JP2003528095A5 - - Google Patents
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- JP2003528095A5 JP2003528095A5 JP2001568932A JP2001568932A JP2003528095A5 JP 2003528095 A5 JP2003528095 A5 JP 2003528095A5 JP 2001568932 A JP2001568932 A JP 2001568932A JP 2001568932 A JP2001568932 A JP 2001568932A JP 2003528095 A5 JP2003528095 A5 JP 2003528095A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methyl
- amino
- group
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000003839 salts Chemical class 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 150000008318 pyrimidones Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- -1 methoxyphenyl Chemical group 0.000 description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 4
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FNSPNJJWDHKURH-UHFFFAOYSA-N 3-methyl-2-(3-phenylpropylamino)-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCCC1=CC=CC=C1 FNSPNJJWDHKURH-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 description 2
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 150000002791 naphthoquinones Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000005751 substituted indanyl group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- AOGWMUZEGUNRTF-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-2-ylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(NC2CC3=CC=CC=C3C2)=NC=1C1=CC=NC=C1 AOGWMUZEGUNRTF-UHFFFAOYSA-N 0.000 description 1
- IUBXUJDMYJSJLL-UHFFFAOYSA-N 2-(2-anilinoethylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCNC1=CC=CC=C1 IUBXUJDMYJSJLL-UHFFFAOYSA-N 0.000 description 1
- XDYBZOOSABMLKX-UHFFFAOYSA-N 2-(2-cyclohexylethylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1CCCCC1 XDYBZOOSABMLKX-UHFFFAOYSA-N 0.000 description 1
- SIZQBTQHFHEAMH-UHFFFAOYSA-N 2-(2-cyclopentylethylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1CCCC1 SIZQBTQHFHEAMH-UHFFFAOYSA-N 0.000 description 1
- NOHBEZNVEDDQJK-UHFFFAOYSA-N 2-(3-cyclohexylpropylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCCC1CCCCC1 NOHBEZNVEDDQJK-UHFFFAOYSA-N 0.000 description 1
- KLTZRQWEHOTASN-UHFFFAOYSA-N 2-(3-ethoxypropylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCOCC)=NC(C=2C=CN=CC=2)=C1 KLTZRQWEHOTASN-UHFFFAOYSA-N 0.000 description 1
- YBYBIGDLPLXTPQ-UHFFFAOYSA-N 2-(3-phenylpropyl)-6-pyridin-4-yl-1h-pyrimidin-4-one Chemical compound N1C(=O)C=C(C=2C=CN=CC=2)N=C1CCCC1=CC=CC=C1 YBYBIGDLPLXTPQ-UHFFFAOYSA-N 0.000 description 1
- KGZISGFROLTSGS-UHFFFAOYSA-N 2-(4-aminobutylamino)-3-(2-phenylethyl)-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CCC1=CC=CC=C1 KGZISGFROLTSGS-UHFFFAOYSA-N 0.000 description 1
- TXQBVNAVVPJSLG-UHFFFAOYSA-N 2-(4-aminobutylamino)-3-benzyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CC1=CC=CC=C1 TXQBVNAVVPJSLG-UHFFFAOYSA-N 0.000 description 1
- KVLFZOYZVKRPCN-UHFFFAOYSA-N 2-(4-hydroxybutylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCO)=NC(C=2C=CN=CC=2)=C1 KVLFZOYZVKRPCN-UHFFFAOYSA-N 0.000 description 1
- QIOSYZQYELNRBQ-UHFFFAOYSA-N 2-(5-aminopentylamino)-3-(2-phenylethyl)-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CCC1=CC=CC=C1 QIOSYZQYELNRBQ-UHFFFAOYSA-N 0.000 description 1
