AU749750B2 - Pyrido {2,3-d} pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation - Google Patents

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Publication number

AU749750B2

AU749750B2 AU66480/98A AU6648098A AU749750B2 AU 749750 B2 AU749750 B2 AU 749750B2 AU 66480/98 A AU66480/98 A AU 66480/98A AU 6648098 A AU6648098 A AU 6648098A AU 749750 B2 AU749750 B2 AU 749750B2

Authority

AU

Australia

Prior art keywords

pyrido

pyrimidin

phenylamino

ethyl

piperidin

Prior art date

1997-02-05

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.)

Ceased

Links

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• 230000004663 cell proliferation Effects 0.000 title claims description 10
• 239000003112 inhibitor Substances 0.000 title abstract description 13
• 150000005007 4-aminopyrimidines Chemical class 0.000 title abstract description 6
• 159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 150
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 69
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 48
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 26
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 25
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims abstract description 19
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims abstract description 19
• 201000011510 cancer Diseases 0.000 claims abstract description 18
• 239000001257 hydrogen Substances 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 230000002062 proliferating effect Effects 0.000 claims abstract description 14
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• 230000001404 mediated effect Effects 0.000 claims abstract description 11
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 11
• 208000037803 restenosis Diseases 0.000 claims abstract description 11
• 239000003102 growth factor Substances 0.000 claims abstract description 10
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 28
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• WDHAAJIGSXNPFO-UHFFFAOYSA-N 8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CN=C2NC(=O)C=CC2=C1 WDHAAJIGSXNPFO-UHFFFAOYSA-N 0.000 claims description 25
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• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 23
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• BETPKCCUZWUHNW-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(C)C(=O)NC2=NC(SC)=NC=C21 BETPKCCUZWUHNW-UHFFFAOYSA-N 0.000 claims description 3
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• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical group CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 229910052700 potassium Inorganic materials 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
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• CYIQWPZMTPNAFQ-UHFFFAOYSA-N 2-(ethylamino)-8-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(NCC)=NC=C2C=CC(=O)N1C1=CC=CC=C1 CYIQWPZMTPNAFQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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• 125000001475 halogen functional group Chemical group 0.000 claims 12
• 230000000052 comparative effect Effects 0.000 claims 9
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• RQUBDOBSPYGIAS-UHFFFAOYSA-N 8-(3-phenylmethoxypropyl)-2-(4-piperidin-1-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(CCCOCC=3C=CC=CC=3)C(=O)C=CC2=CN=C1NC(C=C1)=CC=C1N1CCCCC1 RQUBDOBSPYGIAS-UHFFFAOYSA-N 0.000 claims 1
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