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).

  • Patent number: 9051254
    Abstract: 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: Grant
    Filed: June 11, 2012
    Date of Patent: June 9, 2015
    Assignees: HANGZHOU NORMAL UNIVERSITY, UNIVERSITY OF SHAOXING
    Inventors: Pengfei Zhang, Chao Shen, Runpu Shen, Wei Liu, Chunlei Wu
  • Patent number: 8962827
    Abstract: 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: Grant
    Filed: April 12, 2012
    Date of Patent: February 24, 2015
    Assignee: Zhejiang Medicine Co. Ltd. Xinchang Pharmaceutical Factory
    Inventors: Xiaoyue Jiang, Guofeng Wu, Weidong Ye, Runpu Shen, Xiaohua Song
  • Patent number: 8846968
    Abstract: 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: Grant
    Filed: December 3, 2012
    Date of Patent: September 30, 2014
    Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Patent number: 8765988
    Abstract: 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: Grant
    Filed: March 9, 2011
    Date of Patent: July 1, 2014
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
  • Patent number: 8697918
    Abstract: 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: Grant
    Filed: December 3, 2012
    Date of Patent: April 15, 2014
    Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Chunlei Lv, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Patent number: 8697919
    Abstract: 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: Grant
    Filed: April 6, 2011
    Date of Patent: April 15, 2014
    Assignees: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory, University of Shaoxing
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
  • Publication number: 20140024827
    Abstract: 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: Application
    Filed: April 12, 2012
    Publication date: January 23, 2014
    Applicant: ZHEJIANG MEDICINE CO., LTD XINCHANG PHARMACEUTICAL FACTORY
    Inventors: Xiaoyue Jiang, Guofeng Wu, Weidong Ye, Runpu Shen, Xiaohua Song
  • Publication number: 20140005442
    Abstract: 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: Application
    Filed: December 3, 2012
    Publication date: January 2, 2014
    Applicants: SHAOXING UNIVERSITY, ZHEJIANG MEDICINE CO., LTD. XINCHANG
    Inventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Publication number: 20140005434
    Abstract: 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: Application
    Filed: December 3, 2012
    Publication date: January 2, 2014
    Applicants: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang
    Inventors: Runpu Shen, Chunlei LV, Xiaoyue Jiang, Xuejun Lao, Weidong Ye, Luo Liu, Xiaohua Song, Chunlei Wu
  • Patent number: 8536361
    Abstract: 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: Grant
    Filed: January 30, 2011
    Date of Patent: September 17, 2013
    Inventors: Runpu Shen, Weidong Ye, Shiqing Pi, Xuejun Lao, Luo Liu, Xiaohua Song, Chunlei Wu, Zhigang Wu
  • Publication number: 20130046114
    Abstract: 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: Application
    Filed: April 6, 2011
    Publication date: February 21, 2013
    Applicants: University of Shaoxing, Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutic al Factory
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Xiongsheng Sun, Siping Hu
  • Publication number: 20120330048
    Abstract: 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: Application
    Filed: March 9, 2011
    Publication date: December 27, 2012
    Applicants: UNIVERSITY OF SHAOXING, ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORY
    Inventors: Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
  • Publication number: 20120316366
    Abstract: 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: Application
    Filed: June 11, 2012
    Publication date: December 13, 2012
    Applicants: UNIVERSITY OF SHAOXING, HANGZHOU NORMAL UNIVERSITY
    Inventors: PENGFEI ZHANG, CHAO SHEN, RUNPU SHEN, WEI LIU, CHUNLEI WU
  • Publication number: 20120310002
    Abstract: 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: Application
    Filed: January 30, 2011
    Publication date: December 6, 2012
    Inventors: Runpu Shen, Weidong Ye, Shiqing Pi, Xuejun Lao, Luo Liu, Xiaohua Song, Chunlei Wu, Zhigang Wu
  • Patent number: 7351854
    Abstract: 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: Grant
    Filed: May 17, 2007
    Date of Patent: April 1, 2008
    Assignees: Shaoxing University, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Guoqi Yu, Weidong Ye, Kui Wang, Xuejun Lao
  • Publication number: 20070270607
    Abstract: 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: Application
    Filed: May 17, 2007
    Publication date: November 22, 2007
    Applicants: SHAOXING UNIVERSITY, ZHEJIANG MEDICINE CO., LTD., XINCHANG PHARMACEUTICAL FACTORY
    Inventors: Runpu SHEN, Guoqi YU, Weidong YE, Kui WANG, Xuejun LAO
  • Patent number: 6727381
    Abstract: 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: Grant
    Filed: January 3, 2002
    Date of Patent: April 27, 2004
    Assignee: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
  • Publication number: 20020151742
    Abstract: 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: Application
    Filed: January 3, 2002
    Publication date: October 17, 2002
    Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang