【药物名称】Lansoprazole, AG-1749, ABT-006, CG-4801, A-65006, Ogast, Lanzor, Lanzo, Agopton, Opiren, Bamalite, Takepron, Lansox, Lansox, Ogastro, Monolitum, Prevacid, Zoton
化学结构式(Chemical Structure):
参考文献No.4097
标题:Pyridine derivs. and their production
作者:Nohara, A.; Maki, Y. (Takeda Chemical Industries, Ltd.)
来源:AU 8545895; EP 0174726; ES 8607288; JP 1986050978; US 4628098; US 4689333
合成路线图解说明:

The condensation of 2,3-dimethyl-4-nitropyridine N-oxide (I) with 2,2,2-trifluoroethanol (II) by means of K2CO3 in hot HMPT gives 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine N-oxide (III), which by isomerization in acetic anhydride at 100 C is converted to 2-(hydroxymethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (IV). The reaction of (IV) with SOCl2 in refluxing CHCl3 affords the corresponding chloromethyl derivative (V), which is condensed with 2-mercaptobenzimidazole (VI) by means of sodium methoxide in refluxing methanol to yield 2-(2-benzimidazolylthiomethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin (VII). Finally, this compound is oxidized with m-chloroperbenzoic acid in CHCl3.

参考文献No.53181
标题:Intermediate for the synthesis of lansoprazole and process for obtaining it
作者:Montserrat Vidal, C.; Serra Macia, X. (Laboratorios Salvat SA)
来源:ES 2063705
合成路线图解说明:

The chlorination of 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine-N-oxide (I) with trichloroisocyanuric acid in hot chloroform gives the 2-chloromethyl derivative (II), which is condensed with 2-mercapto-1H-benzimidazole (III) by means of NaOH in methanol to yield the adduct (IV). The reaction of (IV) with PCl3 and acetic acid eliminates the N-oxide group, affording the sulfanylmethylpyridine (V). Finally, this compound is oxidized with tert-butyl hydroperoxide (VI) in ethanol to provide the target sulfoxide. Alternatively, the intermediate adduct (IV) can also be obtained as follows: The chlorination of 2,3-dimethyl-4-nitropyridine-N-oxide (VII) with trichloroisocyanuric acid as before gives the chloromethyl derivative (VIII), which is condensed with 2-mercapto-1H-benzimidazole (III) as before to yield the adduct (IX). Finally, this compound is treated with 2,2,2-trifluoroethanol (X), benzyltrimethylammonium chloride and K2CO3 in acetonitrile to afford the target intermediate (IV).

参考文献No.95999
标题:LANSOPRAZOLE < Prop INN >
作者:Prous, J.; Casta馿r, J.
来源:Drugs Fut 1989,14(7),625
合成路线图解说明:

The condensation of 2,3-dimethyl-4-nitropyridine N-oxide (I) with 2,2,2-trifluoroethanol (II) by means of K2CO3 in hot HMPT gives 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine N-oxide (III), which by isomerization in acetic anhydride at 100 C is converted to 2-(hydroxymethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (IV). The reaction of (IV) with SOCl2 in refluxing CHCl3 affords the corresponding chloromethyl derivative (V), which is condensed with 2-mercaptobenzimidazole (VI) by means of sodium methoxide in refluxing methanol to yield 2-(2-benzimidazolylthiomethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin (VII). Finally, this compound is oxidized with m-chloroperbenzoic acid in CHCl3.

参考文献No.900135
标题:Stabilized pharmaceutical composition comprising a benzimidazole compound, its production and its use as an antiulcer agent.
作者:Makino, T.; Tabata, T.; Hirai, S.
来源:EP 237200; JP 87277322
合成路线图解说明:

The condensation of 2,3-dimethyl-4-nitropyridine N-oxide (I) with 2,2,2-trifluoroethanol (II) by means of K2CO3 in hot HMPT gives 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)pyridine N-oxide (III), which by isomerization in acetic anhydride at 100 C is converted to 2-(hydroxymethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (IV). The reaction of (IV) with SOCl2 in refluxing CHCl3 affords the corresponding chloromethyl derivative (V), which is condensed with 2-mercaptobenzimidazole (VI) by means of sodium methoxide in refluxing methanol to yield 2-(2-benzimidazolylthiomethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridin (VII). Finally, this compound is oxidized with m-chloroperbenzoic acid in CHCl3.

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