Acetylenically Unsaturated Patents (Class 568/873)
  • Patent number: 11814660
    Abstract: The disclosure relates to recombinant microorganisms for the production of fatty amines and derivatives thereof. Further contemplated are cultured recombinant host cells as well as methods of producing fatty amines by employing these host cells.
    Type: Grant
    Filed: December 14, 2020
    Date of Patent: November 14, 2023
    Assignee: Genomatica, Inc.
    Inventors: Stephen B. Del Cardayre, Louis G. Hom
  • Publication number: 20150141709
    Abstract: Subject of the invention is a process for the production of methylbutynol, wherein the process comprises at least one pervaporation step. In a preferred embodiment, the process comprises the steps of (a) providing a feed composition comprising methylbutynol and water, (b) subjecting the feed composition to distillation in a distillation device, (c) removing a sidestream from the distillation device, the sidestream having a higher water content than the feed composition, and (d) subjecting said sidestream to pervaporation, thereby reducing the water content. The invention also relates to uses and devices relating to the inventive process.
    Type: Application
    Filed: July 11, 2013
    Publication date: May 21, 2015
    Inventors: Stefan Ottiger, Thomas Scholl, Stefan Stoffel, Klaus Kalbermatter, Andreas Klein, Kishore Nedungadi
  • Publication number: 20150093354
    Abstract: In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.
    Type: Application
    Filed: December 8, 2014
    Publication date: April 2, 2015
    Applicant: Board of Regents of the Nevada System of Higher Education, on Behalf of the University of Nevada
    Inventors: Claus Tittiger, Rubi Figueroa-Teran, Gary J. Blomquist
  • Publication number: 20150038386
    Abstract: Compounds of formula (I) wherein R is hydrogen and the bond between C-2 and C-3 together with the dotted line represents a double bond, or R is —CH2— and together with C-2 and C-3 represents a cyclopropane ring and the bond between C-2 and C-3 together with the dotted line represents a single bond, having floral rosy odor notes, their use as fragrance and perfumed products comprising them.
    Type: Application
    Filed: May 25, 2012
    Publication date: February 5, 2015
    Applicant: GIVAUDAN S.A.
    Inventors: Hai-Shan Dang, Andreas Goeke, Yue Zou
  • Publication number: 20150018585
    Abstract: The present invention is related to a new metal powder catalytic system (catalyst) comprising a cobalt/chrome-alloy as a carrier, its production and its use in hydrogenation processes.
    Type: Application
    Filed: February 22, 2013
    Publication date: January 15, 2015
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Axel Buss
  • Publication number: 20130289317
    Abstract: A method for converting farnesol to nerolidol in the presence of alpha-bisabolol including providing or preparing a mixture of alpha-bisabolol, farnesol, and one or more catalysts for selective isomerization of farnesol to nerolidol in the presence of alpha-bisabolol, and converting at least a portion of the farnesol to nerolidol.
    Type: Application
    Filed: April 19, 2013
    Publication date: October 31, 2013
    Inventors: Jürgen Siewert, Burghard Wilkening
  • Publication number: 20130281688
    Abstract: Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.
    Type: Application
    Filed: April 22, 2013
    Publication date: October 24, 2013
    Applicant: Elevance Renewable Sciences, Inc
    Inventors: Stephen A. Di Biase, Keith M. Wampler, David R. Allen, Randal J. Bernhardt, Ryan Littich
  • Publication number: 20130035513
    Abstract: The invention relates to the use of EntD polypeptides, polynucleotides encoding the same, and homologues thereof to enhance the production of fatty aldehydes and fatty alcohols in a host cell.
    Type: Application
    Filed: January 26, 2012
    Publication date: February 7, 2013
    Applicant: LS9, INC.
    Inventors: Zhihao HU, Derek L. Greenfield, Vikranth Arlagadda
  • Publication number: 20120197046
    Abstract: The present invention is directed to a process for the manufacture of 2-pentyn-1-ol starting from 2-propyn-1-ol via the following intermediates (I), (II) wherein R1 is H or linear C1-6 alkyl, R2 is linear C1-6 alkyl or branched C3-6 alkyl and R3 is linear C1-6 alkyl, as well as to the intermediates themselves.
    Type: Application
    Filed: August 5, 2010
    Publication date: August 2, 2012
    Inventors: Werner Bonrath, Francesco Pace, Jocelyn Fischesser, Konrad Witzgall
  • Publication number: 20110312904
    Abstract: The present invention provides compounds of Formula (I), compositions comprising an effective amount of a compound of Formula (I), optionally with chemotherapeutic drugs such as a tubulin-binding drug, and methods of their use for reducing the toxicity of cytotoxic agents, treating or preventing cancer or a neuropathic disorder, inducing a chemoprotective phase II enzyme, DNA, or protein synthesis, enhancing the immune system, treating inflammation, improving and enhancing general health or well-being, and methods for making compounds of Formula (I).
    Type: Application
    Filed: August 27, 2009
    Publication date: December 22, 2011
    Applicants: SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH, TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK
    Inventors: Samuel J. Danishefsky, Ting-Chao Chou, Xiaoguang Lei, Heedong Yun, Fay Ng, John Hartung, Dalibor Sames
  • Publication number: 20110236311
    Abstract: The invention relates to radiodiagnostic and radiotherapeutic agents, including biologically active vectors labelled with radionuclides. It further relates to methods and reagents labelling a vector such as a peptide comprising reaction of a compound of formula (I) with a compound of formula (II): or, a compound of formula (III) with a compound of formula (IV) in the presence of a Cu (I) catalyst. The resultant labelled conjugates are useful as diagnostic agents, for example, as radiopharmaceuticals more specifically for use in Positron Emission Tomography (PET) or Single Photon Emission Computed Tomography (SPECT) or for radiotherapy.
    Type: Application
    Filed: June 13, 2011
    Publication date: September 29, 2011
    Applicant: HAMMERSMITH IMANET LIMITED
    Inventors: ERIK ARSTAD, MATTHIAS EBERHARD GLASER
  • Publication number: 20110034565
    Abstract: The invention provides a compound for use in the treatment of symptoms associated with psychosis, schizophrenia, a cognitive impairment disorder, a mood disorder, a nervous system disorder and/or a behavioral disorder. The compound has the formula ? and is administered to a subject in need thereof in an effective amount. The compound Meparfynol (3-methylpent-1-yn-3-ol) has been found to be effective.
    Type: Application
    Filed: April 20, 2009
    Publication date: February 10, 2011
    Applicant: University College Dublin, National University of Ireland, Dublin
    Inventors: Ciaran Regan, Lisa Conboy, Shane Gannon
  • Patent number: 7282614
    Abstract: The present invention provides a process for preparing propargyl alcohol by converting an aqueous formaldehyde solution comprising acetylene over a catalyst comprising copper acetylide at an operating pressure of from 1 to 15 bar and from 70 to 120° C. without forming a continuous gas phase, in which the aqueous formaldehyde solution comprises an organic solvent for acetylene and the catalyst is arranged in a fluidized bed.
    Type: Grant
    Filed: July 3, 2004
    Date of Patent: October 16, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Maximilian Vicari, Martin Rudloff, Andreas Kramer, Ronald Drews
  • Patent number: 7232933
    Abstract: A process for the preparation of diols by a Lewis acid-catalysed aldehyde addition reaction on hydroxyalkynes followed by hydrogenation is described. The process provides a wide range of diols from simple, readily available starting materials. In particular the process is suitable for preparing chiral 1,4-diols suitable for the preparation of chiral phospholane ligands for use in asymmetric catalysis.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: June 19, 2007
    Assignee: Johnson Matthey PLC
    Inventors: Brian Michael Adger, Erick Moran Carreira
  • Patent number: 7183443
    Abstract: Process for the preparation of enantiomerically enriched amino aldehydes and amino alcohols, wherein a corresponding enantiomerically enriched amino nitrile is subjected to hydrogenation in the presence of hydrogen, a hydrogenation catalyst, preferably a Pd-catalyst and a mineral acid. For the preparation of an amino aldehyde hydrogen preferably is present at a hydrogen-pressure between 0.1 and 2 MPa, in particular between 0.5 and 1 MPa. The amino aldehyde preferably is isolated in the form of a chemically and configurationally stable derivative. For the preparation of an amino alcohol, preferably at least during part of the hydrogenation hydrogen is present at a hydrogen-pressure between 2 and 10 MPa, in particular between 4 and 6 MPa. In a preferred embodiment the hydrogen-pressure initially is between 0.5 and 2 MPa and subsequently, after most of the nitrile starting material is converted, the hydrogen pressure is increased to a value between 2 and 10 MPa.
