JP2009511504A5 - - Google Patents
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- Publication number
- JP2009511504A5 JP2009511504A5 JP2008534787A JP2008534787A JP2009511504A5 JP 2009511504 A5 JP2009511504 A5 JP 2009511504A5 JP 2008534787 A JP2008534787 A JP 2008534787A JP 2008534787 A JP2008534787 A JP 2008534787A JP 2009511504 A5 JP2009511504 A5 JP 2009511504A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- methyl
- ethyl
- pyrido
- ethylamino
- 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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- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- JHDJFNOXJGEJCS-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1,2-oxazol-4-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=NOC=1 JHDJFNOXJGEJCS-UHFFFAOYSA-N 0.000 claims description 3
- PNSLJZNTNVQKHL-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=NC=CS1 PNSLJZNTNVQKHL-UHFFFAOYSA-N 0.000 claims description 3
- LXAAVLWRKYXLPP-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1-methylpyrrol-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CN1C LXAAVLWRKYXLPP-UHFFFAOYSA-N 0.000 claims description 3
- PETWXKSNVPOKHU-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1h-pyrazol-4-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=NNC=1 PETWXKSNVPOKHU-UHFFFAOYSA-N 0.000 claims description 3
- SVQPVMARWDTMKG-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CC=C1 SVQPVMARWDTMKG-UHFFFAOYSA-N 0.000 claims description 3
- RSHCHEZCLIFIEP-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-pyrimidin-5-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CN=CN=C1 RSHCHEZCLIFIEP-UHFFFAOYSA-N 0.000 claims description 3
- KEKHVKTZQHDUAE-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CS1 KEKHVKTZQHDUAE-UHFFFAOYSA-N 0.000 claims description 3
- QMFWBMLNHMQKNG-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-thiophen-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CSC=1 QMFWBMLNHMQKNG-UHFFFAOYSA-N 0.000 claims description 3
- SOXRYBWZUVPKSE-UHFFFAOYSA-N 2-amino-8-ethyl-6-(1h-imidazol-5-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CN=CN1 SOXRYBWZUVPKSE-UHFFFAOYSA-N 0.000 claims description 3
- DZKUBTPKXVNNDB-UHFFFAOYSA-N 2-amino-8-ethyl-6-(furan-2-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CO1 DZKUBTPKXVNNDB-UHFFFAOYSA-N 0.000 claims description 3
- ITADRIYKTDHOJF-UHFFFAOYSA-N 2-amino-8-ethyl-6-(furan-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=COC=1 ITADRIYKTDHOJF-UHFFFAOYSA-N 0.000 claims description 3
- CHZVGYLVZMHCSX-UHFFFAOYSA-N 5-(2-amino-8-ethyl-4-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl)thiophene-2-carbonitrile Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=C(C#N)S1 CHZVGYLVZMHCSX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 3
- SNVGNFPYWWJEDD-UHFFFAOYSA-N 2-amino-6-(2,4-dichlorophenyl)-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=C(Cl)C=C1Cl SNVGNFPYWWJEDD-UHFFFAOYSA-N 0.000 claims description 2
- SIQBRKREBNRFFZ-UHFFFAOYSA-N 2-amino-6-(3-chlorophenyl)-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CC(Cl)=C1 SIQBRKREBNRFFZ-UHFFFAOYSA-N 0.000 claims description 2
- ABOPZLXFBVHNMQ-UHFFFAOYSA-N 2-amino-6-(4-chlorophenyl)-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=C(Cl)C=C1 ABOPZLXFBVHNMQ-UHFFFAOYSA-N 0.000 claims description 2
- ROOVRZFTFXTTST-UHFFFAOYSA-N 2-amino-8-ethyl-6-(2-fluorophenyl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CC=C1F ROOVRZFTFXTTST-UHFFFAOYSA-N 0.000 claims description 2
- AMNQMQPWMLMAAY-UHFFFAOYSA-N 2-amino-8-ethyl-6-(3-fluorophenyl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=CC(F)=C1 AMNQMQPWMLMAAY-UHFFFAOYSA-N 0.000 claims description 2
- WRNJSZSXQVCMJN-UHFFFAOYSA-N 2-amino-8-ethyl-6-(4-fluorophenyl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=C(F)C=C1 WRNJSZSXQVCMJN-UHFFFAOYSA-N 0.000 claims description 2
