HRP20110655T1 - 2-amino-7,8-dihidro-6h-pirido(4,3-d)pirimidin-5-oni, postupak njihove proizvodnje i farmaceutski sastavi koji ih sadrže - Google Patents
2-amino-7,8-dihidro-6h-pirido(4,3-d)pirimidin-5-oni, postupak njihove proizvodnje i farmaceutski sastavi koji ih sadrže Download PDFInfo
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- HRP20110655T1 HRP20110655T1 HR20110655T HRP20110655T HRP20110655T1 HR P20110655 T1 HRP20110655 T1 HR P20110655T1 HR 20110655 T HR20110655 T HR 20110655T HR P20110655 T HRP20110655 T HR P20110655T HR P20110655 T1 HRP20110655 T1 HR P20110655T1
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- Prior art keywords
- amino
- phenyl
- pyrimidin
- methyl
- fluoro
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- 238000000034 method Methods 0.000 title claims 2
- CZOQBGHFZWUWPV-UHFFFAOYSA-N 2-amino-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical class O=C1NCCC2=NC(N)=NC=C21 CZOQBGHFZWUWPV-UHFFFAOYSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 30
- 239000001257 hydrogen Substances 0.000 claims abstract 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 23
- 125000003118 aryl group Chemical group 0.000 claims abstract 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 14
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 150000001356 alkyl thiols Chemical class 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 150000003573 thiols Chemical class 0.000 claims abstract 4
- -1 2-methyl-2-morpholinopropyl Chemical group 0.000 claims 320
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 201000011510 cancer Diseases 0.000 claims 9
- 125000001041 indolyl group Chemical group 0.000 claims 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000000335 thiazolyl group Chemical group 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- XQNIXHZQURVQNY-CYBMUJFWSA-N (7r)-2-amino-4-ethyl-7-[4-fluoro-2-(2-methoxy-1,3-thiazol-4-yl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)CC)=CC=C(F)C=C1C1=CSC(OC)=N1 XQNIXHZQURVQNY-CYBMUJFWSA-N 0.000 claims 2
- PYGDPDNOWJKHBZ-CQSZACIVSA-N (7r)-2-amino-4-ethyl-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)CC)=CC=C(F)C=C1C1=CN=CC(OC)=N1 PYGDPDNOWJKHBZ-CQSZACIVSA-N 0.000 claims 2
- QHJOJAPTTNUTLH-MRXNPFEDSA-N (7r)-2-amino-4-ethyl-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)CC)=CC=C(F)C=C1C1=CC=CC(OC)=N1 QHJOJAPTTNUTLH-MRXNPFEDSA-N 0.000 claims 2
- ZRFMJIRKTWKFFF-LLVKDONJSA-N (7r)-2-amino-7-(2-bromo-4-fluorophenyl)-4-ethyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)CC)=CC=C(F)C=C1Br ZRFMJIRKTWKFFF-LLVKDONJSA-N 0.000 claims 2
- JHRBZBFFNJGBDX-SNVBAGLBSA-N (7r)-2-amino-7-(2-bromophenyl)-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)=CC=CC=C1Br JHRBZBFFNJGBDX-SNVBAGLBSA-N 0.000 claims 2
- JETRSAYBEYEUMV-OAHLLOKOSA-N (7r)-2-amino-7-(4-fluoro-2-pyridin-3-ylphenyl)-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@@H]2NC(=O)C3=CN=C(N=C3C2)N)=CC=C(F)C=C1C1=CC=CN=C1 JETRSAYBEYEUMV-OAHLLOKOSA-N 0.000 claims 2
- MVWLENRNKYYEID-MRXNPFEDSA-N (7r)-2-amino-7-[2-(2,3-dimethoxyphenyl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1OC MVWLENRNKYYEID-MRXNPFEDSA-N 0.000 claims 2
- OWKFMMGDGVSSCH-CQSZACIVSA-N (7r)-2-amino-7-[2-(2,4-dimethoxypyrimidin-5-yl)-4-fluorophenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=NC(OC)=NC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 OWKFMMGDGVSSCH-CQSZACIVSA-N 0.000 claims 2
- WWZWNASCKPLORW-CYBMUJFWSA-N (7r)-2-amino-7-[2-(4,5-dimethoxypyrimidin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(OC)C(OC)=CN=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 WWZWNASCKPLORW-CYBMUJFWSA-N 0.000 claims 2
- BGTRYMGNQMHSTP-CQSZACIVSA-N (7r)-2-amino-7-[2-(4-ethoxy-5-fluoropyrimidin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(F)C(OCC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 BGTRYMGNQMHSTP-CQSZACIVSA-N 0.000 claims 2
- ZHLGDCNNFNWSIN-CQSZACIVSA-N (7r)-2-amino-7-[2-(4-ethoxypyrimidin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CCOC1=CC=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 ZHLGDCNNFNWSIN-CQSZACIVSA-N 0.000 claims 2
- OCTZNELAVPCHKI-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5,6-dimethoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(OC)C(OC)=NC=C1C1=CC=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 OCTZNELAVPCHKI-CYBMUJFWSA-N 0.000 claims 2
- CBHLHQSZYFOTRD-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OCC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 CBHLHQSZYFOTRD-CYBMUJFWSA-N 0.000 claims 2
- VBTGUWFNLIKXPW-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)-4-fluorophenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OCC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=C1 VBTGUWFNLIKXPW-CYBMUJFWSA-N 0.000 claims 2
- JRUMJUOFDGKDDW-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OCC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 JRUMJUOFDGKDDW-CYBMUJFWSA-N 0.000 claims 2
- ZOJAOSAXIHOMRQ-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)phenyl]-4-ethyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)CC)=CC=CC=C1C1=CN=C(N)C(OC)=N1 ZOJAOSAXIHOMRQ-CYBMUJFWSA-N 0.000 claims 2
- ZREUAANSOWEBLC-OAHLLOKOSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyridin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 ZREUAANSOWEBLC-OAHLLOKOSA-N 0.000 claims 2
- JDERYWBTAWGGPK-OAHLLOKOSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyridin-2-yl)-4-fluorophenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=C1 JDERYWBTAWGGPK-OAHLLOKOSA-N 0.000 claims 2
- MEGJRXVVTLBCOM-OAHLLOKOSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyridin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(N)C(OC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 MEGJRXVVTLBCOM-OAHLLOKOSA-N 0.000 claims 2
- GSOFQMUSKWIILK-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-chloro-4-methoxypyrimidin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(Cl)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 GSOFQMUSKWIILK-CYBMUJFWSA-N 0.000 claims 2
- CTCIDUPLFJLLEX-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-fluoro-4-methoxypyrimidin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(F)C(OC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 CTCIDUPLFJLLEX-CYBMUJFWSA-N 0.000 claims 2
- AMCUQIOCNNSZOX-CQSZACIVSA-N (7r)-2-amino-7-[2-(6-ethoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CCOC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 AMCUQIOCNNSZOX-CQSZACIVSA-N 0.000 claims 2
- YZMLUOHUAMGPGS-MRXNPFEDSA-N (7r)-2-amino-7-[2-(6-ethoxypyridin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CCOC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 YZMLUOHUAMGPGS-MRXNPFEDSA-N 0.000 claims 2
- LQRMWIFHAFUBHY-CYBMUJFWSA-N (7r)-2-amino-7-[2-(6-methoxypyrazin-2-yl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=N1 LQRMWIFHAFUBHY-CYBMUJFWSA-N 0.000 claims 2
- XTFUULJHEFTUJD-OAHLLOKOSA-N (7r)-2-amino-7-[2-(6-methoxypyridin-2-yl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=N1 XTFUULJHEFTUJD-OAHLLOKOSA-N 0.000 claims 2
- KALCIQWJZRPDNY-MRXNPFEDSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methoxyphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 KALCIQWJZRPDNY-MRXNPFEDSA-N 0.000 claims 2
- BKSRJXJPZGILQE-CYBMUJFWSA-N (7r)-2-amino-7-[4-fluoro-2-(4-methoxypyrimidin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 BKSRJXJPZGILQE-CYBMUJFWSA-N 0.000 claims 2
- DAUZFWLDXPXYFO-QGZVFWFLSA-N (7r)-2-amino-7-[4-fluoro-2-(4-methylphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=CC(C)=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 DAUZFWLDXPXYFO-QGZVFWFLSA-N 0.000 claims 2
- NYVDVTHQVSBUIY-MRXNPFEDSA-N (7r)-2-amino-7-[4-fluoro-2-(4-pyrrolidin-1-ylpyrimidin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)=CC=C(F)C=C1C(N=1)=NC=CC=1N1CCCC1 NYVDVTHQVSBUIY-MRXNPFEDSA-N 0.000 claims 2
- DKQUDOVNDMRXNZ-CYBMUJFWSA-N (7r)-2-amino-7-[4-fluoro-2-(5-methoxythiophen-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OC)=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 DKQUDOVNDMRXNZ-CYBMUJFWSA-N 0.000 claims 2
- GZHQNPWPYAHOLX-SECBINFHSA-N (7r)-2-amino-7-[5-(6-methoxypyrazin-2-yl)-1,3-thiazol-4-yl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C2=C(N=CS2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 GZHQNPWPYAHOLX-SECBINFHSA-N 0.000 claims 2
- PSRJRRKMWYGYOW-LLVKDONJSA-N 2-[(7r)-2-amino-4-methyl-5-oxo-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-7-yl]-5-fluorobenzonitrile Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)=CC=C(F)C=C1C#N PSRJRRKMWYGYOW-LLVKDONJSA-N 0.000 claims 2
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 101100074998 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-2 gene Proteins 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229910052727 yttrium Inorganic materials 0.000 claims 2
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims 1
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- CNWJBTHUHMAMCT-CQSZACIVSA-N (7r)-2-amino-7-(2-cyclopentyloxy-4-fluorophenyl)-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)=CC=C(F)C=C1OC1CCCC1 CNWJBTHUHMAMCT-CQSZACIVSA-N 0.000 claims 1
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- IHBWMFSUJZBNHS-CQSZACIVSA-N (7r)-2-amino-7-(2-cyclopentyloxyphenyl)-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)=CC=CC=C1OC1CCCC1 IHBWMFSUJZBNHS-CQSZACIVSA-N 0.000 claims 1
- WDXWMNUYDISCET-GFCCVEGCSA-N (7r)-2-amino-7-(4-fluoro-2-propan-2-yloxyphenyl)-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC(C)OC1=CC(F)=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 WDXWMNUYDISCET-GFCCVEGCSA-N 0.000 claims 1
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- XCIDJUGADVTBOY-ZCFIWIBFSA-N (7r)-2-amino-7-(5-bromo-1,3-thiazol-4-yl)-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1([C@H]2CC=3N=C(N)N=C(C=3C(=O)N2)C)N=CSC=1Br XCIDJUGADVTBOY-ZCFIWIBFSA-N 0.000 claims 1
- WYLBBGPVCWUWRF-QGZVFWFLSA-N (7r)-2-amino-7-[2-(2,4-dimethoxypyrimidin-5-yl)-4-fluorophenyl]-6-ethyl-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@@H]2N(C(C3=C(C)N=C(N)N=C3C2)=O)CC)=CC=C(F)C=C1C1=CN=C(OC)N=C1OC WYLBBGPVCWUWRF-QGZVFWFLSA-N 0.000 claims 1
- QIVRZIJNOSPKAE-CYBMUJFWSA-N (7r)-2-amino-7-[2-(2-ethoxy-1,3-thiazol-4-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OCC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 QIVRZIJNOSPKAE-CYBMUJFWSA-N 0.000 claims 1
- KLQLELHYCUTHSY-CQSZACIVSA-N (7r)-2-amino-7-[2-(2-ethoxy-1,3-thiazol-4-yl)-4-methoxyphenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OCC)=NC(C=2C(=CC=C(OC)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 KLQLELHYCUTHSY-CQSZACIVSA-N 0.000 claims 1
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- UWFWRCHZCOUSLE-CQSZACIVSA-N (7r)-2-amino-7-[2-(4-methoxy-5-methylpyrimidin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(C)C(OC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 UWFWRCHZCOUSLE-CQSZACIVSA-N 0.000 claims 1
- SDSLCGXITKIRSW-LJQANCHMSA-N (7r)-2-amino-7-[2-(5,6-dimethoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(OC)C(OC)=NC=C1C1=CC(F)=CC=C1[C@@H]1N(CC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 SDSLCGXITKIRSW-LJQANCHMSA-N 0.000 claims 1
- DSICYNWBHUOVGE-HXUWFJFHSA-N (7r)-2-amino-7-[2-(5,6-dimethoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(OC)C(OC)=NC=C1C1=CC(F)=CC=C1[C@@H]1N(CCC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 DSICYNWBHUOVGE-HXUWFJFHSA-N 0.000 claims 1
- ABDXUMYYQCZDEM-OAHLLOKOSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)-4-ethoxyphenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C(OCC)=CC=C([C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)C=1C1=CN=C(N)C(OCC)=N1 ABDXUMYYQCZDEM-OAHLLOKOSA-N 0.000 claims 1
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- DZVNPRWMBZCFPD-CQSZACIVSA-N (7r)-2-amino-7-[2-(5-amino-6-ethylpyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(CC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 DZVNPRWMBZCFPD-CQSZACIVSA-N 0.000 claims 1
- KWVBOJGVFKJJON-CQSZACIVSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-ethoxyphenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C(OCC)=CC=C([C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)C=1C1=CN=C(N)C(OC)=N1 KWVBOJGVFKJJON-CQSZACIVSA-N 0.000 claims 1
- CMXWDYUOYPGVEA-GOSISDBHSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC(C)C)=C1 CMXWDYUOYPGVEA-GOSISDBHSA-N 0.000 claims 1
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- UBZCNOJGKIKFTO-GFCCVEGCSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 UBZCNOJGKIKFTO-GFCCVEGCSA-N 0.000 claims 1
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- GDBNZMPFCWOYAX-OAQYLSRUSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-fluorophenyl]-6-[(2-fluorophenyl)methyl]-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC=2C(=CC=CC=2)F)=C1 GDBNZMPFCWOYAX-OAQYLSRUSA-N 0.000 claims 1
- LHIAMNXIPIYSRC-OAQYLSRUSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-fluorophenyl]-6-[(4-fluorophenyl)methyl]-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC=2C=CC(F)=CC=2)=C1 LHIAMNXIPIYSRC-OAQYLSRUSA-N 0.000 claims 1
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- OJZOYJQVXDIAEP-CYBMUJFWSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-methoxyphenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C(OC)=CC=C([C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)C=1C1=CN=C(N)C(OC)=N1 OJZOYJQVXDIAEP-CYBMUJFWSA-N 0.000 claims 1
- URKCHWNTUXQPQT-GFCCVEGCSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N)C(OC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 URKCHWNTUXQPQT-GFCCVEGCSA-N 0.000 claims 1
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- DQKUYPMPRLSRJL-CQSZACIVSA-N (7r)-2-amino-7-[2-[5-(dimethylamino)-6-methoxypyrazin-2-yl]-4-fluorophenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N(C)C)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 DQKUYPMPRLSRJL-CQSZACIVSA-N 0.000 claims 1
- YBVKFZNMXWXMGY-CQSZACIVSA-N (7r)-2-amino-7-[2-[5-(dimethylamino)-6-methoxypyrazin-2-yl]phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound N1=C(N(C)C)C(OC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 YBVKFZNMXWXMGY-CQSZACIVSA-N 0.000 claims 1
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- BNRHCGPVINGNTO-OAHLLOKOSA-N (7r)-2-amino-7-[4-ethoxy-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C(OCC)=CC=C([C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)C=1C1=CN=CC(OC)=N1 BNRHCGPVINGNTO-OAHLLOKOSA-N 0.000 claims 1
- SDVZGIHLCGTWNP-QGZVFWFLSA-N (7r)-2-amino-7-[4-ethoxy-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C=1C(OCC)=CC=C([C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)C=1C1=CC=CC(OC)=N1 SDVZGIHLCGTWNP-QGZVFWFLSA-N 0.000 claims 1