    Type: Grant
    Filed: April 7, 2003
    Date of Patent: February 27, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
  • Patent number: 7015367
    Abstract: Propargyl bromide is effectively stabilized against shock or thermal decomposition by use therewith of an environmentally acceptable inert liquid solvent that forms an azeotrope with propargyl bromide.
    Type: Grant
    Filed: January 12, 2004
    Date of Patent: March 21, 2006
    Assignee: Albemarle Corporation
    Inventors: Robert C. Herndon, Jr., Robert H. Allen, Noel H. Brantley, Ronny W. Lin, Ralph W. Magin, Mahmood Sabahi
  • Patent number: 6956141
    Abstract: A process for preparing at least one unsaturated alcohol (B) comprises the steps (I) to (III) below: (I) reaction of at least one alkali metal hydroxide or alkaline earth metal hydroxide with at least one alcohol (A) in at least one organic solvent (L) to give a mixture (G-I) comprising at least the alcohol (A), the solvent (L) and an alkoxide (AL); (II) reaction of at least one carbonyl compound of the formula R—CO—R? with at least one alkyne of the formula R?—C?C—H and the mixture (G-I) obtained in step (I) to give a mixture (G-II) comprising at least the alcohol (A), the solvent (L) and an unsaturated alcohol (B); (III) distillation of the mixture (G-II) obtained in step (II) to give the alcohol or alcohols (B) and a mixture (G-III) comprising the solvent (L) and the alcohol (A), wherein the solvent (L) obtained in step (III) and the alcohol (A) obtained in step (III) are recycled as a mixture to step (I).
    Type: Grant
    Filed: February 22, 2000
    Date of Patent: October 18, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Melanie Maas-Brunner, Jochem Henkelmann, Gerd Kaibel, Alois Kindler, Christian Knoll, Harald Rust, Christian Tragut, Manfred Stroezel, Udo Rheude, Rudolf Erich Lorenz, Juan Aiscar
  • Patent number: 6949685
    Abstract: A process for the manufacture of an acetylenically unsaturated alcohol comprising reacting formaldehyde, an aldehyde or a ketone (a carbonyl compound) with acetylene in the presence of ammonia and a strongly basic macroporous anion exchange resin, the latter preferably featuring a polystyrene matrix and quaternary ammonium groups, preferably of type I or Type II. The reaction products, which depending on the starting carbonyl compound are propargyl alcohol or 1-monosubstituted or 1,1-disubstituted derivatives thereof, are of use as intermediates in the synthesis of many useful end products, inter alia in the field of vitamins and carotenoids.
    Type: Grant
    Filed: September 19, 2002
    Date of Patent: September 27, 2005
    Inventors: Werner Bonrath, Bernd Englert, Reinhard Karge, Michael Schneider
  • Patent number: 6710213
    Abstract: Processes are provided for producing propargyl alcohol in an industrially advantageous manner. One of the processes comprises reaction of 1,2,3-trichloropropane with 3 equivalents or more of an alkali compound to produce propargyl alcohol. The other process comprises (1) a first step of reaction of 2,3-dichloro-1-propanol with an amine to produce chloroallyl alcohol, and (2) a second step of reaction of the chloroallyl alcohol obtained in the above step (1) with an alkali compound to produce propargyl alcohol.
    Type: Grant
    Filed: April 2, 2001
    Date of Patent: March 23, 2004
    Assignee: Showa Denko K.K.
    Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami, Makoto Saito, Toshitaka Hiro
  • Patent number: 6610888
    Abstract: A method of reacting a solution comprising a mixture of chemical compounds which are in chemical equilibrium with one another with at least one further chemical compound (9) is provided. The method comprises the following steps: fractionation of the solution by means of a separation method to give at least two fractions (5, 6) which are enriched in different chemical compounds of the mixture; and reaction of a fraction (5) with the further chemical compound or compounds (9). The fractionation is advantageously carried out using a film evaporator (1). Unreacted fractions (6) can be recirculated via a residence time vessel (3) back to the fractionation step. The method is particularly suitable for reactions of an aqueous formaldehyde solution in which various components of the solution (formaldehyde, methylene glycol, polyoxymethylene glycols) react in different ways.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: August 26, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckhard Ströfer, Stephan Scholl, Hans Hasse
  • Patent number: 6586644
    Abstract: A process for producing an optically active propargyl alcohol represented by the following formula (4): wherein R1 is an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylsilyl group, an aromatic hydrocarbon group, a C2-C10 heterocyclic group having 1-3 heteroatoms or a C1-C10 alkyl group having 1-3 heteroatoms, and R2 is an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylsilyl group, an aromatic hydrocarbon group, a C2-C10 heterocyclic group having 1-3 heteroatoms or a C1-C10 alkyl group having 1-3 heteroatoms, which comprises allowing an aldehyde compound represented by the following formula (1): R1—CHO  (1) to react with an alkyne compound represented by the following formula (2): HC≡C—R2  (2) in the presence of an optically active aminoalcohol and a tertiary amine and a zinc halogenated lower alkane sulfonate in an amount of less than equivalent mo
    Type: Grant
    Filed: September 3, 2002
    Date of Patent: July 1, 2003
    Assignees: Sumika Fine Chemicals Company, Limited
    Inventor: Erick M. Carreira
  • Patent number: 6465698
    Abstract: A process for catalytically isomerizing Z-3-methylpent-2-en-4-yn-1-ol to E-3-methylpent-2-en-4-yn-1-ol is provided. This process includes contacting a stereoisomeric mixture containing Z-3-methylpent-2-en-4-yn-1-ol and E-3-methylpent-2-en-4-yn-1-ol with a source of bromine radicals in a two-phase reaction mixture having an aqueous phase and a stereoisomeric mixture phase, intermixing the reaction mixture, and heating the reaction mixture to a temperature from about −10° C. to about 100° C.
    Type: Grant
    Filed: June 11, 2001
    Date of Patent: October 15, 2002
    Assignee: Roche Vitamins, Inc.
    Inventors: Arnold Gloor, Hansjoerg Gruendler, Werner Simon
  • Patent number: 6406793
    Abstract: A silicone pressure sensitive adhesive composition utilizing addition reaction between alkenyl groups of alkenyl group-containing diorganopolysiloxanes and SiH groups of organohydrogenpolysiloxanes, which comprises (A) diorganopolysiloxanes containing alkenyl groups the number of which is on average at least two a molecule, (B) an organopolysiloxane comprising R23SiOC.5 units, wherein R2 is an unsubstituted or substituted 1-10C monovalent hydrocarbon group, and SiO2 units in a R23SiOC.5/SiO2 ratio of from 0.6 to 1.
    Type: Grant
    Filed: September 22, 2000
    Date of Patent: June 18, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventor: Shunji Aoki
  • Publication number: 20020042547
    Abstract: A process for catalytically isomerizing Z-3-methylpent-2-en-4-yn-1-ol to E-3-methylpent-2-en-4-yn-1-ol is provided. This process includes contacting a stereoisomeric mixture containing Z-3-methylpent-2-en-4-yn-1-ol and E-3-methylpent-2-en-4-yn-1-ol with a source of bromine radicals in a two-phase reaction mixture having an aqueous phase and a stereoisomeric mixture phase, intermixing the reaction mixture, and heating the reaction mixture to a temperature from about −10° C. to about 100° C.
    Type: Application
    Filed: June 11, 2001
    Publication date: April 11, 2002
    Applicant: Roche Vitamins Inc.
    Inventors: Arnold Gloor, Hansjoerg Gruendler, Werner Simon
  • Patent number: 6297407
    Abstract: The invention relates to a method for producing alkyne diols by reacting ketones with acetylenic hydrocarbons in an organic solvent in the presence of a base which contains potassium alcoholates of primary and/or secondary alcohols. The alkyne diols are produced while forming adducts which precipitate out of the reaction mixture and which are comprised of alkyne monoalcohols and/or alkyne diols and a base. The stoichiometries of the reaction partners are selected such that gelatinous adducts are formed which comprise a spherical surface, whereby the reaction mixture remains agitable during the entire reaction.
    Type: Grant
    Filed: January 24, 2001
    Date of Patent: October 2, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Alois Kindler, Melanie Brunner, Christian Tragut, Jochem Henkelmann
  • Patent number: 6156913
    Abstract: The invention provides processes for producing phytol, isophytol, and certain phytol derivatives by a method of oxidizing or epoxidizing geranylgeraniol or geranylgeraniol derivatives to form epoxygeranylgeraniol derivatives, reducing or hydrogenating the epoxygeranylgeraniol derivatives to produce epoxyphytol derivatives, and then deoxygenating the epoxyphytol derivatives to produce phytol, isophytol, phytene derivatives, isophytene derivatives, or mixtures thereof. The step of deoxygenating is carried out in the presence of deoxygenation catalysts, including rhenium trioxide compounds. The invention also provides methods for the synthesis of certain novel substituted epoxyphytyl compounds and substituted phytene compounds having removable protecting groups.
    Type: Grant
    Filed: July 6, 1999
    Date of Patent: December 5, 2000
    Assignee: Eastman Chemical Company
    Inventor: John Anthony Hyatt
  • Patent number: 5728376
    Abstract: The present invention is directed to compounds useful as moth attractants and to methods for controlling populations of the tomato moth Scrobipalpuloides absoluta with these compounds. The compounds are 3,8,11-tetradecatrienyl acetates, 3,8-tetradecadienyl acetates, 3,11-tetradecadienyl acetates, and 8,11-tetradecadienyl acetates. Preferred compounds are (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate, (3E,8Z)-3,8-tetradecadienyl acetate, (3E,11Z)-3,11 -tetradecadienyl acetate, and (8Z,11Z)-8-11-tetradecadienyl acetate. The compounds can be used as an attractant in moth traps comprising, in addition to the compounds, a moth restraint. Alternatively, the compounds of the present invention can be combined with a biocontrol agent or an insecticide for use as a moth control composition. Synthesis of (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate is described.
    Type: Grant
    Filed: April 25, 1995
    Date of Patent: March 17, 1998
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
  • Patent number: 5600029
    Abstract: The present invention relates to a process for producing dl-tocopherols and intermediates for the production. dl-Tocopherols obtained by the present invention are useful compounds that are used as food additives, feed and medicaments.
    Type: Grant
    Filed: March 2, 1995
    Date of Patent: February 4, 1997
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tatsuhiko Kaneko, Kenichi Kashiwa
  • Patent number: 5354937
    Abstract: Tert-amyl compounds of the general formula I ##STR1## and novel processes for preparing 2-tert-amylbutadiene by dehydrating 3,4,4-trimethylhex-1-en-3-ol at from 100.degree. to 350.degree. C. and from 0.01 to 50 bar on acidic catalysts, its preparation by partially hydrogenating 3,4,4-trimethyl-hex-1-yn-03-ol at from 0.degree. to 50.degree. C. and from 0.01 to 50 bar and its preparation by reacting tert-amyl methyl ketone (3,3-dimethylpentan-2-one) with acetylene in the presence of basic catalysts at from 0.degree. to 60.degree. C. and from 0.01 to 50 bar, and also the preparation of 2-tert-amylanthraquinone by reacting 2-tert-amylbutadiene with 1,4-naphthoquinone at from 20.degree. to 200.degree. C. and from 0.01 to 50 bar to give 2-tert-amyl-1,4,4a,9a-tetrahydroanthraquinone and then oxidizing the latter in the presence of a strong base at from 0.degree. to 50.degree. C. are described.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: October 11, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ebel, Juergen Schroeder
  • Patent number: 5352845
    Abstract: A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed.
