DE60128457T2 - 1,5-DISUBSTITUIERTE 3,4-DIHYDRO-1H-4,5-DöPYRIMIDIN-2-ON-VERBINDUNGEN UND IHRE VERWENDUNG IN DER BEHANDLUNG VON DURCH CSBP/P38 KINASE BEEINFLUSSTEN KRANKHEITEN - Google Patents

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Publication number

DE60128457T2

DE60128457T2 DE60128457T DE60128457T DE60128457T2 DE 60128457 T2 DE60128457 T2 DE 60128457T2 DE 60128457 T DE60128457 T DE 60128457T DE 60128457 T DE60128457 T DE 60128457T DE 60128457 T2 DE60128457 T2 DE 60128457T2

Authority

DE

Germany

Prior art keywords

alkyl

dihydro

pyrimido

pyrimidin

fluoro

Prior art date

2000-03-02

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.)

Expired - Lifetime

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• 125000000217 alkyl group Chemical group 0.000 claims description 293
• -1 aryl-C 1-10 -alkyl Chemical group 0.000 claims description 172
• 238000000034 method Methods 0.000 claims description 96
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• 150000002431 hydrogen Chemical class 0.000 claims description 55
• 150000003254 radicals Chemical class 0.000 claims description 49
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical group 0.000 claims description 45
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• 125000003107 substituted aryl group Chemical group 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
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• QPZMKCAFTCXOLA-UHFFFAOYSA-N 2-methylsulfanyl-4,8-diphenyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound N=1C(SC)=NC=2N(C=3C=CC=CC=3)C(=O)NCC=2C=1C1=CC=CC=C1 QPZMKCAFTCXOLA-UHFFFAOYSA-N 0.000 claims description 2
• SAYBUHKPFPWVSX-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-2-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-4-(4-fluoro-2-methylphenyl)-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(NC(CO)(CO)CO)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F SAYBUHKPFPWVSX-UHFFFAOYSA-N 0.000 claims description 2
• FWIQAZGOXKXCIO-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-2-methoxy-4-phenyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound N=1C(OC)=NC=2N(C=3C(=CC=CC=3F)F)C(=O)NCC=2C=1C1=CC=CC=C1 FWIQAZGOXKXCIO-UHFFFAOYSA-N 0.000 claims description 2
• BGVFXNCOIUGQSS-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-(2-hydroxyethoxy)-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(OCCO)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F BGVFXNCOIUGQSS-UHFFFAOYSA-N 0.000 claims description 2
• NFCBJEPHFJANDG-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-(2-hydroxyethylamino)-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(NCCO)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F NFCBJEPHFJANDG-UHFFFAOYSA-N 0.000 claims description 2
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• CGRTXKHCITVACI-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(NC(C)(C)CO)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F CGRTXKHCITVACI-UHFFFAOYSA-N 0.000 claims description 2
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• OWJIMCIWDXHGMZ-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-methylsulfonyl-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound CC1=CC(F)=CC=C1C1=NC(S(C)(=O)=O)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F OWJIMCIWDXHGMZ-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• VBPRDTNZCVKPNV-UHFFFAOYSA-N ethyl 1-[8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-7-oxo-5,6-dihydropyrimido[4,5-d]pyrimidin-2-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(N=C1C=2C(=CC(F)=CC=2)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F VBPRDTNZCVKPNV-UHFFFAOYSA-N 0.000 claims description 2
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• ITCXGNOGLOWIDP-UHFFFAOYSA-N 2-[2-(diethylamino)ethylamino]-8-(2,6-difluorophenyl)-4-(2-methylphenyl)-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound N=1C(NCCN(CC)CC)=NC=2N(C=3C(=CC=CC=3F)F)C(=O)NCC=2C=1C1=CC=CC=C1C ITCXGNOGLOWIDP-UHFFFAOYSA-N 0.000 claims 1
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• WSUDMMLLIGODQE-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-4-(4-fluoro-2-methylphenyl)-2-(1-methylpiperidin-4-yl)oxy-5,6-dihydropyrimido[4,5-d]pyrimidin-7-one Chemical compound C1CN(C)CCC1OC(N=C1C=2C(=CC(F)=CC=2)C)=NC2=C1CNC(=O)N2C1=C(F)C=CC=C1F WSUDMMLLIGODQE-UHFFFAOYSA-N 0.000 claims 1
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