HRP20110539T1 - PIRIDINO[3,4-b]PIRAZINONI - Google Patents
PIRIDINO[3,4-b]PIRAZINONI Download PDFInfo
- Publication number
- HRP20110539T1 HRP20110539T1 HR20110539T HRP20110539T HRP20110539T1 HR P20110539 T1 HRP20110539 T1 HR P20110539T1 HR 20110539 T HR20110539 T HR 20110539T HR P20110539 T HRP20110539 T HR P20110539T HR P20110539 T1 HRP20110539 T1 HR P20110539T1
- Authority
- HR
- Croatia
- Prior art keywords
- group
- substituents
- propoxyethyl
- alkyl
- pyrido
- Prior art date
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 51
- 125000001424 substituent group Chemical group 0.000 claims abstract 46
- -1 cyano, hydroxy, carboxy Chemical group 0.000 claims abstract 37
- 229910052736 halogen Inorganic materials 0.000 claims abstract 37
- 150000002367 halogens Chemical group 0.000 claims abstract 37
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 29
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 27
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 26
- 150000003839 salts Chemical class 0.000 claims abstract 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 21
- 239000001257 hydrogen Substances 0.000 claims abstract 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 14
- 150000002431 hydrogen Chemical group 0.000 claims abstract 12
- 125000003118 aryl group Chemical group 0.000 claims abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000005019 carboxyalkenyl group Chemical group 0.000 claims abstract 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims abstract 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000004193 piperazinyl group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 8
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- SPEWXHWTGLOKIR-UHFFFAOYSA-N 1-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-3-yl]piperidine-3-carboxamide Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCCC(C(N)=O)C1 SPEWXHWTGLOKIR-UHFFFAOYSA-N 0.000 claims 1
- MVACPWPVZKOLTI-UHFFFAOYSA-N 1-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-3-yl]piperidine-4-carboxamide Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1N1CCC(C(N)=O)CC1 MVACPWPVZKOLTI-UHFFFAOYSA-N 0.000 claims 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 1
- 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 1
- QDIQYFQPTWVPLK-IAGOWNOFSA-N 3-[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2C(C(N(CCOCCC)C1=C2)=O)=NC1=CN=C2C1=CC=C(OC)N=C1 QDIQYFQPTWVPLK-IAGOWNOFSA-N 0.000 claims 1
- 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 1
- 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 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
- JWKNHXGJPRWPMQ-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)-1,4-diazepan-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=C1N1CCCN(CCO)CC1 JWKNHXGJPRWPMQ-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
- 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 1
- UFRZIRSONMRAPG-UHFFFAOYSA-N 3-[4-(2-hydroxyethyl)piperazin-1-yl]-7-(3-methoxyphenyl)-1-(2-propoxyethyl)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=C(OC)C=CC=3)=NC=C2N=C1N1CCN(CCO)CC1 UFRZIRSONMRAPG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- 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 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
- 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 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
- PEWZFEYDMCHRJT-UHFFFAOYSA-N 3-[4-(3-hydroxypropyl)-1,4-diazepan-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=C1N1CCCN(CCCO)CC1 PEWZFEYDMCHRJT-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- 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 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
