Patents Assigned to SHANGHAI SYNCORES TECHNOLOGIES, INC.
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Patent number: 11420948Abstract: 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.Type: GrantFiled: August 6, 2019Date of Patent: August 23, 2022Assignees: Zhejiang Huahai Pharmaceutical Co., Ltd., SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Wenjing Liao, Jianfeng Ge, Jicheng Zhang, Luning Huang, Anping Tao, Eric Gu
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Patent number: 11365178Abstract: The present invention relates to a method for preparing an intermediate (Formula IV) of sodium elagolix. The intermediate is prepared by the following route. The method has advantages of simple and safe operation, high yield, less environmental pollution, good economic effect and suitability for industrial production, wherein R represents C1-C4 substituted or unsubstituted benzyl or allyl.Type: GrantFiled: December 25, 2018Date of Patent: June 21, 2022Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD., SHANGHAI SYNCORES TECHNOLOGIES, INCInventors: Hu Su, Xiaowen Guo, Yukun Liang, Kaiqiang Shi, Jintao Yang, Kang He, Anping Tao, Luning Huang, Jianguo An, Xi Chen, Hong Gu
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Publication number: 20210300883Abstract: 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.Type: ApplicationFiled: August 6, 2019Publication date: September 30, 2021Applicants: Zhejiang Huahai Pharmaceutical Co., Ltd, SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Wenjing LIAO, Jianfeng GE, Jicheng ZHANG, Luning HUANG, Anping TAO, Eric GU
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Patent number: 10836751Abstract: The present application provides a method for preparing nintedanib. The method of the present application is carried out by using 4-halo-3-nitro-benzoic acid methyl ester (compound II) and 3-oxo-3-phenylpropionate (compound III) as raw materials, and preparing nintedanib via intermediates of methyl 4-(1-alkoxy-1,3-dioxo-3-phenyl propan-2-yl)-3-nitrobenzoate (compound IV) and methyl 3-benzoyl-2-oxoindoline-6-formate (compound V). The method for preparing nintedanib (I) provided by the present application has the advantages of using easily obtained raw materials, having a simple process, being cost effective and environmentally friendly, and is suitable for industrial-scale production.Type: GrantFiled: October 11, 2017Date of Patent: November 17, 2020Assignees: Zhejiang Huahai Pharmaceutical Co., Ltd., Shanghai Syncores Technologies, Inc.Inventors: Zeng Li, Xiaosong Cheng, Xianliang He, Jicheng Zhang, Luning Huang, Anping Tao, Hong Gu
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Patent number: 10766895Abstract: Disclosed is a preparation method for a Palbociclib free base crystal form A as shown in Formula I, comprising the following steps: treating a Palbociclib free base and/or a Palbociclib salt compound by using an inorganic base in a water solvent at the temperature of 35 to 100?C. to obtain a Palbociclib free base crystal form A, the water solvent being water or mixed solvent obtained by water and an organic solvent capable of being mixed and disclosed in the water. Also disclosed is a preparation method for a Palbociclib free base crystal form B, comprising the following steps: treating a Palbociclib salt compound by using an inorganic base in a water solvent at the temperature of 0 to 20° C. to obtain a Palbociclib free crystal form B, the water solvent being water or a mixed solvent obtained by water and an organic solvent capable of being mixed and dissolved in the water. The method is safe and convenient in operation and low in pollution, and facilitates industrial production.Type: GrantFiled: May 7, 2019Date of Patent: September 8, 2020Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD., SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Haisheng Fan, Xiaowen Guo, Luning Huang, Hong Gu
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Patent number: 10385079Abstract: The present invention relates to a preparation method for a tedizolid compound in Formula I. In Formula I, R is selected from hydrogen, formula A, formula B, benzyl or benzyl substituted by a substituent, the substituent is selected from a group consisting of halogen, nitryl, C1-C6 alkyl, and C1-C6 alkoxy, and R1 is C1-C6 alkyl or C1-C6 alkyl substituted by halogen. The method comprises: generating a compound having a structure as shown in Formula C and a compound having a structure as shown in Formula D by a coupled reaction under the catalysis of a metal catalyst, a substituent of R being defined as above, where X is a leaving group, the leaving group comprising chlorine, bromine, iodine, and sulfonyl oxy such as trifluoromethane sulfonic oxy, methylsulfonyl oxy and benzenesulfonyl oxy, or benzenesulfonyl oxy substituted by one or more substituents, the substituent being selected from a group consisting of halogen, C1-C6 alkyl, and C1-C6 alkoxy.Type: GrantFiled: November 2, 2016Date of Patent: August 20, 2019Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD, SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Siyuan Li, Shaoxiao Gui, Jicheng Zhang, Luning Huang, Anping Tao, Hong Gu
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Patent number: 10329290Abstract: Disclosed is a preparation method for a Palbociclib free base crystal form A as shown in Formula I, comprising the following steps: treating a Palbociclib free base and/or a Palbociclib salt compound by using an inorganic base in a water solvent at the temperature of 35 to 100° C. to obtain a Palbociclib free base crystal form A, the water solvent being water or mixed solvent obtained by water and an organic solvent capable of being mixed and disclosed in the water. Also disclosed is a preparation method for a Palbociclib free base crystal form B, comprising the following steps: treating a Palbociclib salt compound by using an inorganic base in a water solvent at the temperature of 0 to 20° C. to obtain a Palbociclib free crystal form B, the water solvent being water or a mixed solvent obtained by water and an organic solvent capable of being mixed and dissolved in the water. The method is safe and convenient in operation and low in pollution, and facilitates industrial production.Type: GrantFiled: November 2, 2016Date of Patent: June 25, 2019Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD, SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Haisheng Fan, Xiaowen Guo, Luning Huang, Hong Gu
