Patents by Inventor Runpu Shen
Runpu Shen has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9051254Abstract: The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of ?40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.Type: GrantFiled: June 11, 2012Date of Patent: June 9, 2015Assignees: HANGZHOU NORMAL UNIVERSITY, UNIVERSITY OF SHAOXINGInventors: Pengfei Zhang, Chao Shen, Runpu Shen, Wei Liu, Chunlei Wu
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Patent number: 8962827Abstract: Provided are a linezolid intermediate and the preparation method thereof and a method for synthesizing linezolid. The structure of the intermediate is shown as formula F2, wherein the compound is prepared by a condensation reaction of (S)—N-(3-chloro-2-hydroxy-1-propyl) acetamide and the compound shown in formula F4. In the preparation methods of the compound shown in formula F2 and linezolid, the reaction system is mild, side reactions are few and the product yield is high.Type: GrantFiled: April 12, 2012Date of Patent: February 24, 2015Assignee: Zhejiang Medicine Co. Ltd. Xinchang Pharmaceutical FactoryInventors: Xiaoyue Jiang, Guofeng Wu, Weidong Ye, Runpu Shen, Xiaohua Song
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Patent number: 8846968Abstract: The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.Type: GrantFiled: December 3, 2012Date of Patent: September 30, 2014Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Patent number: 8765988Abstract: The invention relates to a novel important lycopene intermediate 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.Type: GrantFiled: March 9, 2011Date of Patent: July 1, 2014Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
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Patent number: 8697919Abstract: The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5, 9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.Type: GrantFiled: April 6, 2011Date of Patent: April 15, 2014Assignees: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory, University of ShaoxingInventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
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Patent number: 8697918Abstract: The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.Type: GrantFiled: December 3, 2012Date of Patent: April 15, 2014Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Publication number: 20140024827Abstract: Provided are a linezolid intermediate and the preparation method thereof and a method for synthesizing linezolid. The structure of the intermediate is shown as formula F2, wherein the compound is prepared by a condensation reaction of (S)—N—(3-chloro-2-hydroxy-1-propyl) acetamide and the compound shown in formula F4. In the preparation methods of the compound shown in formula F2 and linezolid, the reaction system is mild, side reactions are few and the product yield is high.Type: ApplicationFiled: April 12, 2012Publication date: January 23, 2014Applicant: ZHEJIANG MEDICINE CO., LTD XINCHANG PHARMACEUTICAL FACTORYInventors: Xiaoyue Jiang, Guofeng Wu, Weidong Ye, Runpu Shen, Xiaohua Song
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Publication number: 20140005434Abstract: The present invention relates to an intermediate (12) of lycopene of 2,6,10-trimethyl-1,1-dialkoxyl-3,5,9-undecantriene of formula, (12) and its intermediate of 4-methyl-5,5-dialkoxyl-1-pentenyl-1-phosphonic acid dialkyl ester of formula (10), and their preparation methods. The process route is simple, the starting materials are available easily, the cost is low, and it is valuable in industry.Type: ApplicationFiled: December 3, 2012Publication date: January 2, 2014Applicants: Shaoxing University, Zhejiang Medicine Co., Ltd. XinchangInventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Publication number: 20140005442Abstract: The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.Type: ApplicationFiled: December 3, 2012Publication date: January 2, 2014Applicants: SHAOXING UNIVERSITY, ZHEJIANG MEDICINE CO., LTD. XINCHANGInventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
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Patent number: 8536361Abstract: 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4), and preparation method thereof are provided. The preparation method comprises: reacting a pseudo ionone of formula (2) with sulfonium salt to prepare a epoxide of formula (9), and then reacting the epoxide of formula (9) with magnesium bromide to prepare a C-14 aldehyde of formula (3); condensing the C-14 aldehyde of formula (3) with tetra-alkyl methylene diphosphonate to obtain 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4). Furthermore, the preparation method of lycopene via 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4) is also provided. The present method has the advantages of short route, easily obtained raw materials, and low cost.Type: GrantFiled: January 30, 2011Date of Patent: September 17, 2013Inventors: Runpu Shen, Weidong Ye, Shiqing Pi, Xuejun Lao, Luo Liu, Xiaohua Song, Chunlei Wu, Zhigang Wu
