ME01952B - 2-amino-7,8-dihydro-6h-pyrido[4,3-d] pyrimidin-5-ones - Google Patents
2-amino-7,8-dihydro-6h-pyrido[4,3-d] pyrimidin-5-onesInfo
- Publication number
- ME01952B ME01952B MEP-2011-334A MEP33411A ME01952B ME 01952 B ME01952 B ME 01952B ME P33411 A MEP33411 A ME P33411A ME 01952 B ME01952 B ME 01952B
- Authority
- ME
- Montenegro
- Prior art keywords
- amino
- pyrimidin
- phenyl
- methyl
- fluoro
- Prior art date
Links
- 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
- -1 2-methyl-2-morpholinopropyl Chemical group 0.000 claims 309
- 150000001875 compounds Chemical class 0.000 claims 43
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 239000001257 hydrogen Substances 0.000 claims 28
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 150000003839 salts Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 7
- 125000001041 indolyl 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
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 150000002357 guanidines Chemical class 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
- 150000001356 alkyl thiols Chemical class 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 239000000651 prodrug Chemical class 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 3
- 150000003573 thiols Chemical class 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- VBWJSOZNRRIJKW-CYBMUJFWSA-N (7r)-2-amino-4-ethyl-7-[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=CC=C1C1=CSC(OC)=N1 VBWJSOZNRRIJKW-CYBMUJFWSA-N 0.000 claims 2
- ZSOOONHJQCGYGH-CQSZACIVSA-N (7r)-2-amino-4-ethyl-7-[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=CC=C1C1=CN=CC(OC)=N1 ZSOOONHJQCGYGH-CQSZACIVSA-N 0.000 claims 2
- PUZHLUJYTGUFDZ-MRXNPFEDSA-N (7r)-2-amino-4-ethyl-7-[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=CC=C1C1=CC=CC(OC)=N1 PUZHLUJYTGUFDZ-MRXNPFEDSA-N 0.000 claims 2
- 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
- JHPAFJTVQHGETR-GFCCVEGCSA-N (7r)-2-amino-7-[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=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 JHPAFJTVQHGETR-GFCCVEGCSA-N 0.000 claims 2
- XDHFEFLWTMOYPX-MRXNPFEDSA-N (7r)-2-amino-7-[2-(3,4-dimethoxyphenyl)-4-fluorophenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 XDHFEFLWTMOYPX-MRXNPFEDSA-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
- 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
- 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
- GEVQNWGODDAVJD-OAHLLOKOSA-N (7r)-2-amino-7-[2-(6-ethoxypyrazin-2-yl)-4-fluorophenyl]-4-ethyl-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(CC)N=C(N)N=C3C2)=N1 GEVQNWGODDAVJD-OAHLLOKOSA-N 0.000 claims 2
- JRWDAMDIXNLHPV-CQSZACIVSA-N (7r)-2-amino-7-[2-(6-ethoxypyrazin-2-yl)-4-fluorophenyl]-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=CN=C(N)N=C3C2)=N1 JRWDAMDIXNLHPV-CQSZACIVSA-N 0.000 claims 2
- BGOLLOXAKPBNOR-CQSZACIVSA-N (7r)-2-amino-7-[2-(6-ethoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CCOC1=CN=CC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 BGOLLOXAKPBNOR-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
- KVFSDPAXFWZEOO-CYBMUJFWSA-N (7r)-2-amino-7-[2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-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=C(C)N=C(N)N=C3C2)=N1 KVFSDPAXFWZEOO-CYBMUJFWSA-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
- 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 2
- URIQODZTLUYWGV-MRXNPFEDSA-N (7r)-2-amino-7-[4-fluoro-2-(4-fluoro-2-methoxyphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC(F)=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 URIQODZTLUYWGV-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
- 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 239000000203 mixture Substances 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
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- 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
- XREFELMPQYYTQL-CYBMUJFWSA-N (7r)-2-amino-7-[2-(2-ethoxy-1,3-thiazol-4-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound S1C(OCC)=NC(C=2C(=CC=CC=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 XREFELMPQYYTQL-CYBMUJFWSA-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
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- 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
- KTNKZWOMALPZFU-CQSZACIVSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)-4-fluorophenyl]-4-ethyl-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(CC)N=C(N)N=C3C2)=C1 KTNKZWOMALPZFU-CQSZACIVSA-N 0.000 claims 1
- ZKSUZLKXPDCNJT-CQSZACIVSA-N (7r)-2-amino-7-[2-(5-amino-6-ethoxypyrazin-2-yl)-4-methoxyphenyl]-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(OC)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=C1 ZKSUZLKXPDCNJT-CQSZACIVSA-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
- 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
- ZTXPMQQFANTVSM-OAQYLSRUSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)-4-fluorophenyl]-6-[(2-chlorophenyl)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)Cl)=C1 ZTXPMQQFANTVSM-OAQYLSRUSA-N 0.000 claims 1
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- 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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- 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 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
- XIXQWXAXKHFMOV-GFCCVEGCSA-N (7r)-2-amino-7-[2-(5-amino-6-methoxypyrazin-2-yl)phenyl]-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=CN=C(N)N=C3C2)=C1 XIXQWXAXKHFMOV-GFCCVEGCSA-N 0.000 claims 1
- 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 1
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- YYVZNVJHYCNNAS-OAHLLOKOSA-N (7r)-2-amino-7-[2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-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=C(C)N=C(N)N=C3C2)=N1 YYVZNVJHYCNNAS-OAHLLOKOSA-N 0.000 claims 1
- 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
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- NEBIQJIIOIAQDK-CQSZACIVSA-N (7r)-2-amino-7-[4-fluoro-2-(2-fluoropyridin-3-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=C1C1=CC=CN=C1F NEBIQJIIOIAQDK-CQSZACIVSA-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
- 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 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
- XPUWYJKHTWTOBQ-OAQYLSRUSA-N (7r)-2-amino-7-[4-fluoro-2-(2-methoxypyridin-3-yl)phenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=NC=CC=C1C1=CC(F)=CC=C1[C@@H]1N(CCC(C)C)C(=O)C2=C(C)N=C(N)N=C2C1 XPUWYJKHTWTOBQ-OAQYLSRUSA-N 0.000 claims 1
- 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
- MJWHLLCUDBSQTP-QGZVFWFLSA-N (7r)-2-amino-7-[4-fluoro-2-(4-fluoro-2-methylphenyl)phenyl]-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC1=CC(F)=CC=C1C1=CC(F)=CC=C1[C@@H]1NC(=O)C2=CN=C(N)N=C2C1 MJWHLLCUDBSQTP-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
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- 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
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- 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
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- XRFHWSYKRFEPRA-CYBMUJFWSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyrazin-2-yl)phenyl]-4-methyl-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CN=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(=O)C3=C(C)N=C(N)N=C3C2)=N1 XRFHWSYKRFEPRA-CYBMUJFWSA-N 0.000 claims 1
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- HGAWINPTRRJJMQ-CYBMUJFWSA-N (7r)-2-amino-7-[4-fluoro-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=C(F)C=2)[C@@H]2NC(=O)C3=CN=C(N)N=C3C2)=N1 HGAWINPTRRJJMQ-CYBMUJFWSA-N 0.000 claims 1
- QDKJJHPEDAWSFV-HXUWFJFHSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-6-(2-methylpropyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=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 QDKJJHPEDAWSFV-HXUWFJFHSA-N 0.000 claims 1
- SHRULSHFCCBDNO-OAQYLSRUSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-6-(3-methylbutyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=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 SHRULSHFCCBDNO-OAQYLSRUSA-N 0.000 claims 1
- QANWJNBGIFWSKZ-JOCHJYFZSA-N (7r)-2-amino-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-6-(oxan-4-ylmethyl)-7,8-dihydropyrido[4,3-d]pyrimidin-5-one Chemical compound COC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2N(C(=O)C3=C(C)N=C(N)N=C3C2)CC2CCOCC2)=N1 QANWJNBGIFWSKZ-JOCHJYFZSA-N 0.000 claims 1
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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
- A61K31/505—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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine 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)
Claims (47)
1. Jedinjenje formule (I): ili stereoizomer, tautomer ili farmaceutski prihvatljiv oblik soli, gde je Ra odabran iz grupe koju čine (1) vodonik, (2) halogen, (3) hidroksil, (4) C1-C6 alkoksi, (5) tiol, (6) C1-C6 alkiltiol, (7) supstituisana ili nesupstituisana C1-C6 alkil grupa, (8) amino ili supstituisana amino grupa, (9) supstitusana ili nesupstituisana aril grupa, (10) supstitusana ili nesupstituisana heteroaril grupa, i (11) supstitusana ili nesupstituisana heterociklil grupa; R je odabran iz grupe koju čine (1) vodonik, (2) supstitusana ili nesupstituisana C1-C6 alkil grupa, (3) supstitusana ili nesupstituisana C2-C6 alkenil grupa, (4) supstitusana ili nesupstituisana C2-C6 alkinil grupa, (5) supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, (6) supstitusana ili nesupstituisana C5-C7 cikloalkenil grupa, (7) supstitusana ili nesupstituisana aril grupa, (8) supstitusana ili nesupstituisana heteroaril grupa, i (9) supstitusana ili nesupstituisana heterociklil grupa; Rbje odabran iz grupe koju čine (1) supstitusan ili nesupstituisan C3-C7 cikloalkil, (2) supstitusan ili nesupstituisan C5-C7 cikloalkenil, (3) supstitusan ili nesupstituisan aril, (4) supstitusan ili nesupstituisan heteroaril, i (5) supstitusan ili nesupstituisan heterociklil; i s tim da kada je Ra amino grupa, tada Rb nije fenil, 4-alkil-fenil, 4-alkoksi-fenil, ili 4-halo-fenil grupa.