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010062237 Renal impairment Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000005977 kidney dysfunction Effects 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 230000035771 neuroregeneration Effects 0.000 claims 1
- 230000036407 pain Effects 0.000 claims 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 230000004936 stimulating effect Effects 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
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
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| PCT/IB2007/001001 WO2007122466A1 (en) | 2006-04-21 | 2007-04-10 | Pyridine[3,4-b]pyrazinones |
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| RS51885B (en) | 2006-04-21 | 2012-02-29 | Pfizer Products Inc. | PYRIDIN [3,4-b] PYRAZINNES |
| DK2101777T3 (en) * | 2006-12-12 | 2015-08-17 | Gilead Sciences Inc | COMPOSITION FOR TREATMENT OF PULMONAL HYPERTENSION |
| BRPI0908569B8 (pt) | 2008-03-05 | 2021-05-25 | Merck Patent Gmbh | estimuladores de secreção de insulina derivados de piridopirazinonas, seu uso, e composição farmacêutica |
| TW201020233A (en) * | 2008-10-09 | 2010-06-01 | Kyorin Seiyaku Kk | Isoquinoline derivative, and pde inhibitor comprising same as active ingredient |
| NZ599549A (en) * | 2009-10-26 | 2013-11-29 | Signal Pharm Llc | Methods of synthesis and purification of heteroaryl compounds |
| EP2637664B1 (en) | 2010-10-15 | 2017-03-29 | Gilead Sciences, Inc. | Compositions and methods of treating pulmonary hypertension |
| ES2602794T3 (es) | 2011-03-31 | 2017-02-22 | Pfizer Inc | Piridinonas bicíclicas novedosas |
| WO2012172449A1 (en) | 2011-06-13 | 2012-12-20 | Pfizer Inc. | Lactams as beta secretase inhibitors |
| JP6043355B2 (ja) | 2011-08-31 | 2016-12-14 | ファイザー・インク | ヘキサヒドロピラノ［３，４−ｄ］［１，３］チアジン−２−アミン化合物 |
| WO2013164730A1 (en) | 2012-05-04 | 2013-11-07 | Pfizer Inc. | Heterocyclic substituted hexahydropyrano [3,4-d] [1,3] thiazin- 2 -amine compounds as inhibitors of app, bace1 and bace 2. |
| CA2882389A1 (en) | 2012-09-20 | 2014-03-27 | Pfizer Inc. | Alkyl-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| WO2014091352A1 (en) | 2012-12-11 | 2014-06-19 | Pfizer Inc. | Hexahydropyrano [3,4-d][1,3]thiazin-2-amine compounds as inhibitors of bace1 |
| CA2893333C (en) | 2012-12-19 | 2017-10-24 | Pfizer Inc. | Carbocyclic-and heterocyclic-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| JP2016507551A (ja) | 2013-02-13 | 2016-03-10 | ファイザー・インク | ヘテロアリール置換ヘキサヒドロピラノ［３，４−ｄ］［１，３］チアジン−２−アミン化合物 |
| US9233981B1 (en) | 2013-02-15 | 2016-01-12 | Pfizer Inc. | Substituted phenyl hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| MD20150071A2 (ro) | 2013-02-19 | 2016-02-29 | Pfizer Inc. | Compuşi azabenzimidazolici ca inhibitori ai PDE4 izoenzimelor pentru tratamentul tulburărilor SNC şi altor afecţiuni |
| EP3052495B1 (en) | 2013-10-04 | 2019-06-26 | Pfizer Inc | Novel bicyclic pyridinones as gamma-secretase modulators |
| JO3466B1 (ar) * | 2013-12-20 | 2020-07-05 | Takeda Pharmaceuticals Co | مواد ضابطة لتترا هيدرو بيريدوبيرازينات من gpr6 |
| CA2944308A1 (en) | 2014-04-01 | 2015-10-08 | Pfizer Inc. | Chromene and 1,1 a,2,7b-tetrahydrocyclopropa[c]chromene pyridopyrazinediones as gamma-secretase modulators |
| MA39866A (fr) | 2014-04-10 | 2017-02-15 | Pfizer | Amides 2-amino-6-méthyl-4,4a,5,6-tétrahydropyrano[3,4-d][1,3]thiazin-8a(8h)-yl-1,3-thiazol-4-yle |
