Patents Assigned to JILIN ASYMCHEM LABORATORIES CO., LTD
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Patent number: 11858873Abstract: Disclosed is a method for continuously synthesizing a propellane compound. The method includes the following steps: using 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane or a derivative thereof as a raw material to form a ring with a lithium metal agent by a continuous reaction, so as to synthesize the propellane compound. A technical scheme of the present disclosure is applied, and a continuous reaction device is used.Type: GrantFiled: June 18, 2019Date of Patent: January 2, 2024Assignee: JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, Enxuan Zhang, Jiangping Lu, Fuliang Wei, Sihang Yang
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Patent number: 11827909Abstract: Provided are a proline hydroxylase and uses thereof. The proline hydroxylase comprises having the amino acid sequence of SEQ ID NO: 2 with the exception of a mutation of one or more amino acids; wherein the mutation of one or more amino acids must comprises E27K, and the mutation of one or more amino acids selected from the group consisting of: H14R, L16N, T25R, F26L, E27K, D30S, S33N, E34N, E34G, E34L, E34S, E34D, Y35W, Y35K, S37W, S37F, S37E, S37N, S37T, S37C, W40F, K41E, D54G, H55Q, S57L, I58T, I58Y, I58A, I58R, I58V, I58S, I58C, K86P, T91A, F95Y, C97Y, I98V, K106V, K106T, K106Q, F111S, K112E, K112R, S154A, K162E, L166M, I118F, I118V, I118R, H119R, H119F, I120V, K123D, K123N, K123Q, K123S, K123I, K123T, T130N, D134G, V135K, N165H, D173G, K209R, I223V and S225A, and having proline hydroxylase activity.Type: GrantFiled: December 10, 2020Date of Patent: November 28, 2023Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD., ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD., TIANJIN ASYMCHEM PHARMACEUTICALS CO., LTD., ASYMCHEM LABORATORIES (FUXIN) CO., LTD., JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, Gage James, Jiangping Lu, Na Zhang, Wenyan Yu, Fang Liu, Yanjun Li, Xin Huang, Juan Gao, Kejian Zhang, Yulei Ma, Junlu Wei
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Patent number: 11162081Abstract: A ketoreductase mutant and use thereof are provided. The amino acid sequence of the ketoreductase mutant is an amino acid sequence obtained by mutation of the amino acid sequence shown in SEQ ID NO: 1, wherein the mutation at least comprises one of the following mutation sites: position 6, position 94, position 96, position 117, position 144, position 156, position 193, position 205, position 224, position 176, position 85 and position 108; alternatively, the amino acid sequence of the ketoreductase mutant has a mutation site in a mutated amino acid sequence and an amino acid sequence having 80% or more homology with the mutated amino acid sequence.Type: GrantFiled: January 22, 2018Date of Patent: November 2, 2021Assignee: JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, Gage James, Jiangping Lu, Xingfu Xu, Wenyan Yu, Na Zhang, Yulei Ma, Yibing Cheng, Huiyan Mu
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Patent number: 10961516Abstract: Provided are a proline hydroxylase and uses thereof. The proline hydroxylase comprises (a) a protein having the amino acid sequence as shown in SEQ ID NO: 2; (b) a protein having an amino acid sequence of SEQ HD NO: 2 with a mutation of one or more amino acids and having a proline hydroxylase activity; or (c) a protein retaining the mutation of one or more amino acids as in (b), and having the proline hydroxylase activity and having at least 78% homology with the amino acid sequence of the protein in (b). Protein having the amino acid sequence as shown in SEQ HD NO: 2 and mutants obtained by genetically engineering have higher catalytic specificity or significantly increased catalytic activity when compared to proline hydroxylases in prior art.Type: GrantFiled: November 4, 2016Date of Patent: March 30, 2021Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD., ASYMCHEM LIFE SCIENCES (TIANJIN) CO., LTD., TIANJIN ASYMCHEM PHARMACEUTICALS CO., LTD., ASYMCHEM LABORATORIES (FUXIN) CO., LTD., JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, Gage James, Jiangping Lu, Na Zhang, Wenyan Yu, Fang Liu, Yanjun Li, Xin Huang, Juan Gao, Kejian Zhang, Yulei Ma, Junlu Wei
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Patent number: 10544119Abstract: The present invention relates to a preparation method for a chiral intermediate for use in statins, acquired with chloroacetic acid and benzyl alcohol as starting materials via a series of reactions, namely etherification, condensation, substitution, and asymmetric reduction. The preparation method provided in the present invention has a novel route of synthesis, allows an intermediate compound to be introduced conveniently into the chiral center of a glycol via enzyme reduction, and not only is low in costs, but also is reliable in quality. The route of synthesis provided in the present invention uses raw materials of low costs, has an easy to operate process, and provides a final product of great purity and high yield.Type: GrantFiled: August 4, 2014Date of Patent: January 28, 2020Assignees: Asymchem Laboratories (Tianjin) Co., Ltd., Asymchem Life Science (Tianjin) Co. Ltd., Tianjin Asymchem Pharmaceutical Co., Ltd., Asymchem Laboratories (Fuxin) Co., Ltd., Jilin Asymchem Laboratories Co., Ltd.Inventors: Hao Hong, Chaoyong Chen, Jiuyuan Li, Litao Shen, Lina Guo, Hongying Tian
