Acetylenically Unsaturated Patents (Class 568/873)
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Patent number: 11814660Abstract: 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: GrantFiled: December 14, 2020Date of Patent: November 14, 2023Assignee: Genomatica, Inc.Inventors: Stephen B. Del Cardayre, Louis G. Hom
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Publication number: 20150141709Abstract: 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: ApplicationFiled: July 11, 2013Publication date: May 21, 2015Inventors: Stefan Ottiger, Thomas Scholl, Stefan Stoffel, Klaus Kalbermatter, Andreas Klein, Kishore Nedungadi
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Publication number: 20150093354Abstract: 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: ApplicationFiled: December 8, 2014Publication date: April 2, 2015Applicant: Board of Regents of the Nevada System of Higher Education, on Behalf of the University of NevadaInventors: Claus Tittiger, Rubi Figueroa-Teran, Gary J. Blomquist
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Publication number: 20150038386Abstract: 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: ApplicationFiled: May 25, 2012Publication date: February 5, 2015Applicant: GIVAUDAN S.A.Inventors: Hai-Shan Dang, Andreas Goeke, Yue Zou
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Publication number: 20150018585Abstract: 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: ApplicationFiled: February 22, 2013Publication date: January 15, 2015Applicant: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Axel Buss
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Publication number: 20130289317Abstract: 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: ApplicationFiled: April 19, 2013Publication date: October 31, 2013Inventors: Jürgen Siewert, Burghard Wilkening
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Publication number: 20130281688Abstract: 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: ApplicationFiled: April 22, 2013Publication date: October 24, 2013Applicant: Elevance Renewable Sciences, IncInventors: Stephen A. Di Biase, Keith M. Wampler, David R. Allen, Randal J. Bernhardt, Ryan Littich
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Publication number: 20130035513Abstract: 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: ApplicationFiled: January 26, 2012Publication date: February 7, 2013Applicant: LS9, INC.Inventors: Zhihao HU, Derek L. Greenfield, Vikranth Arlagadda
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Publication number: 20120197046Abstract: 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: ApplicationFiled: August 5, 2010Publication date: August 2, 2012Inventors: Werner Bonrath, Francesco Pace, Jocelyn Fischesser, Konrad Witzgall
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Publication number: 20110312904Abstract: 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: ApplicationFiled: August 27, 2009Publication date: December 22, 2011Applicants: SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH, TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORKInventors: Samuel J. Danishefsky, Ting-Chao Chou, Xiaoguang Lei, Heedong Yun, Fay Ng, John Hartung, Dalibor Sames
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Publication number: 20110236311Abstract: 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: ApplicationFiled: June 13, 2011Publication date: September 29, 2011Applicant: HAMMERSMITH IMANET LIMITEDInventors: ERIK ARSTAD, MATTHIAS EBERHARD GLASER
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Publication number: 20110034565Abstract: 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: ApplicationFiled: April 20, 2009Publication date: February 10, 2011Applicant: University College Dublin, National University of Ireland, DublinInventors: Ciaran Regan, Lisa Conboy, Shane Gannon
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Patent number: 7282614Abstract: 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: GrantFiled: July 3, 2004Date of Patent: October 16, 2007Assignee: BASF AktiengesellschaftInventors: Maximilian Vicari, Martin Rudloff, Andreas Kramer, Ronald Drews
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Patent number: 7232933Abstract: 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: GrantFiled: April 29, 2002Date of Patent: June 19, 2007Assignee: Johnson Matthey PLCInventors: Brian Michael Adger, Erick Moran Carreira
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Patent number: 7183443Abstract: 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: GrantFiled: April 7, 2003Date of Patent: February 27, 2007Assignee: DSM IP Assets B.V.Inventors: Bernardus Henricus Nicolaas Dassen, Bernardus Kaptein, Quirinus Bernardus Broxterman
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Patent number: 7015367Abstract: 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: GrantFiled: January 12, 2004Date of Patent: March 21, 2006Assignee: Albemarle CorporationInventors: Robert C. Herndon, Jr., Robert H. Allen, Noel H. Brantley, Ronny W. Lin, Ralph W. Magin, Mahmood Sabahi
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Patent number: 6956141Abstract: 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: GrantFiled: February 22, 2000Date of Patent: October 18, 2005Assignee: BASF AktiengesellschaftInventors: Melanie Maas-Brunner, Jochem Henkelmann, Gerd Kaibel, Alois Kindler, Christian Knoll, Harald Rust, Christian Tragut, Manfred Stroezel, Udo Rheude, Rudolf Erich Lorenz, Juan Aiscar
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Patent number: 6949685Abstract: 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: GrantFiled: September 19, 2002Date of Patent: September 27, 2005Inventors: Werner Bonrath, Bernd Englert, Reinhard Karge, Michael Schneider
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Patent number: 6710213Abstract: 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: GrantFiled: April 2, 2001Date of Patent: March 23, 2004Assignee: Showa Denko K.K.Inventors: Takanori Aoki, Takami Ohe, Haruki Ishikami, Makoto Saito, Toshitaka Hiro
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Patent number: 6610888Abstract: 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: GrantFiled: May 31, 2000Date of Patent: August 26, 2003Assignee: BASF AktiengesellschaftInventors: Eckhard Ströfer, Stephan Scholl, Hans Hasse
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Patent number: 6586644Abstract: 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 moType: GrantFiled: September 3, 2002Date of Patent: July 1, 2003Assignees: Sumika Fine Chemicals Company, LimitedInventor: Erick M. Carreira
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Patent number: 6465698Abstract: 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: GrantFiled: June 11, 2001Date of Patent: October 15, 2002Assignee: Roche Vitamins, Inc.Inventors: Arnold Gloor, Hansjoerg Gruendler, Werner Simon
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Patent number: 6406793Abstract: 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: GrantFiled: September 22, 2000Date of Patent: June 18, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Shunji Aoki
