NZ590344A - Isoxazole derivatives and their use as metabotropic glutamate receptor potentiators - Google Patents

Info

Publication number

NZ590344A

NZ590344A NZ590344A NZ59034409A NZ590344A NZ 590344 A NZ590344 A NZ 590344A NZ 590344 A NZ590344 A NZ 590344A NZ 59034409 A NZ59034409 A NZ 59034409A NZ 590344 A NZ590344 A NZ 590344A

Authority

NZ

New Zealand

Prior art keywords

methyl

dihydro

chloro

ethyl

isoxazole

Prior art date

2008-06-06

Links

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• Global Dossier
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• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title description 17
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title description 17
• 150000002545 isoxazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 94
• -1 6-substituted 4-bromo-2-bromomethyl-benzoic acid methyl ester Chemical class 0.000 claims abstract description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
• 238000006243 chemical reaction Methods 0.000 claims abstract description 14
• 239000002253 acid Substances 0.000 claims abstract description 12
• 150000001408 amides Chemical class 0.000 claims abstract description 12
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• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims abstract description 10
• 150000001412 amines Chemical class 0.000 claims abstract description 10
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims abstract description 9
• 229930195712 glutamate Natural products 0.000 claims abstract description 9
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims abstract description 8
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 8
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• UXOLDCOJRAMLTQ-ZZXKWVIFSA-N ethyl (2e)-2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(\Cl)=N/O UXOLDCOJRAMLTQ-ZZXKWVIFSA-N 0.000 claims abstract description 6
• 150000002825 nitriles Chemical class 0.000 claims abstract description 6
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• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 claims abstract description 4
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• HGHRISACSUZVJA-LBPRGKRZSA-N 7-chloro-2-[(1s)-1-cyclopropylethyl]-5-[3-(morpholine-4-carbonyl)-1,2-oxazol-5-yl]-3h-isoindol-1-one Chemical compound C1([C@H](C)N2C(C3=C(Cl)C=C(C=C3C2)C=2ON=C(C=2)C(=O)N2CCOCC2)=O)CC1 HGHRISACSUZVJA-LBPRGKRZSA-N 0.000 claims abstract description 4
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• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 8
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• 229910052736 halogen Inorganic materials 0.000 claims description 3
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• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 3
• NEAGCMRVPAGRKG-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methyl-1,2-oxazole-3-carboxamide Chemical compound OCCN(C)C(=O)C=1C=CON=1 NEAGCMRVPAGRKG-UHFFFAOYSA-N 0.000 claims description 3
• 125000006706 (C3-C6) carbocyclyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
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