Method for enzymatic synthesis of (7S)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-yl) N-methyl methanamine, and use for the synthesis of Ivabradine and the salts thereof 机翻标题: 暂无翻译,请尝试点击翻译按钮。

公开号/公开日
EP2687506 B1 2015-06-24 [EP2687506]EP2687506 A1 2014-01-22 [EP2687506] / 2015-06-242014-01-22
申请号/申请日
2013EP-0176588 / 2013-07-16
发明人
PEDRAGOSA MOREAU SANDRINE;LEFOULON FRANÇOIS;MORIS VARAS FRANCISCO;GONZALEZ SABIN JAVIER;
申请人
SERVIER;
主分类号
IPC分类号
C07C-269/04C07D-223/16C12P-041/00
摘要
(EP2687506) Synthesizing carbamate (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C.  Synthesizing carbamate of formula (IX) comprises performing an enantioselective enzymatic acylation of racemic form of (3,4-dimethoxy-7-bicyclo[4.2.0]octa-1,3,5-trienyl)methanamine of formula (IV) with a lipase (EC 3.1.1.3 in the international classification of enzymes) by carbonate of formula (R1O-(CO)-OR1) with 1-15 molar equivalents in organic solvents, aqueous solvents, a mixture of organic solvents and/or mixture of organic and aqueous solvents at a concentration of 5-500 g/l per liter of solvents and their mixtures, a E/S ratio of 10/1 to 1/100 and a temperature of 25-40[deg] C.  R1 : linear or branched 1-6C-alkyl, allyl or benzyl.  An independent claim is included for synthesis of (7S)-1-(3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-yl) N-methyl methanamine of formula (I) comprising performing enzymatic acylation of (IV) to obtain (IX), and performing reduction step using a reducing agent consisting of lithium tetrahydridoaluminate and sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) to obtain (I).  ACTIVITY : Cardiant; Vasotropic; Antianginal; Antiarrhythmic.  MECHANISM OF ACTION : None given.
机翻摘要
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地址
代理人
代理机构
;
优先权号
2012FR-0056913 2012-07-17
主权利要求
(EP2687506) 1. Process of synthesis of the compound of formula ([IX]): where R [1] represents a grouping alkyl C [1] - C [6] linear or ramified, allyl or benzyl, by [enantioselective] enzymatic [acylation] of the racemic amine of formula (IV): using a lipase (EC. 3.1.1.3 in the international classification of the enzymes): by a carbonate of formula R [1] O (CO) - BUT [1] where R [1] is such as definite previously, in quantity going from 1 to 15 molar equivalents compared to the amine of formula (IV), in an organic solvent, aqueous, a mixture of organic solvents or a mixture of solvents organic and aqueous, with a concentration from 5 to 500 [g]/L of composed of formula (IV) per liter of solvent or mixture of solvents, with a ratio I/o of 10/1 to 1/100, at a temperature of 25.deg.C with 40.deg.C.
法律状态
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