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
Links
- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79397106P | 2006-04-21 | 2006-04-21 | |
| PCT/IB2007/001001 WO2007122466A1 (en) | 2006-04-21 | 2007-04-10 | Pyridine[3,4-b]pyrazinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110539T1 true HRP20110539T1 (hr) | 2011-08-31 |
Family
ID=38431249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110539T HRP20110539T1 (hr) | 2006-04-21 | 2011-07-20 | PIRIDINO[3,4-b]PIRAZINONI |
Country Status (42)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101061328B1 (ko) | 2006-04-21 | 2011-08-31 | 화이자 프로덕츠 인크. | 피리딘[3,4-ｂ]피라지논 |
| HUE025355T2 (en) * | 2006-12-12 | 2016-02-29 | Gilead Sciences Inc | Composition for treating pulmonary hypertension |
| AU2009221213B2 (en) * | 2008-03-05 | 2014-02-27 | Merck Patent Gmbh | Pyridopyrazinones derivatives insulin secretion stimulators, methods for obtaining them and use thereof for the treatment of diabetes |
| WO2010041711A1 (ja) * | 2008-10-09 | 2010-04-15 | 杏林製薬株式会社 | イソキノリン誘導体及びそれらを有効成分とするｐｄｅ阻害剤 |
| MX341704B (es) * | 2009-10-26 | 2016-08-31 | Signal Pharm Llc | Métodos de síntesis y purificación de compuestos de heteroarilo. |
| NZ707213A (en) | 2010-10-15 | 2016-12-23 | Gilead Sciences Inc | Compositions and methods of treating pulmonary hypertension |
| CA2830027C (en) | 2011-03-31 | 2016-04-26 | Pfizer Inc. | Novel bicyclic pyridinones |
| WO2012172449A1 (en) | 2011-06-13 | 2012-12-20 | Pfizer Inc. | Lactams as beta secretase inhibitors |
| EP2751116B1 (en) | 2011-08-31 | 2016-10-12 | Pfizer Inc | Hexahydropyrano [3,4-d][1,3]thiazin-2-amine compounds |
| JP6110937B2 (ja) | 2012-05-04 | 2017-04-05 | ファイザー・インク | ＡＰＰ、ＢＡＣＥ１、およびＢＡＣＥ２の阻害剤としての複素環式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 |
| JP2015529239A (ja) | 2012-09-20 | 2015-10-05 | ファイザー・インク | アルキ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 |
| UA110688C2 (uk) | 2012-09-21 | 2016-01-25 | Пфайзер Інк. | Біциклічні піридинони |
| EP2931731A1 (en) | 2012-12-11 | 2015-10-21 | Pfizer Inc. | Hexahydropyrano [3,4-d][1,3]thiazin-2-amine compounds as inhibitors of bace1 |
| EP2935282A1 (en) | 2012-12-19 | 2015-10-28 | Pfizer Inc. | CARBOCYCLIC- AND HETEROCYCLIC-SUBSTITUTED HEXAHYDROPYRANO[3,4-d][1,3]THIAZIN-2-AMINE COMPOUNDS |
| CA2897678A1 (en) | 2013-02-13 | 2014-08-21 | Pfizer Inc. | Heteroaryl-substituted hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| US9233981B1 (en) | 2013-02-15 | 2016-01-12 | Pfizer Inc. | Substituted phenyl hexahydropyrano[3,4-d][1,3]thiazin-2-amine compounds |
| JP6505023B2 (ja) | 2013-02-19 | 2019-04-24 | ファイザー・インク | Ｃｎｓおよび他の障害を治療するための、ｐｄｅ４アイソザイムの阻害薬としてのアザベンゾイミダゾール化合物 |
| CA2925743C (en) | 2013-10-04 | 2018-03-06 | 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 |
| AU2015245260A1 (en) | 2014-04-10 | 2016-10-06 | Pfizer Inc. | 2-amino-6-methyl-4,4a,5,6-tetrahydropyrano[3,4-d][1,3]thiazin-8a(8H)-yl-1,3-thiazol-4-yl amides |
| EP3172210B1 (en) | 2014-07-24 | 2020-01-15 | Pfizer Inc | Pyrazolopyrimidine compounds |
| MX2017001565A (es) | 2014-08-06 | 2017-04-27 | Pfizer | Compuestos de imidazopiridazina. |
| EA033423B1 (ru) | 2015-02-03 | 2019-10-31 | Pfizer | Циклопропанбензофуранилпиридопиразиндионы |
| HUE059372T2 (hu) | 2015-06-17 | 2022-11-28 | Pfizer | Triciklusos vegyületek és azok alkalmazása foszfodiészteráz inhibitorként |