| JP6713982B2 (ja) | 2014-07-24 | 2020-06-24 | ファイザー・インク | ピラゾロピリミジン化合物 |
| JP6506833B2 (ja) | 2014-08-06 | 2019-04-24 | ファイザー・インク | イミダゾピリダジン化合物 |
| EA033423B1 (ru) | 2015-02-03 | 2019-10-31 | Pfizer | Циклопропанбензофуранилпиридопиразиндионы |
| DK3766885T3 (da) | 2015-06-17 | 2022-08-01 | Pfizer | Tricykliske forbindelser og deres anvendelse som phoshodiesteraseinhibitorer |
| JP2018531923A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | Ｎ−［２−（２−アミノ−６，６−二置換−４，４ａ，５，６−テトラヒドロピラノ［３，４−ｄ］［１，３］チアジン−８ａ（８Ｈ）−イル）−１，３−チアゾール−４−イル］アミド |
| EP3353174A1 (en) | 2015-09-24 | 2018-08-01 | Pfizer Inc | N-[2-(3-amino-2,5-dimethyl-1,1-dioxido-5,6-dihydro-2h-1,2,4-thiadiazin-5-yl)-1,3-thiazol-4-yl]amides useful as bace inhibitors |
| JP2018531924A (ja) | 2015-09-24 | 2018-11-01 | ファイザー・インク | テトラヒドロピラノ［３，４−ｄ］［１，３］オキサジン誘導体、およびｂａｃｅ阻害剤としてのその使用 |
| AU2017223132B2 (en) | 2016-02-23 | 2019-12-05 | Pfizer Inc. | 6,7-Dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxamide compounds |
| CN109641898B (zh) | 2016-07-01 | 2022-04-08 | 辉瑞公司 | 用于治疗神经和神经退行性疾病的5,7-二氢-吡咯并-吡啶衍生物 |
| CN110944998B (zh) | 2017-06-22 | 2022-08-16 | 辉瑞大药厂 | 二氢-吡咯并-吡啶衍生物 |
| WO2019005980A1 (en) * | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| HUE061533T2 (hu) | 2018-03-23 | 2023-07-28 | Pfizer | Piperazin azaspiro származékok |
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| FR1361652A (fr) | 1963-06-21 | 1964-05-22 | Ciba Geigy | Procédé de préparation de diazines, entre autres de la 2-méthyl-6-hydroxy-7-morpholino-ptéridine |
| DK0556393T3 (da) * | 1990-11-06 | 2000-10-16 | Yamanouchi Pharma Co Ltd | Tilkondenseret pyrazinderivat |
| TW274550B (xx) * | 1992-09-26 | 1996-04-21 | Hoechst Ag | |
| JP2000154139A (ja) | 1998-09-16 | 2000-06-06 | Kyowa Hakko Kogyo Co Ltd | 縮環ピラジン誘導体 |
| US6369056B1 (en) * | 1999-05-04 | 2002-04-09 | American Home Products Corporation | Cyclic urea and cyclic amide derivatives |
| US6465465B1 (en) * | 2000-03-14 | 2002-10-15 | Arzneimittelwerk Dresden Gmbh | Process for the treatment of erectile dysfunction and product therefor |
| EP1364950A4 (en) * | 2001-02-26 | 2005-03-09 | Tanabe Seiyaku Co | PYRIDOPYRIMIDINE OR NAPHTHYRIDINE DERIVATIVE |
| WO2002076954A1 (en) | 2001-03-23 | 2002-10-03 | Smithkline Beecham Corporation | Compounds useful as kinase inhibitors for the treatment of hyperproliferative diseases |
| US20030114469A1 (en) * | 2001-09-27 | 2003-06-19 | Cohen David Saul | Combinations |
| US7067658B2 (en) * | 2002-09-30 | 2006-06-27 | Bristol-Myers Squibb Company | Pyridino and pyrimidino pyrazinones |
| JP2007504283A (ja) * | 2003-05-20 | 2007-03-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | β−アミロイド斑に作用物質を結合させる方法 |
| JP4705912B2 (ja) * | 2003-06-26 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | ベンゾジアゼピンｃｇｒｐ受容体拮抗物質 |
| DE102004033670A1 (de) * | 2004-07-09 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel |
| EP1833803A4 (en) * | 2005-01-03 | 2009-08-05 | Myriad Genetics Inc | PHARMACEUTICAL COMPOUNDS COMPRISING CASPASE ACTIVATORS AND INDUCERS OF APOPTOSIS AND THE USE THEREOF |
| WO2006126082A2 (en) * | 2005-05-24 | 2006-11-30 | Pharmacia & Upjohn Company Llc | Pyridine [3,4-b] pyrazinones as pde-5 inhibitors |
| WO2007022638A1 (en) * | 2005-08-26 | 2007-03-01 | Methylgene Inc. | Benzodiazepine and benzopiperazine analog inhibitors of histone deacetylase |
| WO2007112347A1 (en) * | 2006-03-28 | 2007-10-04 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| RS51885B (en) | 2006-04-21 | 2012-02-29 | Pfizer Products Inc. | PYRIDIN [3,4-b] PYRAZINNES |
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