Processes Patents (Class 549/513)
  • Patent number: 5254694
    Abstract: An optically active epoxycyclohexane derivative represented by the general formula: ##STR1## wherein R represents a 4-oxycarbonyl-1-hydroxy-3-methyl-3(Z)-buten-1-yl or 4-hydroxycarbonyl-3-methyl-1(E),3(Z)-butadien-1-yl group; and R.sup.1 and R.sup.2 each represent a lower alkoxy group or together form a 1,3-dioxolane ring together with the carbon atom to which they are bonded,and an enantiometer thereof.An optically active epoxycyclohexanone derivative represented by the general formula: ##STR2## wherein R.sup.3 represents a hydrogen atom or a lower alkyl, allyl, aralkyl or aryl group,and an enantiomer thereof.Further, the process for preparing these compounds, is also disclosed.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: October 19, 1993
    Assignee: Sagami Chemical Research Center
    Inventors: Kunikazu Sakai, Kyoko Takahashi
  • Patent number: 5252759
    Abstract: Organic sulfonate derivatives of optically active epoxy alcohols such as (R)- or (S)- glycidol are conveniently prepared from aqueous solutions of the epoxy alcohols.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: October 12, 1993
    Assignee: Arco Chemical Technology, L.P.
    Inventor: Wilfred P. Shum
  • Patent number: 5216181
    Abstract: Liquid telechelic polymers are made from dienes and are produced via anionic polymerization. While having low molecular weight, for example less than 15,000, the telechelic polymers are generally gel-free, have high amounts of trans-1,4 structure, low vinyl unsaturation and low bulk viscosities. The liquid telechelic polymers are made utilizing a trimetallic initiator comprised of (1) an organopolylithium compound and (2) a complex of a trialiphatic substituted aluminum compound or derivative thereof and a barium salt of an organic alcohol.
    Type: Grant
    Filed: August 26, 1991
    Date of Patent: June 1, 1993
    Assignee: GenCorp Inc.
    Inventors: I. Glen Hargis, Hubert J. Fabris, John A. Wilson, Russell A. Livigni
  • Patent number: 5198557
    Abstract: A process for the kinetic resolution of cis or trans enantiomeric mixtures of the compounds of formula ##STR1## wherein R.sub.3 and X have the meanings reported in the specification and the asterisks mark the asymmetric carbon atoms, is described.The compounds of formula III-A are intermediates useful in the preparation of compounds active on the cardiovascular system.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: March 30, 1993
    Assignee: Zambon Group S.p.A.
    Inventors: Claudio Giordano, Roberto Casagrande
  • Patent number: 5191094
    Abstract: A process is described for the preparation of mono (2-ammonium-2-hydroxymethyl-1,3-propanediol) (2R,cis)-1,2-epoxypropyl-phosphonate with improved characteristics of stability, of processing for the preparation of pharmaceutical forms and of stability of the pharmaceutical forms that contain it.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: March 2, 1993
    Assignee: Zambon Group S.p.A.
    Inventors: Dario Tentorio, Graziano Castaldi, Claudio Girodano, Franco Pozzi
  • Patent number: 5155233
    Abstract: Compositions are provided containing epoxysilanes and diphenylamine in an amount at least sufficient to inhibit degradation. Methods for producing such compositions are also provided.
    Type: Grant
    Filed: December 24, 1991
    Date of Patent: October 13, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Shiu-Chin Su, Frederick D. Osterholtz
  • Patent number: 5145974
    Abstract: A continuous process for producing nitratoalkyl-substituted cyclic ethers which consists of (a) cocurrently mixing a stream of N.sub.2 O.sub.5 and a stream of a hydroxyalkyl-substituted cyclic ether each dissolved in an inert organic solvent, followed by (b) rapidly separating the nitric acid and nitratoalkyl coproducts before they can react together to rupture the ether ring. Step (b) is conveniently performed by quenching the product stream within approximately 15 seconds of its formation, in a basic aqueous solution into which the nitric acid is transferred from the organic phase and is neutralized. Examples of products which may be prepared by this process are nitratoalkyl-substituted oxiranes and oxetanes.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: September 8, 1992
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Norman C. Paul, Ross W. Millar, Peter Golding
  • Patent number: 5145880
    Abstract: A reactive composition, rapidly polymerizable already starting from room temperature, comprises a liquid mixture consituted by at least one organic polyisocyanate, at least one compound containing one or more epoxy groups and a liquid catalyst constituted by, or containing, at least one compound falling within the scope of the general formula ##STR1## in which the substituents have the meanings reported in the following; the compound which contains the epoxy group(s) can be constituted by the catalyst only.Such a composition can turn into a polymeric material having softening temperatures as high as 300.degree. C. and even higher.