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Publication number: 20020042547Abstract: 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: ApplicationFiled: June 11, 2001Publication date: April 11, 2002Applicant: Roche Vitamins Inc.Inventors: Arnold Gloor, Hansjoerg Gruendler, Werner Simon
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Patent number: 6297407Abstract: 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: GrantFiled: January 24, 2001Date of Patent: October 2, 2001Assignee: BASF AktiengesellschaftInventors: Alois Kindler, Melanie Brunner, Christian Tragut, Jochem Henkelmann
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Patent number: 6156913Abstract: 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: GrantFiled: July 6, 1999Date of Patent: December 5, 2000Assignee: Eastman Chemical CompanyInventor: John Anthony Hyatt
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Patent number: 5728376Abstract: 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: GrantFiled: April 25, 1995Date of Patent: March 17, 1998Assignee: Cornell Research Foundation, Inc.Inventors: Athula B. Attygalle, Gulab N. Jham, Ales Svatos, Rosa T.S. Frighetto
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Patent number: 5600029Abstract: 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: GrantFiled: March 2, 1995Date of Patent: February 4, 1997Assignee: Takeda Chemical Industries, Ltd.Inventors: Tatsuhiko Kaneko, Kenichi Kashiwa
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Patent number: 5354937Abstract: 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: GrantFiled: September 30, 1993Date of Patent: October 11, 1994Assignee: BASF AktiengesellschaftInventors: Klaus Ebel, Juergen Schroeder
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Patent number: 5352845Abstract: 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: GrantFiled: March 25, 1993Date of Patent: October 4, 1994Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5258529Abstract: 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: GrantFiled: June 15, 1990Date of Patent: November 2, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiaki Oda, Sanshiro Matsuo, Kenji Saito
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Patent number: 5243097Abstract: 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: GrantFiled: November 20, 1992Date of Patent: September 7, 1993Assignee: Rhone-Poulenc Sante Les MiroirsInventors: Gerard Mignani, Didier Morel
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Patent number: 5243096Abstract: 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: GrantFiled: April 30, 1992Date of Patent: September 7, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5157167Abstract: 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: GrantFiled: January 31, 1992Date of Patent: October 20, 1992Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Jonathan C. Evans, Christian T. Goralski
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Patent number: 5093536Abstract: 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: GrantFiled: November 8, 1989Date of Patent: March 3, 1992Assignee: Kenkel Research CorporationInventors: James M. Renga, Alan G. Olivero, Mark Bosse
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Patent number: 5073572Abstract: 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: GrantFiled: February 16, 1990Date of Patent: December 17, 1991Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Sarath P. Gunasekera, Glynn T. Faircloth, Amy E. Wright, Winnie C. Thompson, Neal Burres
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Patent number: 5049681Abstract: 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: GrantFiled: July 8, 1988Date of Patent: September 17, 1991Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 5043495Abstract: 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: GrantFiled: January 30, 1990Date of Patent: August 27, 1991Assignee: Ube Industries, Ltd.Inventors: Fumio Toda, Koichi Tanaka, Kikuo Ataka
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Patent number: 4967019Abstract: 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: GrantFiled: May 22, 1989Date of Patent: October 30, 1990Assignee: Gaf-Huels Chemie GMBHInventors: Helmut Westernacher, Karl Aertken, Thomas Stieren
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Patent number: 4871868Abstract: 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: GrantFiled: March 3, 1988Date of Patent: October 3, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Yuzuru Saito, Kokichi Yoshida
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Patent number: 4855516Abstract: 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: GrantFiled: March 10, 1988Date of Patent: August 8, 1989Assignee: Gaff-Huels Chemie GmbHInventors: Helmut Westernacher, Karl Aertken, Thomas Stieren
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Patent number: 4751245Abstract: 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: GrantFiled: June 25, 1986Date of Patent: June 14, 1988Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, Robert Zahler
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Patent number: 4620045Abstract: Eneynols are prepared from terminal acetylenes and propargylic alcohols using a Cu.sup.+, Ag.sup.+ and/or Au.sup.+ halide catalyst.Type: GrantFiled: March 19, 1985Date of Patent: October 28, 1986Assignee: The Dow Chemical CompanyInventors: Giffin D. Jones, Harold E. Doorenbos
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Patent number: 4588828Abstract: 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: GrantFiled: August 23, 1984Date of Patent: May 13, 1986Assignee: E. R. Squibb & Sons, Inc.Inventors: Gregory S. Bisacchi, William H. Koster
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Patent number: 4467118Abstract: 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: GrantFiled: March 3, 1982Date of Patent: August 21, 1984Assignee: Givaudan CorporationInventors: Alan J. Chalk, Steven A. Magennis, Vasile S. Wertheimer, Richard E. Naipawer
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Patent number: 4317905Abstract: 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: GrantFiled: May 21, 1979Date of Patent: March 2, 1982Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
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Patent number: 4311645Abstract: 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: GrantFiled: March 24, 1980Date of Patent: January 19, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Michael Rosenberger
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Patent number: 4263463Abstract: 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: GrantFiled: October 26, 1976Date of Patent: April 21, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeyoshi Kitamura, Norbushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
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Patent number: 4233453Abstract: 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: GrantFiled: June 7, 1979Date of Patent: November 11, 1980Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4232166Abstract: 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: GrantFiled: June 7, 1979Date of Patent: November 4, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner