen Inorganic materials 0.000 claims description 116
• 229910052739 hydrogen Inorganic materials 0.000 claims description 108
• 239000001257 hydrogen Substances 0.000 claims description 108
• 150000002367 halogens Chemical class 0.000 claims description 92
• 125000004076 pyridyl group Chemical group 0.000 claims description 80
• 125000000623 heterocyclic group Chemical group 0.000 claims description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims description 75
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 69
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
• 125000004043 oxo group Chemical group O=* 0.000 claims description 65
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 62
• 150000002431 hydrogen Chemical class 0.000 claims description 57
• 125000002757 morpholinyl group Chemical group 0.000 claims description 56
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
• 150000003839 salts Chemical class 0.000 claims description 50
• 125000000304 alkynyl group Chemical group 0.000 claims description 43
• 125000003342 alkenyl group Chemical group 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 41
• 125000001153 fluoro group Chemical group F* 0.000 claims description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
• 125000001544 thienyl group Chemical group 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 25
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 24
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 19
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 19
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
• 125000005016 hydroxyalkynyl group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 9
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
• QZRFBQWPAKTWDH-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-piperazin-1-yl-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCNCC1 QZRFBQWPAKTWDH-UHFFFAOYSA-N 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 3
• MCVVKULRMVPCPN-UHFFFAOYSA-N 2-[4-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-3-yl]piperazin-1-yl]acetic acid Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CC(O)=O)CC1 MCVVKULRMVPCPN-UHFFFAOYSA-N 0.000 claims description 3
• ZVWRYJRTXGTMQE-UHFFFAOYSA-N 7-(4-fluoro-3-methylphenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(C)C(F)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 ZVWRYJRTXGTMQE-UHFFFAOYSA-N 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• CYLNBQNJAOVCQH-UHFFFAOYSA-N 3-(3-hydroxypyrrolidin-1-yl)-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCC(O)C1 CYLNBQNJAOVCQH-UHFFFAOYSA-N 0.000 claims description 2
• YIDUAHHKCUXUPG-UHFFFAOYSA-N 3-(4-ethylpiperazin-1-yl)-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CC)CC1 YIDUAHHKCUXUPG-UHFFFAOYSA-N 0.000 claims description 2
• VJKXLUFHNZFVDW-SFHVURJKSA-N 3-[(3s)-4-(2-hydroxyethyl)-3-methylpiperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CCO)[C@@H](C)C1 VJKXLUFHNZFVDW-SFHVURJKSA-N 0.000 claims description 2
• SYMRULYCDZKABS-UHFFFAOYSA-N 3-[3-(hydroxymethyl)piperidin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCCC(CO)C1 SYMRULYCDZKABS-UHFFFAOYSA-N 0.000 claims description 2
• SVHKUKDOJOYIMM-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(2-hydroxyphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=CC=CC=3)O)=NC=C2N=C1N1CCN(CCO)CC1 SVHKUKDOJOYIMM-UHFFFAOYSA-N 0.000 claims description 2
• GBDNVSRJMRNGGU-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(3-methylphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(C)C=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 GBDNVSRJMRNGGU-UHFFFAOYSA-N 0.000 claims description 2
• BJOASBSDIQNYJB-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(4-hydroxyphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(O)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 BJOASBSDIQNYJB-UHFFFAOYSA-N 0.000 claims description 2
• RALGFLBLQQDLCM-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(4-methoxy-3-methylphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(C)C(OC)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 RALGFLBLQQDLCM-UHFFFAOYSA-N 0.000 claims description 2
• ATHOAOZEBCPBRJ-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(4-methylphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(C)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 ATHOAOZEBCPBRJ-UHFFFAOYSA-N 0.000 claims description 2
• MNLNAGRCHNMKKJ-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 MNLNAGRCHNMKKJ-UHFFFAOYSA-N 0.000 claims description 2
• JISPWAKJBNANOA-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)-3,5-dimethylpiperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CC(C)N(CCCO)C(C)C1 JISPWAKJBNANOA-UHFFFAOYSA-N 0.000 claims description 2
• FHFJVFOTDIRAOD-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CCCO)CC1 FHFJVFOTDIRAOD-UHFFFAOYSA-N 0.000 claims description 2
• ZZHCAPMRVHYZMC-RTBURBONSA-N 3-[4-[(2r,3r)-3-hydroxybutan-2-yl]piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN([C@H](C)[C@@H](C)O)CC1 ZZHCAPMRVHYZMC-RTBURBONSA-N 0.000 claims description 2
• ZZHCAPMRVHYZMC-RBUKOAKNSA-N 3-[4-[(2s,3r)-3-hydroxybutan-2-yl]piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN([C@@H](C)[C@@H](C)O)CC1 ZZHCAPMRVHYZMC-RBUKOAKNSA-N 0.000 claims description 2
