Processes For Forming The Isothiocyanate Group Patents (Class 558/18)
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Patent number: 10640464Abstract: The present invention relates to methods and compositions for the prevention and treatment of keratin-based skin diseases. In particular, the application describes compositions and methods of treating a patient suffering from skin blistering comprising the use of phase II enzyme inducers and/or activity modifiers.Type: GrantFiled: July 9, 2019Date of Patent: May 5, 2020Assignee: The William M. Yarbrough FoundationInventor: Michael E. Silver
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Patent number: 9169331Abstract: An exemplary multimodal chromatographic medium of the invention includes one or more strong anion exchange, weak anion exchange, strong cation exchange and/or weak cation exchange binding sites in combination with one or more reverse phase and/or hydrophilic interaction chromatography binding site. In an exemplary embodiment, the sites interact with one or more glycans in a mixture of glycans in a manner that allows separation of glycans in the mixture and analysis of the glycan mixture. The media are incorporated into devices and systems for chromatographic analysis. Also provided are methods of using the multimodal media of the invention to analyze glycans.Type: GrantFiled: December 21, 2012Date of Patent: October 27, 2015Assignee: DIONEX CORPORATIONInventors: Xiaodong Liu, Udayanath Aich, Christopher A. Pohl
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Publication number: 20150110863Abstract: The present invention relates to a new series of compounds having general formula (I) and the optical isomer or enantiomer forms thereof, which belong to the family of sulforaphane derivatives. The invention also relates to the production method thereof. The invention further relates to the multiple medical (pharmaceutical, homeopathic and phytotherapeutic), food, cosmetic and dietary uses of said series of compounds, especially the use thereof in the prevention and/or treatment of diseases and any type of illness or damage associated with an oxidative process or which, although not involved in said process, are mediated by the Nrf2 transcription factor, such as, for example, cancer. The compounds can be used alone or, alternatively, encapsulated in cyclodextrins.Type: ApplicationFiled: March 6, 2013Publication date: April 23, 2015Applicants: Univerversidad De Sevilla, Consejo Superior De Investigaciones CientÍficas (CSIC)Inventors: Noureddine Khiar El Wahabi, Inmaculada Fernández Fernández, Rocío Recio Jiménez
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Publication number: 20130310555Abstract: Stereoselective and regioselective synthesis of compounds via nucleophilic ring opening reactions of aziridinium ions for use in stereoselective and regioselective synthesis of therapeutic and diagnostic compounds.Type: ApplicationFiled: May 17, 2013Publication date: November 21, 2013Applicant: Illinois Institute of TechnologyInventor: Hyun-Soon Chong
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Patent number: 8541611Abstract: A process for preparing phenyl iso(thio)cyanates of the formula I in which a compound of the formula II or its HCl adduct is reacted with a phosgenating agent where W is oxygen or sulfur and Ar and A are as defined in claim 1 is described. Moreover, the invention relates to the use of the phenyl iso(thio)cyanates for preparing crop protection agents.Type: GrantFiled: June 28, 2012Date of Patent: September 24, 2013Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
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Publication number: 20130245305Abstract: The object of the present invention is to provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) by a reaction of the corresponding amino compound having a carboxyl group(s), thiocarbonyldiimidazole and a base, in one step with high purity. An amino compound having a carboxyl group(s) is reacted with thiocarbonyldiimidazole in a solvent in the presence of a base to obtain an isothiocyanate compound having a carboxyl group(s).Type: ApplicationFiled: November 29, 2010Publication date: September 19, 2013Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Junko Takada, Shunsuke Iwamoto, Satoshi Nakano
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Publication number: 20130142739Abstract: A method for synthesizing an isothiocyanate of general formula (I) SCN—R1—R4—R2??(I) wherein R1 and R2 represent independently of each other an alkyl-aryl or aryl group, R4 represents a carbonyl, sulfinyl, sulfonyl group or a sulfide group and of its derivatives comprising a step for reacting an alkylalkylamine having the general formula (II) NH2—R1—R4—R2??(II) wherein R1 and R2 represent independently of each other an alkyl, aryl or alkylaryl group, R4 represents a carbonyl, sulfinyl, sulfonyl or sulfide group, in the presence of carbon sulfide and of di-tert-butyl dicarbonate with formation of the corresponding aforesaid isothiocyanate, compounds obtained by this method as well as their uses.Type: ApplicationFiled: July 20, 2011Publication date: June 6, 2013Applicant: Auriga InternationalInventors: Jacques Dubois, Alfred Marchal, Damien Lacroix, Jérôme Cabou
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Patent number: 8367857Abstract: To provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) from the corresponding amino compound having a carboxyl group(s). A method for producing an isothiocyanate compound which has a carboxyl group(s) and is represented by the formula (2). And the method comprises reacting an amino compound which has a carboxyl group(s) and is represented by the formula (1) (wherein A is e.g. a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group, and B is e.g. a single bond, a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group), in a solvent, with carbon disulfide (CS2) and then with a halogen as a simple substance.Type: GrantFiled: February 27, 2009Date of Patent: February 5, 2013Assignee: Nissan Chemical Industries, Ltd.Inventors: Satoshi Nakano, Daisuke Saito
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Publication number: 20120271049Abstract: A process for preparing phenyl iso(thio)cyanates of the formula I in which a compound of the formula II or its HCl adduct is reacted with a phosgenating agent where W is oxygen or sulfur and Ar and A are as defined in claim 1 is described. Moreover, the invention relates to the use of the phenyl iso(thio)cyanates for preparing crop protection agents.Type: ApplicationFiled: June 28, 2012Publication date: October 25, 2012Applicant: BASF AKTIENGESELLSCHAFTInventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
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Patent number: 8232421Abstract: A process for preparing phenyl iso(thio)cyanates of the formula I in which a compound of the formula II or its HCl adduct is reacted with a phosgenating agent where W is oxygen or sulfur and Ar and A are as defined in claim 1 is described. Moreover, the invention relates to the use of the phenyl iso(thio)cyanates for preparing crop protection agents.Type: GrantFiled: September 21, 2010Date of Patent: July 31, 2012Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
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Publication number: 20110009640Abstract: A process for preparing phenyl iso(thio)cyanates of the formula I in which a compound of the formula II or its HCl adduct is reacted with a phosgenating agent where W is oxygen or sulfur and Ar and A are as defined in claim 1 is described. Moreover, the invention relates to the use of the phenyl iso(thio)cyanates for preparing crop protection agents.Type: ApplicationFiled: September 21, 2010Publication date: January 13, 2011Applicant: BASF AKTIENGESELLSCHAFTInventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
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Publication number: 20100312000Abstract: To provide a novel method for producing an isothiocyanate compound having a carboxyl group(s) from the corresponding amino compound having a carboxyl group(s). A method for producing an isothiocyanate compound which has a carboxyl group(s) and is represented by the formula (2). And the method comprises reacting an amino compound which has a carboxyl group(s) and is represented by the formula (1) (wherein A is e.g. a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group, and B is e.g. a single bond, a C6-14 aromatic hydrocarbon group or a C1-12 saturated hydrocarbon group), in a solvent, with carbon disulfide (CS2) and then with a halogen as a simple substance.Type: ApplicationFiled: February 27, 2009Publication date: December 9, 2010Applicant: Nissan Chemical Industries LimitedInventors: Satoshi Nakano, Daisuke Saito