2. Jedinjenje iz patentnog zahteva 1, naznačen time, što je Ra C1-C6 alkil ili halo C1-C6 alkil grupa.
3. Jedinjenje iz patentnog zahteva 1, naznačen time, što je Rb aril ili heteroaril grupa.
4. Jedinjenje iz patentnog zahteva 3, naznačen time, što je Rb neki iz grupe koju čine fenil, piridil, pirimidinil, pirazinil, indolil, tiazolil i tienil.
5. Jedinjenje iz patentnog zahteva 1, naznačen time, što je Rb jedan iz grupe koju čine fenil, supstituisani piridil, supstituisani pirimidinil, supstituisani pirazinil, supstituisani indolil, supstituisani tiazolil, i supstituisani tienil.
6. Jedinjenje iz patentnog zahteva 5, naznačen time, što je pomenuti fenil, piridil, pirimidinil, pirazinil, indolil, tiazolil i tienil zamenjen sa supstituisanom ili nesupstituisanom aril ili supstituisanom ili
7. Jedinjenje iz patentnog zahteva 5, naznačen time, što je pomenuti fenil, piridil, pirimidinil, pirazinil, indolil, tiazoiil i tienil zamenjen sa halo grupom.
8. Jedinjenje iz patentnog zahteva 7, naznačen time, što je pomenuta halo grupa ovde fluoro.
9. Jedinjenje iz patentnog zahteva 1, naznačen time, što je R jedan iz grupe koju čine vodonik, nesupstituisana alkil i substituisana alkil grupa.
10. Jedinjenje iz patentnog zahteva 9, naznačen time, što je R jedan iz grupe koju čine vodonik, benzil, 1-(4-metoksifenil)etil, metil, 3-aminopropil i 2-metil-2-morfolinopropil.
11. Jedinjenje iz patentnog zahteva 1 formule (la) naznačen time što su, R, Ra i Rb prethodno definisani za formulu (I).
12. Jedinjenje iz patentnog zahteva 1 formule (II): ili stereoizomer, tautomer ili farmaceutski prihvatljiv oblik soli ili prolek, gde je n 0 ili 1, gde je Ra odabran iz grupe koju čine: (1) vodonik, (2) halogen, (3) hidroksil, (4) C1-C6 alkoksi, (5) tiol, (6) C1-C6 alkiltiol, (7) supstitusana ili nesupstituisana C1-C6 alkil grupa, (8) amino ili supstituisana amino grupa, (9) supstitusana ili nesupstituisana aril grupa, (10) supstitusana ili nesupstituisana heteroaril grupa i (11) supstitusana ili nesupstituisana heterociklil grupa; gde je R odabran iz grupe koju čine (1) vodonik, (2) supstitusana ili nesupstituisana C1-C6 alkil grupa, (3) supstitusana ili nesupstituisana C2-C6 alkenil grupa, (4) supstitusana ili nesupstituisana C2-C6 alkinil grupa, (5) supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, (6) supstitusana ili nesupstituisana C5-C7 cikloalkenil grupa, (7) supstitusana ili nesupstituisana aril grupa, (8) supstitusana ili nesupstituisana heteroaril grupa i (9) supstitusana ili nesupstituisana heterociklil grupa, gde je kada je n 1, X je C, Y je na svakoj poziciji nezavisno odabran iz CQ1 i N, a Z je odabran iz CR2 i N pod uslovom da ne više od 3 Y i Z grupa su N, i gde je kada je n 0, X je C ili N, Y je na svakoj poziciji nezavisno odabran iz CQ' N, NQ2, O, i S pod uslovom da ne više od 4 X i Y grupa je N i NQ2 i ne više od 1 Y grupe je S ili O; gde je Q1 na svakoj poziciji nezavisno odabran iz grupe koju čine (1) vodonik, (2) halogen, (3) supstitusana ili nesupstituisana C1-C6 alkil grupa, (4) supstitusana ili nesupstituisana C2-C6 alkenil grupa, (5) supstitusana ili nesupstituisana C2-C6 alkinil grupa, (6) supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, (7) supstitusana ili nesupstituisana C5-C7 cycloalkenil grupa, (8) supstitusana ili nesupstituisana aril grupa, (9) supstitusana ili nesupstituisana heteroaril grupa, (10) supstitusana ili nesupstituisana heterociklil grupa, (11) supstitusana ili nesupstituisana amino grupa, (12) -OR3 ili -SR3 (13) -C(O)R3, -CO2R3, -C(O)N(R3)2, -S(O)R3, -SO2R3, ili - SO2N(R3)2, (14) -OC(O)R3, -N(R3)C(O)R3, ili -N(R3)SO2R3, (15) -CN, i (16) -N02; gde je Q2 na svakoj poziciji nezavisno odabran iz grupe koju čine (1) vodonik, (3) supstitusana ili nesupstituisana C1-C6 alkil grupa, (4) supstitusana ili nesupstituisana C2-C6 alkenil grupa, (5) supstitusana ili nesupstituisana C2-C6 alkinil grupa, (6) supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, (7) supstitusana ili nesupstituisana C5-C7 cikloalkenil grupa, (8) supstitusana ili nesupstituisana aril grupa, (9) supstitusana ili nesupstituisana heteroaril grupa, i (10) supstitusana ili nesupstituisana heterociklil grupa; gde je R2 odabran iz grupe koju čine (1) vodonik, (2) halogen, (3) supstitusana ili nesupstituisana C1-C3 alkil grupa, i (4) -OR3, -SR3, ili -NHR3; gde je R3 na svakoj poziciji nezavisno odabran iz grupe koju čine (1) vodonik, (2) supstitusana ili nesupstituisana C1-C6 alkil grupa, (3) supstitusana ili nesupstituisana C2-C6 alkenil grupa, (4) supstitusana ili nesupstituisana C2-C6 alkinil grupa, (5) supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, (6) supstitusana ili nesupstituisana C5-C7 cikloalkenil grupa, (7) supstitusana ili nesupstituisana aril grupa, (8) supstitusana ili nesupstituisana heteroaril grupa, i Pod uslovom da kada je Ra amino grupa, tada X, Y, Z, i n zajedno ne formiraju fenil, 4-alkil-fenil, 4-alkoksi-fenil, ili 4-halo-fenil grupu.
13. Jedinjenje iz patentnog zahteva 12, naznačen time, što je jedan od Q1 ili Q2 odabran iz grupe koju čine supstitusana ili nesupstituisana aril grupa, supstitusana ili nesupstituisana heterociklil grupa, supstitusana ili nesupstituisana heteroaril grupa, supstitusana ili nesupstituisana C3-C7 cikloalkil grupa, i supstitusana ili nesupstituisana C5-C7 cikloalkenil grupa.
14. Jedinjenje iz patentnog zahteva 13, naznačen time, što su pomenute aril, heterociklil, heteroaril, C3-C7 cikloalkil, i C5-C7 cikloalkenil grupa odabrani iz grupe koju čine fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, furanil, hinolinil, izohinolinil, izoksazolil, oksazolil, tiazolil, morfolin, piperidinil, pirolidinil, tienil, cikloheksil, ciklopentil, cikloheksenil, i ciklopentenil.
15. Jedinjenje iz patentnog zahteva 14, naznačen time, što je jedan od Q1 ili Q2 odabran iz grupe koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1H-pirazol-4-il, 1 -metil-1 H-pirazol-4-il, 1 -metil-1 H-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-hloro-4-metoksi-pirimidin-5-il, 2-hloro-5-fluoro-piridin-3-il, 2-hloro-fenil, 2-hloro-piridin-3-il, 2-hloro-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-izohinolin-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-hloro-pirazin-2-il, 3-cianofenil, 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-hloro-2, 5-dimetoksi-fenil, 4-hloro-2-fluoro-fenil, 4-hloro-2-metoksi-5-metil-fenil, 4-hloro-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-1 H-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-hloro-4-metoksi-pirimidin-2-il, 5-hloro-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-hloro-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. Jedinjenje iz patentnog zahteva 12 formule (IIa): ili tautomer, ili farmaceutski prihvatljiv oblik soli, gde su Ra, R, X, Y, Z, i n prethodno definisani za formulu (II).
17. Jedinjenje iz patentnog zahteva 1 formule (III): ili stereoizomer, tautomer ili farmaceutski prihvatljiv oblik soli, gde je Ra odabran iz grupe koju čine (1) vodonik, (2) halogen, (3) hidroksilna grupa, (4) C1-C6 alkoksi grupa, (5) tiol, (6) C1-C6 alkiltiol, (7) supstitusana ili nesupstituisana C1-C6 alkil grupa, (8) amino ili supstituisana amino grupa (9) supstitusana ili nesupstituisana aril grupa, (10) supstitusana ili nesupstituisana heteroaril grupa, i (11) supstitusana ili nesupstituisana heterociklil grupa; R4 je vodonik ili supstitusana ili nesupstituisana C1-C6 alkil grupa; R5 je vodonik, alkil, alkoksi, ili halo grupa; R6, R7, R8, i R9 su svaki za sebe, nezavisno odabrani iz grupe koju čine vodonik, alkil grupa, alkoksi grupa, halo grupa, supstitusana ili nesupstituisana aril grupa, i supstitusana ili nesupstituisana heteroaril grupa; ili stereoizomer, tautomer, ili farmaceutski prihvatljiv oblik soli i pod uslovom da kada je Ra amino grupa i kada je R6, R7, R8, i R9 je vodonik, tada R5 nije vodonik, alkil, alkoksi, ili halo grupa.
18. Jedinjenje iz patentnog zahteva 1, 12 ili 17, naznačen time, što je Ra vodonik.
19. Jedinjenje iz patentnog zahteva 12 ili 17, naznačen time, što je Ra supstitusan ili ne supstituisan C1-C6 alkil.
20. Jedinjenje iz patentnog zahteva 2 ili 19 naznačen time, što je Ra metil.
21. jJdinjenje iz patentnog zahteva 20, naznačen time, što je R4 odabran iz grupe koju čine vodonik, benzil, 1-(4-metoksifenil)etil, metil, 3-aminopropil, i 2-metil-2-morfolinopropil.
22. Jedinjenje iz patentnog zahteva 21, naznačen time, što je R4 vodonik.
23. Jedinjenje iz patentnog zahteva 17, naznačen time, što je svaki od R7, R8, i R9 vodonik.
24. Jedinjenje iz patentnog zahteva 17, naznačen time, što je R6 odabran iz grupe koju čine supstituisana aril i supstituisana heteroaril grupa.
25. Jedinjenje iz patentnog zahteva 24, naznačen time, što su pomenuti aril i heteroaril odabrani iz grupe koju čine furanil, pirrolil, fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, hinolinil, izohinolinil, izoksazolil, oksazolil, tiazolil, i tienil.
26. Jedinjenje iz patentnog zahteva 25, naznačen time, što je R6 odabran iz grupe koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1 H-pirazol-4-il, 1 -metil-1 H-pirazol-4-il, 1 -metil-1 H-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-hloro-4-metoksi-pirimidin-5-il, 2-hloro-5-fluoro-piridin-3-il, 2-hloro-fenil, 2-hloro-piridin-3-il, 2-hloro-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-izohinolin-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-hloro-pirazin-2-il, 3-cianofenil, 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-trifiuorometilfenil, 4, 5-dimetoksi-pirimidin-2-il, 4-amino-5-fluoro-pirimidin-2-il, 4-hloro-2, 5-dimetoksi-fenil, 4-hloro-2-fluoro-fenil, 4-hloro-2-metoksi-5-metil-fenil, 4-hloro-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-1 H-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-hloro- 4- metoksi-pirimidin-2-il, 5-hloro-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-hloro-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-ii, 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.
27. Jedinjenje iz patentnog zahteva 17 formule (IIIa): ili tautomer ili farmaceutski prihvatljiv oblik soli, ili prolek, gde su Ra, R4, X, Y, Z, i n prethodno definisani za formulu (III) u uz uslov da kada je Ra amino grupa i R6, R7, R8, i R9 su vodonik, tada R5 nije vodonik, alkil, alkoksi, ili halo grupa.
28. Jedinjenje iz patentnog zahteva 1 formule (IV): ili stereoizomer, tautomer, ili farmaceutski prihvatljiv oblik soli, ili prolek, gde je, R4 je vodonik ili supstitusana ili nesupstituisana C1-C6 alkil grupa R5 je vodonik ili halo grupa, R6a je odabran iz grupe koju čine vodonik, halo, supstitusana ili nesupstituisana aril, i supstitusana ili nesupstituisana heteroaril grupa.
29. Jedinjenje iz patentnog zahteva 28, naznačen time, što je R4 odabran iz grupe koju čine vodonik, benzil, 1 -(4-metoksifenil)etil, metil, 3-aminopropil, i 2-metil-2-morfolinopropil grupa.
30. Jedinjenje iz patentnog zahteva 1 7 ili 29, naznačen time, što je R5 vodonik ili fluoro.
31. Jedinjenje iz patentnog zahteva 28, naznačen time, što je R6a odabran iz grupe koju čine supstituisana aril i supstituisana heteroaril grupa.
32. Jedinjenje iz patentnog zahteva 31, naznačen time, što su pomenute aril i heteroaril grupa odabrane iz grupe koju čine furanil, pirrolil, fenil, piridil, pirazinil, pirimidinil, piridazinil, pirazolil, imidazolil, triazolil, indolil, oksadiazol, tiadiazol, hinolinil, izohinolinil, izoksazolil, oksazolil, tiazolil, i tienil.
33. Jedinjenje iz patentnog zahteva 32, naznačen time, što je R6a odabran iz grupe koju čine (2-hidroksi-etilamino)-pirazin-2-il, 1 H-pirazol-4-il, 1 -metil-1 H-pirazol-4-il, 1 -metil-1 H-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-hloro-4-metoksi-pirimidin-5-il, 2-hloro-5-fluoro-piridin-3-il, 2-hloro-fenil, 2-hloro-piridin-3-il, 2-hloro-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-izohinolin-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-hloro-pirazin-2-il, 3-cianofenil, 3-dimetilaminofenil, 3-etoksi-feni!, 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-hloro-2, 5-dimetoksi-fenil, 4-hloro-2-fluoro-fenil, 4-hloro-2-metoksi-5-metil-fenil, 4-hloro-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-1 H-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-T -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-cloro- 4- metoksi-pirimidin-2-il, 5-hloro-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-hloro-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.
34. Jedinjenje iz patentnog zahteva 28 formule (IVa): ili tautomer ili farmaceutski prihvatljiv oblik soli, naznačen time, što su R4, R5, i R6a prethodno definisani za formulu (IV).
35. Jedinjenje iz patentnog zahteva 12 formule (V): naznačen time, što su R10 i R11 svaki za sebe Q1 a Ra, R, Q1 i Q2 su prethodno definisani za formulu (II).
36. Jedinjenje iz patentnog zahteva 35 formule (Va): gde su R10 i R11 svaki za sebe Q1 a Ra, R, Q1 i Q2 su prethodno definisani za formulu (V).
37. Jedinjenje ili stereoizomer, tautomer, ili farmaceutski prihvatljiv oblik soli iz patentnog zahteva 1 odabran od (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-hloro-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-izohinolin-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-hloro-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-metii-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-1 H-pirazol-4-il)-fenil]-4-metil-7, 8-dihidro-6H-pirido[4, 3-d]pirimidin-5-on; 2-amino-7-[4-fluoro-2-(1 H-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-fluoro-benzonitril; (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-hloro-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-[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)-4-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-rnetoksi-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-hloro-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-hloro-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-hloro-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-hloro-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-il-metil-7, 8-dihidro-6H-pirido[4, 3-d]pirimidin-5-on; (R)-2-amino-7-[4-fluoro-2-(6-rnetoksi-pirazin-2-il)-fenil]-4-metil-6-piridin-4-il-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-6-piridin-4-il-metil-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-hloro-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-hloro-benzil)-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-hloro-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-il-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-(tetrahidropiran-4-il-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-(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’-rnetoksi-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[4t3-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-rrietil-7T8-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-dJpirimidin-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-rnetoksi-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]pinmidin-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-arnino-6-metoksi-pirazin-2-il)-4-fluoro-fenil]-6-izibutil- 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-il-metil-7, 8-dihidro-6H-pirido[4, 3-d]pirimidin-5-on; Terc-butil ester {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}- karbaminske kiseline; (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; Terc-butil ester {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}- karbaminske kiseline; (R)-2-amino-6-(3-amino-propil)-7-(4-fluoro-2-piridin-3-il-fenil)-4-metii- 7. 8- dihidro-6H-pirido[4, 3-d]pirimidin-5-on; Terc-butil ester (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}-karbaminske kiseline; (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-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-(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-hloro-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-i! )-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-arriino-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-fluoro-benzonitril; (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, 2, 3]-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-tiazoi-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’]bipiridin-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-fiuorofenil)-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]pirimidin-5(6H)-on; (R)-2-amino-7-((R)-2-(6-metoksipiridin-2-il)-4-metilfenil)-4-metil-7, 8- dihidropirido[4, 3-d]pirimidin-5(6H)-on; (R)-2-amino-7-((R)-5-fluoro-2-(6-metoksipirazin-2-il)fenil)-4-metil- 7, 8-dihidropirido[4, 3-d]pirimidin-5(6H)-on; (R)-2-amino-7-((R)-2-(6-metoksipirazin-2-il)-4-metilfenil)-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)-4-metil-7, 8-dihidropirido[4, 3-djpirimidin-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-6-(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. Jedinjenje strukturne formule