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- ARFDWRCGNZTJPI-HXUWFJFHSA-N (7r)-2-amino-7-[4-fluoro-2-(2-fluoropyridin-3-yl)phenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound C1([C@@H]2N(C(C3=C(C)N=C(N)N=C3C2)=O)CCC(C)C)=CC=C(F)C=C1C1=CC=CN=C1F ARFDWRCGNZTJPI-HXUWFJFHSA-N 0.000 claims 1
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- BNOYRDUPHFYYTI-GFCCVEGCSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methoxy-1,3-thiazol-4-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 BNOYRDUPHFYYTI-GFCCVEGCSA-N 0.000 claims 1
- ZDVWPCBCFQRVOL-GFCCVEGCSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methoxy-1,3-thiazol-5-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OC)=NC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 ZDVWPCBCFQRVOL-GFCCVEGCSA-N 0.000 claims 1
- RGMRIVCMJKMUGX-HXUWFJFHSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methoxypyridin-3-yl)phenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=NC=CC=C1C1=CC(F)=CC=C1[C@@H]1N(CC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 RGMRIVCMJKMUGX-HXUWFJFHSA-N 0.000 claims 1
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- KDONHFIXUCEHJH-QGZVFWFLSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methylphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 KDONHFIXUCEHJH-QGZVFWFLSA-N 0.000 claims 1
- WJIVZYGWMWGPEU-QGZVFWFLSA-N (7r)-2-amino-7-[4-fluoro-2-(3-methylphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=C1 WJIVZYGWMWGPEU-QGZVFWFLSA-N 0.000 claims 1
- IAKZMEKRMJBGOI-CQSZACIVSA-N (7r)-2-amino-7-[4-fluoro-2-(4-methoxy-5-methylpyrimidin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(C)C(OC)=NC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 IAKZMEKRMJBGOI-CQSZACIVSA-N 0.000 claims 1
- XCZWEHQTNQUMSG-HXUWFJFHSA-N (7r)-2-amino-7-[4-fluoro-2-(4-methoxypyridin-3-yl)phenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=NC=C1C1=CC(F)=CC=C1[C@@H]1N(CC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 XCZWEHQTNQUMSG-HXUWFJFHSA-N 0.000 claims 1
- RBWYWCZCZNEVKM-OAQYLSRUSA-N (7r)-2-amino-7-[4-fluoro-2-(4-methoxypyridin-3-yl)phenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=NC=C1C1=CC(F)=CC=C1[C@@H]1N(CCC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 RBWYWCZCZNEVKM-OAQYLSRUSA-N 0.000 claims 1
- FJMVDJBVWSKJEB-LLVKDONJSA-N (7r)-2-amino-7-[4-fluoro-2-(5-methoxy-1,3,4-oxadiazol-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound O1C(OC)=NN=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=C(C)N=C(N)N=C2C1 FJMVDJBVWSKJEB-LLVKDONJSA-N 0.000 claims 1
- OYZQWJNSTBRXOZ-LJQANCHMSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC(C)C)=N1 OYZQWJNSTBRXOZ-LJQANCHMSA-N 0.000 claims 1
- MIOGXGVTLHKICS-HXUWFJFHSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CCC(C)C)=N1 MIOGXGVTLHKICS-HXUWFJFHSA-N 0.000 claims 1
- AQUWQQXPWXUZFH-OAQYLSRUSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-6-(oxan-4-ylmethyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC2CCOCC2)=N1 AQUWQQXPWXUZFH-OAQYLSRUSA-N 0.000 claims 1
- CPEKJNQQDIZMGS-OAQYLSRUSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-6-(pyridin-3-ylmethyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC=2C=NC=CC=2)=N1 CPEKJNQQDIZMGS-OAQYLSRUSA-N 0.000 claims 1
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Classifications
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- 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
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Abstract
Spoj formule (I): ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol, naznačen time, daRa je odabran iz skupine koju čine (1) vodik, (2) halogen, (3) hidroksil, (4) C1-C6 alkoksi, (5) tiol, (6) C1-C6 alkiltiol, (7) supstituirani ili nesupstituirani C1-C6 alkil, (8) amino ili supstituirani amino, (9) supstituirani ili nesupstituirani aril, (10) supstituirani ili nesupstituirani heteroaril, i (11) supstituirani ili nesupstituirani heterociklil; R je odabran iz skupine koju čine (1) vodik, (2) supstituirani ili nesupstituirani C1-C6 alkil, (3) supstituirani ili nesupstituirani C2-C6 alkenil, (4) supstituirani ili nesupstituirani C2-C6 alkinil, (5) supstituirani ili nesupstituirani C3-C7 cikloalkil, (6) supstituirani ili nesupstituirani C5-C7 cikloalkenil, (7) supstituirani ili nesupstituirani aril, (8) supstituirani ili nesupstituirani heteroaril, i (9) supstituirani ili nesupstituirani heterociklil; Rb je odabran iz skupine koju čine (1) supstituirani ili nesupstituirani C3-C7 cikloalkil, (2) supstituirani ili nesupstituirani C5-C7 cikloalkenil, (3) supstituirani ili nesupstituirani aril, (4) supstituirani ili nesupstituirani heteroaril, i (5) supstituirani ili nesupstituirani heterociklil; i pod uvjetom da kada Ra je amino, tada Rb nije fenil, 4-alkil-fenil, 4-alkoksi-fenil ili 4-halo-fenil. Patent sadrži još 46 patentnih zahtjeva.
Claims (47)
1. Spoj formule (I):
[image]
ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol,
naznačen time, da
Ra je odabran iz skupine koju čine
(1) vodik,
(2) halogen,
(3) hidroksil,
(4) C1-C6 alkoksi,
(5) tiol,
(6) C1-C6 alkiltiol,
(7) supstituirani ili nesupstituirani C1-C6 alkil,
(8) amino ili supstituirani amino,
(9) supstituirani ili nesupstituirani aril,
(10) supstituirani ili nesupstituirani heteroaril, i
(11) supstituirani ili nesupstituirani heterociklil;
R je odabran iz skupine koju čine
(1) vodik,
(2) supstituirani ili nesupstituirani C1-C6 alkil,
(3) supstituirani ili nesupstituirani C2-C6 alkenil,
(4) supstituirani ili nesupstituirani C2-C6 alkinil,
(5) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(6) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(7) supstituirani ili nesupstituirani aril,
(8) supstituirani ili nesupstituirani heteroaril, i
(9) supstituirani ili nesupstituirani heterociklil;
Rb je odabran iz skupine koju čine
(1) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(2) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(3) supstituirani ili nesupstituirani aril,
(4) supstituirani ili nesupstituirani heteroaril, i
(5) supstituirani ili nesupstituirani heterociklil; i
pod uvjetom da kada Ra je amino, tada Rb nije fenil, 4-alkil-fenil, 4-alkoksi-fenil ili 4-halo-fenil.
2. Spoj prema zahtjevu 1, naznačen time, da Ra je C1-C6 alkil ili halo C1-C6 alkil.
3. Spoj prema zahtjevu 1, naznačen time, da Rb je aril ili heteroaril.
4. Spoj prema zahtjevu 3, naznačen time, da Rb je odabran iz skupine koju čine fenil, piridil, pirimidinil, pirazinil, indolil, tiazolil i tienil.
5. Spoj prema zahtjevu 1, naznačen time, da Rb je odabran iz skupine koju čine supstituirani fenil, supstituirani piridil, supstituirani pirimidinil, supstituirani pirazinil, supstituirani indolil, supstituirani tiazolil i supstituirani tienil.
6. Spoj prema zahtjevu 5, naznačen time, da su spomenuti fenil, piridil, pirimidinil, pirazinil, indolil, tiazolil i tienil supstituirani sa supstituiranim ili nesupstituiranim arilom ili sa supstituiranim ili nesupstituiranim heteroarilom.
7. Spoj prema zahtjevu 5, naznačen time, da su spomenuti fenil, piridil, pirimidinil, pirazinil, indolil, tiazolil i tienil supstituirani s halo.
8. Spoj prema zahtjevu 7, naznačen time, da spomenuti halo je fluor.
9. Spoj prema zahtjevu 1, naznačen time, da je R odabran iz skupine koju čine vodik, nesupstituirani alkil i supstituirani alkil.
10. Spoj prema zahtjevu 9, naznačen time, da je R odabran iz skupine koju čine vodik, benzil, 1-(4-metoksifenil)etil, metil, 3-aminopropil i 2-metil-2-morfolinopropil.