| BR112018003489A2 (pt) | 2015-09-24 | 2018-09-25 | Pfizer | n-[2-(2-amino-6,6-dissubstituído-4,4a,5,6-tetra-hidropirano[3,4-d][1,3]tiazin-8a(8h)-il)-1,3-tiazol-4-il]amidas |
| WO2017051294A1 (en) | 2015-09-24 | 2017-03-30 | 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 |
| WO2017051303A1 (en) | 2015-09-24 | 2017-03-30 | Pfizer Inc. | Tetrahydropyrano[3,4-d][1,3]oxazin derivatives and their use as bace inhibitors |
| PL3419979T3 (pl) | 2016-02-23 | 2020-06-29 | Pfizer Inc. | Związki 6,7-dihydro-5h-pirazolo[5,1-b][1,3]oksazyno-2- karboksyamidowe |
| WO2018002760A1 (en) | 2016-07-01 | 2018-01-04 | Pfizer Inc. | 5,7-dihydro-pyrrolo-pyridine derivatives for treating neurological and neurodegenerative diseases |
| CN110944998B (zh) | 2017-06-22 | 2022-08-16 | 辉瑞大药厂 | 二氢-吡咯并-吡啶衍生物 |
| CA3067591A1 (en) * | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | Methods for treating huntington's disease |
| DK3768669T3 (da) | 2018-03-23 | 2023-04-24 | Pfizer | Piperazinazaspiroderivater |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE69132340T2 (de) * | 1990-11-06 | 2001-02-08 | Yamanouchi Pharma Co Ltd | Kondensiertes pyrazinderivat |
| TW274550B (es) * | 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 |
| JP4166991B2 (ja) * | 2001-02-26 | 2008-10-15 | 田辺三菱製薬株式会社 | ピリドピリミジンまたはナフチリジン誘導体 |
| 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 |
| EP1624900A4 (en) * | 2003-05-20 | 2007-05-02 | Univ California | METHOD OF BINDING AGENTS AT BETA AMYLOID PLAQUE |
| CA2529196A1 (en) * | 2003-06-26 | 2005-02-17 | Merck & Co., Inc. | Benzodiazepine cgrp receptor antagonists |
| 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 |
| WO2006074223A2 (en) * | 2005-01-03 | 2006-07-13 | Myriad Genetics, Inc. | Pharmaceutical compounds as activators of caspases 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 |
| CA2620414A1 (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 |
| KR101061328B1 (ko) | 2006-04-21 | 2011-08-31 | 화이자 프로덕츠 인크. | 피리딘[3,4-ｂ]피라지논 |
-
2007
- 2007-04-10 KR KR1020087028465A patent/KR101061328B1/ko not_active IP Right Cessation
- 2007-04-10 ME MEP-238/08A patent/MEP23808A/xx unknown
- 2007-04-10 ES ES07734320T patent/ES2366239T3/es active Active
- 2007-04-10 MX MX2008012456A patent/MX2008012456A/es active IP Right Grant
- 2007-04-10 CA CA2649775A patent/CA2649775C/en not_active Expired - Fee Related
- 2007-04-10 RS RSP-2008/0484A patent/RS20080484A/sr unknown
- 2007-04-10 BR BRPI0710658-0A patent/BRPI0710658A2/pt not_active IP Right Cessation
- 2007-04-10 WO PCT/IB2007/001001 patent/WO2007122466A1/en active Application Filing
- 2007-04-10 DK DK07734320.0T patent/DK2013208T3/da active
- 2007-04-10 RS RS20110363A patent/RS51885B/en unknown
- 2007-04-10 PL PL07734320T patent/PL2013208T3/pl unknown
- 2007-04-10 JP JP2009505983A patent/JP4436892B2/ja not_active Expired - Fee Related
- 2007-04-10 AP AP2008004640A patent/AP2408A/xx active
- 2007-04-10 MY MYPI20084131A patent/MY148583A/en unknown
- 2007-04-10 CN CN2007800198932A patent/CN101454320B/zh not_active Expired - Fee Related
- 2007-04-10 SI SI200730675T patent/SI2013208T1/sl unknown
- 2007-04-10 AU AU2007242555A patent/AU2007242555B2/en not_active Ceased
- 2007-04-10 NZ NZ571540A patent/NZ571540A/en not_active IP Right Cessation
- 2007-04-10 AT AT07734320T patent/ATE513831T1/de active
- 2007-04-10 EP EP07734320A patent/EP2013208B1/en active Active
