【药物名称】Milameline hydrochloride, Miramelin, CI-979, RU-35926, PD-129409
化学结构式(Chemical Structure):
参考文献No.7328
标题:1,2,5,6-Tetrahydropyridine-3-carboxaldehyde oxime derivs., process for their preparation, their application as medicaments and compsns. containing them
作者:Galliani, G.; Barzaghi, F.; Butti, A.; Bonetti, C.; Toja, E. (Aventis Pharma SA)
来源:EP 0239445; JP 1987252767; US 5219872
合成路线图解说明:

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

参考文献No.8515
标题:O-Substd. tetrahydropyridine oxime cholinergic agents
作者:Bergmeier, S.C.; Downs, D.A.; Moos, W.H.; Moreland, D.W.; Tecle, H. (Pfizer Inc.)
来源:AU 8781102; EP 0271798; JP 1988215664; US 4710508
合成路线图解说明:

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

参考文献No.378254
标题:Milameline Hydrochloride
作者:Graul, A.; Casta馿r, J.
来源:Drugs Fut 1996,21(11),1124
合成路线图解说明:

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

参考文献No.384425
标题:1-Alkyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde-O-alkyl-oximes: A new class of potent orally active muscarinic agonists related to arecoline
作者:Toja, E.; Bonetti, C.; Butti, A.; Hunt, P.; Fortin, M.; Barzaghi, F.; Formento, M.L.; Maggioni, A.; Nencioni, A.; Galliani, G.
来源:Eur J Med Chem 1991,26(9),853-68
合成路线图解说明:

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

Drug Information Express,Drug R&D,Chemical Database,Patent Search.
Copyright © 2006-2024 Drug Future. All rights reserved.Contact Us