- GKWRRVVLRVJJRX-UHFFFAOYSA-N 2-amino-8-ethyl-6-(4-methoxyphenyl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CC=C(OC)C=C1 GKWRRVVLRVJJRX-UHFFFAOYSA-N 0.000 claims description 2
- -1 cyano, amino Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 4
- RGHYDLZMTYDBDT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1H-pyrazol-5-yl)-7-pyrido[2,3-d]pyrimidinone Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 RGHYDLZMTYDBDT-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000001724 1,2,3-oxadiazol-4-yl group Chemical group [H]C1=C(*)N=NO1 0.000 claims 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 2
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 2
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 2
- JMNLUUPZYOLBHN-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-6-(1H-pyrazol-5-yl)-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1NC2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 JMNLUUPZYOLBHN-UHFFFAOYSA-N 0.000 claims 2
- IRHDSXMLSTVXEQ-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 IRHDSXMLSTVXEQ-UHFFFAOYSA-N 0.000 claims 2
- ZHRYNYKDUYSRGB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1N1C=CC=N1 ZHRYNYKDUYSRGB-UHFFFAOYSA-N 0.000 claims 2
- HSEBQNPXSICMIB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CS1 HSEBQNPXSICMIB-UHFFFAOYSA-N 0.000 claims 2
- QRJXSWSAFBXPGH-UHFFFAOYSA-N 2-(ethylamino)-6-(furan-3-yl)-4-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=COC=1 QRJXSWSAFBXPGH-UHFFFAOYSA-N 0.000 claims 2
- LRBPZCIDQVONRS-UHFFFAOYSA-N 2-amino-4,8-diethyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C=1C=2C(CC)=NC(N)=NC=2N(CC)C(=O)C=1C1=CC=NN1 LRBPZCIDQVONRS-UHFFFAOYSA-N 0.000 claims 2
- HZRBHCGEYZORAK-UHFFFAOYSA-N 2-amino-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 HZRBHCGEYZORAK-UHFFFAOYSA-N 0.000 claims 2
- JHXCMDLLRNPOOU-UHFFFAOYSA-N 2-amino-8-benzyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1CC1=CC=CC=C1 JHXCMDLLRNPOOU-UHFFFAOYSA-N 0.000 claims 2
- BGBWOFOWRGIYJH-UHFFFAOYSA-N 2-amino-8-cyclopentyl-4-methyl-6-(1,3-thiazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C=2SC=NC=2)=CC=2C(C)=NC(N)=NC=2N1C1CCCC1 BGBWOFOWRGIYJH-UHFFFAOYSA-N 0.000 claims 2
- QSWPHEWUFGXYPX-UHFFFAOYSA-N 2-amino-8-cyclopentyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1C1CCCC1 QSWPHEWUFGXYPX-UHFFFAOYSA-N 0.000 claims 2
- DMRXBVGEQSWGNY-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(2h-tetrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=NN=NN1 DMRXBVGEQSWGNY-UHFFFAOYSA-N 0.000 claims 2
- RXZGFXKARYPDCT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(2h-triazol-4-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CN=NN1 RXZGFXKARYPDCT-UHFFFAOYSA-N 0.000 claims 2
- BYOHGQCLGOTIRV-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(4-methylthiophen-3-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C1=CSC=C1C BYOHGQCLGOTIRV-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- DGRRKSNJOVHVFZ-UHFFFAOYSA-N 6-(5-chlorothiophen-2-yl)-8-ethyl-2-(ethylamino)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=C(Cl)S1 DGRRKSNJOVHVFZ-UHFFFAOYSA-N 0.000 claims 2
- XMEZKAIELOKSNK-UHFFFAOYSA-N 8-cyclohexyl-2-(ethylamino)-4-methyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C2CCCCC2)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CS1 XMEZKAIELOKSNK-UHFFFAOYSA-N 0.000 claims 2
- YELSUCDKJBIDHK-UHFFFAOYSA-N 8-cyclopentyl-2-(ethylamino)-4-methyl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C2CCCC2)C2=NC(NCC)=NC(C)=C2C=C1N1C=CC=N1 YELSUCDKJBIDHK-UHFFFAOYSA-N 0.000 claims 2
- QJPJYBSSDNQQRU-UHFFFAOYSA-N 8-ethyl-2-(2-fluoroethylamino)-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCCF)=NC(C)=C2C=C1C1=CC=NN1 QJPJYBSSDNQQRU-UHFFFAOYSA-N 0.000 claims 2
- XEIHFSVZTFDIGS-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(1,3-thiazol-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=NC=CS1 XEIHFSVZTFDIGS-UHFFFAOYSA-N 0.000 claims 2
- YJMFDEYHLMFOSN-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=NN1 YJMFDEYHLMFOSN-UHFFFAOYSA-N 0.000 claims 2
- BEPVPUYZYQRJAQ-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(1h-pyrrol-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CN1 BEPVPUYZYQRJAQ-UHFFFAOYSA-N 0.000 claims 2
- NLRSTBWELKXVHN-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(4-methylthiophen-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC(C)=CS1 NLRSTBWELKXVHN-UHFFFAOYSA-N 0.000 claims 2
- XFVJUMGGCIFZBT-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(4-methylthiophen-3-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CSC=C1C XFVJUMGGCIFZBT-UHFFFAOYSA-N 0.000 claims 2
- WOQNWAFKWIBAFO-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-(5-phenylthiophen-2-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C(S1)=CC=C1C1=CC=CC=C1 WOQNWAFKWIBAFO-UHFFFAOYSA-N 0.000 claims 2
- CSPSPXHFDYRQAI-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1N1C=CC=N1 CSPSPXHFDYRQAI-UHFFFAOYSA-N 0.000 claims 2
- UGWQQIPKTBUFRP-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-pyrimidin-5-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CN=CN=C1 UGWQQIPKTBUFRP-UHFFFAOYSA-N 0.000 claims 2
- IYROWIUMRWBPSD-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CS1 IYROWIUMRWBPSD-UHFFFAOYSA-N 0.000 claims 2
- UCNWJNJPCDCHIR-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-thiophen-3-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CSC=1 UCNWJNJPCDCHIR-UHFFFAOYSA-N 0.000 claims 2
- HIGCMWPMIDVKLQ-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-6-(1h-indol-6-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C2C=CNC2=CC(C2=CC3=C(C)N=C(N=C3N(CC)C2=O)NCC)=C1 HIGCMWPMIDVKLQ-UHFFFAOYSA-N 0.000 claims 2
- LIJZDASQNMTIQH-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-6-(3-fluoropyridin-4-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=NC=C1F LIJZDASQNMTIQH-UHFFFAOYSA-N 0.000 claims 2
- VJEUHYDFQNWESU-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-6-(furan-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C=1C=COC=1 VJEUHYDFQNWESU-UHFFFAOYSA-N 0.000 claims 2
- WPQXBIFIGCHPPR-UHFFFAOYSA-N 8-ethyl-4-methyl-2-(methylamino)-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NC)=NC(C)=C2C=C1C1=CC=NN1 WPQXBIFIGCHPPR-UHFFFAOYSA-N 0.000 claims 2
- VZKDEUQOMRCYFB-UHFFFAOYSA-N 8-ethyl-4-methyl-6-(1h-pyrazol-5-yl)-2-(2,2,2-trifluoroethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC(F)(F)F)=NC(C)=C2C=C1C1=CC=NN1 VZKDEUQOMRCYFB-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
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2006
- 2006-10-09 HR HRP20130902TT patent/HRP20130902T1/hr unknown
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- 2006-10-09 NZ NZ566903A patent/NZ566903A/en not_active IP Right Cessation
- 2006-10-09 KR KR1020087008369A patent/KR101538412B1/ko not_active Expired - Fee Related
- 2006-10-09 KR KR1020137026515A patent/KR101492795B1/ko not_active Expired - Fee Related
- 2006-10-09 EP EP11157050.3A patent/EP2322523B1/en active Active
- 2006-10-09 RS RS20130400A patent/RS52953B/sr unknown
- 2006-10-09 CN CNA2006800370996A patent/CN101395155A/zh active Pending
- 2006-10-09 EA EA200800760A patent/EA016945B1/ru unknown
- 2006-10-09 AU AU2006302078A patent/AU2006302078B2/en not_active Ceased
- 2006-10-09 KR KR1020147023011A patent/KR20140105621A/ko not_active Ceased
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- 2006-10-09 DK DK06825768.2T patent/DK1940839T3/da active
- 2006-10-09 US US11/988,848 patent/US8044062B2/en active Active
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2008
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