CA2518218A1 - Tetrazole and oxadiazolone substituted .beta.-amino acid derivatives - Google Patents

Info

Publication number

CA2518218A1

CA2518218A1 CA002518218A CA2518218A CA2518218A1 CA 2518218 A1 CA2518218 A1 CA 2518218A1 CA 002518218 A CA002518218 A CA 002518218A CA 2518218 A CA2518218 A CA 2518218A CA 2518218 A1 CA2518218 A1 CA 2518218A1

Authority

CA

Canada

Prior art keywords

tetrazol

pain

disorders

disorder

methyl

Prior art date

2003-03-07

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
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• 150000003536 tetrazoles Chemical group 0.000 title abstract description 9
• ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical group O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 153
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 73
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 210000003169 central nervous system Anatomy 0.000 claims abstract description 4
• 150000003839 salts Chemical class 0.000 claims description 77
• 208000002193 Pain Diseases 0.000 claims description 59
• 241000124008 Mammalia Species 0.000 claims description 58
• 208000035475 disorder Diseases 0.000 claims description 57
• 238000000034 method Methods 0.000 claims description 56
• -1 more particularly Diseases 0.000 claims description 48
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
• 239000002253 acid Substances 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 229940079593 drug Drugs 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
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• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 8
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• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 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 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
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• IRGUQCXZQYDFIB-UHFFFAOYSA-N 2-cyclopentyl-2-(2h-tetrazol-5-yl)ethanamine Chemical compound N=1N=NNC=1C(CN)C1CCCC1 IRGUQCXZQYDFIB-UHFFFAOYSA-N 0.000 claims description 4
• XZTNSYTXLIHCOV-UHFFFAOYSA-N 4-methyl-2-(2h-tetrazol-5-yl)hexan-1-amine Chemical compound CCC(C)CC(CN)C1=NN=NN1 XZTNSYTXLIHCOV-UHFFFAOYSA-N 0.000 claims description 4
• HEYQMGOIQCPCJR-UHFFFAOYSA-N 4-propyl-2-(2h-tetrazol-5-yl)heptan-1-amine Chemical compound CCCC(CCC)CC(CN)C1=NN=NN1 HEYQMGOIQCPCJR-UHFFFAOYSA-N 0.000 claims description 4
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• HRQYYBXGEHDLNQ-UHFFFAOYSA-N 2-(3,5-dimethylcyclohexyl)-2-(2h-tetrazol-5-yl)ethanamine Chemical compound C1C(C)CC(C)CC1C(CN)C1=NN=NN1 HRQYYBXGEHDLNQ-UHFFFAOYSA-N 0.000 claims description 3
• IKXDKDIBPYBTQF-UHFFFAOYSA-N 3-methyl-2-(2h-tetrazol-5-yl)-4-[3-(trifluoromethyl)phenyl]butan-1-amine Chemical compound N=1N=NNC=1C(CN)C(C)CC1=CC=CC(C(F)(F)F)=C1 IKXDKDIBPYBTQF-UHFFFAOYSA-N 0.000 claims description 3
• RNWBSZAHGAQFRT-UHFFFAOYSA-N 3-methyl-5-phenyl-2-(2h-tetrazol-5-yl)pentan-1-amine Chemical compound N=1N=NNC=1C(CN)C(C)CCC1=CC=CC=C1 RNWBSZAHGAQFRT-UHFFFAOYSA-N 0.000 claims description 3
• WWJNGJMHBAWIBF-UHFFFAOYSA-N 3-phenyl-2-(2h-tetrazol-5-yl)propan-1-amine Chemical compound N=1N=NNC=1C(CN)CC1=CC=CC=C1 WWJNGJMHBAWIBF-UHFFFAOYSA-N 0.000 claims description 3
• NIAFYYRJRTUUMY-UHFFFAOYSA-N 4,4-dimethyl-2-(2h-tetrazol-5-yl)pentan-1-amine Chemical compound CC(C)(C)CC(CN)C1=NN=NN1 NIAFYYRJRTUUMY-UHFFFAOYSA-N 0.000 claims description 3
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