11. Spoj prema zahtjevu 1, naznačen time, da ima formulu (Ia)
[image]
gdje su R, Ra i Rb prethodno određeni za formulu (I).
12. Spoj prema zahtjevu 1, naznačen time, da ima formulu (II):
[image]
ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol, gdje n je 0 ili 1, pri čemu je Ra odabran iz skupine koju čine
(1) vodik,
(2) halogen,
(3) hidroksil,
(4) C1-C6 alkoksi,
(5) tiol,
(6) C1-C6 alkiltiol,
(7) supstituirani ili nesupstituirani C1-C6 alkil,
(8) amino ili supstituirani amino,
(9) supstituirani ili nesupstituirani aril,
(10) supstituirani ili nesupstituirani heteroaril, i
(11) supstituirani ili nesupstituirani heterociklil;
gdje je R odabran iz skupine koju čine
(1) vodik,
(2) supstituirani ili nesupstituirani C1-C6 alkil,
(3) supstituirani ili nesupstituirani C2-C6 alkenil,
(4) supstituirani ili nesupstituirani C2-C6 alkinil,
(5) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(6) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(7) supstituirani ili nesupstituirani aril,
(8) supstituirani ili nesupstituirani heteroaril, i
(9) supstituirani ili nesupstituirani heterociklil,
pri čemu kada n je 1, X je C, a Y je na svakoj poziciji neovisno odabran od CQ1 i N, tada je Z odabran od CR2 i N pod uvjetom da ne više od tri skupine Y i Z su N, i pri čemu kada n je 0, X je C ili N, a Y je na svakoj poziciji neovisno odabran od CQ1, N, NQ2, O i S pod uvjetom da ne više od četiri skupine X i Y su N i NQ2 i ne više od jedne skupine Y je S ili O, te gdje je Q1 na svakoj poziciji neovisno odabran iz skupine koju čine
(1) vodik,
(2) halogen,
(3) supstituirani ili nesupstituirani C1-C6 alkil,
(4) supstituirani ili nesupstituirani C2-C6 alkenil,
(5) supstituirani ili nesupstituirani C2-C6 alkinil,
(6) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(7) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(8) supstituirani ili nesupstituirani aril,
(9) supstituirani ili nesupstituirani heteroaril,
(10) supstituirani ili nesupstituirani heterociklil,
(11) supstituirani ili nesupstituirani amino,
(12) -OR3 ili -SR3
(13) -C(O)R3, -CO2R3, -C(O)N(R3)2, -S(O)R3, -SO2R ili -SO2N(R3)2,
(14) OC(O)R3, -N(R3)C(O)R3ili -N(R3)SO2R3,
(15) -CN, i
(16) -NO2;
gdje je Q2 na svakoj poziciji neovisno odabran iz skupine koju čine
(1) vodik,
(3) supstituirani ili nesupstituirani C1-C6 alkil,
(4) supstituirani ili nesupstituirani C2-C6 alkenil,
(5) supstituirani ili nesupstituirani C2-C6 alkinil,
(6) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(7) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(8) supstituirani ili nesupstituirani aril,
(9) supstituirani ili nesupstituirani heteroaril, i
(10) supstituirani ili nesupstituirani heterociklil;
gdje R2 je odabran iz skupine koju čine
(1) vodik,
(2) halogen,
(3) supstituirani ili nesupstituirani C1-C3 alkil, i
(4) -OR3, -SR3 ili -NHR3;
gdje je R3 na svakoj poziciji neovisno odabran iz skupine koju čine
(1) vodik,
(2) supstituirani ili nesupstituirani C1-C6 alkil,
(3) supstituirani ili nesupstituirani C2-C6 alkenil,
(4) supstituirani ili nesupstituirani C2-C6 alkinil,
(5) supstituirani ili nesupstituirani C3-C7 cikloalkil,
(6) supstituirani ili nesupstituirani C5-C7 cikloalkenil,
(7) supstituirani ili nesupstituirani aril,
(8) supstituirani ili nesupstituirani heteroaril, i
(9) supstituirani ili nesupstituirani heterociklil,
pod uvjetom da kada je Raamino, tada X, Y, Z i n zajedno ne tvore fenil, 4-alkil-fenil, 4-alkoksi-fenil ili 4-halo-fenil skupinu.
13. Spoj prema zahtjevu 12, naznačen time, da jedan od Q1ili Q2je odabran iz skupine koju čine supstituirani ili nesupstituirani aril, supstituirani ili nesupstituirani heterociklil, supstituirani ili nesupstituirani heteroaril, supstituirani ili nesupstituirani C3-C7 cikloalkil i supstituirani ili nesupstituirani C5-C7 cikloalkenil.
14. Spoj prema zahtjevu 13, naznačen time, da spomenuti aril, heterociklil, heteroaril, C3-C7 cikloalkil i C5-C7 cikloalkenil su odabrani iz skupine koju čine fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, furanil, kinolinil, izokinolinil, izoksazolil, oksazolil, tiazolil, morfolino, piperidinil, pirolidinil, tienil, cikloheksil, ciklopentil, cikloheksenil i ciklopentenil.
15. Spoj prema zahtjevu 14, naznačen time, da jedan od Q1 ili Q2 je odabran iz skupine koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1H-pirazol-4-il, 1-metil-1H-pirazol-4-il, 1-metil-1H-pirazol-4-il, 2-(5-metil-piridin-2-il)-fenil, 2,3-difluoro-fenil, 2,3-dimetoksi-fenil, 2,4-difluoro-fenil, 2,4-dimetoksi-fenil, 2,4-dimetoksi-pirimidin-5-il, 2,5-difluoro-fenil, 2,6-difluoro-fenil, 2,6-dimetil-piridin-3-il, 2-acetamidofenil, 2-aminokarbonil-fenil, 2-amino-pirimidin-5-il, 2-kloro-4-metoksi-pirimidin-5-il, 2-kloro-5-fluoro-piridin-3-il, 2-kloro-fenil, 2-kloro-piridin-3-il, 2-kloro-piridin-4-il, 2-difluoro-3-metoksifenil, 2-etil-fenil, 2-etoksi-tiazol-4-il, 2-fluoro-3-metoksi-fenil, 2-fluoro-3-metilfenil, 2-fluoro-4-metil-fenil, 2-fluoro-5-metoksi-fenil, 2-fluoro-5-metilfenil, 2-fluorofenil, 2-fluoro-piridin-3-il, 2-hidroksimetil-3-metoksifenil, 2-hidroksimetilfenil, 2-izokinolin-4-il, 2-metoksi-5-trifluorometil-fenil, 2-metoksi-fenil, 2-metoksi-piridin-3-il, 2-metoksi-pirimidin-4-il, 2-metoksi-tiazol-4-il, 2-metil-fenil, 2-metil-piridin-3-il, 2-okso-1,2-dihidro-piridin-3-il, 2-fenoksifenil, 2-piridin-3-il, 2-pirimidin-5-il, 2-trifluorometoksifenil, 2-trifluorometoksi-fenil, 3,4-dimetoksi-fenil, 3,5-dimetil-izoksazol-4-il, 3,6-dimetil-pirazin-2-il, 3-acetamidofenil, 3-aminokarbonilfenil, 3-bromo-fenil, 3-kloro-pirazin-2-il, 3-cijanofenil, 3-dimetilaminofenil, 3-etoksi-fenil, 3-etil-4-metil-fenil, 3-etinil-fenil, 3-fluoro-6-metoksi-piridin-2-il, 3-fluorofenil, 3-fluoro-pirazin-2-il, 3-metansulfonamidofenil, 3-metoksikarbonilfenil, 3-metoksifenil, 3-metoksi-pirazin-2-il, 3-metil-3H-imidazo[4,5-b]pirazin-5-il, 3-metilfenil, 3-metil-piridin-2-il, 3-trifluorometoksifenil, 3-trifluorometilfenil, 4,5-dimetoksi-pirimidin-2-il, 4-amino-5-fluoro-pirimidin-2-il, 4-kloro-2,5-dimetoksi-fenil, 4-kloro-2-fluoro-fenil, 4-kloro-2-metoksi-5-metil-fenil, 4-kloro-piridin-3-il, 4-difluoro-2-metil-fenil, 4-etoksi-5-fluoro-pirimidin-2-il, 4-etoksi-pirimidin-2-il, 4-etoksi-pirimidin-5-il, 4-etil-1H-pirazol-3-il, 4-fluoro-2-metoksi-fenil, 4-fluoro-2-metil-fenil, 4-fluorofenil, 4-metoksi-5-metil-pirimidin-2-il, 4-metoksi-piridin-3-il, 4-metoksi-pirimidin-2-il, 4-metoksi-pirimidin-5-il, 4-metil-fenil, 4-metil-piridin-2-il, 4-metil-piridin-3-il, 4-pirolidin-1-il-pirimidin-2-il, 5,6-dimetoksi-pirazin-2-il, 5-acetil-tiofen-2-il, 5-amino-6-etoksi-pirazin-2-il, 5-amino-6-metoksi-3-metil-pirazin-2-il, 5-amino-6-metoksi-piridin-2-il, 5-kloro-4-metoksi-pirimidin-2-il, 5-kloro-6-metoksi-pirazin-2-il, 5-dimetilamino-6-metoksi-pirazin-2-il, 5-fluoro-2-metoksifenil, 5-fluoro-4-metoksi-pirimidin-2-il, 5-fluoro-6-metoksi-pirazin-2-il, 5-fluoro-piridin-2-il, 5-metoksi-piridin-3-il, 5-metoksi-tiofen-2-il, 5-trifluorometil-pirimidin-2-il, 6-acetil-piridin-2-il, 6-kloro-pirazin-2-il, 6-etoksi-pirazin-2-il, 6-etoksi-piridin-2-il, 6-fluoro-piridin-2-il, 6-fluoro-piridin-3-il, 6-hidroksi-piridin-2-il, 6-metoksi-5-metilamino-pirazin-2-il, 6-metoksi-5-metil-pirazin-2-il, 6-metoksi-pirazin-2-il, 6-metoksi-piridin-2-il, 6-metoksi-piridin-3-il, 6-metilamino-pirazin-2-il, 6-metil-piridin-2-il, 5-amino-6-(2,2,2-trifluoroetoksi) pirazin-2-il i 6-trifluorometil-piridin-2-il.