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Patent number: 10189760Abstract: 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.Type: GrantFiled: October 9, 2015Date of Patent: January 29, 2019Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD., SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Jian Hong, Yusheng Wang, Boyu Wang, Luning Huang, Eric Gu
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Patent number: 9951036Abstract: 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.Type: GrantFiled: June 19, 2015Date of Patent: April 24, 2018Assignees: SHANGHAI SYNCORES TECHNOLOGIES INC. LTD., ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTDInventors: Wenjing Liao, Xiaowen Guo, Luning Huang, Eric Gu
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Patent number: 9926286Abstract: 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.Type: GrantFiled: March 25, 2015Date of Patent: March 27, 2018Assignees: SHANGHAI SYNCORES TECHNOLOGIES INC. LTD., ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTDInventors: Caide Tang, Gang Wang, Boyu Wang, Luning Huang, Eric Gu
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Patent number: 9873651Abstract: 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.Type: GrantFiled: October 9, 2015Date of Patent: January 23, 2018Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD, SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Jian Hong, Yusheng Wang, Boyu Wang, Luning Huang, Eric Gu
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Publication number: 20170305822Abstract: 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.Type: ApplicationFiled: October 9, 2015Publication date: October 26, 2017Applicants: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD., SHANGHAI SYNCORES TECHNOLOGIES INC.LTD.Inventors: Jian Hong, Yusheng Wang, Boyu Wang, Luning Huang, Eric Gu
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Patent number: 9745264Abstract: Provided is a method for preparing silodosin. Also provided is a method for preparing an organic acid salt of a new intermediate 3-(7-cyano-5-((R)-2-((R)-1-phenylethylamino)propyl)-1-hydrogen-indolyl) propyl alcohol (ester or ether), and a new intermediate 3-(7-cyano-5-((R)-2-(((R)-1-phenethyl)(2-(2-(trifluoroethoxy)phenoxy) ethyl)amino)propyl)1-hydrogen-indolyl)propyl alcohol (ester or ether) and a salt thereof. The method has the following advantages: raw materials are cheap and easy to obtain, the operation is simple, the intermediate and product are easy to purify, the yield is high, and the method is applicable to industrial production.Type: GrantFiled: October 20, 2014Date of Patent: August 29, 2017Assignees: Shanghai Syncores Technologies, Inc., Zhejiang Huahai Pharmaceuticals Co., Ltd.Inventors: Hong Gu, Jian Cao, Liushan Chen, Luning Huang
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Patent number: 9656958Abstract: The invention relates to a method for synthesizing an intermediate of Apixaban comprising reacting a compound of formula I with 5-chloro-valeryl chloride in the presence of inorganic base in an inert solvent to obtain a compound of formula II, with the reaction formula of (A), wherein R is selected from nitro group and the group (B). The method is mild in reaction condition, simple in operation, easy in purification, inexpensive in production cost, environmental-friendly, and suitable for industrial production.Type: GrantFiled: July 29, 2014Date of Patent: May 23, 2017Assignees: Shanghai Syncores Technologies Inc. Ltd., Zhejiang Huahai Pharmaceutical Co., Ltd.Inventors: Boyu Wang, Jinfeng Yao, Luning Huang, Jeannie Zhang
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Publication number: 20170044129Abstract: 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.Type: ApplicationFiled: June 19, 2015Publication date: February 16, 2017Applicants: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD., SHANGHAI SYNCORES TECHNOLOGIES INC. LTD., SHANGHAI SYNCORES TECHNOLOGIES INC. LTD.Inventors: Wenjing Liao, Xiaowen Guo, Luning Huang, Eric Gu
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Patent number: 9126990Abstract: The present invention discloses novel methods for synthesizing Rivaroxaban intermediate, i.e., 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one. The novel methods provided in the present invention involve mild reaction conditions, convenient operations, easy purification, and low production costs, and thus the process is environmental-friendly and suitable for industrial production.Type: GrantFiled: January 18, 2012Date of Patent: September 8, 2015Assignees: ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTD, SHANGHAI SYNCORES TECHNOLOGIES, INC.Inventors: Chunpeng Zi, Luning Huang, Jeannie Zhang
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Publication number: 20140114066Abstract: The present invention discloses novel methods for synthesizing Rivaroxaban intermediate, i.e., 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3 -oxazolidin-3 -yl]phenyl}morpholin-3-one. The novel methods provided in the present invention involve mild reaction conditions, convenient operations, easy purification, and low production costs, and thus the process is environmental-friendly and suitable for industrial production.Type: ApplicationFiled: January 18, 2012Publication date: April 24, 2014Applicants: SHANGHAI SYNCORES TECHNOLOGIES, INC., ZHEJIANG HUAHAI PHARMACEUTICAL CO., LTDInventors: Chunpeng Zi, Luning Huang, Jeannie Zhang