Patents Examined by Paul A. Zucker
  • Patent number: 10710955
    Abstract: Methods and systems for producing alkyl hydroxyalkanoate from hydroxy carboxylic acid recovery bottoms. The methods generally comprise the steps of obtaining a hydroxy carboxylic acid recovery bottom, adding a mono-alcohol to the hydroxy carboxylic acid recovery bottom to obtain a first mixture, heating the first mixture in the presence of a catalyst to form a reaction product, distilling the reaction product, and recovering an alkyl hydroxyalkanoate fraction.
    Type: Grant
    Filed: May 23, 2019
    Date of Patent: July 14, 2020
    Assignee: CARGILL, INCORPORATED
    Inventors: Timothy Walter Abraham, Anthony Louis Duran, Stephen C. Edgar, Ravi R. Gokarn
  • Patent number: 10711031
    Abstract: A method for extracting phytosterols from tall oil pitch. The method involves saponifying tall oil pitch using an alkali in a polyatomic alcohol, extracting unsaponified matter from the alkali-alcohol solution using a hydrocarbon solvent, subsequently removing the solvent by distillation, and concentrating the phytosterols, wherein a mixture of paraffin hydrocarbons is used as said hydrocarbon solvent, and, following extraction from the extraction solution, betulin is isolated by crystallization and the phytosterols are then concentrated by means of rectification. This method enables an increase in the extraction rate of phytosterols from a saponified tall oil pitch up to 95%, producing the end product with phytosterol content of at least 65% with unwanted betulin impurities at no more than 0.3%.
    Type: Grant
    Filed: May 8, 2018
    Date of Patent: July 14, 2020
    Assignee: ORGKHIM BCH MANAGEMENT COMPANY, JSC
    Inventors: Ilia Nikolaevich Chernov, Alexey Olegovich Korshunov, Taras Ivanovich Dolinskiy, Mikhail Alekseevich Lazarev, Ekaterina Aleksandrovna Mavrina, Ilia Sergeevich Ilichev, Arkadiy Benyuminovich Radbil
  • Patent number: 10707424
    Abstract: A method of making a chemical product includes reacting a compound represented by Chemical Formula 1 with a metal alkyl chalcogenide using a palladium catalyst and a tertiary phosphine catalyst to obtain a first intermediate represented by Chemical Formula 2, obtaining a second intermediate represented by Chemical Formula 3 from the first intermediate, obtaining a third intermediate from the second intermediate and a compound represented by Chemical Formula 4, obtaining a fourth intermediate including a chalcogen-containing ring from the third intermediate, and performing a cyclization reaction of the fourth intermediate to obtain a fused heteroaromatic compound. A fused heteroaromatic compound obtained by the method, an intermediate thereof, and a synthetic method of the intermediate are disclosed.
    Type: Grant
    Filed: July 10, 2017
    Date of Patent: July 7, 2020
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Eun Kyung Lee, Eigo Miyazaki, Jeong Il Park, Hyun Bum Kang
  • Patent number: 10696617
    Abstract: Provided is a method for the alcoholysis of an amide. The method comprises subjecting an amide-containing compound to alcoholysis under alkaline conditions using an epoxy compound as an accelerant of alcoholysis, the method comprising: mixing the amide-containing compound, the epoxy compound, a pH adjuster and a solvent to form an alkaline reaction system, the pH of the alkaline reaction system being 7.5-9.5; reacting the alkaline reaction system at 50° C. ˜150° C. to subject the amide-containing compound to alcoholysis.
    Type: Grant
    Filed: May 8, 2017
    Date of Patent: June 30, 2020
    Assignee: ASYMCHEM LABORATORIES (TIANJIN) CO., LTD
    Inventors: Jiangping Lu, Qinglan Pei, Jinquan Yu, Enxuan Zhang
  • Patent number: 10689338
    Abstract: Novel amisulpride derivatives and pharmaceutical compositions thereof are disclosed. The amisulpride derivative disclosed herein or a pharmaceutical composition thereof may have better membrane permeability compared to amisulpride. The amisulpride derivative disclosed herein or a pharmaceutical composition thereof may be used for antagonizing dopamine and/or serotonin (e.g., 5-HT2a) and/or ?2 receptor in a subject, either individually or in combination with other CNS active agents. The amisulpride derivative disclosed herein or a pharmaceutical composition thereof may be used for treating one or more conditions responsive to modulation of dopamine and/or serotonin (e.g., 5-HT2a) and/or ?2 receptor in a subject, either individually or in combination with other CNS active agents.