16. Spoj prema zahtjevu 12, naznačen time, da ima formulu (IIa):
[image]
ili njegov tautomer ili njegova farmaceutski prihvatljiva sol, gdje su Ra, R, X, Y, Z i n prethodno određeni za formulu (II).
17. Spoj prema zahtjevu 1, naznačen time, da ima formulu (III):
[image]
ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol, gdje je Ra odabran iz skupine koju čine
(1) vodik,
(2) halogen,
(3) hidroksil,
(4) C1-C6 alkoksi,
(5) tiol,
(6) C1-C6 alkiltiol,
(7) supstituirani ili nesupstituirani C1-C6 alkil,
(8) amino ili supstituirani amino
(9) supstituirani ili nesupstituirani aril,
(10) supstituirani ili nesupstituirani heteroaril, i
(11) supstituirani ili nesupstituirani heterociklil;
R4 je vodik ili supstituirani ili nesupstituirani C1-C6 alkil;
R5 je vodik, alkil, alkoksi ili halo;
svaki od R6,R7,R8 i R9 su neovisno odabrani iz skupine koju čine vodik, alkil, alkoksi, halo, supstituirani ili nesupstituirani aril i supstituirani ili nesupstituirani heteroaril; ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol, te pod uvjetom da kada je Raamino i R6, R7, R8 i R9 su vodik, tada R5 nije vodik, alkil, alkoksi ili halo.
18. Spoj prema zahtjevu 1, 12 ili 17, naznačen time, da Ra je vodik.
19. Spoj prema zahtjevu 12 ili 17, naznačen time, da Ra je supstituirani ili nesupstituirani C1-C6 alkil.
20. Spoj prema zahtjevu 2 ili 19, naznačen time, da Ra je metil.
21. Spoj prema zahtjevu 20, naznačen time, da R4 je odabran iz skupine koju čine vodik, benzil, 1-(4-metoksifenil)etil, metil, 3-aminopropil i 2-metil-2-morfolinopropil.
22. Spoj prema zahtjevu 21, naznačen time, da R4 je vodik.
23. Spoj prema zahtjevu 17, naznačen time, da su svaki od R7, R8 i R9 vodik.
24. Spoj prema zahtjevu 17, naznačen time, da R6 je odabran iz skupine koju čine supstituirani aril i supstituirani heteroaril.
25. Spoj prema zahtjevu 24, naznačen time, da je spomenuti aril i heteroaril odabran iz skupine koju čine furanil, pirolil, fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, kinolinil, izokinolinil, izoksazolil, oksazolil, tiazolil i tienil.
26. Spoj prema zahtjevu 25, naznačen time, da je R6 odabran iz skupine koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1H-pirazol-4-il, 1-metil-1H-pirazol-4-il, 1-metil-1H-pirazol-4-il, 2-(5-metil-piridin-2-il)-fenil, 2,3-difluoro-fenil, 2,3-dimetoksi-fenil, 2,4-difluoro-fenil, 2,4-dimetoksi-fenil, 2,4-dimetoksi-pirimidin-5-il, 2,5-difluoro-fenil, 2,6-difluoro-fenil, 2,6-dimetil-piridin-3-il, 2-acetamidofenil, 2-aminokarbonilfenil, 2-amino-pirimidin-5-il, 2-kloro-4-metoksi-pirimidin-5-il, 2-kloro-5-fluoro-piridin-3-il, 2-kloro-fenil, 2-kloro-piridin-3-il, 2-kloro-piridin-4-il, 2-difluoro-3-metoksifenil, 2-etil-fenil, 2-etoksi-tiazol-4-il, 2-fluoro-3-metoksi-fenil, 2-fluoro-3-metilfenil, 2-fluoro-4-metil-fenil, 2-fluoro-5-metoksi-fenil, 2-fluoro-5-metilfenil, 2-fluorofenil, 2-fluoro-piridin-3-il, 2-hidroksimetil-3-metoksifenil, 2-hidroksimetilfenil, 2-izokinolin-4-il, 2-metoksi-5-trifluorometilfenil, 2-metoksi-fenil, 2-metoksi-piridin-3-il, 2-metoksi-pirimidin-4-il, 2-metoksi-tiazol-4-il, 2-metil-fenil, 2-metil-piridin-3-il, 2-okso-1,2-dihidro-piridin-3-il, 2-fenoksifenil, 2-piridin-3-il, 2-pirimidin-5-il, 2-trifluorometoksifenil, 2-trifluorometoksi-fenil, 3,4-dimetoksi-fenil, 3,5-dimetil-izoksazol-4-il, 3,6-dimetil-pirazin-2-il, 3-acetamidofenil, 3-aminokarbonilfenil, 3-bromo-fenil, 3-kloro-pirazin-2-il, 3-cijanofenil, 3-dimetilaminofenil, 3-etoksi-fenil, 3-etil-4-metil-fenil, 3-etinil-fenil, 3-fluoro-6-metoksi-piridin-2-il, 3-fluorofenil, 3-fluoro-pirazin-2-il, 3-metansulfonamidofenil, 3-metoksikarbonilfenil, 3-metoksifenil, 3-metoksi-pirazin-2-il, 3-metil-3H-imidazo[4,5-b]pirazin-5-il, 3-metilfenil, 3-metil-piridin-2-il, 3-trifluorometoksifenil, 3-trifluorometilfenil, 4,5-dimetoksi-pirimidin-2-il, 4-amino-5-fluoro-pirimidin-2-il, 4-kloro-2,5-dimetoksi-fenil, 4-kloro-2-fluoro-fenil, 4-kloro-2-metoksi-5-metil-fenil, 4-kloro-piridin-3-il, 4-difluoro-2-metil-fenil, 4-etoksi-5-fluoro-pirimidin-2-il, 4-etoksi-pirimidin-2-il, 4-etoksi-pirimidin-5-il, 4-etil-1H-pirazol-3-il, 4-fluoro-2-metoksi-fenil, 4-fluoro-2-metil-fenil, 4-fluorofenil, 4-metoksi-5-metil-pirimidin-2-il, 4-metoksi-piridin-3-il, 4-metoksi-pirimidin-2-il, 4-metoksi-pirimidin-5-il, 4-metil-fenil, 4-metil-piridin-2-il, 4-metil-piridin-3-il, 4-pirolidin-1-il-pirimidin-2-il, 5,6-dimetoksi-pirazin-2-il, 5-acetil-tiofen-2-il, 5-amino-6-etoksi-pirazin-2-il, 5-amino-6-metoksi-3-metil-pirazin-2-il, 5-amino-6-metoksi-piridin-2-il, 5-kloro-4-metoksi-pirimidin-2-il, 5-kloro-6-metoksi-pirazin-2-il, 5-dimetilamino-6-metoksi-pirazin-2-il, 5-fluoro-2-metoksifenil, 5-fluoro-4-metoksi-pirimidin-2-il, 5-fluoro-6-metoksi-pirazin-2-il, 5-fluoro-piridin-2-il, 5-metoksi-piridin-3-il, 5-metoksi-tiofen-2-il, 5-trifluorometil-pirimidin-2-il, 6-acetil-piridin-2-il, 6-kloro-pirazin-2-il, 6-etoksi-pirazin-2-il, 6-etoksi-piridin-2-il, 6-fluoro-piridin-2-il, 6-fluoro-piridin-3-il, 6-hidroksi-piridin-2-il, 6-metoksi-5-metilamino-pirazin-2-il, 6-metoksi-5-metil-pirazin-2-il, 6-metoksipirazin-2-il, 6-metoksi-piridin-2-il, 6-metoksi-piridin-3-il, 6-metil-amino-pirazin-2-il, 6-metil-piridin-2-il, 5-amino-6-(2,2,2-trifluoroetoksi)pirazin-2-il i 6-trifluorometil-piridin-2-il.