    Type: Grant
    Filed: April 12, 1991
    Date of Patent: September 8, 1992
    Assignee: Enichem S.p.A.
    Inventors: Fabrizio Parodi, Carlo Belgiovine
  • Patent number: 5136062
    Abstract: A method of preparing a nitrate ester of an epoxy alcohol, which consists of reacting an epoxy alcohol with N.sub.2 O.sub.5 in an inert solvent at a temperature of -10.degree. C. to -40.degree. C., followed by quenching the reaction mixture in aqueous solution. Quenching separates the nitric acid and nitrate ester coproducts into aqueous and organic phases respectively to prevent subsequent reaction between the two. Reaction between the nitric acid coproduct and epoxy alcohol reagent to produce acyclic contaminants is supressed by adding the epoxy alcohol to excess N.sub.2 O.sub.5, thereby rapidly converting available alcohol to nitrate ester.
    Type: Grant
    Filed: March 22, 1991
    Date of Patent: August 4, 1992
    Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: Ross W. Millar, Norman C. Paul, Peter Golding
  • Patent number: 5110959
    Abstract: This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: May 5, 1992
    Assignee: Smithkline Beckman Corp.
    Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
  • Patent number: 5107002
    Abstract: The method for the separating methyl formate from lower alkylene oxide such as propylene oxide which comprises contacting the impure alkylene oxide with basic ion exchange resin and separating alkylene oxide reduced in methyl formate content.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: April 21, 1992
    Assignee: Arco Chemical Technology, L.P.
    Inventor: T. Thomas Shih
  • Patent number: 5084582
    Abstract: The invention relates to a method of oxidizing epoxyalcohols, in a medium containing an organic solvent and water, by means of a solid oxidizing compound, in the presence of a catalyst based on a ruthenium salt. The proportion of water relative to that of organic solvent is sufficiently small for at least the major part of the oxidizing compound to remain in the solid state in the reaction medium, which is heterogeneous.
    Type: Grant
    Filed: January 18, 1991
    Date of Patent: January 28, 1992
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Jean-Pierre Genet, Dominique Pons, Sylvain Juge
  • Patent number: 5057624
    Abstract: New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: October 15, 1991
    Assignee: ALFA Wassermann S.p.A.
    Inventors: Vincenzo Cannata, Giancarlo Tamerlani, Graziano Zagnoni
  • Patent number: 5015744
    Abstract: Process for the preparation of a taxol intermediate comprising contacting an alcohol with an oxazinone having the formula: ##STR1## wherein R.sub.1 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; R.sub.2 is hydrogen, ethoxyethyl, 2,2,2-trichloroethoxymethyl or other hydroxyl protecting group; and R.sub.3 is aryl, substituted aryl, alkyl, alkenyl, or alkynyl; the contacting of said alcohol and oxazinone being carried out in the presence of a sufficient amount of an activating agent under effective conditions to cause the oxazinone to react with the alcohol to form a .beta.-amido ester which is suitable for use as an intermediate in the synthesis of taxol.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: May 14, 1991
    Assignee: Florida State University
    Inventor: Robert A. Holton
  • Patent number: 4987236
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom, R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: January 22, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4931584
    Abstract: The invention relates to novel monoesters and diesters of 9,10-endoethano-9,10-dihydroanthracene-11,11-dicarboxylic acid.These novel monoesters and diesters correspond to the following structural chemical formula (II): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and can represent H, an alkali metal or alkaline earth metal atom, a linear or branched alkyl group having from 1 to 6 carbon atoms, an alicyclic group having from 3 to 6 carbon atoms, an alkenyl group having from 2 to 6 carbon atoms, defined in their cis or trans variety, or an alkynyl group having from 2 to 6 carbon atoms, the said groups optionally being substituted by one or more functional groups such as ether, epoxide, halogeno, cyano, ester, aldehyde, ketone, aryl etc., where R.sup.1 and R.sup.2 cannot be H or ethyl simultaneously. These addition products constitute valuable intermediates for the preparation of methylidenemalonates in high yields and with a high purity.
    Type: Grant
    Filed: March 1, 1988
    Date of Patent: June 5, 1990
    Assignee: Laboratoires UPSA
    Inventors: Nicole Bru-Magniez, Christian De Cock, Jacques Poupaert, Jean-Luc De Keyser, Pierre Dumont
  • Patent number: 4902812
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: February 20, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4886893
    Abstract: Process for the production of modified triglycerides which contain epoxide groups, secondary hydroxyl groups and ether groups. The invention particularly relates to the production of reaction products of epoxidized triglycerides, for example epoxidized soy oil, with polyfunctional alcohols, for example glycols. The products so prepared are valuable starting materials, particularly for the production of alkyd resins.