• ZSNODUPUFUVGAV-UHFFFAOYSA-N 7-(2,3-difluorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=C(F)C=CC=3)F)=NC=C2N=C1N1CCN(CCO)CC1 ZSNODUPUFUVGAV-UHFFFAOYSA-N 0.000 claims description 2
• OXNAGYXWQOFMEG-UHFFFAOYSA-N 7-(2,4-difluorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=CC(F)=CC=3)F)=NC=C2N=C1N1CCN(CCO)CC1 OXNAGYXWQOFMEG-UHFFFAOYSA-N 0.000 claims description 2
• LWKSQBYHCUSZTE-UHFFFAOYSA-N 7-(2-fluoro-3-methoxyphenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=C(OC)C=CC=3)F)=NC=C2N=C1N1CCN(CCO)CC1 LWKSQBYHCUSZTE-UHFFFAOYSA-N 0.000 claims description 2
• QAICVOHXYNMHJJ-UHFFFAOYSA-N 7-(2-fluorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=CC=CC=3)F)=NC=C2N=C1N1CCN(CCO)CC1 QAICVOHXYNMHJJ-UHFFFAOYSA-N 0.000 claims description 2
• MFUGFRGCIJAGHU-UHFFFAOYSA-N 7-(3-chlorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(Cl)C=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 MFUGFRGCIJAGHU-UHFFFAOYSA-N 0.000 claims description 2
• JDWLXXLWUBYDGZ-UHFFFAOYSA-N 7-(3-ethoxyphenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(OCC)C=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 JDWLXXLWUBYDGZ-UHFFFAOYSA-N 0.000 claims description 2
• LMUUQOWEKJCFPZ-UHFFFAOYSA-N 7-(3-fluoro-4-methoxyphenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(F)C(OC)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 LMUUQOWEKJCFPZ-UHFFFAOYSA-N 0.000 claims description 2
• VERGKMWTTUSCQG-UHFFFAOYSA-N 7-(4-chlorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(Cl)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 VERGKMWTTUSCQG-UHFFFAOYSA-N 0.000 claims description 2
• LYZRVRLBCRJEJE-UHFFFAOYSA-N 7-(4-ethoxyphenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(OCC)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 LYZRVRLBCRJEJE-UHFFFAOYSA-N 0.000 claims description 2
• YXARUBQOXPCFHT-UHFFFAOYSA-N 7-(5-acetylthiophen-2-yl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3SC(=CC=3)C(C)=O)=NC=C2N=C1N1CCN(CCO)CC1 YXARUBQOXPCFHT-UHFFFAOYSA-N 0.000 claims description 2
• KMXOYONUVSEKLB-UHFFFAOYSA-N 7-(5-chloro-2-fluorophenyl)-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=CC=C(Cl)C=3)F)=NC=C2N=C1N1CCN(CCO)CC1 KMXOYONUVSEKLB-UHFFFAOYSA-N 0.000 claims description 2
• ABEPDSNVMMDBNZ-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-3-morpholin-4-yl-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCOCC1 ABEPDSNVMMDBNZ-UHFFFAOYSA-N 0.000 claims description 2
• VLSMUWVURGNLSJ-UHFFFAOYSA-N 7-[4-(dimethylamino)-2-methylphenyl]-3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C(=CC(=CC=3)N(C)C)C)=NC=C2N=C1N1CCN(CCO)CC1 VLSMUWVURGNLSJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• QRDSPYIGRCQYGI-UHFFFAOYSA-N 1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound C1=NC=C2N=CC(=O)N(CCOCCC)C2=C1 QRDSPYIGRCQYGI-UHFFFAOYSA-N 0.000 claims 1
• GXHQTFMCJBDCKQ-UHFFFAOYSA-N 3-(3-hydroxypiperidin-1-yl)-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCCC(O)C1 GXHQTFMCJBDCKQ-UHFFFAOYSA-N 0.000 claims 1
• QYCPKCWJSXULEG-UHFFFAOYSA-N 3-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CC(C)(C)O)CC1 QYCPKCWJSXULEG-UHFFFAOYSA-N 0.000 claims 1
• DOXUOKHYYJENKH-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-propoxyethyl)-7-pyridin-3-ylpyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 DOXUOKHYYJENKH-UHFFFAOYSA-N 0.000 claims 1
• OEGBMFWFOKVZKI-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(4-methoxyphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(OC)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 OEGBMFWFOKVZKI-UHFFFAOYSA-N 0.000 claims 1
• IVCUZGCZGTVUPU-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(4-propan-2-yloxyphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=CC(OC(C)C)=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 IVCUZGCZGTVUPU-UHFFFAOYSA-N 0.000 claims 1
• XQGLARBEKFQKOD-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-isoquinolin-5-yl-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C4=CC=NC=C4C=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 XQGLARBEKFQKOD-UHFFFAOYSA-N 0.000 claims 1
• JWZQBERYCMZHJF-GOSISDBHSA-N 3-[4-[(2r)-2-hydroxypropyl]piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(C[C@@H](C)O)CC1 JWZQBERYCMZHJF-GOSISDBHSA-N 0.000 claims 1
• JWZQBERYCMZHJF-SFHVURJKSA-N 3-[4-[(2s)-2-hydroxypropyl]piperazin-1-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(C[C@H](C)O)CC1 JWZQBERYCMZHJF-SFHVURJKSA-N 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• 125000005019 carboxyalkenyl group Chemical group 0.000 claims 1
• 125000000262 haloalkenyl group Chemical group 0.000 claims 1
• 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 1
• QWKKVSCYKPHTIS-UHFFFAOYSA-N tert-butyl 2-[4-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-3-yl]piperazin-1-yl]acetate Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCN(CC(=O)OC(C)(C)C)CC1 QWKKVSCYKPHTIS-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 238000000034 method Methods 0.000 description 49
• 238000006243 chemical reaction Methods 0.000 description 43
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
• 125000005843 halogen group Chemical group 0.000 description 34
• 239000000243 solution Substances 0.000 description 33
• 239000002904 solvent Substances 0.000 description 32
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 30
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 30
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