Abstract: New aminooxylipids of general formula I, wherein n1=5-30 and X is polymethylene linker of the general formula II where n2=2-10, or X is polyethylene glycol linker of the general formula III, wherein n3=1-14 are provided. A method of preparation of the aminooxylipids of general formula I characterized in that the acylation of N-tert-butoxycarbonyl-polymethylenediamine {(CH3)3C—O—(C?O)—HN—(CH2)n—NH2, n=2-13}, or N-tert-butoxycarbonyl-polyethyleglycoldiamine {(CH3)3C—O—(C?O)—HN—(CH2)2—[O—(CH2)]n—O—(CH2)2NH2, n=1-14} with in position C(2) symmetrically branched fatty acids of general formula IV, wherein n1=5-30, in the presence of condensation reagent, or from acid of general formula IV derived acylchloride of general formula V wherein n1=5-30, produces N-Boc-aminolipids of general formula VI, wherein n1=5-30 a X is polymethylene linker of the general formula II or X is polyethylene glycol linker of the general formula III.
Type:
Grant
Filed:
November 2, 2017
Date of Patent:
November 8, 2022
Assignees:
VYSOKA SKOLA CHEMICKO-TECHNOLOGICKA V PRAZE, VYZKUMNY USTAV VETERINARNIHO LEKARSTVI, V. V. I., APIGENEX S.R.O.
Inventors:
Miroslav Ledvina, Roman Effenberg, Jaroslav Turanek, Elissa Bartheldyova, Ladislav Droz, Josef Masek, Frantisek Hubatka
Abstract: The present invention relates to a process for purifying ethylenediamine, in which a) a mixture comprising water (H2O), ethylenediamine (EDA) and N-methylethylenediamine (NMEDA) is introduced into a rectification column (NMEDA removal column), where the mixture introduced comprises at least the amount of water as required for the formation of a high-boiling azeotrope of EDA and water at the appropriate bottom temperature; and the EDA-comprising bottom product from the NMEDA removal column is introduced into a second rectification column (EDA dewatering column), wherein the pressure at the top of the EDA dewatering column is adjusted such that the boiling temperature of the mixture obtained at the top is 10° C.
Abstract: A production method for producing a 1,4-cyclohexanedicarboxylic acid derivative, involves subjecting an aqueous ammonia solution of 1,4-cyclohexanedicarboxylic acid to heat concentration, thereby precipitating a 1,4-cyclohexanedicarboxylic acid derivative as a crystal.
Abstract: The present invention relates to an improved process for the preparation of metformin hydrochloride, an important drug in the first line treatment of Type II Diabetes.
Type:
Grant
Filed:
February 5, 2019
Date of Patent:
October 11, 2022
Assignee:
Merck Patent GmbH
Inventors:
Camille Correia, Renaud Poli, Serge Gerbaut, Marc Dittmann, David Maillard, Sebastian Haertner
Abstract: The present invention provides a route for synthesizing monofunctional thiuram compounds that is safe, environmentally friendly, and cost effective. This method specifically involves synthesizing a monofunctional thiuram by (1) reacting a tetraorganylthiuram disulfide with an organyl mercaptan to produce the monofunctional thiuram and a dithiocarbamate metal salt or a dithiocarbamate metalloid salt under basic conditions, (2) separating the monofunctional thiuram in an organic phase from the dithiocarbamate metal salt or the dithiocarbamate metalloid salt in an aqueous phase, and (3) recovering the monofunctional thiuram from the aqueous phase. The monofunctional thiuram compounds made in accordance with this invention are of particular value as accelerators for use in the vulcanization of rubber. The use of these monofunctional thiuram compounds as accelerators provides good cure rates and as well as good scorch safety.
Type:
Grant
Filed:
December 10, 2020
Date of Patent:
October 11, 2022
Inventors:
Thomas Franklin Spilker, Ji Yang Jin, Frank J. Feher
Abstract: Provided is a method of preparation of (1R, 3S)-3-amino-1-cyclopentanol, the method including: contacting N-acylhydroxyamine and cyclopentadiene for an asymmetric cycloaddition, to yield a first intermediate I; hydrogenating the first intermediate I to yield a second intermediate II; hydrolyzing, ammonolyzing, hydrazinolyzing, or alcoholyzing an amido bond of the second intermediate II to yield a third intermediate III; and hydrogenating the third intermediate III to yield (1R, 3S)-3-amino-1-cyclopentanol.
Abstract: A viscoelastic surfactant (VES) for a self-diverting acid under high temperature has a structural formula shown as formula (I), wherein, n is saturated hydrocarbon with 2 to 8 carbon atoms; R1 is saturated or unsaturated hydrocarbon with 18 to 28 carbon atoms; R2 and R3 are independently methyl, ethyl or hydrogen, and R2 and R3 can be the same or different; and X? is any one of Cl?, Br?, CO32?, SO42?, HCOO? and CH3COO?. The method for preparing the surfactant includes subjecting a fatty acid and an organic amine to acid-amine condensation to obtain an intermediate. The intermediate reacts with a metal hydride to obtain a fatty amine. Then, an acid solution is used to protonate the fatty amine to obtain an ultra-long-chain viscoelastic cationic surfactant. The present invention also provides use of the surfactant as a thickener for a self-diverting acid.
Abstract: The present invention provides zuclomiphene salts, zuclomiphene binaphthyl hydrogen phosphate salt (1-A)·(BPA) and zuclomiphene oxalate salt (1-A)·(OXL), crystalline forms thereof and processes for the preparation thereof.
Type:
Grant
Filed:
November 11, 2020
Date of Patent:
September 13, 2022
Assignee:
Apotex Inc.
Inventors:
Mohammed Abdul Raheem, Siva Ramarao Kakani, Minh T. N. Nguyen, Yajun Zhao, Stuart P. Green, Fabio E. S. Souza, Alexander J. Stirk, Fatemeh Mohammadpourmir
Abstract: The present invention relates novel methods of synthesizing terphenyl compounds and in particular to novel methods for the synthesis of a compound of Formula I or intermediates thereof.
Type:
Grant
Filed:
July 1, 2020
Date of Patent:
August 2, 2022
Assignee:
VECTUS BIOSYSTEMS LIMITED
Inventors:
Anthony Kaye, Nurul Quazi, George Feast, Marshnil Lakshman
Abstract: Processes and reaction mixtures including non-aqueous solvent mixtures are presented. Non-aqueous solvent mixtures including fluoride salt and non-aqueous solvent combinations are provided that possess high fluoride ion concentrations useful for a range of applications, including organic synthesis. Further non-aqueous solvent mixtures are provided including a salt possessing a non-fluoride anion and a non-aqueous solvent that, when contacted with aqueous fluoride-containing reagents, extract fluoride ions to form non-aqueous fluoride-ion solutions possessing high fluoride-ion concentrations. The salts include an organic cation that does not possess a carbon in the ?-position or does not possess a carbon in the ?-position having a bound hydrogen. This salt structure facilitates its ability to be made anhydrous without decomposition. Example anhydrous fluoride salts include (2,2-dimethylpropyl)trimethylammonium fluoride and bis(2,2-dimethylpropyl)dimethylammonium fluoride.
Type:
Grant
Filed:
September 25, 2019
Date of Patent:
July 26, 2022
Assignees:
California Institute of Technology, The Regents of the University of California
Inventors:
Simon C. Jones, Victoria K. Davis, Christopher M. Bates, Nebojsa Momcilovic, Brett M. Savoie, Michael A. Webb, Thomas F. Miller, III, Robert H. Grubbs, Jennifer M. Murphy
Abstract: The invention concerns a new, efficient process for the preparation of enantiomerically pure norepinephrine (also known as noradrenaline), or an addition salt thereof, using a catalytic hydrogenation system under hydrogen donor transfer. The invention also discloses a novel intermediate and the process for the preparation thereof.
Abstract: The present invention provides novel, stable, processable and pharmaceutically acceptable salt forms of 2R,6R-hydroxynorketamine or 2S,6S-hydroxynorketamine with high aqueous solubility.
Type:
Grant
Filed:
July 31, 2018
Date of Patent:
July 5, 2022
Assignee:
SMALL PHARMA LTD.
Inventors:
David Pearson, Lorraine Sharp, Alan Armstrong, Richard Myerson, Jonathan Hull, Paul Blaney, Peter Rands, Marie Layzell, Zelah Joel
Abstract: A method of preparing pentachlorodisilane is disclosed. The method comprises partially reducing hexachlorodisilane with a metal hydride compound to give a reaction product comprising pentachlorodisilane. The method further comprises purifying the reaction product to give a purified reaction product comprising the pentachlorodisilane. The purified reaction product comprising pentachlorodisilane formed in accordance with the method is also disclosed.
Type:
Grant
Filed:
July 30, 2018
Date of Patent:
June 28, 2022
Assignee:
Jiangsu Nata Opto-Electronic Materials Co. Ltd.
