JP5964974B2 - キナーゼ活性のモジュレーターとしての新規イミダゾールアミン - Google Patents

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Publication number

JP5964974B2

JP5964974B2 JP2014529985A JP2014529985A JP5964974B2 JP 5964974 B2 JP5964974 B2 JP 5964974B2 JP 2014529985 A JP2014529985 A JP 2014529985A JP 2014529985 A JP2014529985 A JP 2014529985A JP 5964974 B2 JP5964974 B2 JP 5964974B2

Authority

JP

Japan

Prior art keywords

imidazol

phenyl

fluoro

trifluoromethyl

ethyl

Prior art date

2011-09-12

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 - Fee Related

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• 230000000694 effects Effects 0.000 title description 10
• 108091000080 Phosphotransferase Proteins 0.000 title description 6
• 102000020233 phosphotransferase Human genes 0.000 title description 6
• DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical class NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 title description 2
• -1 isopropyloxy, ethyl Chemical group 0.000 claims description 1056
• 150000001875 compounds Chemical class 0.000 claims description 518
• 238000000034 method Methods 0.000 claims description 94
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 49
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 35
• 239000012453 solvate Substances 0.000 claims description 30
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 27
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 239000000543 intermediate Substances 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 20
• 201000011510 cancer Diseases 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 11
• 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 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 8
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• 125000003118 aryl group Chemical group 0.000 claims description 5
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• MRYHAUHEHQAMRQ-UHFFFAOYSA-N 4-amino-6-[4-[4-(4-fluoro-3-methylphenyl)-1-[2-(methylamino)ethyl]imidazol-2-yl]piperidin-1-yl]pyrimidine-5-carboxamide Chemical compound CNCCN1C=C(C=2C=C(C)C(F)=CC=2)N=C1C(CC1)CCN1C1=NC=NC(N)=C1C(N)=O MRYHAUHEHQAMRQ-UHFFFAOYSA-N 0.000 claims description 2
• MOQRMWMUHUDDJL-UHFFFAOYSA-N 4-amino-6-[4-[4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-[2-(propan-2-ylamino)ethyl]imidazol-2-yl]piperidin-1-yl]pyrimidine-5-carboxamide Chemical compound CC(C)NCCN1C=C(C=2C=C(C(F)=CC=2)C(F)(F)F)N=C1C(CC1)CCN1C1=NC=NC(N)=C1C(N)=O MOQRMWMUHUDDJL-UHFFFAOYSA-N 0.000 claims description 2
• GAYRMKRSQCSTHF-UHFFFAOYSA-N 4-amino-6-[4-[4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-pyrrolidin-3-ylimidazol-2-yl]piperidin-1-yl]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=C(N)N=CN=C1N1CCC(C=2N(C=C(N=2)C=2C=C(C(F)=CC=2)C(F)(F)F)C2CNCC2)CC1 GAYRMKRSQCSTHF-UHFFFAOYSA-N 0.000 claims description 2
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