Abstract: This application relates to pharmaceutical engineering, and more particularly to a continuous-flow preparation method of diclofenac sodium. The continuous-flow preparation method includes: subjecting aniline and chloroacetic acid to amidation to obtain 2-chloro-N-phenylacetamide (3); subjecting 2-chloro-N-phenylacetamide (3) and 2,6-dichlorophenol to continuous condensation to obtain N-(2,6-dichlorophenyl)-2-hydroxy-N-phenylacetamide (5); subjecting N-(2,6-dichlorophenyl)-2-hydroxy-N-phenylacetamide (5) and thionyl chloride to chlorination to obtain N-(2,6-dichlorophenyl)-2-chloro-N-phenylacetamide (6); subjecting N-(2,6-dichlorophenyl)-2-chloro-N-phenylacetamide (6) to Friedel-Crafts alkylation in the presence of aluminum chloride to obtain 1-(2,6-dichlorophenyl)-1,3-dihydro-2H-indol-2-one (7); and subjecting 1-(2,6-dichlorophenyl)-1,3-dihydro-2H-indol-2-one (7) to hydrolysis to obtain the diclofenac sodium.
Type:
Grant
Filed:
February 22, 2023
Date of Patent:
December 5, 2023
Assignee:
Fudan University
Inventors:
Fener Chen, Dang Cheng, Lulu Wang, Ge Meng, Yingtang Ning
Abstract: A method of making N-(2,4-dinitrophenyl)-4-nitrobenzamide from a mixture of 2,4-dinitroaniline, 4-nitrobenzoyl chloride, and solid acid catalyst in an organic solvent, wherein the solid acid catalyst is not soluble in the organic solvent, the solid acid catalyst being an acidic clay, an ion exchange resin, a beta zeolite, a sulfonated tetrafluoroethylene-based fluoropolymer-copolymer, or some mixture of these.
Type:
Grant
Filed:
May 18, 2021
Date of Patent:
December 5, 2023
Assignee:
DUPONT SAFETY & CONSTRUCTION, INC.
Inventors:
James A. Schultz, Sourav Kumar Sengupta, Venkateswara Rao Surisetty
Abstract: Provided are a quaternary ammonium salt and a preparation method and use thereof as an inhibitor, and a water-based drilling fluid and use thereof. The quaternary ammonium salt has a structure shown in formula I, wherein, in the formula I, R1 is selected from the group consisting of —H and —COOH; R2 is selected from the group consisting of —H and —CH2—COOH; R3 is selected from the group consisting of —NH—CH2—CH2—CH2—NH2, —NH—CH2—CH2—NH2, —NH—CH2—CH2—OH, —O—CH2—CH2—NH2, —N—(CH2—CH2—OH)2, and —O—CH2—CH2—NH—CH2—CH2—OH; and n and m are independently 10 to 15.
Abstract: Novel 85Rb-enriched rubidium salt compounds of general formula 1, below and novel compounds of general formula 2, below. Compositions that contain at least one of the novel compounds and optionally further contain an antitumor drug. Methods that entail administering such compounds and compositions to treat cancer, optionally in combination with a conventional form of cancer therapy, such as chemotherapy and radiation treatment. When administered with a conventional form of cancer therapy, the compounds and compositions of the invention may be administered before, simultaneously with, or after administration of the conventional form of cancer therapy.
Type:
Grant
Filed:
March 16, 2022
Date of Patent:
November 28, 2023
Assignee:
Vector Vitale IP LLC
Inventors:
Peter Novak, Maxim Temnikov, Oleksandr Balakin
Abstract: Provided is a boron-containing compound suitable for the material of a blue light-emitting diode and an organic light-emitting diode using the same. The boron-containing compound has a structure represented by the formula (1): X is each independently —NR1—, —CR2R3—, —O— or —S—. In the —NR1— and —CR2R3—, R1 to R3 are each independently hydrogen, deuterium, an alkyl group having 1 to 6 carbon atoms or an aryl group having 5 to 30 core atoms, and R2 and R3 may connect with each other to form a ring. Cy1 is an aryl group having 5 to 30 core atoms. All or part of hydrogen atoms in the formula (1) may be substituted by deuterium, a halogen, an alkyl group having 1 to 6 carbon atoms, an aryl group having 5 to 30 core atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, or cyano group.