Inventors:
Barry Ketola, Noel Mower Chang, Jeanette Young, Xiaobing Zhou
Abstract: The present invention provides a novel method for producing an ester group-containing compound and a derivative produced using the compound as a synthetic intermediate. The invention also provides a polymerizable composition containing the compound obtained by the production method and a film-shaped polymer obtained by polymerizing the polymerizable composition. The present invention is a method for producing an ester group-containing compound, the method including a mixing step of mixing a condensing agent, a Bronsted acid, a carboxylic acid, and a phenol or an alcohol to prepare a reaction mixture. The Bronsted acid selected is other than the condensing agent, the carboxylic acid, and the phenol.
Abstract: Described herein are antifungal peptoids, the development and characterization of the antifungal peptoids, methods of making the antifungal peptoids, and methods of using the antifungal peptoids. In some embodiments, the antifungal peptoids may be administered to a subject infected with or at risk of being infected with pathogenic fungi including, for example Cryptococcus spp. In some embodiments, the Cryptococcus spp. may include C. neoformans or C. gattii or both.
Type:
Grant
Filed:
December 18, 2019
Date of Patent:
June 28, 2022
Assignee:
Middle Tennessee State University
Inventors:
Kevin L. Bicker, Madyson P. Middleton, Scott A. Armstrong
Abstract: The present invention provides crystalline forms of Acalabrutinib, Specific crystalline forms provided by the present invention include Acalabrutinib Form APO-I, a co-crystal of Acalabrutinib and urea; APO-II, a co-crystal of Acalabrutinib and nicotinamide; APO-III, a co-crystal of Acalabrutinib and L-sorbitol; APO-IV, a crystalline form of Acalabrutinib; and APO-V, a co-crystal of Acalabrutinib and urea.
Type:
Grant
Filed:
August 23, 2018
Date of Patent:
May 31, 2022
Assignee:
Apotex Inc.
Inventors:
Fabio E. S. Souza, Bahareh Khalili, Annyt Bhattacharyya, Wancheng Guo, Jingda Zhang, Kun Cheng, Kangying Li
Abstract: Here are described processes for the preparation of sulfamic acid derivatives, for instance, halogenated derivatives and their metallic or organic salts. The present document also describes the sulfamic acid derivatives thus produced and to their uses, for instance, in electrolyte compositions for electrochemical applications.
Abstract: A process to convert cyclic alkylene ureas into their corresponding alkylene amines is provided. An exemplary process includes reacting the cyclic alkylene ureas with an amine compound chosen from the group of primary amines or secondary amines that have a higher boiling point than the alkylene amines formed during the process, wherein the process is a reactive separation process and the reaction mixture contains less than about 10 wt % of water on the basis of total weight of the reaction mixture.
Type:
Grant
Filed:
August 7, 2018
Date of Patent:
May 24, 2022
Assignee:
NOURYON CHEMICALS INTERNATIONAL B.V.
Inventors:
Rens Veneman, Antoon Jacob Berend Ten Kate, Karl Fredrik Lake, Eike Nicolas Kantzer, Slavisa Jovic, Rolf Krister Edvinsson, Ina Ehlers, Hendrik Van Dam, Michiel Jozef Thomas Raaijmakers
Abstract: The present invention relates to a novel and improved process for preparing (3S)-3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)-3-cyclopropylpropanoic acid of the formula (I), to the compound of the formula (I) in crystalline form and to their use for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular, cardiopulmonary and cardiorenal disorders.
Type:
Grant
Filed:
November 26, 2018
Date of Patent:
May 17, 2022
Assignee:
BAYER PHARMA AKTIENGESELLSCHAFT
Inventors:
Peter Fey, Philipp Rubenbauer, Kai Lovis, Britta Olenik, Julia Kusel, Felix Spindler
Abstract: Chiral spirobiindane skeleton compound and preparation method thereof is disclosed in the present invention. The spirobiindane skeleton compound of the present invention having the structure formula of I or I?; the preparation method for synthesizing the spirobiindane skeleton compound of the present invention comprising the following steps: in the presence of solvent and catalysts, the structure formula compound III reacted through intramolecular Friedel-Crafts reaction to obtain the compound of formula I; the catalyst is a Browsteric acidor Lewis acid. The preparation method of chiral fused spirobiindane skeleton compound of the present invention does not need to adopt chiral starting materials or chiral resolving agents, does not require chiral resolving steps, is simple in method, is simple in post-treatment, and is economic and environment friendly. High product yield, high product optical purity and chemical purity.