27. Spoj prema zahtjevu 17, naznačen time, da ima formulu (IIIa):
[image]
ili njegov tautomer ili njegova farmaceutski prihvatljiva sol, gdje su Ra, R4, X, Y, Z i n prethodno određeni za formulu (III) te uz uvjet da kada Ra je amino i R6, R7, R8 i R9 su vodik, tada R5 nije vodik, alkil, alkoksi ili halo.
28. Spoj prema zahtjevu 1, naznačen time, da ima formulu (IV):
[image]
ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol, gdje
R4 je vodik ili supstituirani ili nesupstituirani C1-C6 alkil,
R5 je vodik ili halo,
R6aje odabran iz skupine koju čine vodik, halo, supstituirani ili nesupstituirani aril i supstituirani ili nesupstituirani heteroaril.
29. Spoj prema zahtjevu 28, naznačen time, da je R4 odabran iz skupine koju čine vodik, benzil, 1-(4-metoksifenil)etil, metil, 3-aminopropil i 2-metil-2-morfolinopropil.
30. Spoj prema zahtjevu 17 ili 29, naznačen time, da R5 je vodik ili fluor.
31. Spoj prema zahtjevu 28, naznačen time, da je R6aodabran iz skupine koju čine supstituirani aril i supstituirani heteroaril.
32. Spoj prema zahtjevu 31, naznačen time, da su spomenuti aril i heteroaril odabrani iz skupine koju čine furanil, pirolil, fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, kinolinil, izokinolinil, izoksazolil, oksazolil, tiazolil i tienil.
33. Spoj prema zahtjevu 32, naznačen time, da je R6a odabran iz skupine koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1H-pirazol-4-il, 1-metil-1H-pirazol-4-il, 2-(5-metil-piridin-2-il)-fenil, 2,3-difluoro-fenil, 2,3-dimetoksi-fenil, 2,4-difluoro-fenil, 2,4-dimetoksi-fenil, 2,4-dimetoksi-pirimidin-5-il, 2,5-difluoro-fenil, 2,6-difluoro-fenil, 2,6-dimetil-piridin-3-il, 2-acetamidofenil, 2-aminokarbonilfenil, 2-amino-pirimidin-5-il, 2-kloro-4-metoksi-pirimidin-5-il, 2-kloro-5-fluoro-piridin-3-il, 2-kloro-fenil, 2-kloro-piridin-3-il, 2-kloro-piridin-4-il, 2-difluoro-3-metoksifenil, 2-etil-fenil, 2-etoksi-tiazol-4-il, 2-fluoro-3-metoksi-fenil, 2-fluoro-3-metilfenil, 2-fluoro-4-metil-fenil, 2-fluoro-5-metoksi-fenil, 2-fluoro-5-metilfenil, 2-fluorofenil, 2-fluoro-piridin-3-il, 2-hidroksimetil-3-metoksifenil, 2-hidroksimet-ilfenil, 2-izokinolin-4-il, 2-metoksi-5-trifluorometilfenil, 2-metoksi-fenil, 2-metoksi-piridin-3-il, 2-metoksi-pirimidin-4-il, 2-metoksi-tiazol-4-il, 2-metil-fenil, 2-metil-piridin-3-il, 2-okso-1,2-dihidro-piridin-3-il, 2-fenoksifenil, 2-piridin-3-il, 2-pirimidin-5-il, 2-trifluorometoksifenil, 2-trifluorometoksi-fenil, 3,4-dimetoksi-fenil, 3,5-dimetil-izoksazol-4-il, 3,6-dimetil-pirazin-2-il, 3-acetamidofenil, 3-aminokarbonilfenil, 3-bromo-fenil, 3-kloro-pirazin-2-il, 3-cijanofenil, 3-dimetilaminofenil, 3-etoksi-fenil, 3-etil-4-metil-fenil, 3-etinil-fenil, 3-fluoro-6-metoksi-piridin-2-il, 3-fluorofenil, 3-fluoro-pirazin-2-il, 3-metansulfonamidofenil, 3-metoksikarbonilfenil, 3-metoksifenil, 3-metoksi-pirazin-2-il, 3-metil-3H-imidazo[4,5-b]pirazin-5-il, 3-metilfenil, 3-metil-piridin-2-il, 3-trifluorometoksifenil, 3-trifluorometilfenil, 4,5-dimetoksi-pirimidin-2-il, 4-amino-5-fluoro-pirimidin-2-il, 4-kloro-2,5-dimetoksi-fenil, 4-kloro-2-fluoro-fenil, 4-kloro-2-metoksi-5-metil-fenil, 4-kloro-piridin-3-il, 4-difluoro-2-metil-fenil, 4-etoksi-5-fluoro-pirimidin-2-il, 4-etoksi-pirimidin-2-il, 4-etoksi-pirimidin-5-il, 4-etil-1H-pirazol-3-il, 4-fluoro-2-metoksi-fenil, 4-fluoro-2-metil-fenil, 4-fluorofenil, 4-metoksi-5-metil-pirimidin-2-il, 4-metoksi-piridin-3-il, 4-metoksi-pirimidin-2-il, 4-metoksi-pirimidin-5-il, 4-metil-fenil, 4-metil-piridin-2-il, 4-metil-piridin-3-il, 4-pirolidin-1-il-pirimidin-2-il, 5,6-dimetoksi-pirazin-2-il, 5-acetil-tiofen-2-il, 5-amino-6-etoksi-pirazin-2-il, 5-amino-6-metoksi-3-metil-pirazin-2-il, 5-amino-6-metoksi-piridin-2-il, 5-kloro-4-metoksi-pirimidin-2-il, 5-kloro-6-metoksi-pirazin-2-il, 5-dimetilamino-6-metoksi-pirazin-2-il, 5-fluoro-2-metoksifenil, 5-fluoro-4-metoksi-pirimidin-2-il, 5-fluoro-6-metoksi-pirazin-2-il, 5-fluoro-piridin-2-il, 5-metoksi-piridin-3-il, 5-metoksi-tiofen-2-il, 5-trifluorometil-pirimidin-2-il, 6-acetil-piridin-2-il, 6-kloro-pirazin-2-il, 6-etoksi-pirazin-2-il, 6-etoksi-piridin-2-il, 6-fluoro-piridin-2-il, 6-fluoro-piridin-3-il, 6-hidroksi-piridin-2-il, 6-metoksi-5-metilamino-pirazin-2-il, 6-metoksi-5-metil-pirazin-2-il, 6-metoksipirazin-2-il, 6-metoksi-piridin-2-il, 6-metoksi-piridin-3-il, 6-metilamino-pirazin-2-il, 6-metil-piridin-2-il, 5-amino-6-(2,2,2-trifluoroetoksi)pirazin-2-il i 6-trifluorometil-piridin-2-il.