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Publication number: 20130046114Abstract: The invention discloses an intermediate 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and a preparation method and uses thereof. In the synthesis method for the current lycopene intermediate 2-pos double bond C-14 aldehyde (2,6,10-trimethyl-2,5,9-undecatriene-1-aldehyde), expensive methyl iodide, polluting dimethyl sulphide and dangerous strong base are needed, so that the method is hardly applied to industrial production. The invention provides a new compound 1-methoxyl-2,6,10-trimethyl-1,3,5,9-undec-tetraene, and pure 2-pos double bond C-14 aldehyde can be prepared by hydrolyzing and refining the compound. The synthetic route is simplified and the great suitability for industrial production is achieved.Type: ApplicationFiled: April 6, 2011Publication date: February 21, 2013Applicants: University of Shaoxing, Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutic al FactoryInventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
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Publication number: 20120330048Abstract: The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.Type: ApplicationFiled: March 9, 2011Publication date: December 27, 2012Applicants: UNIVERSITY OF SHAOXING, ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORYInventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
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Publication number: 20120316366Abstract: The present invention describes a novel synthetic method for preparing the key intermediate 2,6,10-trimethyl-1,1-dialkoxy-3,5,9-undecatriene of lycopene. An existing synthetic method have some disadvantages that it is very difficult to gain the raw material dialkyl 4-methyl-5,5-diakoxy-1-pentene-1-phosphonate (10) because no effective synthetic method can be adopted, and furthermore the obtained target compound is composed of several cis/trans isomers. This invention relates to a process comprising a condensation step wherein a starting C10-phosphonate is changed to its carbanion completely at a temperature of ?40˜30 under an atmosphere of a non-reactive gas in an organic solvent catalyzed by base, and then C4-dialkyl is added to undergo Wittig-Horner condensation. This invention affords all trans C14-acetal and this method is characterized with the advantages of simple procedure, easy access to raw material and low cost, which makes it has the value of industrial application.Type: ApplicationFiled: June 11, 2012Publication date: December 13, 2012Applicants: UNIVERSITY OF SHAOXING, HANGZHOU NORMAL UNIVERSITYInventors: PENGFEI ZHANG, CHAO SHEN, RUNPU SHEN, WEI LIU, CHUNLEI WU
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Publication number: 20120310002Abstract: 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4), and preparation method thereof are provided. The preparation method comprises: reacting a pseudo ionone of formula (2) with sulfonium salt to prepare a epoxide of formula (9), and then reacting the epoxide of formula (9) with magnesium bromide to prepare a C-14 aldehyde of formula (3); condensing the C-14 aldehyde of formula (3) with tetra-alkyl methylene diphosphonate to obtain 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4). Furthermore, the preparation method of lycopene via 1,4,6,10-tetra-double bond pentadec-carbon phosphonate of formula (4) is also provided. The present method has the advantages of short route, easily obtained raw materials, and low cost.Type: ApplicationFiled: January 30, 2011Publication date: December 6, 2012Inventors: Runpu Shen, Weidong Ye, Shiqing Pi, Xuejun Lao, Luo Liu, Xiaohua Song, Chunlei Wu, Zhigang Wu
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Patent number: 7351854Abstract: 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.Type: GrantFiled: May 17, 2007Date of Patent: April 1, 2008Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Guoqi Yu, Weidong Ye, Kui Wang, Xuejun Lao
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Publication number: 20070270607Abstract: 1-Chloro-2-methyl-4-acyloxy-2-butene derivatives can be synthesized in good yields and high purity starting from isoprene and employing a chlorohydrin formation reaction in a system made of N-chloroisocyanuric acid derivatives and water, followed by esterification and rearrangement of the crude product mixture.Type: ApplicationFiled: May 17, 2007Publication date: November 22, 2007Applicants: SHAOXING UNIVERSITY, ZHEJIANG MEDICINE CO., LTD., XINCHANG PHARMACEUTICAL FACTORYInventors: Runpu SHEN, Guoqi YU, Weidong YE, Kui WANG, Xuejun LAO
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Patent number: 6727381Abstract: The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.Type: GrantFiled: January 3, 2002Date of Patent: April 27, 2004Assignee: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
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Publication number: 20020151742Abstract: The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.Type: ApplicationFiled: January 3, 2002Publication date: October 17, 2002Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang