NZ564255A - Novel heterocyclic compounds as positive allosteric modulators of metabotropic glutamate receptors - Google Patents

Info

Publication number

NZ564255A

NZ564255A NZ564255A NZ56425506A NZ564255A NZ 564255 A NZ564255 A NZ 564255A NZ 564255 A NZ564255 A NZ 564255A NZ 56425506 A NZ56425506 A NZ 56425506A NZ 564255 A NZ564255 A NZ 564255A

Authority

NZ

New Zealand

Prior art keywords

alkyl

oxadiazol

piperidin

fluoro

methanone

Prior art date

2005-05-18

Links

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• Global Dossier
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• 230000003281 allosteric effect Effects 0.000 title abstract description 22
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title description 12
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title description 12
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 142
• 239000000203 mixture Substances 0.000 claims abstract description 55
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• 125000000217 alkyl group Chemical group 0.000 claims description 404
• 125000003118 aryl group Chemical group 0.000 claims description 153
• 125000001072 heteroaryl group Chemical group 0.000 claims description 114
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 66
• -1 substituted Chemical class 0.000 claims description 63
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 57
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 50
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 50
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 239000001257 hydrogen Substances 0.000 claims description 49
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
• 238000002360 preparation method Methods 0.000 claims description 24
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• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 150000001204 N-oxides Chemical class 0.000 claims description 13
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• 239000012453 solvate Substances 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
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• QVBBSMSTRBNOMJ-AWEZNQCLSA-N (4-chlorophenyl)-[(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 QVBBSMSTRBNOMJ-AWEZNQCLSA-N 0.000 claims description 3
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• PWEZDXFTPKFAAL-AWEZNQCLSA-N [(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(3-fluorophenyl)methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C=CC=2)=C1 PWEZDXFTPKFAAL-AWEZNQCLSA-N 0.000 claims description 3
• MUMITROLTOTPRS-AWEZNQCLSA-N [(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=C(F)C=CC=3)N=2)CCC1 MUMITROLTOTPRS-AWEZNQCLSA-N 0.000 claims description 3
• KBTHKZSHURSRDH-HNNXBMFYSA-N [(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=C(F)C=CC=3)N=2)CCC1 KBTHKZSHURSRDH-HNNXBMFYSA-N 0.000 claims description 3
• MUMITROLTOTPRS-UHFFFAOYSA-N [3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(OC=3C=C(F)C=CC=3)N=2)CCC1 MUMITROLTOTPRS-UHFFFAOYSA-N 0.000 claims description 3
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• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 2
• RFSWMYADYIKSGY-KRWDZBQOSA-N (4-methylphenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 RFSWMYADYIKSGY-KRWDZBQOSA-N 0.000 claims description 2
• DLHCRKQPDNCDPF-AWEZNQCLSA-N (6-fluoropyridin-3-yl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 DLHCRKQPDNCDPF-AWEZNQCLSA-N 0.000 claims description 2
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• KKOQSEWPKNKOPH-INIZCTEOSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-phenylmethanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2C=CC=CC=2)=NC=1OC1=CC=CC=C1 KKOQSEWPKNKOPH-INIZCTEOSA-N 0.000 claims description 2
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• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 4
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