    Type: Grant
    Filed: September 5, 2019
    Date of Patent: June 23, 2020
    Assignee: LB Pharmaceuticals Inc.
    Inventors: Andrew R. Vaino, Vincent T. Grattan, Zachary Prensky
  • Patent number: 10683265
    Abstract: The present invention relates to a cannabidiol-3-sulfonic acid, a preparation method and application thereof, and a cannabidiol derivative. The present invention introduces a sulfonic acid group in a molecular structure of cannabidiol, and the sulfonic acid group as a polar group can increase the polarity of cannabidiol, thereby improving the water solubility thereof. The cannabidiol-3-sulfonic acid can be subjected to a salt forming reaction with an inorganic base or an organic base, so that the water solubility of the cannabidiol is further improved, and the druggability of a drug based on a parent nucleus and physiological activity of the CBD structure can be enhanced. The newly introduced sulfonic acid group in the cannabidiol-3-sulfonic acid provided by the present invention can be used as a new action site to react with a specific group, and the research and application range of the cannabidiol-3-sulfonic acid is further broadened.
    Type: Grant
    Filed: October 7, 2019
    Date of Patent: June 16, 2020
    Assignee: YANTAI HEMP BIOTECHNOLOGY CO., LTD.
    Inventors: Guiwu Qu, Ming Cui
  • Patent number: 10676500
    Abstract: The present invention relates to processes for preparing compounds of Formula (I) and compounds of Formula (II): These compounds are useful as FXR or TGR5 modulators.
    Type: Grant
    Filed: April 9, 2018
    Date of Patent: June 9, 2020
    Assignee: Enanta Pharmaceuticals, Inc.
    Inventors: Guoqiang Wang, Yong He, Brett Granger, Xuechao Xing, Yat Sun Or
  • Patent number: 10676418
    Abstract: The present invention addresses the problem of providing a method for efficiently producing uniform microparticles of curcumin and/or ?-oryzanol at a higher yield. The target microparticles are produced by dissolving a starting material in a solvent to give a starting material solution and then subjecting the starting material solution to crystallization by a poor solvent method to thereby deposit the starting material. To prepare the starting material solution, curcumin and/or ?-oryzanol are used as the starting material(s) and ethanol is used as the solvent. The starting material(s) and the solvent are stirred in a pressurized state at a temperature of 78.3-130° C. inclusive to give the starting material solution. Then, the starting material solution thus obtained is subjected to crystallization by the poor solvent method and thus the target microparticles are produced.
    Type: Grant
    Filed: September 5, 2017
    Date of Patent: June 9, 2020
    Assignee: M. TECHNIQUE CO., LTD.
    Inventors: Masakazu Enomura, Kaeko Araki
  • Patent number: 10669225
    Abstract: Linear ?, ?-nonadecanediester derivatives and methods of making the derivatives are described. The methods include reacting a linear ?, ?-nonadecanediester or a linear ?, ?-nonadecanedicarboxylic acid with a reactant optionally in the presence of at least one of a solvent and a catalyst to form the ?, ?-nonadecanediester derivative. Methods of making linear ?, ?-nonadecanediester or diester derivatives are also described.
    Type: Grant
    Filed: November 9, 2016
    Date of Patent: June 2, 2020
    Assignee: Battelle Memorial Institute
    Inventors: Ramanathan S. Lalgudi, Jeffrey Cafmeyer, Robert J. Cain, Daniel Garbark
  • Patent number: 10669233
    Abstract: The present invention provides a process for purifying methionine. A methionine product having a purity of up to 99% or higher is obtained by separating methionine from a salt by-product through a process comprising adsorption and desorption using a macroporous adsorption resin, where the methionine content in the salt by-product is ?0.03%. The yield of methionine extracted with the resin is up to 98% or higher. By using the process of the present invention, the existing production process is simplified, the quality of the methionine product is improved, and the production costs for methionine are reduced.
    Type: Grant
    Filed: March 19, 2019
    Date of Patent: June 2, 2020
    Assignees: SUNRESIN NEW MATERIALS CO. LTD., XI'AN, Bluestar Adisseo Nanjing Co., Ltd.
    Inventors: Xiaokang Kou, Risheng Wang, Gang Wang, Qiong Liu, Wanping Ren, Julien Boutet, Yuanbin Yang, Valentin Guidal
  • Patent number: 10662146
    Abstract: Disclosed herein are pharmaceutical compositions with fencamfamine or fencamfamine related prodrug derivatives. The pharmaceutical compositions are for targeted therapeutic applications including, but not limited to, treating cancer-related fatigue, apathy in Alzheimer's Disease, major depression, and attention deficit-hyperactivity disorder. Also disclosed are methods of synthesizing the pharmaceutical compositions with fencamfamine or fencamfamine related prodrug derivatives.
    Type: Grant
    Filed: September 13, 2016
    Date of Patent: May 26, 2020
    Assignee: PRAXIS BIORESEARCH, LLC
    Inventors: Sandeep Patil, Ron Bihovsky, Steven A. Smith, Yuhua Ji, Valentino Stella, Daniel D. Long, Daniel Marquess
  • Patent number: 10661196
    Abstract: A process for separating or removing permanganate reducing compounds (PRC's) from a first mixture containing at least one PRC, methyl iodide, and water comprises the steps of: feeding the first mixture to a feed port of a distillation column, and distilling and separating the first mixture into an upper stream and a lower stream, wherein the distillation of the first mixture forms a second mixture at an upper position than the feed port, and the process further comprises the steps of: withdrawing the second mixture as the upper stream, and withdrawing the lower stream from a lower position than the feed port.
    Type: Grant
    Filed: November 16, 2018
    Date of Patent: May 26, 2020
    Assignee: DAICEL CORPORATION
    Inventors: Masahiko Shimizu, Yoshihisa Mizutani, Hiroyuki Miura
  • Patent number: 10654794
    Abstract: Disclosed are a fused tricyclic ?-amino acid derivative and a medical use thereof, in particular, the present invention relates to a fused cyclic ?-amino acid derivative as shown in general formula (I), or a stereoisomer, solvate, metabolite, prodrug, pharmaceutically acceptable salt or eutectic thereof, a pharmaceutical composition containing same, and the use of a compound or the composition in the field of analgesia, wherein the definitions of each substituent in general formula (I) are the same as the definitions in the description.
    Type: Grant
    Filed: September 12, 2017
    Date of Patent: May 19, 2020
    Assignee: SICHUAN HAISO PHARMACEUTICAL CO., LTD.
    Inventors: Yao Li, Zongjun Shi, Bo Xu
  • Patent number: 10654885
    Abstract: The present invention refers to a new process for the synthesis of (9?,10?)-pregn-4-ene-3,20-dione, commonly known as retroprogesterone, having the formula (1) shown below.
    Type: Grant
    Filed: January 18, 2018
    Date of Patent: May 19, 2020
    Assignee: INDUSTRIALE CHIMCA S.R.L.
    Inventors: Roberto Lenna, Claudio Delfrate, Davide Rigamonti
  • Patent number: 10654798
    Abstract: A process for the continuous industrial preparation of an alkane-sulphonic acid, from the corresponding alkane and sulphur trioxide, said process being carried out in a solvent which is the alkane-sulphonic acid. The process includes e1) addition of sulphur trioxide in order to maintain an initial molar ratio (alkanesulphonic acid)/(sulphur trioxide), addition of alkane in order to maintain a molar ratio (alkane)/(sulphur trioxide) comprised between 4/1 and 2/1, and continuous withdrawal of the alkanesulphonic acid.
    Type: Grant
    Filed: February 28, 2019
    Date of Patent: May 19, 2020
    Assignee: ARKEMA FRANCE
    Inventor: Jean-Luc Dubois
  • Patent number: 10647656
    Abstract: The invention relates to an integrated process for the production of ethylene and vinyl acetate (VAM), comprising contacting in a first reaction zone a gas stream comprising ethane and optionally ethylene with an oxygen-containing gas stream in the presence of a oxydehydrogenation catalyst under oxidative dehydrogenation conditions to produce a first product stream comprising ethane, ethylene, acetic acid and water, and optionally other compounds, separating said first product stream in a vapor permeation unit into a second stream comprising water and a third stream comprising ethane, ethylene, acetic acid, and optionally other gaseous compounds, contacting in a second reaction zone all or at least a portion of said third stream with a stream comprising concentrated acetic acid and with an oxygen-containing gas stream in the presence of a VAM catalyst, to produce a fourth product stream comprising vinyl acetate, acetic acid, ethane, ethylene, water, carbon dioxide, and optionally other compounds, separating s
    Type: Grant
    Filed: December 18, 2017
    Date of Patent: May 12, 2020
    Assignee: Shell Oil Company
    Inventor: Jean Paul Andre Marie Joseph Ghislain Lange
  • Patent number: 10647651
    Abstract: The invention relates to a process for the production of 1,6-difunctionalized hexane derivatives from 1,3-diunsaturated hydrocarbons, preferably butadiene, wherein a hydroformylation with carbon monoxide and hydrogen is performed in the presence of an at least dihydric alkanol and during the hydroformylation the temperature is increased. The reaction yields the acetals of the 1,6-hexanedial derivatives which are isolated and further reacted to obtain the desired 1,6-difunctionalized hexane derivatives, in particular 1,6-hexanediamine, 1,6-hexanediol and adipic acid.
    Type: Grant
    Filed: October 11, 2016
    Date of Patent: May 12, 2020
    Assignee: BASF SE
    Inventors: Thomas Schaub, Rocco Paciello, Martin Ernst, Jaroslaw Mormul, Peter Hofmann, Jan Breitenfeld, Oliver Trapp
  • Patent number: 10647676
    Abstract: This invention pertains to bivalent linkers, and the synthesis and use thereof. In particular, this invention pertains to the synthesis and use of bivalent linkers in preparing vitamin, drug, diagnostic agent, and/or imaging agent conjugates. The present invention includes divalent linkers, which are alternatively referred to as bivalent linkers, that may be used to couple, link, bond, attach, or otherwise associate two or more chemical entities. This coupling, linking, attachment, or association may be used in the formation of conjugates of such chemical entities. Those chemical entities include targeting ligands and receptor-binding ligands, such as vitamins. Those chemical entities also include drugs for treating various diseases or disease states, and imaging and diagnostic agents for diagnosing, detecting, or otherwise monitoring various diseases or disease states.
    Type: Grant
    Filed: June 18, 2019
    Date of Patent: May 12, 2020
    Assignee: Endocyte, Inc.
    Inventors: Iontcho R. Vlahov, Christopher P. Leamon, Apparao Satyam, Stephen J. Howard
  • Patent number: 10640449
    Abstract: The present invention provides methods comprising washing or, preferably, washing and neutralizing a sulfur acid containing crude MMA stream to generate a two phase stream containing at least methacrylic acid, methacrylamide (MAM), water and methanol, and an organic component containing methyl methacrylate and thereby form an aqueous component; including in any of the organic component, the aqueous component of a neutralized sulfur acid containing crude methyl methacrylate (MMA) stream or the organic component of a neutralized sulfur acid containing crude methyl methacrylate (MMA) stream one or more N-oxyl compound polymerization inhibitor; followed by separating the aqueous component from the organic component, thereby forming a treated crude MMA stream and an aqueous stream to remove residual (meth) acrylic acid.
    Type: Grant
    Filed: December 8, 2017
    Date of Patent: May 5, 2020
    Assignees: Dow Global Technologies LLC, Rohm and Haas Company
    Inventors: Joseph Atkins, Philippe P. Maillot, Joy L. Mendoza, Alan E. Sopchik, Mingyu Ye
  • Patent number: 10640519
    Abstract: This invention provides a method for producing organometallic compounds RnM (M=alkali or alkaline earth element, R=alkyl residue) where n=valence of the metal M- and R=alkyl residue with 2 to 18 C atoms. In the method of this invention, an olefin is hydrometalated in an alkyl methyl ether, or in a solvent mixture containing an alkyl methyl ether, by means of the metal M and in the presence of a hydrogen source and in the presence of a transition metal catalyst, wherein the molar ratio between alkyl methyl ether and metal M is at least 0.01:1 and at most 50:1.
    Type: Grant
    Filed: October 30, 2018
    Date of Patent: May 5, 2020
    Inventors: Ulrich Wietelmann, Christopher Kurth, Stefan Scherer, Peter Rittmeyer, Armin Stoll