CA2668579A1 - Cis-cyclohexyl substituted pyrimidinone derivatives - Google Patents

Info

Publication number

CA2668579A1

CA2668579A1 CA002668579A CA2668579A CA2668579A1 CA 2668579 A1 CA2668579 A1 CA 2668579A1 CA 002668579 A CA002668579 A CA 002668579A CA 2668579 A CA2668579 A CA 2668579A CA 2668579 A1 CA2668579 A1 CA 2668579A1

Authority

CA

Canada

Prior art keywords

compound

hydrate

salt

pain

patient

Prior art date

2006-11-06

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title abstract description 19
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• 241001465754 Metazoa Species 0.000 claims abstract description 30
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• 238000000338 in vitro Methods 0.000 claims abstract description 21
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• 108010062740 TRPV Cation Channels Proteins 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 82
• YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 77
• 210000004027 cell Anatomy 0.000 claims description 66
• 238000003556 assay Methods 0.000 claims description 57
• -1 hydroxy, amino Chemical group 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 44
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• 238000009739 binding Methods 0.000 claims description 40
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
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• IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims description 7
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• 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 6
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• FSKYZRCACCHDGR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-4-one Chemical compound C1=CN=C2C(=O)N=CNC2=C1 FSKYZRCACCHDGR-UHFFFAOYSA-N 0.000 claims description 3
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• SHBDCXWCHZVXDX-TXEJJXNPSA-N C1C[C@H](C(F)(F)F)CC[C@@H]1C1=NC2=CC=CN=C2C(=O)N1C1=CC=C(Cl)N=C1 Chemical compound C1C[C@H](C(F)(F)F)CC[C@@H]1C1=NC2=CC=CN=C2C(=O)N1C1=CC=C(Cl)N=C1 SHBDCXWCHZVXDX-TXEJJXNPSA-N 0.000 claims description 2
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
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• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
• AYGLTQXKFKWBDG-UHFFFAOYSA-N 1-(4-fluorophenyl)-9-methyl-2-[4-(trifluoromethyl)cyclohexyl]purin-6-one Chemical compound CN1C=NC(C(N2C=3C=CC(F)=CC=3)=O)=C1N=C2C1CCC(C(F)(F)F)CC1 AYGLTQXKFKWBDG-UHFFFAOYSA-N 0.000 claims 1
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