- FFMVEZPXTUKPDV-UHFFFAOYSA-N 2-(5-aminopentylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCCN)=NC(C=2C=CN=CC=2)=C1 FFMVEZPXTUKPDV-UHFFFAOYSA-N 0.000 description 1
- UWDWHLGHESXJEW-UHFFFAOYSA-N 2-(5-hydroxypentylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCCO)=NC(C=2C=CN=CC=2)=C1 UWDWHLGHESXJEW-UHFFFAOYSA-N 0.000 description 1
- AMGXUHRKXDEHMP-UHFFFAOYSA-N 2-(6-aminohexylamino)-3-(2-phenylethyl)-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CCC1=CC=CC=C1 AMGXUHRKXDEHMP-UHFFFAOYSA-N 0.000 description 1
- WJDVOTZYKDAVOG-UHFFFAOYSA-N 2-(6-aminohexylamino)-3-(3-phenylpropyl)-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CCCC1=CC=CC=C1 WJDVOTZYKDAVOG-UHFFFAOYSA-N 0.000 description 1
- KROXOPHTLDAAOU-UHFFFAOYSA-N 2-(6-aminohexylamino)-3-benzyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound NCCCCCCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1CC1=CC=CC=C1 KROXOPHTLDAAOU-UHFFFAOYSA-N 0.000 description 1
- ZKXFFBWTNYXQTN-UHFFFAOYSA-N 2-(benzylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC1=CC=CC=C1 ZKXFFBWTNYXQTN-UHFFFAOYSA-N 0.000 description 1
- JUBKIXBILWHKRM-UHFFFAOYSA-N 2-(butylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCC)=NC(C=2C=CN=CC=2)=C1 JUBKIXBILWHKRM-UHFFFAOYSA-N 0.000 description 1
- CRAPXBOBZXDVJS-UHFFFAOYSA-N 2-(cyclohexylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NC1CCCCC1 CRAPXBOBZXDVJS-UHFFFAOYSA-N 0.000 description 1
- GAPVSUZWYPHFBD-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC1CCCCC1 GAPVSUZWYPHFBD-UHFFFAOYSA-N 0.000 description 1
- MCFNREXCIOPMEQ-UHFFFAOYSA-N 2-(cyclopentylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NC1CCCC1 MCFNREXCIOPMEQ-UHFFFAOYSA-N 0.000 description 1
- BGHLCXGBDYUABT-UHFFFAOYSA-N 2-(decylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCCCCCCC)=NC(C=2C=CN=CC=2)=C1 BGHLCXGBDYUABT-UHFFFAOYSA-N 0.000 description 1
- PFUINUAXKPHHNQ-UHFFFAOYSA-N 2-(ethylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCC)=NC(C=2C=CN=CC=2)=C1 PFUINUAXKPHHNQ-UHFFFAOYSA-N 0.000 description 1
- OOLYLNQGOBDTGD-UHFFFAOYSA-N 2-(heptylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCCCC)=NC(C=2C=CN=CC=2)=C1 OOLYLNQGOBDTGD-UHFFFAOYSA-N 0.000 description 1
- ANDODQCLSFETGX-UHFFFAOYSA-N 2-(hexylamino)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound O=C1N(C)C(NCCCCCC)=NC(C=2C=CN=CC=2)=C1 ANDODQCLSFETGX-UHFFFAOYSA-N 0.000 description 1
- HLHSBTANQKHKAP-UHFFFAOYSA-N 2-[(2-hydroxy-2-phenylethyl)amino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC(O)C1=CC=CC=C1 HLHSBTANQKHKAP-UHFFFAOYSA-N 0.000 description 1
- KTQIRHPUSBDGGQ-UHFFFAOYSA-N 2-[2-(1-adamantyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(NCCC23CC4CC(CC(C4)C2)C3)=NC=1C1=CC=NC=C1 KTQIRHPUSBDGGQ-UHFFFAOYSA-N 0.000 description 1
- PTOYZHWKZSVSKL-UHFFFAOYSA-N 2-[2-(1h-indol-3-yl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(NCCC=2C3=CC=CC=C3NC=2)=NC=1C1=CC=NC=C1 PTOYZHWKZSVSKL-UHFFFAOYSA-N 0.000 description 1
- YGWJRXNEIGCXHK-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(Cl)C=C1Cl YGWJRXNEIGCXHK-UHFFFAOYSA-N 0.000 description 1