    Type: Grant
    Filed: April 9, 1987
    Date of Patent: December 12, 1989
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Alfred Meffert, Hermann Kluth
  • Patent number: 4868208
    Abstract: Novel semi-synthetic antifungal compounds which may be produced from 10-[(3-chloro-4-methoxyphenyl)methyl]-6- methyl-3-(2-methylpropyl)-16-[1-(3-phenyloxiranyl)ethyl]-1,4-dioxa- 8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone isolated from the fermentation of a cyanobacterium (Nostoc sp.) are described.
    Type: Grant
    Filed: July 15, 1988
    Date of Patent: September 19, 1989
    Assignee: Merck & Co., Inc.
    Inventors: David F. Sesin, Jerrold M. Liesch
  • Patent number: 4864041
    Abstract: A novel process for the homogenous oxidation of organic substrates is disclosed. This process uses a transition metal-substituted polyoxometalate catalyst, which in the presence of an oxygen donor, catalyses the carbon-hydrogen bond (e.g., alkane) hydroxylation reaction and/or epoxidation reaction of the organic substrate.
    Type: Grant
    Filed: February 4, 1987
    Date of Patent: September 5, 1989
    Assignee: Emory University
    Inventor: Craig L. Hill
  • Patent number: 4857645
    Abstract: A process for introducing thiocarboxylic ester at ortho-position of phenols or phenylamines which comprises reacting a phenyl compound having group or optionally substituted amino or cyclic amino group, of which at least one ortho-position is vacant, with C.sub.1 -C.sub.5 alkyl thiocyanate, C.sub.7 -C.sub.13 aralkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and hydrolyzing the resultant product under acidic conditions is provided, and said process is useful in the synthesis of medicinals, pesticides and dyes.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: August 15, 1989
    Assignee: Shionogi & Co., Ltd.
    Inventors: Adachi Makoto, Hiromu Matsumura, Tsutomu Sugasawa
  • Patent number: 4751312
    Abstract: A new process for the controlled synthesis of the two diasteromeric forms of triazolyl-O,N-acetals of the formula ##STR1## in which R represents optionally substituted phenyl, optionally substituted phenoxy, optionally substituted alkoxy, optionally substituted alkoxy, optionally substituted alkylthio, alkylcarbonyl, nitro or halogen andn represents an integer from 0 to 5, with the proviso that R can represent identical or different radicals, if n represents an integer from 2 to 5.New trans-substituted oxiranes and their use as intermediates for the synthesis of compounds of the formula (I).
    Type: Grant
    Filed: July 19, 1985
    Date of Patent: June 14, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Johann Gasteiger, Karlheinz Kaufmann, Rudolf Mengel
  • Patent number: 4642361
    Abstract: A novel process for the manufacture of quinone derivatives which are suitable as intermediates for the manufacture of (2RS,4'R,8'R)-tocopherol is described.
    Type: Grant
    Filed: September 18, 1985
    Date of Patent: February 10, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: August Ruttimann
  • Patent number: 4485251
    Abstract: Disclosed is a process for the preparation of a bis(perfluoroalkyl-alkylthio)alkanoic acid of the formula ##STR1## wherein each R.sub.f is independently perfluoroalkyl of 3 to 18 carbon atoms or perfluoroalkoxyperfluoroalkyl of 3 to 18 carbon atoms, or mixtures thereof;each A is independently alkylene of up to 6 carbon atoms or said alkylene interrupted by --O--; N(H)-- or --N(lower alkyl)--;R is hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.1 is hydrogen or lower alkyl; andR.sub.2 is hydrogen, lower alkyl, aryl or aryl substituted lower alkyl;by reacting a perfluoroalkyl-alkyl mercaptan of the formulaR.sub.f --A--SH (II)with a lactone of the formula ##STR2## in the presence of a catalytic amount of a Lewis acid to form a perfluoroalkyl-alkylthio lactone of the formula ##STR3## and reacting said perfluoroalkyl-alkylthio lactone with additional perfluoroalkyl-alkylmercaptan of the formulaR.sub.
