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1. 发明申请

US20170305822A1 METHOD FOR PREPARING SITAGLIPTIN INTERMEDIATE VIA ASYMMETRICAL REDUCTION METHOD 审中-公开
公开(公告)号：US20170305822A1
公开(公告)日：2017-10-26
申请号：US15319370
申请日：2015-10-09
申请人： ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD. , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Jian Hong , Yusheng Wang , Boyu Wang , Luning Huang , Eric Gu
IPC分类号： C07C29/153 , C07C25/13 , B01J27/18 , C07D487/04 , C07C29/151
CPC分类号： C07C29/153 , B01J27/18 , B01J2231/44 , B01J2531/004 , C07C25/13 , C07C29/1514 , C07C227/32 , C07C229/34 , C07C269/04 , C07C271/22 , C07D487/04
摘要： Disclosed is a method for synthesizing a sitagliptin intermediate, the method comprising: in the presence of hydrogen and a transition metal catalyst having a chiral phosphine ligand, subjecting a compound of formula II to an asymmetric reductive amination with ammonia or ammonium salt in a proper organic solvent under the condition of adding an acidic additive to produce a compound of formula I, wherein, an R- or S-configuration of a stereocenter is represented by *; the compound of formula I of R configuration can be used to prepare sitagliptin, and a reaction formula is as follows: R1 and R2 are each independently selected from hydrogen, C1-C12 linear or branched alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C2-C12 alkynyl and C7-C12 arylalkyl. The method has a high yield and a high ee % value, a mild reaction condition and a low production cost, and is simple to operate, convenient to purify, environmental friendly and suitable for industrial production.

2. 发明授权

US10189760B2 Method for preparing sitagliptin intermediate via asymmetrical reduction method 有权
公开(公告)号：US10189760B2
公开(公告)日：2019-01-29
申请号：US15319370
申请日：2015-10-09
申请人： ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD. , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Jian Hong , Yusheng Wang , Boyu Wang , Luning Huang , Eric Gu
IPC分类号： C07C229/00 , C07C29/153 , B01J27/18 , C07C25/13 , C07D487/04 , C07C29/151
CPC分类号： C07C29/153 , B01J27/18 , B01J2231/44 , B01J2531/004 , C07C25/13 , C07C29/1514 , C07C227/32 , C07C229/34 , C07C269/04 , C07C271/22 , C07D487/04
摘要： Disclosed is a method for synthesizing a sitagliptin intermediate, the method comprising: in the presence of hydrogen and a transition metal catalyst having a chiral phosphine ligand, subjecting a compound of formula II to an asymmetric reductive amination with ammonia or ammonium salt in a proper organic solvent under the condition of adding an acidic additive to produce a compound of formula I, wherein, an R- or S-configuration of a stereocenter is represented by *; the compound of formula I of R configuration can be used to prepare sitagliptin, and a reaction formula is as follows: R1 and R2 are each independently selected from hydrogen, C1-C12 linear or branched alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C2-C12 alkynyl and C7-C12 arylalkyl. The method has a high yield and a high ee % value, a mild reaction condition and a low production cost, and is simple to operate, convenient to purify, environmental friendly and suitable for industrial production.

3. 发明申请

US20170044129A1 METHOD FOR PREPARING CANAGLIFLOZIN INTERMEDIATE 2-(2-METHYL-5-BROMOBENZYL)-5-(4-FLUOROPHENYL)THIOPHENE 有权
标题翻译：中间体2-（2-甲基-5-溴甲基）-5-（4-氟代戊基）噻吩的制备方法
公开(公告)号：US20170044129A1
公开(公告)日：2017-02-16
申请号：US15308456
申请日：2015-06-19
申请人： ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD. , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Wenjing Liao , Xiaowen Guo , Luning Huang , Eric Gu
IPC分类号： C07D333/12
CPC分类号： C07D333/12
摘要： Provide in the present invention is a method for preparing canagliflozin intermediate 2-(2-methyl-5-bromobenzyl)-5-(4-fluorobenzene)thiophene. The method comprises a compound, shown as formula (II), of (5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]ketone being reduced under the action of a directly used borane solution or borane locally produced by reacting alkali metal borohydride with a Lewis acid in a suitable solvent and at a suitable temperature, so as to obtain the compound of formula (I) of 2-(2-methyl-5-bromobenzyl)-5-(4-fluorobenzene)thiophene. The preparation method avoids the use of expensive reductive agents and guarantees the complete conversion of raw materials, wherein the post-treatment is simple, the purity of product obtained is high, the reaction yield is high, in the preparation method is simple and convenient, and can easily be used in industry.
摘要翻译：在本发明中提供了制备canagliflozin中间体2-（2-甲基-5-溴苄基）-5-（4-氟苯）噻吩的方法。该方法包括在直接使用的硼烷溶液的作用下还原的（5-溴-2-甲基苯基）[5-（对氟苯基）噻吩-2-基]酮的式（II）化合物，或硼烷在局部通过碱金属硼氢化物与路易斯酸在合适的溶剂中和在合适的温度下反应，得到2-（2-甲基-5-溴苄基）-5-（4）的式（I）化合物 - 氟苯）噻吩。制备方法避免使用昂贵的还原剂，保证原料完全转化，其中后处理简单，得到的产物纯度高，反应收率高，制备方法简单方便，并且可以很容易地在工业中使用。

4. 发明授权

US09951036B2 Method for preparing canagliflozin intermediate 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene 有权
公开(公告)号：US09951036B2
公开(公告)日：2018-04-24
申请号：US15308456
申请日：2015-06-19
申请人： ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD. , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Wenjing Liao , Xiaowen Guo , Luning Huang , Eric Gu
IPC分类号： C07D333/12
CPC分类号： C07D333/12
摘要： Provide in the present invention is a method for preparing canagliflozin intermediate 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene. The method comprises a compound, shown as formula (II), of (5-bromo-2-methylphenyl)[5-(p-fluorophenyl)thiophene-2-yl]ketone being reduced under the action of a directly used borane solution or borane locally produced by reacting alkali metal borohydride with a Lewis acid in a suitable solvent and at a suitable temperature, so as to obtain the compound of formula (I) of 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene. The preparation method avoids the use of expensive reductive agents and guarantees the complete conversion of raw materials, wherein the post-treatment is simple, the purity of product obtained is high, the reaction yield is high, in the preparation method is simple and convenient, and can easily be used in industry.

5. 发明授权

US09873651B2 Method for preparing sitagliptin intermediate via asymmetrical reduction method 有权
公开(公告)号：US09873651B2
公开(公告)日：2018-01-23
申请号：US15319370
申请日：2015-10-09
申请人： ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD. , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Jian Hong , Yusheng Wang , Boyu Wang , Luning Huang , Eric Gu
IPC分类号： C07C229/00 , C07C29/153 , C07C29/151 , C07C25/13 , C07D487/04 , B01J27/18
摘要： Disclosed is a method for synthesizing a sitagliptin intermediate, the method comprising: in the presence of hydrogen and a transition metal catalyst having a chiral phosphine ligand, subjecting a compound of formula II to an asymmetric reductive amination with ammonia or ammonium salt in a proper organic solvent under the condition of adding an acidic additive to produce a compound of formula I, wherein, an R- or S-configuration of a stereocenter is represented by *; the compound of formula I of R configuration can be used to prepare sitagliptin, and a reaction formula is as follows: R1 and R2 are each independently selected from hydrogen, C1-C12 linear or branched alkyl, C3-C12 cycloalkyl, C2-C12 alkenyl, C2-C12 alkynyl and C7-C12 arylalkyl. The method has a high yield and a high ee % value, a mild reaction condition and a low production cost, and is simple to operate, convenient to purify, environmental friendly and suitable for industrial production.

6. 发明授权

US11420948B2 Synthesis method for cariprazine 有权
公开(公告)号：US11420948B2
公开(公告)日：2022-08-23
申请号：US17266955
申请日：2019-08-06
申请人： Zhejiang Huahai Pharmaceutical Co., Ltd , SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.
发明人： Wenjing Liao , Jianfeng Ge , Jicheng Zhang , Luning Huang , Anping Tao , Eric Gu
IPC分类号： C07D295/135 , C07B43/06
摘要： The present application relates to a synthesis method for cariprazine, comprising performing an acylation reaction between a compound represented by formula (I) and dimethylcarbamoyl chloride in a reaction solvent in the presence of an aqueous solution of an inorganic base, so as to obtain the cariprazine compound represented by formula (II). The synthesis method overcomes defects in the prior art such as a long reaction time, large size impurities and the difficulty of purification, and provides a new method suitable for commercial production wherein the reaction is fast, impurity sizes are small, the product is easily purified, the purity of the product can reach 99.0% or more, and the yield is high.

7. 发明授权

US09926286B2 Vortioxetine intermediate and synthesis process thereof 有权
公开(公告)号：US09926286B2
公开(公告)日：2018-03-27
申请号：US15126890
申请日：2015-03-25
申请人： SHANGHAI SYNCORES TECHNOLOGIES INC. LTD. , ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD
发明人： Caide Tang , Gang Wang , Boyu Wang , Luning Huang , Eric Gu
IPC分类号： C07D295/096 , C07D295/185
CPC分类号： C07D295/096 , C07D295/185 , C07D295/205
摘要： The present invention provides a new intermediate II and a method for synthesizing the same. The method comprises: (a) firstly diazotizing a compound of formula I as a raw material, and then halogenating to obtain an intermediate II; and (b) reacting the intermediate II with a compound III to obtain a compound IV, hydrolyzing the obtained compound IV directly without being separated to obtain Vortioxetine represented by compound V. The intermediate II can be used for synthesizing Vortioxetine.

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