- KGQHGDLVGYYEPV-UHFFFAOYSA-N 2-[2-(2,5-dimethoxyphenyl)ethyl-methylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=C(OC)C(CCN(C)C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 KGQHGDLVGYYEPV-UHFFFAOYSA-N 0.000 description 1
- XCQRETFBJPMMJO-UHFFFAOYSA-N 2-[2-(2,5-dimethoxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=C(OC)C(CCNC=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 XCQRETFBJPMMJO-UHFFFAOYSA-N 0.000 description 1
- JDHPQHTYBJJUPX-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=CC=C1Cl JDHPQHTYBJJUPX-UHFFFAOYSA-N 0.000 description 1
- NLUJFYPBCBIJPI-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=CC=C1F NLUJFYPBCBIJPI-UHFFFAOYSA-N 0.000 description 1
- IHXUFXFWCMSEFY-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC=C1CCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1C IHXUFXFWCMSEFY-UHFFFAOYSA-N 0.000 description 1
- NIIORIQATVWLHP-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1C NIIORIQATVWLHP-UHFFFAOYSA-N 0.000 description 1
- WULIJGZCGDGIFK-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=CC(Cl)=C1 WULIJGZCGDGIFK-UHFFFAOYSA-N 0.000 description 1
- HOQCPKWNWIMAMK-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=CC(F)=C1 HOQCPKWNWIMAMK-UHFFFAOYSA-N 0.000 description 1
- SCRWLELQJFUGNQ-UHFFFAOYSA-N 2-[2-(3-methoxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC=CC(CCNC=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 SCRWLELQJFUGNQ-UHFFFAOYSA-N 0.000 description 1
- OSURWZPJNWZKGX-UHFFFAOYSA-N 2-[2-(4-aminophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(N)C=C1 OSURWZPJNWZKGX-UHFFFAOYSA-N 0.000 description 1
- KSUUUKMNOQKMBQ-UHFFFAOYSA-N 2-[2-(4-bromophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(Br)C=C1 KSUUUKMNOQKMBQ-UHFFFAOYSA-N 0.000 description 1
- HJWZFWAGBIQARQ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(Cl)C=C1 HJWZFWAGBIQARQ-UHFFFAOYSA-N 0.000 description 1
- WUSPECDVZDICNQ-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(F)C=C1 WUSPECDVZDICNQ-UHFFFAOYSA-N 0.000 description 1
- VYQVEGBZHSOEOH-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCCC1=CC=C(O)C=C1 VYQVEGBZHSOEOH-UHFFFAOYSA-N 0.000 description 1
- CWPSQSTWQJFISU-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1CCNC1=NC(C=2C=CN=CC=2)=CC(=O)N1C CWPSQSTWQJFISU-UHFFFAOYSA-N 0.000 description 1
- AITJIVBPVPIEDD-UHFFFAOYSA-N 2-[2-(5-methoxy-1h-indol-3-yl)ethylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C12=CC(OC)=CC=C2NC=C1CCNC(N(C(=O)C=1)C)=NC=1C1=CC=NC=C1 AITJIVBPVPIEDD-UHFFFAOYSA-N 0.000 description 1
- MARMTRXHOPJVNJ-UHFFFAOYSA-N 2-[3-cyclohexylpropyl(methyl)amino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1N(C)CCCC1CCCCC1 MARMTRXHOPJVNJ-UHFFFAOYSA-N 0.000 description 1
- ZSTRDIPXJSHMJU-UHFFFAOYSA-N 2-[4-aminobutyl(2-phenylethyl)amino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N(CCCCN)CCC=2C=CC=CC=2)=NC=1C1=CC=NC=C1 ZSTRDIPXJSHMJU-UHFFFAOYSA-N 0.000 description 1
- MBIRRCWABHLJSK-UHFFFAOYSA-N 2-[5-aminopentyl(2-phenylethyl)amino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N(CCCCCN)CCC=2C=CC=CC=2)=NC=1C1=CC=NC=C1 MBIRRCWABHLJSK-UHFFFAOYSA-N 0.000 description 1
