EA016388B1 - Соединения пиридо[2,3-d]пиримидинона и их применение в качестве pi3 ингибиторов - Google Patents

Info

Publication number

EA016388B1

EA016388B1 EA200970207A EA200970207A EA016388B1 EA 016388 B1 EA016388 B1 EA 016388B1 EA 200970207 A EA200970207 A EA 200970207A EA 200970207 A EA200970207 A EA 200970207A EA 016388 B1 EA016388 B1 EA 016388B1

Authority

EA

Eurasian Patent Office

Prior art keywords

amino

pyrimidin

methyl

trans

cyclohexyl

Prior art date

2006-09-15

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 274
• 239000003112 inhibitor Substances 0.000 title abstract description 49
• UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 title description 7
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• 238000000034 method Methods 0.000 claims abstract description 56
• 230000002159 abnormal effect Effects 0.000 claims abstract description 27
• 230000010261 cell growth Effects 0.000 claims abstract description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 241000124008 Mammalia Species 0.000 claims abstract description 18
• -1 5-fluoro-6-methoxypyridin-3-yl Chemical group 0.000 claims description 367
• 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 87
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 82
• 206010028980 Neoplasm Diseases 0.000 claims description 49
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 22
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 20
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
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• YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
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• 230000002401 inhibitory effect Effects 0.000 claims description 7
• JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 5
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• 230000002255 enzymatic effect Effects 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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• 101000605639 Homo sapiens Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform Proteins 0.000 abstract description 2
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• XDLYKKIQACFMJG-UHFFFAOYSA-N 2-amino-8-[4-(2-hydroxyethoxy)cyclohexyl]-6-(6-methoxypyridin-3-yl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=NC(OC)=CC=C1C(C1=O)=CC2=C(C)N=C(N)N=C2N1C1CCC(OCCO)CC1 XDLYKKIQACFMJG-UHFFFAOYSA-N 0.000 abstract 1
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• 238000003756 stirring Methods 0.000 description 23
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• 239000002585 base Substances 0.000 description 20
• 229910000027 potassium carbonate Inorganic materials 0.000 description 20
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
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