    Type: Grant
    Filed: December 23, 1982
    Date of Patent: November 27, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert A. Falk
  • Patent number: 4473371
    Abstract: Perfluoroalkyl esters of the formula ##STR1## wherein R.sub.1 denotes C.sub.2 -C.sub.20, preferably C.sub.4 -C.sub.14 -perfluoroalkyl or perfluoroalkoxyperfluoroalkyl, R.sub.2 denotes C.sub.3 -C.sub.4 -alkylene, R.sub.3 denotes C.sub.2 -C.sub.5 -.omega.-epoxyalkyl or C.sub.1 -C.sub.18, preferably C.sub.1 -C.sub.5 -alkyl, which can be substituted by 1 or 2 halogen atoms, preferably chlorine atoms, by hydroxyl groups, by a group of the formula ##STR2## by 1 to 3 groups of the formula --OCO--CX.dbd.CY--COO--(CH.sub.2).sub.m --R.sub.1 or by, in each case, one lower alkoxy, epoxy, lower acyloxy, lower alkoxycarbonyl, lower acylamino, lower hydroxylalkylthio, lower trialkylamino, lower trialkylammonium, phenyl, phenoxy or furanyl group or R.sub.3, in the case where b=0, also denotes C.sub.3 -C.sub.18 -alkenyl, which can be subsituted by hydroxyl groups or a phenyl group; C.sub.3 -C.sub.8 -alkynyl, which can be substituted by hydroxyl groups; cyclohexyl; phenyl, which can be substituted by 1-3 C.sub.1 -C.sub.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erich Schinzel, Emmerich Paszthory
  • Patent number: 4401673
    Abstract: Novel 3-(buta-1',3'-dienyl)-cyclopropane-1-carboxylic acid compounds of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually a halogen and A is selected from the group consisting of (A) benzyl optionally substituted (B) ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen and --CH.sub.3 and R.sub.2 is selected from the group consisting of aryl and --CH.sub.2 --C.tbd.CH, (C) ##STR3## wherein R.sub.3 is an aliphatic of 2 to 6 carbon atoms containing at least one carbon-carbon unsaturation, (D) ##STR4## wherein R'.sub.1 and R'.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and cyano and R.sub.3 has the above definition, (E) ##STR5## wherein R.sub.4 is selected from the group consisting of hydrogen, --CN, --CH.sub.3, --CONH.sub.2, --CSNH.sub.2 and --C.tbd.CH, R.sub.5 is selected from the group consisting of chlorine and --CH.sub.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: August 30, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Pierre Girault
  • Patent number: 4400559
    Abstract: Ethylene glycol is prepared by a process in which ethylene oxide is extracted from an aqueous solution with near-critical or super-critical carbon dioxide. Thereafter an ethylene oxide--carbon dioxide--water mixture is contacted with a catalyst to form ethylene carbonate, which is then hydrolyzed to ethylene glycol in the presence of the same catalyst. The ethylene glycol is separated as product and the carbon dioxide and the catalyst are recycled.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: August 23, 1983
    Assignee: The Halcon SD Group, Inc.
    Inventor: Vijay S. Bhise
  • Patent number: 4353922
    Abstract: Compounds of the formula ##STR1## wherein the serrated lines denote both endo and exo forms; R.sub.1 and R.sub.2 are the same or different and are C.sub.1 to C.sub.6 alkyl, C.sub.5 or C.sub.6 cycloalkyl, C.sub.5 or C.sub.6 cycloalkenyl, phenyl optionally substituted with C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy or halo, or 5 or 6 membered heterocyclic aryl wherein the heteroatom is oxygen, nitrogen or sulfur; R.sub.3 is a C.sub.1 to C.sub.6 alkyl radical; R.sub.4 and X are optionally present, and when present R.sub.4 is a C.sub.1 to C.sub.6 alkyl radical or hydrogen and X is an inorganic or organic anion which forms a pharmaceutically acceptable salt. Methods for preparing these compounds are also disclosed. The compounds of the present invention are useful as anticholinergic agents.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: October 12, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jurg R. Pfister
  • Patent number: 4352757
    Abstract: Esters of leukotriene A are conveniently prepared by reacting 9-oxo-5,6-trans-epoxynon-7(E)-enoates with 11-triphenylphosphoranylidene undec-6(Z),9(Z)-diene. Esters of leukotriene-A are useful intermediates in the synthesis of naturally occurring leukotrienes, which have been shown to be potent broncho-constricting substances. Novel intermediates to the esters of leukotriene A, 9-oxo-5,6-transepoxynon-7(E)-enoates and 7-oxo-5,6-transepoxyheptanoates, are disclosed.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: October 5, 1982
    Assignee: SmithKline Beckman Corporation
    Inventors: John G. Gleason, Charles M. Kinzig, Deborah L. Bryan