    Type: Grant
    Filed: March 25, 1993
    Date of Patent: October 4, 1994
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5258529
    Abstract: The present invention provides a process for producing a propargylcarbinol compound of formula (I): ##STR1## where R.sup.1 and R.sup.2 are as defined herein. The process comprises reacting a haloallycarbinol compound of formula (II) with a base. The present invention also relates to a process for producing the haloallylcarbinol compound. The above propargylcarbinol compound is useful as an intermediate for agrochemicals, pharmaceuticals, perfumes, resin monomers, and the like.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: November 2, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
  • Patent number: 5243097
    Abstract: Acetylenic derivatives of general formula ##STR1## in which R.sub.1 denotes a hydrogen atom or a phenyl radical or a radical of general formula ##STR2## in which R.sub.2 and R.sub.3, which may be identical or different, denote a hydrogen atom or a saturated or unsaturated aliphatic radical, substituted if appropriate, or form together a cycloaliphatic radical, R.sub.4 denotes a hydrogen atom or a saturated or unsaturated aliphatic radical, a hydroxy, alkyloxy, methanesulphonyloxy, benzenesulpnonyloxy or p-toluenesulphonyloxy radical, R.sub.5 denotes a hydrogen atom or a saturated aliphatic radical, R.sub.6 denotes a hydrogen atom or a saturated or unsaturated aliphatic radical are made by reaction of an acetylenic derivative of general formulaR.sub.1 --C.tbd.C--H (III)with an allyl derivative of general formula ##STR3## in the presence of a cuprous salt and an anhydrous organic base. The compounds of formula (I) are useful in organic synthesis, in particular in the preparation of the vitamins A and E.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: September 7, 1993
    Assignee: Rhone-Poulenc Sante Les Miroirs
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 5243096
    Abstract: An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and the chiral central carbon atoms marked with symbols *, # and .thrfore.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: September 7, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5157167
    Abstract: The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: October 20, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Jonathan C. Evans, Christian T. Goralski
  • Patent number: 5093536
    Abstract: Functional internal alkynes are conveniently and economically prepared by dehydrohalogenating a dibromide with an alkali metal hydroxide in the presence of a phase transfer catalyst.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: March 3, 1992
    Assignee: Kenkel Research Corporation
    Inventors: James M. Renga, Alan G. Olivero, Mark Bosse
  • Patent number: 5073572
    Abstract: Novel acetylenic alcohols were isolated from the known marine sponge Cribrochalina vasculum. These compounds, and derivatives thereof, are useful agents for the treatment of cancers of humans and animals. Also, these compounds and their derivatives can be used as immunosuppressive agents for humans and animals.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: December 17, 1991
    Assignee: Harbor Branch Oceanographic Institution, Inc.
    Inventors: Sarath P. Gunasekera, Glynn T. Faircloth, Amy E. Wright, Winnie C. Thompson, Neal Burres
  • Patent number: 5049681
    Abstract: A novel optically active allyl alcohol derivative represented by the following general formulae (I), (II), (III) and (IV): ##STR1## The novel optically active allyl alcohol can be used effectively for producing leucotrienes B.sub.4 by the process of reacting an optically active halogen substituted allyl alcohol and a novel optically active acetylene-substituted allyl alcohol.
    Type: Grant
    Filed: July 8, 1988
    Date of Patent: September 17, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 5043495
    Abstract: A process of separation and purification of a propargyl alcohol which comprises treating a propargyl alcohol represented by Formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituent which is different from each other, and is selected from the group consisting of a C.sub.1 -C.sub.8 alkyl group, a phenyl group; a halophenyl group, a phenyl group having at least one methyl substituent, an aralkyl group and a cycloalkyl group,which is chemically or optically impure,with a tertiary diamine represented by Formula (II): ##STR2## wherein each of R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be the same or different and represents an aralkyl group or an alkyl group having 1 to 6 carbon atoms; and R.sub.3, R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: January 30, 1990
    Date of Patent: August 27, 1991
    Assignee: Ube Industries, Ltd.
    Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
  • Patent number: 4967019
    Abstract: A method of manufacturing 2-propyn-1-ol by decomposing 2-butyn-1,4-diol in the presence of a copper acetylide catalyst. 2-propyn-1-ol is produced at high conversion, yield, and purity.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: October 30, 1990
    Assignee: Gaf-Huels Chemie GMBH
    Inventors: Helmut Westernacher, Karl Aertken, Thomas Stieren
  • Patent number: 4871868
    Abstract: A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula ofA--X (I)wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula ofM--C.tbd.C--B (II)wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of--C.tbd.C--M (III)wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of ##STR1## wherein R.sup.1 and R.sup.2 independently represent a lower alkyl, and R.sup.3 represents a hydrogen or a lower alkyl.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: October 3, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yuzuru Saito, Kokichi Yoshida
  • Patent number: 4855516
    Abstract: A method of manufacturing 2-propyn-1-ol by decomposing 2-butyn-1,4-diol in the presence of a copper acetylide catalyst. 2-propyn-1-ol is produced at high conversion, yield, and purity.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: August 8, 1989
    Assignee: Gaff-Huels Chemie GmbH
    Inventors: Helmut Westernacher, Karl Aertken, Thomas Stieren
  • Patent number: 4751245
    Abstract: N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine derivatives are provided having the general formula ##STR1## wherein R.sub.1 is methoxy, iminomethyl or 1-iminoethyl and R.sub.2 and R.sub.3 are each hydrogen; or R.sub.1 is methyl and one of R.sub.2 and R.sub.3 is hydrogen and the other is halogen.The above compounds as well as acid-addition salts thereof are useful as antifungal agents.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: June 14, 1988
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Gregory S. Bisacchi, Robert Zahler
  • Patent number: 4620045
    Abstract: Eneynols are prepared from terminal acetylenes and propargylic alcohols using a Cu.sup.+, Ag.sup.+ and/or Au.sup.+ halide catalyst.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: October 28, 1986
    Assignee: The Dow Chemical Company
    Inventors: Giffin D. Jones, Harold E. Doorenbos
  • Patent number: 4588828
    Abstract: Antimicrobial activity is exhibited by compounds having the formula ##STR1## wherein R.sub.1 is hydrogen or aryl;R.sub.2 is hydroxymethyl, carboxyaldehyde, propenalyl, 3-hydroxy-1-propenyl, or 3-hydroxy-1,2-epoxypropyl; andn is 2 and m is 1 or n is 3 and m is 0; with the proviso that if R.sub.1 is hydrogen, n is 2 and m is 1.
    Type: Grant
    Filed: August 23, 1984
    Date of Patent: May 13, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Gregory S. Bisacchi, William H. Koster
  • Patent number: 4467118
    Abstract: There is disclosed a novel process for converting allylic amines, having a hydrogen bonded to a carbon .delta. to the amino group, to a diene in the presence of a zero valent palladium phosphine complex and a weak acid. The process has been used to make novel compositions containing 7-methoxy-3,7-dimethyloctadienes which are useful as odorants and flavorants.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: August 21, 1984
    Assignee: Givaudan Corporation
    Inventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
  • Patent number: 4317905
    Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
  • Patent number: 4311645
    Abstract: A chemical synthesis of an SRS-A active compound from the reaction product of 1-halo-2-octyne and the ether of 2-penten-4-yn-1-ol including intermediates in the synthesis, some of which being antagonists of SRS-A useful for treating allergic reactions.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: January 19, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4263463
    Abstract: Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: April 21, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeyoshi Kitamura, Norbushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
  • Patent number: 4233453
    Abstract: This invention disclosed herein relates to pharmacologically active 15-deoxy-16-hydroxy prostaglandin derivatives of the E and F series wherein C.sub.16 is substituted with allenyl.These compounds are active as hypotensives, antisecretory, bronchodilating and fertility control agents.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: November 11, 1980
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4232166
    Abstract: The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E and F series wherein C-16 is substituted with hydroxy and methyl and a double bond is introduced between C-19 and C-20. These compounds are active as bronchodilators, anti-ulcer agents and fertility control agents.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: November 4, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner