JP2005522492A5 - - Google Patents

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Publication number

JP2005522492A5

JP2005522492A5 JP2003583416A JP2003583416A JP2005522492A5 JP 2005522492 A5 JP2005522492 A5 JP 2005522492A5 JP 2003583416 A JP2003583416 A JP 2003583416A JP 2003583416 A JP2003583416 A JP 2003583416A JP 2005522492 A5 JP2005522492 A5 JP 2005522492A5

Authority

JP

Japan

Prior art keywords

group

methyl

pyridin

substituted

trimethoxyphenyl

Prior art date

2003-04-11

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.)

Pending

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• 150000003839 salts Chemical class 0.000 claims description 14
• -1 cyclic amine compound Chemical class 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 9
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 239000012830 cancer therapeutic Substances 0.000 claims description 4
• 238000001415 gene therapy Methods 0.000 claims description 4
• 239000003276 histone deacetylase inhibitor Substances 0.000 claims description 4
• 229940121372 histone deacetylase inhibitor Drugs 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 30
• 125000001072 heteroaryl group Chemical group 0.000 claims 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 24
• 125000000217 alkyl group Chemical group 0.000 claims 22
• 125000003545 alkoxy group Chemical group 0.000 claims 18
• 125000003118 aryl group Chemical group 0.000 claims 18
• 125000005843 halogen group Chemical group 0.000 claims 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
• 125000002252 acyl group Chemical group 0.000 claims 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
• 125000004414 alkyl thio group Chemical group 0.000 claims 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 12
• 125000004475 heteroaralkyl group Chemical group 0.000 claims 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims 6
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 6
• 125000003342 alkenyl group Chemical group 0.000 claims 6
• 125000005530 alkylenedioxy group Chemical group 0.000 claims 6
• 125000000304 alkynyl group Chemical group 0.000 claims 6
• 125000003277 amino group Chemical group 0.000 claims 6
• NLGSNZVQUOCQJN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-n,1-bis[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN(C3CCN(CC=4C=C(N=CC=4)C=4C=C(OC)C(OC)=C(OC)C=4)CC3)C=3C=C4OCOC4=CC=3)C=2)=C1 NLGSNZVQUOCQJN-UHFFFAOYSA-N 0.000 claims 6
• WCQNPRXILHBFLX-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)-n,1-bis[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound COC1=CC(OC)=CC(N(CC=2C=C(N=CC=2)C=2C=C(OC)C(OC)=C(OC)C=2)C2CCN(CC=3C=C(N=CC=3)C=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 WCQNPRXILHBFLX-UHFFFAOYSA-N 0.000 claims 6
• HLFPVNRCIWSFNV-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1N(C1CCN(CC=2C=C(N=CC=2)C=2C=C(OC)C(OC)=C(OC)C=2)CC1)CC1=CN=CC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 HLFPVNRCIWSFNV-UHFFFAOYSA-N 0.000 claims 6
• FCMRKIJWSJURDE-UHFFFAOYSA-N n-(4-methoxyphenyl)-n,1-bis[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical group C1=CC(OC)=CC=C1N(C1CCN(CC=2C=C(N=CC=2)C=2C=C(OC)C(OC)=C(OC)C=2)CC1)CC1=CC=NC(C=2C=C(OC)C(OC)=C(OC)C=2)=C1 FCMRKIJWSJURDE-UHFFFAOYSA-N 0.000 claims 6
• AVFGUYNXNVEQFK-UHFFFAOYSA-N n-methyl-n,1-bis[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2N=CC=C(CN(C)C3CCN(CC=4C=C(N=CC=4)C=4C=C(OC)C(OC)=C(OC)C=4)CC3)C=2)=C1 AVFGUYNXNVEQFK-UHFFFAOYSA-N 0.000 claims 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
• OOAMKQROPFDCBV-UHFFFAOYSA-N n-(4-methylsulfanylphenyl)-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-n-[[5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]methyl]piperidin-4-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(CN(C3CCN(CC=4C=C(N=CC=4)C=4C=C(OC)C(OC)=C(OC)C=4)CC3)C=3C=CC(SC)=CC=3)C=NC=2)=C1 OOAMKQROPFDCBV-UHFFFAOYSA-N 0.000 claims 4
• 125000001424 substituent group Chemical group 0.000 claims 4
• 239000003112 inhibitor Substances 0.000 claims 3
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
• 239000003814 drug Substances 0.000 claims 1
• 230000001737 promoting effect Effects 0.000 description 1