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Patent number: 10131926Abstract: A transaminase and a use thereof are provided. The transaminase has the amino acid sequences as shown in SEQ ID NO: 2 or 4, or has at least 80% identity to the amino acid sequences as shown in SEQ ID NO: 2 or 4, or has amino acid sequences which are obtained by the substitution, deletion or addition of one or more amino acids and have an the activity of an omega-transaminase with high stereoselective R-configuration catalytic activity, wherein the high stereoselective refers to the content of one of the stereoisomers being at least about 1.1 times that of the other.Type: GrantFiled: October 31, 2014Date of Patent: November 20, 2018Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD, ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD, TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD, ASYMCHEM LABORATORIES (FUXIN) CO., LTD, JILIN ASYMCHEM LABORATORIES CO., LTDInventors: Hao Hong, Feng Gao, Yanjun Li, Yan Zhang, Shaohe Li
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Patent number: 10131883Abstract: The application provides a Diketoreductase (DKR) mutant, its nucleotide coding sequence, and an expression cassette, recombinant vector and host cell containing the sequence, as well as a method for application of the mutant to the preparation of 3R,5S-dicarbonyl compound. An ee value of the obtained 3R,5S-dicarbonyl compound is higher than 99%, and a de value is about 90%. The DKR mutant is a key pharmaceutical intermediate, and particularly provides an efficient catalyst for synthesis of a chiral dicarbonyl hexanoic acid chain of a statin drug.Type: GrantFiled: August 4, 2014Date of Patent: November 20, 2018Assignees: Asymchem Laboratories (Tianjin) Co., Ltd, Asymchem Life Science (Tianjin) Co., Ltd, Tianjin Asymchem Pharmaceutical Co., Ltd, Asymchem Laboratories (Fuxin) Co., Ltd, Jilin Asymchem Laboratories Co., LtdInventors: Hao Hong, James Gage, Feng Gao, Lihui Liu, Wenyan Yu, Fang Liu, Lina Guo, Na Zhang
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Patent number: 10000470Abstract: A method for preparing nilotinib includes the following steps: performing an aminocarbonylation reaction on a compound A and 3-(4-methyl-1H-imidazole-1-yl)-5-(trifluoromethyl) aniline to obtain an amination product; and performing deprotection treatment of an R group on the amination product to obtain the nilotinib, wherein the compound A has a structure shown in formula I, and in formula I, an R group is selected from benzyl, —COCF3, —CHO or —CO2R?, where an R? group is C1˜C10 alkyl, C1˜C3 alkoxy ethyl or C7˜C19 aralkyl.Type: GrantFiled: May 26, 2015Date of Patent: June 19, 2018Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD, TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD, JILIN ASYMCHEM LABORATORIES CO., LTD, ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD, ASYMCHEM LABORATORIES (FUXIN) CO., LTDInventors: Hao Hong, Gage James, Jiuyuan Li, Changfeng Li, Gaochao Huang
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Patent number: 9926283Abstract: Provided are an intermediate compound for preparing rosuvastatin calcium and a preparation method of the rosuvastatin calcium. The method comprises: using the foregoing intermediate compound as a raw material, and subjecting the raw material to a step of Wittig reaction, a step of protecting group removal and hydrolysis and a step of calcium salt formation, so as to obtain the rosuvastatin calcium. The product, which is prepared from the intermediate compound, can be substantially enhanced in stereoselectivity and also notably improved in purity and yield; in addition, the method for preparing rosuvastatin calcium from the intermediate compound is simple, convenient and low in cost.Type: GrantFiled: March 7, 2014Date of Patent: March 27, 2018Assignees: Asymchem Laboratories (Tianjin) Co., Ltd., Asymchem Life Science (Tianjin) Co., Ltd., Tianjin Asymchem Pharmaceutical Co., Ltd., Asymchem Laboratories (Fuxin) Co., Ltd., Jilin Asymchem Laboratories Co., Ltd.Inventors: Hao Hong, James Gage, Jiuyuan Li, Litao Shen, Lei Zhang, Changming Dong