34. Spoj prema zahtjevu 28, naznačen time, da ima formulu (IVa):
[image]
ili njegov tautomer ili njegova farmaceutski prihvatljiva sol, gdje su R4, R5 i R6a prethodno određeni za formulu (IV).
35. Spoj prema zahtjevu 12, naznačen time, da ima formulu (V):
[image]
gdje su R10 i R11 neovisno Q1, a Ra, R, Q1 i Q2 su prethodno određeni za formulu (II).
36. Spoj prema zahtjevu 35, naznačen time, da ima formulu (Va):
[image]
gdje su R10 i R11 neovisno Q1, a Ra, R, Q1 i Q2 su prethodno određeni za formulu (V).
37. Spoj ili njegov stereoizomer, tautomer ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time, da je odabran iz skupine koju čine
(R)-2-amino-7-[2-(2-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on; (S)-2-amino-6-benzil-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-6-[(S)-1-(4-metoksi-fenil)-etil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4,6-dimetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4,6-dimetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(6-metoksipiridin-2-il)fenil]-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
2-amino-7-[2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4,6-dimetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(2-metoksi-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5,2’-difluoro-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5-fluoro-2’-trifluorometoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(2-kloro-piridin-3-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(6-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-izokinolin-4-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5,3’-difluoro-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(4-kloro-piridin-3-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5,2’-difluoro-3’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5,4’-difluoro-2’-metil-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5-fluoro-2’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-pirimidin-5-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido [4,3-d] pirimidin-5-on;
2-amino-7-(5-fluoro-3’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(3-amino-propil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-piridin-3-il-fenil)-4-metil-7,8-dihidro-6H-pirido [4,3-d]pirimidin-5-on;
2-amino-7-(5,2’-difluoro-4’-metil-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(1-metil-1H-pirazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(1H-pirazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-4-metil-7-(5,2’,3’-trifluoro-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(2-bromo-4-fluoro-fenil)-4-metil-6-(2-metil-2-morfolin-4-il-propil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(3’-dimetilamino-5-fluoro-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(2,4-dimetoksi-pirimidin-5-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(5-metoksi-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-pirimidin-5-il-fenil)-4-metil-6-(2-metil-2-morfolin-4-il-propil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-4-metil-6-(2-metil-2-morfolin-4-il-propil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5-fluoro-3’-metoksi-bifenil-2-il)-4-metil-6-(2-metil-2-morfolin-4-il-propil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-metoksi-5-metil-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-furan-3-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4-etoksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-metoksi-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-pirolidin-1-il-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-((R)-2-amino-4-metil-5-okso-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-7-il)-5-fluorobenzonitril;
(R)-2-amino-7-[2-(4,5-dimetoksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-kloro-4-metoksi-pirimidin-2-il)-4-tluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,5’-difluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,4’-difluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-3’,4’-dimetoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-3’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3,d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-4’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,4’-difluoro-2’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(4-fluoro-2-piridin-3-il-fenil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2,4-dimetoksi-pirimidin-5-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-fluoro-4-metoksi-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(5-metoksi-tiofen-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2-metoksi-tiazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5,6-dimetoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4-etoksi-5-fluoro-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-2’,3’-dimetoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-piridin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-fenil]-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(2-metoksi-tiazol-4-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(2-metoksi-tiazol-4-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-etil-7,8-dihidro-6H-pirido[4,3 d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-(6-metoksi-pirazin-2-il)-tiazol-4-il]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5-fluoro-2’-trifluorometil-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(4-fluoro-2-piridin-4-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-(5,3’-difluoro-4’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-4-metil-7-fenil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-6-(2-amino-etil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-metoksi-tiazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(4-fluoro-fenil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(S)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(4-fluoro-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-metil-7-fenil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-6-alil-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-etil-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-etil-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-etil-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-etil-7-(5-fluoro-3’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-etil-7-(4-fluoro-2-piridin-3-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2,4-dimetoksi-pirimidin-5-il)-4-fluoro-fenil]-6-etil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[2-(5-kloro-4-hidroksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-6-(2-hidroksi-etil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-6-(2,4-dimetoksi-benzil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(3-kloro-benzil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(3-kloro-benzil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(3-kloro-benzil)-7-[2-(5,6-dimetoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2,4-dimetoksi-benzil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2,4-dimetoksi-benzil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-6-piridin-4-ilmetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-piridin-4-ilmetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-6-piridin-4-ilmetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2-fluoro-benzil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-6-(2-fluoro-benzil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2-kloro-benzil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-6-(2-klorobenzil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-(3-trifluorometil-benzil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-6-(3-trifluorometil-benzil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2-fluoro-benzil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(2-kloro-benzil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-(tetrahidropiran-4-ilmetil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-6-(tetrahidropiran-4-ilmetil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-(2-metil-2-morfolin-4-il-propil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-(5-fluoro-3’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-4-metil-7-(5,2’,3’-trifluoro-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-(5,3’-difluoro-4’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-(4-fluoro-2-piridin-3-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[2-(2,4-dimetoksi-pirimidin-5-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-(5,2’-difluoro-4’-metil-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-benzil-7-(5,2’-difluoro-3’-metoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-amino-7-[2-(5,6-dimetoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5,6-dimetoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d] pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-metoksi-piridin-3-il)-fenil]-4-metil-6-(3-metil-butil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5,6-dimetoksi-pirazin-2-il)-4-fluoro-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-metoksi-piridin-3-il)-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido [4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-metoksi-piridin-3-il)-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(4-fluoro-benzil)-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(4-fluoro-benzil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-6-(4-fluoro-benzil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-6-izobutil-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-6-piridin-3-ilmetil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
{3-[(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-4-metil-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-propil}-karbaminska kiselina tert-butil ester;
(R)-2-amino-6-(3-amino-propil)-7-(2-bromo-4-fluoro-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
{3-[(R)-2-amino-7-(4-fluoro-2-piridin-3-il-fenil)-4-metil-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il]-propil}-karbaminska kiselina tert-butil ester;
(R)-2-amino-6-(3-amino-propil)-7-(4-fluoro-2-piridin-3-il-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(3-{(R)-2-amino-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-5-okso-7,8-dihidro-5H-pirido[4,3-d]pirimidin-6-il}-propil)-karbaminska kiselina tert-butil ester;
