AU2006248649B2 - Novel oxadiazole derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors - Google Patents

Info

Publication number

AU2006248649B2

AU2006248649B2 AU2006248649A AU2006248649A AU2006248649B2 AU 2006248649 B2 AU2006248649 B2 AU 2006248649B2 AU 2006248649 A AU2006248649 A AU 2006248649A AU 2006248649 A AU2006248649 A AU 2006248649A AU 2006248649 B2 AU2006248649 B2 AU 2006248649B2

Authority

AU

Australia

Prior art keywords

phenyl

oxadiazol

fluoro

piperidin

methanone

Prior art date

2005-05-18

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 230000003281 allosteric effect Effects 0.000 title claims description 25
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims description 14
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims description 14
• 150000004866 oxadiazoles Chemical class 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 239
• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims abstract description 58
• 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims abstract description 58
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• 230000002265 prevention Effects 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
• 238000000034 method Methods 0.000 claims description 276
• -1 methanone { (S)-3-[3-(4-Fluoro-phenyl)-[ 1,2,4]oxadiazol-5-yl]-piperidin- l-yl} -(2,4,6-trifluoro phenyl)-methanone Chemical compound 0.000 claims description 57
• 239000000203 mixture Substances 0.000 claims description 40
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• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 12
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• PYUPTXHFQPNYMS-NSHDSACASA-N [(3s)-3-[3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2C(=CC(F)=CC=2)F)=C1C PYUPTXHFQPNYMS-NSHDSACASA-N 0.000 claims description 5
• QNFBKFBGEBITCP-LBPRGKRZSA-N [(3s)-3-[3-(2,4-difluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound FC1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=N1 QNFBKFBGEBITCP-LBPRGKRZSA-N 0.000 claims description 5
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• QRRNOELOFVMJSB-INIZCTEOSA-N [(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(1,2,5-trimethylpyrrol-3-yl)methanone Chemical compound CN1C(C)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2C=CC(F)=CC=2)=C1C QRRNOELOFVMJSB-INIZCTEOSA-N 0.000 claims description 2
• CXIBEVBSQCBRSY-UQKRIMTDSA-N [(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-pyridin-2-ylmethanone;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2N=CC=CC=2)=N1 CXIBEVBSQCBRSY-UQKRIMTDSA-N 0.000 claims description 2
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• SOWWXUOAKQFNCQ-INIZCTEOSA-N cyclohexyl-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C2CCCCC2)=N1 SOWWXUOAKQFNCQ-INIZCTEOSA-N 0.000 claims description 2
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