39. Mešavina koja obuhvata farmaceutski prihvatljiv nosač i jedinjenje prema bilo kojem od patentnih zahteva od 1 do 38.
40. Mešavina prema patentnom zahtevu 39, naznačen time, što dalje obuhvata bar još jedno sredstvo odabrano iz grupe koju čine irinotekan, topotekan, gemkitabin, imatinib, trastuzumab, 5’fluorouracil, leukovorin, karboplatin, cisplatin, taksani, tezacinatibin, ciklofosfamid, vinka alkaloidi, geftinib, vatalanib, sunitinib, sorafenib, erlotinib, deksrazoksan, antraciklini i rituksimab.
41. Jedinjenje prema patentnom zahtevu 39, naznačen time, što se koristi za lečenje kancera.
42. Jedinjenje prema bilo kojem patentnom zahtevu od 1 do 38, naznačen time, što se koristi za lečenje kancera.
43. Jedinjenje prema patentnom zahtevu 41 ili jedinjenje prema patentnom zahtevu 42, naznačen time, što se koristi za lečenje kancera, kada se radi o kanceru iz grupe koju čine kancer pluća i bronhija; prostate; tumor testisa; dojke; pankreasa; kancer debelog creva i rektuma; štitaste žlezde; stomaka; jetre i žučne kese; kancer bubrega; karlice; kancer bešike, materice; grlića materice; jajnika; multipli mijelom; jednjaka; akutna mijelogena leukemija; hronična mijelogena leukemija, limfocitna leukemia; limfom; mijeloidna leukemija; leukemija mast ćelija, tumor mozga; usna duplja i farinks; larinks; glave; vrata; glioblastom; tanko crevo; gastrointestinalni stromalni tumori (GIST); tumor želudca; ne-hodžkinsov limfom; melanom; i vilozni adenom kolona.
44. Postupak za dobijanje jedinjenja prema patentnom zahtevu 1 formule (I) ili stereoizomera, tautomera ili farmaceutski prihvatljivog oblika soli, naznačen time, što obuhvata (a) reakciju jedinjenja formule (I) sa kiselinom da bi se dobila kisela adiciona so; ili b) reakciju kisele adicion soli formule (I) da bi se dobila slobodna baza formule (I); ili c) reakciju intermedijarnog jedinjenja formule (VI) sa gvanidinom ili derivatom gvanidina (VI) gde su Ra, R, i Rb definisani za formulu (I) i W je O ili NR'R" gde su R' i R" nezavisno H ili alkil da bi obrazovali jedinjenje formule (I).
45. Intermedijarno jedinjenje prema patentnom zahtevu 44, naznačen time, što je Ra metil.
46. Intermedijarno jedinjenje prema patentnom zahtevu 44 formule naznačen time, što je R je definisan za formulu (VI); R5 je vodonik ili halo grupa; a R6a je odabran iz grupe koju čine halo, supstituisan ili nesupstituisan aril i supstituisan ili nesupstituisan heteroaril.
47. Kombinacija koja obuhvata jedinjenje prema bilo kojem od patentnih zahteva od 1 do 38 zajedno sa jednim ili više dodatnih agenasa, za davanje u isto ili različito vreme, za lečenje kancera.
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| PCT/US2006/038181 WO2007041362A1 (en) | 2005-09-30 | 2006-09-28 | 2-amino-7,8-dihydro-6h-pyrido[4,3-d] pyrimidin-5-ones |
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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. |
| CN101225083A (zh) * | 2007-01-16 | 2008-07-23 | 北京摩力克科技有限公司 | 四氢喹唑啉酮类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| GB2449293A (en) * | 2007-05-17 | 2008-11-19 | Evotec | Compounds having Hsp90 inhibitory activity |
| ES2475206T3 (es) * | 2008-02-01 | 2014-07-10 | Takeda Pharmaceutical Company Limited | Derivados de oxima como inhibidores de HSP90 |
| JP2012503619A (ja) | 2008-09-26 | 2012-02-09 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Ｈｃｖ感染に対する抗ウイルス治療のための標的としての宿主細胞キナーゼ |
| CN105727297A (zh) * | 2008-11-28 | 2016-07-06 | 诺华股份有限公司 | 包含hsp90抑制剂和mtor抑制剂的药物组合 |
| MA32933B1 (fr) * | 2008-11-28 | 2012-01-02 | Novartis Ag | Combinaison d'inhibiteurs de hspo90 et d'herceptine |
| BRPI0924107A2 (pt) * | 2008-11-28 | 2019-09-24 | Novartis Ag | inibidores de hsp90 para tratamento terapêutico |
| AR075180A1 (es) * | 2009-01-29 | 2011-03-16 | Novartis Ag | Formulaciones orales solidas de una pirido-pirimidinona |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| SG10201407012XA (en) * | 2009-10-29 | 2014-11-27 | Genosco | Kinase inhibitors |
| WO2012104823A2 (en) | 2011-02-04 | 2012-08-09 | Novartis Ag | Pyridopyrimidinone compounds in the treatment of neurodegenerative diseases |
| MX2014004559A (es) | 2011-10-14 | 2014-08-01 | Novartis Ag | Derivados de 2-carboxamida cicloamino urea en combinacion con inhibidores de hsp90 para el tratamiento de enfermedades proliferativas. |
| ITTO20111013A1 (it) | 2011-11-03 | 2013-05-04 | Dac Srl | Composti farmaceutici |
| CN103664938A (zh) * | 2012-09-12 | 2014-03-26 | 山东亨利医药科技有限责任公司 | 含有嘧啶并环的syk抑制剂 |
| WO2014074580A1 (en) | 2012-11-07 | 2014-05-15 | Novartis Ag | Combination therapy |
| US9677907B2 (en) * | 2013-03-14 | 2017-06-13 | Itron Inc | Intelligent receptacle |
| GB201306610D0 (en) * | 2013-04-11 | 2013-05-29 | Almac Discovery Ltd | Pharmaceutical compounds |
| HUE053617T2 (hu) * | 2013-09-30 | 2021-07-28 | Taiho Pharmaceutical Co Ltd | Kombinációs rákterápia azabiciklo vegyületet felhasználva |
| RU2690853C2 (ru) * | 2014-09-02 | 2019-06-06 | Пьер Фабр Медикамент | Производные изохинолинона, полезные для лечения рака |
| KR20160035411A (ko) * | 2014-09-23 | 2016-03-31 | 주식회사 오스코텍 | LRRK2 (Leucine Rich Repeat Kinase 2) 키나제 억제제로서의 피리도피리미딘 유도체 화합물 |
| 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 |
| RU2629599C1 (ru) * | 2016-09-28 | 2017-08-30 | Государственное бюджетное учреждение здравоохранения Московской области "Московский областной научно-исследовательский клинический институт им. М.Ф. Владимирского" (ГБУЗ МО МОНИКИ им. М.Ф. Владимирского) | Способ химиолучевого лечения опухолей прямой кишки и анального канала |
| WO2018225851A1 (ja) | 2017-06-09 | 2018-12-13 | 中外製薬株式会社 | Ｎ－置換アミノ酸を含むペプチドの合成方法 |
| CN115916752B (zh) * | 2020-06-26 | 2025-05-06 | 日本农药株式会社 | 芳基四氢吡啶衍生物或其盐类、和含有该化合物的杀虫剂及其使用方法 |
| AU2022234998B2 (en) * | 2021-03-08 | 2025-04-10 | Jinan University | Pyridopyrimidine compounds and applications thereof |
| WO2026027375A1 (de) | 2024-07-29 | 2026-02-05 | Bayer Aktiengesellschaft | Hydroxy-dihydropyridinon carboxamide als schädlingsbekämpfungsmittel |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| US4734418A (en) * | 1984-12-14 | 1988-03-29 | Mitsui Petrochemical Industries, Ltd. | Quinazoline compounds and antihypertensives |
| MA21177A1 (fr) * | 1987-02-11 | 1988-10-01 | May & Baker Ltd | Diones cycliques. |
| DE60206363T2 (de) * | 2001-02-12 | 2006-07-06 | F. Hoffmann-La Roche Ag | 6-substituierte pyridopyrimidine |
| DE102004018198A1 (de) * | 2004-04-15 | 2005-11-03 | Merck Patent Gmbh | Sulfonamide |
| WO2006045010A2 (en) | 2004-10-20 | 2006-04-27 | Resverlogix Corp. | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| US20100152206A1 (en) * | 2005-01-07 | 2010-06-17 | Ralph Mazitschek | Bicyclic Dihydropyrimidines and Uses Thereof |
| US20070027150A1 (en) * | 2005-04-14 | 2007-02-01 | Bellamacina Cornelia R | 2-Amino-quinazolin-5-ones |
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