- LPGMNPGBYOKHSZ-UHFFFAOYSA-N 2-[[3-(3-aminopropoxy)phenyl]methylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC1=CC=CC(OCCCN)=C1 LPGMNPGBYOKHSZ-UHFFFAOYSA-N 0.000 description 1
- IVJWREKBFVNMRS-UHFFFAOYSA-N 2-[[3-(3-hydroxypropoxy)phenyl]methylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC1=CC=CC(OCCCO)=C1 IVJWREKBFVNMRS-UHFFFAOYSA-N 0.000 description 1
- WJRAQZGXWRRQDC-UHFFFAOYSA-N 2-[[3-(aminomethyl)phenyl]methylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(C)C=1NCC1=CC=CC(CN)=C1 WJRAQZGXWRRQDC-UHFFFAOYSA-N 0.000 description 1
- PVGDQVJEEDRQQW-UHFFFAOYSA-N 2-[[3-[3-(dimethylamino)propoxy]phenyl]methylamino]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound CN(C)CCCOC1=CC=CC(CNC=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)=C1 PVGDQVJEEDRQQW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- KCCGMZLDFDTGSG-UHFFFAOYSA-N 3-(2-aminoethyl)-2-(3-phenylpropylamino)-6-pyridin-4-ylpyrimidin-4-one Chemical compound N=1C(C=2C=CN=CC=2)=CC(=O)N(CCN)C=1NCCCC1=CC=CC=C1 KCCGMZLDFDTGSG-UHFFFAOYSA-N 0.000 description 1
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| TW201041580A (en) * | 2001-09-27 | 2010-12-01 | Alcon Inc | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma |
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| TWI301834B (en) | 2001-10-22 | 2008-10-11 | Eisai R&D Man Co Ltd | Pyrimidone compound and pharmaceutical composition including the same |
| CN1726209B (zh) | 2002-12-16 | 2011-04-13 | 三菱制药株式会社 | 3-取代的-4-嘧啶酮衍生物 |
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| TWI357408B (en) * | 2003-03-26 | 2012-02-01 | Mitsubishi Tanabe Pharma Corp | 3-substituted-4-pyrimidone derivatives |
| KR20060041309A (ko) | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | ４-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
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| US20070117818A1 (en) * | 2004-02-04 | 2007-05-24 | Masaichi Hasegawa | Pyrimidinone compounds useful as kinase inhibitors |
| UA85871C2 (uk) | 2004-03-15 | 2009-03-10 | Такеда Фармасьютікал Компані Лімітед | Інгібітори дипептидилпептидази |
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| AR050865A1 (es) | 2004-09-09 | 2006-11-29 | Sanofi Aventis | Derivados de 2- morfolino-4-pirimidona |
| CN101048397A (zh) | 2004-09-29 | 2007-10-03 | 三菱制药株式会社 | 作为τ蛋白激酶1抑制剂的6－（吡啶基）－4－嘧啶酮衍生物 |
| JP2008524331A (ja) | 2004-12-21 | 2008-07-10 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤 |
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| EP2275095A3 (en) | 2005-08-26 | 2011-08-17 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| MY147393A (en) | 2005-09-14 | 2012-11-30 | Takeda Pharmaceutical | Administration of dipeptidyl peptidase inhibitors |
| CA2622642C (en) | 2005-09-16 | 2013-12-31 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| AU2006308889A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | GABA receptor mediated modulation of neurogenesis |
