JP4677518B2 - 新規ピペリジニルアミノ−チエノ［２，３−ｄ］ピリミジン化合物 - Google Patents

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Publication number

JP4677518B2

JP4677518B2 JP2006509547A JP2006509547A JP4677518B2 JP 4677518 B2 JP4677518 B2 JP 4677518B2 JP 2006509547 A JP2006509547 A JP 2006509547A JP 2006509547 A JP2006509547 A JP 2006509547A JP 4677518 B2 JP4677518 B2 JP 4677518B2

Authority

JP

Japan

Prior art keywords

compound

thieno

amine

piperidin

pyrimidin

Prior art date

2003-03-31

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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• ADSGKJVJNPJWJS-UHFFFAOYSA-N n-piperidin-1-ylthieno[2,3-d]pyrimidin-2-amine Chemical class C1CCCCN1NC1=NC=C(C=CS2)C2=N1 ADSGKJVJNPJWJS-UHFFFAOYSA-N 0.000 title abstract description 5
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 208000019695 Migraine disease Diseases 0.000 claims abstract description 18
• 206010027599 migraine Diseases 0.000 claims abstract description 18
• 208000015114 central nervous system disease Diseases 0.000 claims abstract description 14
• 229940127239 5 Hydroxytryptamine receptor antagonist Drugs 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 264
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 152
• 239000000203 mixture Substances 0.000 claims description 86
• -1 (1-naphthalen-2-ylmethyl-piperidin-4-yl)-(5,6,7,8-tetrahydro-benzo [4,5] thieno [2,3-d] pyrimidin-4-yl) Chemical group 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 15
• 208000037905 systemic hypertension Diseases 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 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 8
• 229940044551 receptor antagonist Drugs 0.000 claims description 8
• 239000002464 receptor antagonist Substances 0.000 claims description 8
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 125000002723 alicyclic group Chemical group 0.000 claims description 5
• YWDUHOZXYSVKQP-UHFFFAOYSA-N CC(C1=CC=CC=C1)N2CCC(CC2)NC3=C4C5=C(CCCC5)SC4=NC=N3 Chemical compound CC(C1=CC=CC=C1)N2CCC(CC2)NC3=C4C5=C(CCCC5)SC4=NC=N3 YWDUHOZXYSVKQP-UHFFFAOYSA-N 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims description 2
• 239000003420 antiserotonin agent Substances 0.000 claims description 2
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
• 125000004404 heteroalkyl group Chemical group 0.000 claims 2
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
• 125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims 1
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 1
• JXZYICYIKCJUID-UHFFFAOYSA-N n-(1-benzhydrylpiperidin-4-yl)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine Chemical compound C1CCCC(C=23)=C1SC3=NC=NC=2NC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 JXZYICYIKCJUID-UHFFFAOYSA-N 0.000 claims 1
• 239000002400 serotonin 2A antagonist Substances 0.000 claims 1
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• 239000003814 drug Substances 0.000 description 41
• 239000000243 solution Substances 0.000 description 37
• 235000002639 sodium chloride Nutrition 0.000 description 29
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
• 102000005962 receptors Human genes 0.000 description 25
• 108020003175 receptors Proteins 0.000 description 25
• 125000000304 alkynyl group Chemical group 0.000 description 23
• 125000000623 heterocyclic group Chemical group 0.000 description 22
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• 125000003342 alkenyl group Chemical group 0.000 description 20
• 238000009472 formulation Methods 0.000 description 19
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 125000003545 alkoxy group Chemical group 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 241000124008 Mammalia Species 0.000 description 14
• 239000002775 capsule Substances 0.000 description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 239000005557 antagonist Substances 0.000 description 13
• 239000007788 liquid Substances 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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• 239000004615 ingredient Substances 0.000 description 11
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 10
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
• 208000019553 vascular disease Diseases 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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• 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 9
• 229910019142 PO4 Inorganic materials 0.000 description 9
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 125000004442 acylamino group Chemical group 0.000 description 9
• 125000003282 alkyl amino group Chemical group 0.000 description 9
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• 239000000935 antidepressant agent Substances 0.000 description 9
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• 125000004658 aryl carbonyl amino group Chemical group 0.000 description 9
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 9
• 125000001072 heteroaryl group Chemical group 0.000 description 9
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• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
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• FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 8
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