Processes For Forming The Isothiocyanate Group Patents (Class 558/18)
  • Patent number: 10640464
    Abstract: 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: Grant
    Filed: July 9, 2019
    Date of Patent: May 5, 2020
    Assignee: The William M. Yarbrough Foundation
    Inventor: Michael E. Silver
  • Patent number: 9169331
    Abstract: 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: Grant
    Filed: December 21, 2012
    Date of Patent: October 27, 2015
    Assignee: DIONEX CORPORATION
    Inventors: Xiaodong Liu, Udayanath Aich, Christopher A. Pohl
  • Publication number: 20150110863
    Abstract: 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: Application
    Filed: March 6, 2013
    Publication date: April 23, 2015
    Applicants: Univerversidad De Sevilla, Consejo Superior De Investigaciones CientÍficas (CSIC)
    Inventors: Noureddine Khiar El Wahabi, Inmaculada Fernández Fernández, Rocío Recio Jiménez
  • Publication number: 20130310555
    Abstract: 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: Application
    Filed: May 17, 2013
    Publication date: November 21, 2013
    Applicant: Illinois Institute of Technology
    Inventor: Hyun-Soon Chong
  • Patent number: 8541611
    Abstract: 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: Grant
    Filed: June 28, 2012
    Date of Patent: September 24, 2013
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
  • Publication number: 20130245305
    Abstract: 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: Application
    Filed: November 29, 2010
    Publication date: September 19, 2013
    Applicant: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Junko Takada, Shunsuke Iwamoto, Satoshi Nakano
  • Publication number: 20130142739
    Abstract: 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: Application
    Filed: July 20, 2011
    Publication date: June 6, 2013
    Applicant: Auriga International
    Inventors: Jacques Dubois, Alfred Marchal, Damien Lacroix, Jérôme Cabou
  • Patent number: 8367857
    Abstract: 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: Grant
    Filed: February 27, 2009
    Date of Patent: February 5, 2013
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoshi Nakano, Daisuke Saito
  • Publication number: 20120271049
    Abstract: 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: Application
    Filed: June 28, 2012
    Publication date: October 25, 2012
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
  • Patent number: 8232421
    Abstract: 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: Grant
    Filed: September 21, 2010
    Date of Patent: July 31, 2012
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
  • Publication number: 20110009640
    Abstract: 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: Application
    Filed: September 21, 2010
    Publication date: January 13, 2011
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Gerhard Hamprecht, Michael Puhl, Bernd Wolf, Norbert Götz, Michael Keil, Robert Reinhard, Ingo Sagasser, Werner Seitz
  • Publication number: 20100312000
    Abstract: 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: Application
    Filed: February 27, 2009
    Publication date: December 9, 2010
    Applicant: Nissan Chemical Industries Limited
    Inventors: Satoshi Nakano, Daisuke Saito
  • Publication number: 20080227995
    Abstract: 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: Application
    Filed: July 20, 2006
    Publication date: September 18, 2008
    Applicant: Schwarz Pharma AG
    Inventors: Jorg Hamann, Ralf Kanzler, Youxin Li
  • Publication number: 20030235634
    Abstract: 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: Application
    Filed: June 21, 2002
    Publication date: December 25, 2003
    Applicant: ACCESS BUSINESS GROUP INTERNATIONAL LLC.
    Inventors: Donald J. Pusateri, Tamara R. Kizer, Alex L. Lowry
  • Patent number: 6420556
    Abstract: 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: Grant
    Filed: June 12, 2001
    Date of Patent: July 16, 2002
    Assignee: The Procter & Gamble Company
    Inventor: Lawrence Joseph Wilson
  • Patent number: 5250717
    Abstract: 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: Grant
    Filed: June 1, 1992
    Date of Patent: October 5, 1993
    Assignee: Ethyl Corporation
    Inventor: Gordon G. Knapp
  • Patent number: 5208361
    Abstract: 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: Grant
    Filed: January 15, 1991
    Date of Patent: May 4, 1993
    Assignee: Degussa Aktiengesellschaft
    Inventors: Gunter Giesselmann, Kurt Gunther
  • Patent number: 5098934
    Abstract: 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: Grant
    Filed: June 22, 1990
    Date of Patent: March 24, 1992
    Assignee: Roussel Uclaf
    Inventors: Jean-Paul Vevert, Francoise Delevallee, Rogert Deraedt
  • Patent number: 5043442
    Abstract: 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: Grant
    Filed: April 2, 1990
    Date of Patent: August 27, 1991
    Assignee: Chemsyn Science Laboratories
    Inventors: Paul Ruehle, Amy M. Bunker
  • Patent number: 4849130
    Abstract: 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: Grant
    Filed: March 31, 1988
    Date of Patent: July 18, 1989
    Assignees: Wojskowa Akademia Techniczna, Zaklady Kineskopowe "Unitra-Polkolor" Zaklady Kineskopow Kolorowych
    Inventors: Roman Dabrowski, Jerzy Dziaduszek, Tomasz Szczucinnski, Witold Drzewinski, Zofia Stolarz, Jozef Zmija, Janusz Parka, Bozena Sosnowska
  • Patent number: 4713467
    Abstract: 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: Grant
    Filed: November 6, 1986
    Date of Patent: December 15, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Jeffrey E. Telschow, Danielle A. Bright
  • Patent number: 4636574
    Abstract: Arylisothiocyanates are prepared by reacting a primary arylamine with carbon disulfide in the presence of a tertiary amine.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: January 13, 1987
    Assignee: Ethyl Corporation
    Inventor: Kju H. Shin
  • Patent number: 4614798
    Abstract: 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: Grant
    Filed: April 9, 1985
    Date of Patent: September 30, 1986
    Assignee: Vetamix
    Inventors: Richard L. Elliott, Paul H. Ruehle