- 2007-04-10 EA EA200801998A patent/EA014919B1/ru not_active IP Right Cessation
- 2007-04-11 NL NL2000583A patent/NL2000583C2/nl not_active IP Right Cessation
- 2007-04-18 AR ARP070101657A patent/AR060525A1/es not_active Application Discontinuation
- 2007-04-18 UY UY30291A patent/UY30291A1/es not_active Application Discontinuation
- 2007-04-19 PE PE2007000483A patent/PE20080192A1/es not_active Application Discontinuation
- 2007-04-19 GT GT200700035A patent/GT200700035A/es unknown
- 2007-04-20 US US11/737,966 patent/US7902195B2/en not_active Expired - Fee Related
- 2007-04-20 DO DO2007000080A patent/DOP2007000080A/es unknown
- 2007-04-20 PA PA20078724201A patent/PA8724201A1/es unknown
- 2007-04-20 TW TW096114037A patent/TWI337609B/zh not_active IP Right Cessation
- 2007-10-04 UA UAA200812397A patent/UA92637C2/ru unknown
-
2008
- 2008-09-29 NO NO20084129A patent/NO20084129L/no not_active Application Discontinuation
- 2008-09-29 ZA ZA200808283A patent/ZA200808283B/xx unknown
- 2008-09-30 CR CR10327A patent/CR10327A/es unknown
- 2008-10-07 IL IL194591A patent/IL194591A/en not_active IP Right Cessation
- 2008-10-08 EC EC2008008803A patent/ECSP088803A/es unknown
- 2008-10-17 CU CU20080194A patent/CU23777B7/es active IP Right Grant
- 2008-10-17 TN TNP2008000408A patent/TNSN08408A1/fr unknown
- 2008-10-21 SV SV2008003074A patent/SV2008003074A/es unknown
- 2008-10-21 MA MA31321A patent/MA30352B1/fr unknown
-
2009
- 2009-11-10 HK HK09110478.1A patent/HK1133875A1/xx not_active IP Right Cessation
-
2011
- 2011-07-20 HR HR20110539T patent/HRP20110539T1/hr unknown
- 2011-07-25 CY CY20111100731T patent/CY1111739T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20110539T1 (hr) | PIRIDINO[3,4-b]PIRAZINONI | |
| JP2009534368A5 (es) | ||
| ES2893621T3 (es) | Métodos para el tratamiento de los síntomas residuales de la esquizofrenia | |
| CN104583213B (zh) | 取代的吡啶唑并嘧啶-5-(6h)-酮化合物 | |
| ES2697174T3 (es) | Compuestos para tratar atrofia muscular espinal | |
| KR101720824B1 (ko) | 카테콜 ｏ-메틸 트랜스퍼라제의 억제제 및 정신병적 장애의 치료에서의 그의 용도 | |
| HRP20200624T1 (hr) | Derivati 2-(2,4,5-supstituiranog-anilino)pirimidina kao modulatori egfr korisni za liječenje raka | |
| US9428506B2 (en) | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders | |
| CN112409363B (zh) | 用于治疗认知损害的苯并二氮杂䓬衍生物、组合物和方法 | |
| JP2009524676A5 (es) | ||
| HRP20160647T1 (hr) | Novi heterociklički derivati i njihova uporaba u liječenju neuroloških poremećaja | |
| CN101534824A (zh) | 作为化学活素受体拮抗剂的氨基吡咯烷 | |
| WO2004087677A3 (en) | Pyrimidin-4-one derivatives and their use as p38 kinase modulators | |
| CN102387704A (zh) | S1p5受体的激动剂和拮抗剂，和其用法 | |
| CN105294655A (zh) | Cdk类小分子抑制剂的化合物及其用途 | |
| WO2015154030A1 (en) | Organic compounds | |
| CN101448829A (zh) | 4-氨基-吡啶并[3,2-e]吡嗪类，其作为磷酸二酯酶10的抑制剂的用途以及制备它们的方法 | |
| CN102816175A (zh) | 一种杂环并吡啶酮类化合物,其中间体、制备方法和用途 | |
| AR053011A1 (es) | Compuestos de heteroarilo como inhibidores del receptor p2y1, composiciones farmaceuticas que los contienen y su uso en la manufactura de un medicamento para el tratamiento de un trastorno tromboembolico | |
| JP2014503544A5 (es) | ||
| CN110088107A (zh) | 化合物、组合物及其用途 | |
| JP2021528427A (ja) | 認知障害を処置するためのベンゾジアゼピン誘導体、組成物および方法 | |
| JP2019510039A (ja) | 新規組成物および方法 | |
| RU2016110483A (ru) | Производные пирролопиридина или пиразолопиридина | |
| JP6285610B2 (ja) | アゼチジニルオキシフェニルピロリジン化合物 |