(R)-2-amino-6-(3-amino-propil)-7-[4-fluoro-2-(2-fluoro-piridin-3-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-6-(3-amino-propil)-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-(6-metoksi-piridin-2-il)-tiazol-4-il]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-bromo-tiazol-4-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4-etoksi-5-fluoro-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,5’-difluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,4’-difluoro-2’-metoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-3’,4’-dimetoksi-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-3’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-2’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-4’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5,4’-difluoro-2’-metil-bifenil-2-il)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4,5-dimetoksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-(6-metoksi-pirazin-2-il)-tiazol-4-il]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-piridin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2-metoksi-tiazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5,6-dimetoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(4-fluoro-2-piridin-3-il-fenil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2,4-dimetoksi-pirimidin-5-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4-etoksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-mcthoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-metoksi-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido [4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-fenil]-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[2-(2-metoksi-tiazol-4-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-kloro-4-metoksi-pirimidin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-fluoro-4-metoksi-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(4-pirolidin-1-il-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-piridin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(5-metoksi-tiofen-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-fluoro-fenil)-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-fluoro-2’,3’-dimetoksi-bifenil-2-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-4-etil-7-[4-fluoro-2-(2-metoksi-tiazol-4-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-fluoro-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
2-((R)-2-amino-4-metil-5-okso-5,6,7,8-tetrahidro-pirido[4,3-d]pirimidin-7-il)-5-fluorobenzonitril;
(R)-2-amino-7-[2-(6,etoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(4-metoksi-5-metil-pirimidin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(5-okso-4,5-dihidro-[1,3,4]oksadiazol-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(5-metoksi-[1,3,4]oksadiazol-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(S)-2-amino-7-[5-(6-metoksi-pirazin-2-il)-tiazol-4-il]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(2-metoksi-tiazol-5-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-fluoro-fenil]-4-etil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-metoksi-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-fenil)-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2-etoksi-tiazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2-etoksi-tiazol-4-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(S)-2-amino-7-[5-(6-metoksi-piridin-2-il)-tiazol-4-il]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(S)-2-amino-7-[5-(6-metoksi-pirazin-2-il)-tiazol-4-il]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etil-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-bromo-4-metoksi-fenil)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-metoksi-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-metoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-etoksi-pirazin-2-il)-4-metoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-metoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-metoksi-2-(2-metoksi-tiazol-4-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(2-etoksi-tiazol-4-il)-4-metoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(6-metoksi-5-metilamino-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-fluoro-2-(6-metoksi-5-metilamino-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-metoksi-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-metoksi-2-(6-metoksi-pirazin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-dimetilamino-6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-dimetilamino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(5-bromo-2-metoksi-piridin-4-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(6,6’-dimetoksi-[2,3’]bipiridinil-4’-il)-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-metoksi-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[5-metoksi-2-(6-metoksi-piridin-2-il)-fenil]-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-etoksi-pirazin-2-il)-4-etoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[2-(5-amino-6-metoksi-pirazin-2-il)-4-etoksi-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-etoksi-2-(6-metoksi-piridin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-[4-etoksi-2-(6-metoksi-pirazin-2-il)-fenil]-4-metil-7,8-dihidro-6H-pirido[4,3-d]pirimidin-5-on;
(R)-2-amino-7-(2-(ciklopentiloksi)-4-fluorofenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-(ciklopentiloksi)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(4-fluoro-2-izopropoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-5-fluoro-2-(6-metoksipiridin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimi-din-5(6H)-on;
(R)-2-amino-7-((R)-2-(6-metoksipiridin-2-il)-4-metilfenil)-4-metil-7,8-dihidropirido[4,3-d]pirimi-din-5(6H)-on;
(R)-2-amino-7-((R)-5-fluoro-2-(6-metoksipirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimi-din-5(6H)-on;
(R)-2-amino-7-((R)-2-(6-metoksipirazin-2-il)-4-metilfenil)-4-metil-7,8-dihidropirido[4,3-d]pirimi-din-5(6H)-on;
(R)-2-amino-7-(2-((R)-5-amino-6-(2,2,2-trifluoroetoksi)pirazin-2-il)-4-fluorofenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-5-fluoro-2-(2-metoksitiazol-4-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-2-(5-amino-6-metoksipirazin-2-il)-5-fluorofenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-2-(2-metoksitiazol-4-il)-4-metilfenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-2-(5-amino-6-metoksipirazin-2-il)-4-metilfenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-(ciklopentiloksi)-4-fluorofenil)-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-((R)-5-amino-b-(2,2,2-trifluoroetoksi)pirazin-2-il)fenil)-7,8-dihidropirido [4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-((R)-5-amino-6-(2,2,2-trifluoroetoksi)pirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-((R)-5-amino-6-(2,2,2-trifluoroetoksi)pirazin-2-il)-4-fluorofenil)-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-2-(5-amino-6-metoksipirazin-2-il)-4-fluoro-5-metoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-4-fluoro-5-metoksi-2-(6-metoksipirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(4-fluoro-5-metoksi-2-((S)-6-metoksipiridin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-4-fluoro-5-metoksi-2-(2-metoksitiazol-4-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-2-(5-amino-6-metoksipirazin-2-il)-4-izopropoksi-5-metoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-4-izopropoksi-5-metoksi-2-(6-metoksipirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(4-izopropoksi-5-metoksi-2-((S)-6-metoksipiridin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-4-izopropoksi-5-metoksi-2-(2-metoksitiazol-4-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-4,5-dimetoksi-2-(6-metoksipiridin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-4,5-dimetoksi-2-(6-metoksipirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-bromo-4,5-dimetoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-4,5-dimetoksi-2-(2-metoksitiazol-4-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-2-(5-amino-6-etoksipirazin-2-il)-4,5-dimetoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-bromo-4-etoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((S)-4-fluoro-2-(6-hidroksipiridin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-((R)-4-fluoro-2-(6-hidroksipirazin-2-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on;
(R)-2-amino-7-(2-bromo-4,5-dietoksifenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on; i
(R)-2-amino-7-((R)-4-fluoro-2-(2-hidroksitiazol-4-il)fenil)-4-metil-7,8-dihidropirido[4,3-d]pirimidin-5(6H)-on.
38. Spoj, naznačen time, da ima sljedeću strukturu
[image]
39. Sastav, naznačen time, da sadrži farmaceutski prihvatljiv nosač i spoj prema bilo kojem zahtjevu od 1 do 38.
40. Sastav prema zahtjevu 39, naznačen time, da sadrži nadalje najmanje jedno dodatno sredstvo odabrano iz skupine koju čine irinotekan, topotekan, gemcitabin, imatinib, trastuzumab, 5-fluorouracil, leukovorin, karboplatin, cisplatin, taksani, tezacitabin, ciklofosfamid, vinca alkaloidi, geftinib, vatalanib, sunitinib, sorafenib, erlotinib, deksrazoksan, antraciklini i rituksimab.
41. Sastav prema zahtjevu 39, naznačen time, da služi za liječenje raka.
42. Spoj prema bilo kojem zahtjevu od 1 do 38, naznačen time, da služi za liječenje raka.
43. Sastav prema zahtjevu 41 ili spoj prema zahtjevu 42, naznačen time, da služi za liječenje raka, pri čemu je rak odabran od raka pluća i bronhija; raka prostate; tumora testisa; raka dojke; raka gušterače; raka debelog i zadnjeg crijeva; raka tiroidne žlijezde; raka želuca; raka jetre i unutar-jetrenog žučovoda; raka bubrega i bubrežnih kanala; karličnog raka; raka mokraćnog mjehura; raka tijela maternice; raka grlića maternice; raka jajnika; višestrukog mijeloma; ezofagusa; akutne mijelogene leukemije; kronične mijelogene leukemije; limfocitne leukemije; limfoma; mijeloidne leukemije; leukemije glavnih stanica; raka mozga; raka usne šupljine i ždrijela; raka grla; tumora glave; vratnih tumora; glioblastoma; raka tankog crijeva; gastrointestinalnih stromalnih tumora (GIST); gastričkog tumora; ne-hodgkin limfoma; melanoma; i villous adenoma debelog crijeva.
44. Postupak za pripravu spoja prema zahtjevu 1 formule (I) ili njegovog stereoizomera, tautomera ili njegove farmaceutski prihvatljive soli, naznačen time, da obuhvaća
(a) reakciju spoja formule (I) s kiselinom za tvorbu dodatne kiselinske soli; ili
(b) reakciju dodatne kiselinske soli formule (I) za tvorbu spoja formule (I) sa slobodnom bazom; ili
(c) reakciju intermedijernog spoja formule (VI) s guanidinom ili s derivatom guanidina,
[image]
pri čemu su Ra, R, i Rb određeni za formulu (I), a W je O ili NR’R'' gdje su R’ i R" neovisno H ili alkil, za tvorbu spoja formule (I).
45. Intermedijerni spoj prema zahtjevu 44, naznačen time, da ima formulu (VI) gdje Ra je metil.
46. Intermedijerni spoj prema zahtjevu 44, naznačen time, da ima formulu (VII)
[image]
Gdje
R je određen za formulu (VI);
R5 je vodik ili halo; a R6a je odabran iz skupine koju čine halo, supstituirani ili nesupstituirani aril, isupstituirani ili nesupstituirani heteroaril.
47. Kombinacija, naznačena time, da sadrži spoj prema bilo kojem zahtjevu od 1 do 38 zajedno s jednim ili više dodatnih sredstava, za davanje istovremeno ili u različitim vremenskim intervalima, u svrhu liječenja raka.
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CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
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KR101653560B1 (ko) * | 2016-02-02 | 2016-09-12 | 한국화학연구원 | 신규한 화합물 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 함유하는 인플루엔자 바이러스 감염으로 인한 질환의 예방 또는 치료용 약학적 조성물 |
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JPS6165873A (ja) | 1984-09-07 | 1986-04-04 | Mitsui Petrochem Ind Ltd | 2−ピペラジノピリミジン誘導体 |
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