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| TW200813015A (en) * | 2006-03-15 | 2008-03-16 | Mitsubishi Pharma Corp | 2-(cyclic amino)-pyrimidone derivatives |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| CN101528729A (zh) * | 2006-08-23 | 2009-09-09 | 辉瑞产品公司 | 作为gsk-3抑制剂的嘧啶酮化合物 |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| AR076014A1 (es) | 2009-04-02 | 2011-05-11 | Sanofi Aventis | Derivados de 3- (1,4) oxazepan -4-pirimidona |
| JP5442852B2 (ja) | 2009-08-13 | 2014-03-12 | 田辺三菱製薬株式会社 | タウプロテインキナーゼ１阻害剤としてのピリミドン誘導体 |
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| EP3741375A1 (en) | 2014-07-17 | 2020-11-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for treating neuromuscular junction-related diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4935631B1 (https=) | 1970-12-28 | 1974-09-25 | ||
| JPS4935633B1 (https=) | 1970-12-30 | 1974-09-25 | ||
| JPS559099B2 (https=) * | 1972-08-07 | 1980-03-07 | ||
| JPS4935633A (https=) | 1972-08-09 | 1974-04-02 | ||
| US4460589A (en) * | 1980-10-03 | 1984-07-17 | The Upjohn Company | Process for treating hypertension |
| TW229142B (https=) * | 1992-04-15 | 1994-09-01 | Nissan Detrochem Corp | |
| WO1998016528A1 (en) * | 1996-10-11 | 1998-04-23 | Chiron Corporation | Purine inhibitors of glycogen synthase kinase 3 (gsk3) |
| TW520362B (en) * | 1996-12-05 | 2003-02-11 | Amgen Inc | Substituted pyrimidine compounds and pharmaceutical composition comprising same |
| EP0948496A2 (en) * | 1996-12-05 | 1999-10-13 | Amgen inc. | Substituted pyrimidinone and pyridone compounds and methods of use |
| AR023052A1 (es) * | 1998-09-25 | 2002-09-04 | Mitsuharu Yoshimura Milton | Derivados de pirimidona |
| EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
-
2000
- 2000-03-23 EP EP00400800A patent/EP1136482A1/en not_active Withdrawn
-
2001
- 2001-03-22 US US10/221,598 patent/US6844335B2/en not_active Expired - Fee Related
- 2001-03-22 ES ES01959921T patent/ES2296783T3/es not_active Expired - Lifetime
- 2001-03-22 AT AT01959921T patent/ATE380806T1/de active
- 2001-03-22 AU AU2001281487A patent/AU2001281487A1/en not_active Abandoned
- 2001-03-22 DE DE60131844T patent/DE60131844T2/de not_active Expired - Lifetime
- 2001-03-22 DK DK01959921T patent/DK1276738T3/da active
- 2001-03-22 CN CNB018069916A patent/CN1247567C/zh not_active Expired - Fee Related
- 2001-03-22 CN CNA2006100061354A patent/CN1891220A/zh active Pending
- 2001-03-22 PT PT01959921T patent/PT1276738E/pt unknown
- 2001-03-22 KR KR1020027012431A patent/KR100820543B1/ko not_active Expired - Fee Related
- 2001-03-22 CA CA2401241A patent/CA2401241C/en not_active Expired - Fee Related
- 2001-03-22 EP EP01959921A patent/EP1276738B8/en not_active Expired - Lifetime
- 2001-03-22 JP JP2001568932A patent/JP4778657B2/ja not_active Expired - Fee Related
- 2001-03-22 WO PCT/EP2001/003640 patent/WO2001070729A1/en not_active Ceased
- 2001-03-22 SI SI200130806T patent/SI1276738T1/sl unknown
- 2001-03-23 AR ARP010101372A patent/AR028280A1/es active IP Right Grant
-
2005
- 2005-01-13 US US11/035,264 patent/US7378413B2/en not_active Expired - Fee Related
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2008
- 2008-03-07 CY CY20081100270T patent/CY1107236T1/el unknown
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