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Publication number: 20170190684Abstract: The present invention relates to a preparation method for a chiral intermediate for use in statins, acquired with chloroacetic acid and benzyl alcohol as starting materials via a series of reactions, namely etherification, condensation, substitution, and asymmetric reduction. The preparation method provided in the present invention has a novel route of synthesis, allows an intermediate compound to be introduced conveniently into the chiral center of a glycol via enzyme reduction, and not only is low in costs, but also is reliable in quality. The route of synthesis provided in the present invention uses raw materials of low costs, has an easy to operate process, and provides a final product of great purity and high yield.Type: ApplicationFiled: August 4, 2014Publication date: July 6, 2017Applicants: Asymchem Laboratories (Tianjin) Co., Ltd., Asymchem Life Science (Tianjin) Co., Ltd., Tianjin Asymchem Pharmaceutical Co., Ltd., Asymchem Laboratories (Fuxin) Co., Ltd., Jilin Asymchem Laboratories Co., Ltd.Inventors: Hao Hong, Chaoyong Chen, Jiuyuan Li, Litao Shen, Lina Guo, Hongying Tian
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Publication number: 20170152488Abstract: The application provides a Diketoreductase (DKR) mutant, its nucleotide coding sequence, and an expression cassette, recombinant vector and host cell containing the sequence, as well as a method for application of the mutant to the preparation of 3R,5S-dicarbonyl compound. An ee value of the obtained 3R,5S-dicarbonyl compound is higher than 99%, and a de value is about 90%. The DKR mutant is a key pharmaceutical intermediate, and particularly provides an efficient catalyst for synthesis of a chiral dicarbonyl hexanoic acid chain of a statin drug.Type: ApplicationFiled: August 4, 2014Publication date: June 1, 2017Applicants: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD., ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD., TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD., ASYMCHEM LABORATORIES (FUXIN) CO., LTD., JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, James Gage, Feng Gao, Lihui Liu, Wenyan Yu, Fang Liu, Lina Guo, Na Zhang
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Publication number: 20170022169Abstract: Provided are an intermediate compound for preparing rosuvastatin calcium and a preparation method of the rosuvastatin calcium. The method comprises: using the foregoing intermediate compound as a raw material, and subjecting the raw material to a step of Wittig reaction, a step of protecting group removal and hydrolysis and a step of calcium salt formation, so as to obtain the rosuvastatin calcium. The product, which is prepared from the intermediate compound, can be substantially enhanced in stereoselectivity and also notably improved in purity and yield; in addition, the method for preparing rosuvastatin calcium from the intermediate compound is simple, convenient and low in cost.Type: ApplicationFiled: March 7, 2014Publication date: January 26, 2017Applicants: Asymchem Laboratories (Tianjin) Co., Ltd., Asymchem Life Science (Tianjin) Co., Ltd., Tianjin Asymchem Pharmaceutical Co., Ltd., Asymchem Laboratories (Fuxin) Co., Ltd., Jilin Asymchem Laboratories Co., Ltd.Inventors: Hao HONG, James GAGE, Jiuyuan LI, Litao SHEN, Lei ZHANG, Changming DONG
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Patent number: 9371326Abstract: Disclosed is a method for synthesizing sapropterin dihydrochloride. The present disclosure reduces a synthesis route of the sapropterin dihydrochloride, and resolves a racemate intermediate or an intermediate having a low antimer isomerism value by using a chiral resolving reagent, thereby obtaining an intermediate having a high antimer isomerism value. Raw materials are cheap and readily available, and the cost is significantly reduced, hence providing an effective scheme for mass industrial production of the sapropterin dihydrochloride.Type: GrantFiled: December 27, 2012Date of Patent: June 21, 2016Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD, ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD, TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD, ASYMCHEM LABORATORIES (FUXIN) CO., LTD, JILIN ASYMCHEM LABORATORIES CO., LTDInventors: Hao Hong, James Gage, Chaoyong Chen, Jiangping Lu, Yan Zhou, Shuangyong Liu
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Patent number: 9365573Abstract: Disclosed is a method for synthesizing sapropterin dihydrochloride. The present disclosure reduces a synthesis route of the sapropterin dihydrochloride, introduces a chiral center in an asymmetric synthesis manner, in which a tetrahydrofuran solution containing a samarium catalyst is adopted as a catalyst, and obtains a target compound having a high antimer isomerism value by means of selective catalysis. The yield is improved, raw materials are cheap and readily available, and the cost is significantly reduced, hence providing an effective scheme for mass industrial production of the sapropterin dihydrochloride.Type: GrantFiled: December 27, 2012Date of Patent: June 14, 2016Assignees: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD, ASYMCHEM LIFE SCIENCE (TIANJIN) CO., LTD, ASYMCHEM LABORATORIES (FUXIN) CO., LTD, JILIN ASYMCHEM LABORATORIES CO., LTD, TIANJIN ASYMCHEM PHARMACEUTICAL CO., LTD.Inventors: Hao Hong, James Gage, Chaoyong Chen, Jiangping Lu, Yan Zhou, Shuangyong Liu