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Publication number: 20080227995Abstract: A process of producing a compound of the following formula (3): wherein R1 is a C1-5 alkyl group, R2 is a halogen atom, a C1-5 alkyl group, a C2-5 alkenyl group, a C2-5 alkynyl group, a C1-5 alkyl group, a C1-5 alkoxy group, a nitro group, or a hydroxy group, wherein multiple R2 may be the same or may be different, and a is an integer of from 0 to 4, comprising reacting a compound of the following formula (2): wherein R2 and a are as defined above with a C1-5-alkanesulfonyl chloride or C1-5-alkanesulfonic acid anhydride followed by hydrolyzing an N,N-disulfonated derivative of compound (3) to the compound of formula (3).Type: ApplicationFiled: July 20, 2006Publication date: September 18, 2008Applicant: Schwarz Pharma AGInventors: Jorg Hamann, Ralf Kanzler, Youxin Li
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Publication number: 20030235634Abstract: A method of extracting non-polar isothiocyanates from a plant includes providing fresh or dehydrated plant material that contains at least one glucosinolate that will form a corresponding non-polar isothiocyanate, and endogenous myrosinase enzyme. Water is added to the plant material and milled, and oil is added thereafter to the water and plant mixture. This mixture is then homogenized after which the oil phase is separated from water phase and solids, such that the non-polar isothiocyanate(s) partition into the oil phase. A stable composition made according to the method includes at least one non-polar isothiocyanate and a vegetable oil. A dietary supplement may be formulated from the stable composition.Type: ApplicationFiled: June 21, 2002Publication date: December 25, 2003Applicant: ACCESS BUSINESS GROUP INTERNATIONAL LLC.Inventors: Donald J. Pusateri, Tamara R. Kizer, Alex L. Lowry
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Patent number: 6420556Abstract: The subject invention involves novel acyl isothiocyanate resins of formula (I) and processes for making them: (a) starting with a phenyl carboxy resin, treating the resin with any reagent that converts the carboxy to an acyl halide, followed by treatment with tetranikylammonium thiocyanate or an alkali metal salt thereof, to provide the acyl isothiocyanate resin. The subject invention also involves processes for making guanidine compounds and related cyclized compounds using an acyl isothiocyanate resin, comprising the following steps: (b) reacting the acyl isothiocyanate resin with a primary amine; (c) reacting the product from Step (b) with a sulfur activating agent and ammonia or a primary or secondary amine; (d) treating the product from Step (c) with a strong base or medium strength acid to cleave product from the resin, providing the guanidine compound or/and the related cyclized compound.Type: GrantFiled: June 12, 2001Date of Patent: July 16, 2002Assignee: The Procter & Gamble CompanyInventor: Lawrence Joseph Wilson
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Patent number: 5250717Abstract: Isothiocyanates of the formula ##STR1## where R, R.sub.1, and R.sub.2 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl and thioureas of the formula ##STR2## where R, R.sub.1, and R.sub.2 are defined above, are disclosed. Processes for their preparation are also disclosed.Type: GrantFiled: June 1, 1992Date of Patent: October 5, 1993Assignee: Ethyl CorporationInventor: Gordon G. Knapp
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Patent number: 5208361Abstract: Alkylisothiocyanic acid esters having the formula R--N.dbd.C.dbd.S can be prepared by reacting N-alkyldithiocarbamates with hydrogen peroxide in aqueous phase at 95.degree. to 130.degree. C. The aqueous solution of N-alkyldithiocarbamate is reacted with a 20 to 40% by weight aqueous solution of hydrogen peroxide in a volumetric ratio of 1 to 0.8 to 1 while maintaining a pH of 1.5 to 4.5. The solutions are preferably sprayed into a reactor, at which time the alkylisothiocyanate formed distills off in vapor form and an aqueous phase containing the byproducts collects in the reactor. The method is capable of significantly increasing the space-time yield because much less sulfur is formed in comparison to the previously known method, which takes place at pH 5 to 9, thereby minimizing the shutdown times previously required for cleaning the reactor.Type: GrantFiled: January 15, 1991Date of Patent: May 4, 1993Assignee: Degussa AktiengesellschaftInventors: Gunter Giesselmann, Kurt Gunther
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Patent number: 5098934Abstract: Novel .omega.-mercaptopropanamides and their homologs of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and ##STR2## R.sub.1 ' is selected from the group consisting of alkyl of 1 to 5 carbon atoms and aryl optionally substituted with at least one member of the group consisting of --OH, alkyl and alkoxy of 1 to 5 carbon atoms, --NO.sub.2 and halogen, n is an integer from 1 to 5, R.sub.2 is selected from the group consisting of hydrogen alkyl of 1 to 5 carbon atoms and aryl and aralkyl of 6 to 15 carbon atoms optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, --OH, halogen and --CF.sub.3, R.sub.3 is selected from the group consisting of a) hydrogen, b) phenyl optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, --OH, --NO.sub.2, halogen, --CF.sub.Type: GrantFiled: June 22, 1990Date of Patent: March 24, 1992Assignee: Roussel UclafInventors: Jean-Paul Vevert, Francoise Delevallee, Rogert Deraedt
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Patent number: 5043442Abstract: A process for preparing 2,6-dimethylphenylisothiocyanate comprises the steps of dissolving 2,6-dimethylaniline in carbon disulfide and ammonium hydroxide to form a dithiocarbamate salt. The salt is reacted with ethyl chloroformate to form 2,6-dimethylphenylisothiocyanate, which may thereafter be reacted with 3-amino-1-propanol and subsequently cyclized, by treating with hydrochloric acid, to form xylazine.Type: GrantFiled: April 2, 1990Date of Patent: August 27, 1991Assignee: Chemsyn Science LaboratoriesInventors: Paul Ruehle, Amy M. Bunker
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Patent number: 4849130Abstract: Liquid crystalline ethane derivatives by the described method in order to form liquid crystalline compositions with known liquid crystalline compounds have a general formula I: ##STR1## wherein, if ring A idicates a 1,4-substituted benzene ring, then ring B indicates 1.4-substituted benzene ring or 1.4-trans-substituted cyclohexane ring or 1.4-substituted bicyclo[2,2,2]octane ring or 2.5-substituted pyrimidine ring or 2.5-substituted 1.3- dioxane ring, or if ring B indicates a 1.4-substituted benzene ring, then A indicates 1.4-trans-substituted cyclohexane ring or 1.4-substituted bicylo[2,2,2]octane ring or 2.5-substituted pyrimidine ring or 2.5-substituted 1.3-dioxane ring, and R indicates a normal alkyl chain C.sub.n H.sub.2n+1 or a non-branched alkoxy group C.sub.n H.sub.2n+1 O or an alkylcarboxylic group C.sub.n H.sub.2n+1 COO or an alkyl carbonato group C.sub.n H.sub.2n+1 OCOO or a branched alkyl chain CH.sub.3 --CH.sub.2 --CH(CH.sub.3)--(CH.sub.2).sub.k -- or a branched alkoxy group CH.sub.3 --CH.sub.Type: GrantFiled: March 31, 1988Date of Patent: July 18, 1989Assignees: Wojskowa Akademia Techniczna, Zaklady Kineskopowe "Unitra-Polkolor" Zaklady Kineskopow KolorowychInventors: Roman Dabrowski, Jerzy Dziaduszek, Tomasz Szczucinnski, Witold Drzewinski, Zofia Stolarz, Jozef Zmija, Janusz Parka, Bozena Sosnowska
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Patent number: 4713467Abstract: Isothiocyanates are formed by oxidizing, with gaseous oxygen or air, in the presence of a metal oxidation catalyst a dithiocarbamate with appropriate control of the pH of the reaction medium to suppress the formation of by-products. Optionally a quaternary ammonium halide catalyst can be used to increase product yield.Type: GrantFiled: November 6, 1986Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventors: Jeffrey E. Telschow, Danielle A. Bright
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Patent number: 4636574Abstract: Arylisothiocyanates are prepared by reacting a primary arylamine with carbon disulfide in the presence of a tertiary amine.Type: GrantFiled: November 4, 1985Date of Patent: January 13, 1987Assignee: Ethyl CorporationInventor: Kju H. Shin
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Patent number: 4614798Abstract: In the preparation of 2,6-dimethylphenylisothiocyanate by reacting N-(2,6-dimethylphenyl)acetamide with sodium hydride in an organic solvent to form the corresponding anion of said amide, then reacting carbon disulfide with said anion to form said 2,6-dimethylphenylisothiocyanate, unexpectedly high yields are obtained by using as the organic solvent tetrahydrofuran or a mixture of N,N-dimethylacetamide and toluene. 2,6-Dimethylphenylisothiocyanate is an intermediate in the preparation of xylazine useful, for instance, as a sedative, an analgesic and muscle relaxant.Type: GrantFiled: April 9, 1985Date of Patent: September 30, 1986Assignee: VetamixInventors: Richard L. Elliott, Paul H. Ruehle