Type:
Grant
Filed:
January 5, 2021
Date of Patent:
November 21, 2023
Assignee:
FLASK CORPORATION C/O YONEZAWA CAMPUS, NATIONAL UNIVERSITY CORPORATION YAMAGATA UNIVERSITY
Abstract: The present invention generally relates to processes for the catalytic hydrogenation of halonitroaromatics. In particular, the present invention includes processes for the catalytic hydrogenation of halonitroaromatics such as 2,5-dicloronitrobenzene to 2,5-dichloroaniline over a platinum-containing catalyst. The present invention also relates to processes for producing 3,6-dichloro-2-methoxybenzoic acid.
Abstract: Methods are disclosed including methods for crystallizing a material such as a drug. An example method may include combining a nucleation initiator, a surfactant solution, and an amorphous form of a drug to form a drug precursor dispersion/suspension. The method may also include incubating the drug precursor dispersion/suspension to allow the drug to convert from the amorphous form to a crystalline form.
Type:
Grant
Filed:
March 12, 2021
Date of Patent:
November 14, 2023
Assignee:
Boston Scientific Scimed, Inc.
Inventors:
Hongxia Zeng, Jonathan Pascal Chaky, Yen-Lane Chen
Abstract: The present invention relates to a method of separating amino acids from an aqueous solution comprising amino acids as well as proteins and/or protein decomposition products by combining phosphoric acid with the aqueous solution to precipitate an amino acid monophosphate. The precipitate so formed may be separated from the aqueous solution and used as such, e.g. in plant fertilizer compositions. The precipitate may be redissolved in a suitable liquid, after which phosphate and amino acid may be separated following conventional methods. In either case, the present invention enables highly selective precipitation of arginine and/or lysine monophosphate as crystals.
Type:
Grant
Filed:
March 5, 2019
Date of Patent:
November 14, 2023
Assignee:
AREVO AB
Inventors:
Torgny Näsholm, Jonathan Love, Mattias Holmlund, Nils Bertil Skoglund
Abstract: Disclosed are compounds that can penetrate the mitochondrial membrane and that are able to deliver cargo (e.g., therapeutic agents) specifically to the mitochondria.
Type:
Grant
Filed:
May 6, 2019
Date of Patent:
November 14, 2023
Assignee:
OHIO STATE INNOVATION FOUNDATION
Inventors:
Dehua Pei, George Appiah Kubi, Ziqing Qian
Abstract: The invention relates to a process for the preparation of Melphalan (4-[bis(2-5 chloroethyl)amino]-L-phenylalanine of formula (I) said process comprising the reaction of a 4-amino-L-phenylalanine protected at the carboxy and amino aminoacidic groups with an agent able to convert the aromatic amino group into a group of formula: —N(CH2CH2OS(O)nO—)2, wherein n is 1 or 2 followed by conversion of the ?N(CH2CH2OS(O)nO—)2 group into a —N(CH2CH2Cl)2 group. The invention also provides novel intermediates useful for the preparation of Melphalan.
Type:
Grant
Filed:
December 21, 2020
Date of Patent:
October 17, 2023
Assignee:
Indena S.P.A.
Inventors:
Pietro Allegrini, Andrea Bonetti, Marco Molinari, Andrea Gambini
Abstract: A preparation method according to the present invention makes it possible to industrially produce large amounts of highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield by use of commercially available reagents and solvents. In addition, the use of novel intermediates according to the present invention makes it possible to produce highly pure optically active tert-butyl 3-methyl-4-oxopiperidine-1-carboxylate in high yield.
Type:
Grant
Filed:
January 7, 2022
Date of Patent:
October 10, 2023
Inventors:
Jae Hong Kweon, Eun Sun Kim, Hyuk Woo Lee, Dong Hyun Ko, Chae Young Ryu, Kwang Do Choi, SeungPyeong Heo
Abstract: The present invention is directed to a method of producing active pharmaceutical ingredients (APIs). The method includes subjecting a reaction mixture with an API precursor to solvent extraction to produce a reactant stream with the API precursor. The method includes concentrating the API precursor in the reactant stream using at least one membrane. The method includes carrying out a reaction in a membrane reactor. The method includes separating the API precursor from the reaction stream using a separator. The method includes crystallizing the API precursor using a crystallizer to produce APIs.
Abstract: Provided is a photo-oxidation reaction of benzylic C—H bonds of an aromatic compound under the catalysis of an acid catalyst. The method aims to synthesize aromatic acids and acetophenones. The acid catalyst is one of Bronsted acids, including one or a mixture of two or more selected from the group consisting of hydrochloric acid, phosphoric acid, sulfuric acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, trifluoroacetic acid, and potassium hydrogen sulfate, as well as N-propylsulfonate pyridinium hydrogensulfate, N-butylsulfonate pyridinium hydrogensulfate, N-propylsulfonate pyridinium trifluoromethanesulfonate, N-butylsulfonate pyridinium trifluoromethanesulfonate, N-propylsulfonate pyridinium tetrafluoroborate, and N-butylsulfonate pyridinium tetrafluoroborate. The oxidation reaction is conducted under mild conditions (normal temperature and pressure) using air or oxygen as the oxidant in the presence of recyclable catalyst and solvent.
Type:
Grant
Filed:
January 19, 2022
Date of Patent:
October 3, 2023
Assignee:
NANJING TECH UNIVERSITY
Inventors:
Yufeng Li, Hongjun Zhu, Hongfei Ma, Hongzhong Bu, Jieqing Wu, Jiefan Gu, Jiwei Chen, Haoyue Zhang, Chen Wang
Abstract: A composition comprises one or more trimesic acid derivatives of Formula (I) in which R1, R2, and R3 are independently selected from the group consisting of alkyl groups. A polymer composition comprises a composition as described above and a polyolefin polymer. The polymer compositions containing a trimesic acid derivative of Formula (I) exhibit very low haze levels and minimal extraction of the trimesic acid derivative.
Type:
Grant
Filed:
December 2, 2021
Date of Patent:
October 3, 2023
Assignee:
Milliken & Company
Inventors:
Daniel Kremer, Hans-Werner Schmidt, Paul Smith, John David Anderson, Suchitra Datta, Keith Keller, Nathan Mehl, Walter Scrivens
Abstract: In one aspect, the present disclosure provides methods of preparing a secondary amine. In some embodiments, the secondary amine comprises two different groups or two identical groups. Also provided herein are compositions for use in the preparation of the secondary amine.
Type:
Grant
Filed:
May 17, 2018
Date of Patent:
September 26, 2023
Assignee:
William Marsh Rice University
Inventors:
Padmanabha Venkatesh Kattamuri, Laszlo Kurti
Abstract: Disclosed is a method for efficiently synthesizing primary amines, which comprises using carbonyl compounds or alcohol compounds as reaction substrate, liquid ammonia or alcohol solutions of ammonia as nitrogen source, and hydrogen as hydrogen source, and reacting in reaction medium catalyzed by a cobalt-based catalyst to obtain the primary amines. Due to high catalytic activity, the method can realize the reductive amination of carbonyl compounds and the hydrogen-borrowing amination of alcohol compounds at low temperatures in a short time to obtain the primary amines with high yield, and is applicable to a wide range of substrates. The obtained primary amines can be used as raw materials with high extra value for producing polymers, medicines, dyes and surfactants. Further, the cobalt-based catalyst has a good industrial application prospect because it is magnetic which can facilitate separation and recycling of the catalyst.
Type:
Grant
Filed:
December 28, 2021
Date of Patent:
September 26, 2023
Assignee:
East China University of Science and Technology
Abstract: The present invention provides a method for producing primary amines and secondary amines, the method being characterized by reducing a primary amide or a secondary amide in the presence of a reducing agent and an organic metal halide of a group-2 element.
Abstract: A process for continuous production of C2-C4-monoalkanolamines by reaction of a corresponding C2-C4-alkylene oxide with a molar excess of ammonia (NH3), wherein aqueous ammonia is employed, in the liquid phase and in the presence of an acidic cation exchanger as catalyst which contains a crosslinked copolymer comprising acidic functional groups as the carrier matrix, wherein the cation exchanger has a total exchange capacity of not less than 1.8 eq/L.
Type:
Grant
Filed:
January 28, 2019
Date of Patent:
September 12, 2023
Assignee:
BASF SE
Inventors:
Christian Gruenanger, Gabriele Iffland, Zeljko Kotanjac, Hermann Luyken, Thomas Krug, Jian Zhong Yi, Johann-Peter Melder
Abstract: A method of reducing color in an alkanolamine is described. The method includes contacting the alkanolamine with a color-reducing amount of a borane complex effective to provide a color-reduced alkanolamine composition having a Platinum-Cobalt Color Value, according to Test Method ASTM D1209, of less than 50.