Halogen Containing Patents (Class 568/495)
  • Patent number: 8865947
    Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).
    Type: Grant
    Filed: December 6, 2012
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, Sheng Peng
  • Publication number: 20140309452
    Abstract: Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ?-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).
    Type: Application
    Filed: April 9, 2014
    Publication date: October 16, 2014
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Miyoshi Yamashita, Takehiko Fukumoto, Takeshi Kinsho
  • Publication number: 20120288445
    Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.
    Type: Application
    Filed: April 13, 2012
    Publication date: November 15, 2012
    Applicant: The University of Manchester
    Inventor: Christian PRENANT
  • Publication number: 20120207858
    Abstract: Provided are biocide compositions and bleach compositions comprising organic acyl polyoxychlorine and related methods. The reduction of the acyl polyoxychlorine group releases a reactive intermediate that undergoes a series of cascading reduction steps, resulting in termination products Generally Recognized As Safe.
    Type: Application
    Filed: January 11, 2012
    Publication date: August 16, 2012
    Applicant: TRUOX, INC.
    Inventor: Roy W. Martin
  • Publication number: 20100068139
    Abstract: The invention relates to conjugates of formula (V) or (VI): wherein X is —CO—NH—, —NH—, —O—, —NHCONH—, or —NHCSNH—; their use as radiopharmaceuticals, processes for their preparation, and synthetic intermediates used in such processes.
    Type: Application
    Filed: March 12, 2004
    Publication date: March 18, 2010
    Inventors: Alan Cuthbertson, Magne Solbakken, Joseph Maduabuchi Arukwe, Hege Karlsen, Matthias Eberhard Glaser
  • Publication number: 20090302262
    Abstract: Claimed are fluorous telomeric compounds of the formula: RF-A-[CH2]cCR2R3-Z where RF is a perfluoroalkyl radical of 1 to 20 carbon atoms, A is a group of the formulae R1 is CF3 OR4, Cl, Br or I, R2 and R3 are H, alkyl or aryl R4 is perfluoromethyl, perfluoropropyl or perfluoropropyloxypropyl X and Y are H, Cl or F Z is —OH, —OCOCH?CH2 or —OCOCCH3?CH2 a is from 0 to 10, b is from 1 to 30 and c is from 1 to 30. These compounds are copolymerized with further monomers. The copolymers thus obtained are useful for water-, oil- and soil-repellent finishing of fibrous substrates.
    Type: Application
    Filed: December 22, 2006
    Publication date: December 10, 2009
    Applicant: CLARIANT INTERNATIONAL LTD
    Inventors: Hans Götz, Wolfgang Knaup, Anton Probst, Christian Ahollinger
  • Publication number: 20080274046
    Abstract: Compounds of the formula (I) are disclosed: 18F—(CHR)n(CH2)mCHO ??(I) in which n and m are independently 0 and 1 with at least one of n and m being 1, and R (if present) is a hydrogen atom or a methyl group, subject to the proviso that if n is 1 and R is methyl then m is 0. Synthesis of the compounds is described together with their use in radiolabelling reactions, e.g. for the radiolabelling of peptides to facilitate detection by Positron Emission Tomography (PET) imaging. The preferred compound is [18F]Fluoroacetaldehyde.
    Type: Application
    Filed: February 20, 2008
    Publication date: November 6, 2008
    Inventor: Christian Prenant
  • Patent number: 5583208
    Abstract: A ganglioside GM3 derivative containing fluorine atoms in a ceramide portion thereof, represented by the formula: ##STR1## in which m is an integer of at least 2, n is an integer of 0 to 7 provided that m is larger than n, and R represents an alkyl group or a fluoroalkyl group is disclosed.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: December 10, 1996
    Assignee: Daikin Industries, Ltd.
    Inventors: Takao Iida, Yutaka Ohira
  • Patent number: 5563235
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: October 8, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5550298
    Abstract: The catalytic process obtains a methyl tertiary butyl ether by feeding methanol over a solid catalyst section in a rectifying column having vertical layers in which a catalyst material is enclosed. At least one of the enclosing walls is impermeable to the catalyst material while being permeable to the methanol. A reactant comprising a mixture of saturated and unsaturated 4 carbon-chain hydrocarbons is fed into the solid catalyst section with methanol to produce a methyl tertiary butyl ether.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: August 27, 1996
    Assignee: Sulzer Brothers Limited
    Inventors: Ronald Shelden, Jean-Paul Stringaro
  • Patent number: 5512652
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: February 14, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5498802
    Abstract: A process for preparing 6-chloro-2-hexanone which comprises the steps of (a) dehydrating cyclohexanol in the presence of a suitable catalyst and at a suitable temperature and for a sufficient period of time to form cyclohexene; (b) rearranging said cyclohexene at a higher temperature than in step (a) in the presence of a suitable catalyst and for a sufficient period of time to form 1-methylcyclopentene; (c) hydrating said 1-methylcyclopentene at a temperature lower than step (b) and in the presence of a resin catalyst for a sufficient period of time to form 1-methylcyclopentanol; (d) reacting said 1-methylcylcopentanol with a suitable amount of an alkali metal hypochlorite in the presence of a carboxylic acid to form 1-methylcyclopentyl hypochlorite; and (e) heating said 1-methylcyclopentyl hypochlorite for a sufficient period of time to form 6-chloro-2-hexanone.
    Type: Grant
    Filed: February 28, 1995
    Date of Patent: March 12, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Diane E. Allen, Ramakrishnan Chidambaram
  • Patent number: 5414139
    Abstract: A process for manufacturing monochloroacetaldehyde trimer and chloral together by effectively utilizing a raw material acetaldehyde or para-aldehyde. The process comprises a step of chlorinating acetaldehyde or para-aldehyde to produce a chlorinated liquid of which the major component is monochloroacetaldehyde, a step comprising adding chloral to said chlorinated liquid and distilling the mixture to obtain a fraction of which the major components are monochloroacetaldehyde and chloral, a step of trimerizing monochloroacetaldehyde by reacting said fraction in the presence of a trimerization catalyst and separating the MCA trimer by filtration, and a step of chlorinating other fractions from said distillation step and the filtrate from said trimerization step to produce chloral. According to this process all raw material aldehydes and components derived from aldehydes which have not been consumed for the production of MCA trimer can be easily converted into chloral which is useful as an industrial chemical.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: May 9, 1995
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Takashi Wakasugi, Tadashi Miyakawa, Fukuichi Suzuki
  • Patent number: 5414140
    Abstract: Fluorinated aldehydes are made by reacting a fluorinated acyl chloride with a silicon hydride in the presence of palladium. Also disclosed are fluorinated ether aldehydes and their polymers, a process for making fluorinated aldehydes polymers using titanium or aluminum alkoxide catalysts, and a process for endcapping fluorinated polymers using perfluoroallyl fluorosulfate or fluorine.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: May 9, 1995
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: William B. Farnham
  • Patent number: 5405870
    Abstract: Compounds of formula (Ic): ##STR1## having valuable platelet-aggregation inhibitory activities useful for the prophylaxis and treatment of such diseases as thrombosis and pharmaceutical compositions containing said compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: April 11, 1995
    Assignee: Sankyo Company, Limited
    Inventors: Kazuo Koyama, Shigeo Amemiya, Koichi Kojima, Shinsaku Kobayashi
  • Patent number: 5386063
    Abstract: (all-E)-2,7,-dimethylocta-2,4,6-triene-1,8-dial-.sup.13 C.sub.4 is synthesized from commercially available and relatively inexpensive starting compounds, and the key starting compound is triethyl phosphonoacetate-.sup.13 C.sub.2. The .sup.13 C labeled dial is useful as an intermediate in synthesizing .sup.13 C labeled carotenoids.
    Type: Grant
    Filed: June 16, 1993
    Date of Patent: January 31, 1995
    Assignees: The Catholic University of America, The United States of America as represented by the Secretary of Agriculture
    Inventors: Frederick Khachik, Gary R. Beecher, Betty W. Li
  • Patent number: 5304661
    Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: April 19, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5292911
    Abstract: Novel monocyclic terpene derivative of the formula: ##STR1## wherein R is hydrogen atom, trimethylsilyl group or 1-ethoxyethyl group, and novel intermediates therefor. The terpene derivative (I) is a useful intermediate for preparing Sarcophytol A having an anti-carcinogenesis promoter activity and an antitumor activity.
    Type: Grant
    Filed: March 10, 1992
    Date of Patent: March 8, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5278338
    Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.
    Type: Grant
    Filed: November 4, 1992
    Date of Patent: January 11, 1994
    Assignee: Ethyl Corporation
    Inventor: Rhonda L. Trace
  • Patent number: 5248832
    Abstract: A process for the manufacture of trifluoroacetaldehyde, or a hydrate or hemiacetal thereof, which comprises reduction of an ester of trifluoroacetic acid with a borohydride reducing agent in a hydroxylic solvent to form trifluoroacetaldehyde hydrate or hemiacetal; whereafter if the free aldehyde is required, water or alcohol is removed from the hydrate or hemiacetal respectively using conventional procedures.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: September 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: Stanley A. Lee
  • Patent number: 5166373
    Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.
    Type: Grant
    Filed: December 30, 1991
    Date of Patent: November 24, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 5077439
    Abstract: Compounds of formula I ##STR1## wherein R is C.sub.1 -C.sub.4 alkyl or benzyl, are prepared by reacting a butanal of formula II ##STR2## wherein X and Y are each independently of the other chloro, bromo or iodo, in an inert solvent, with a compound of formula IIIR-S-Me (III)wherein R is as defined above and Me is an alkali metal cation, and converting the resultant compound of formula IV ##STR3## wherein X and R are as defined above, in an inert solvent and in the presence of a base, into a compound of formula I.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: December 31, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5068390
    Abstract: 1,1,1-trifluoro-2-propene compounds which are useful in the preparation of insecticidal, acaricidal and nematicidal arylpyrrole compounds are described. A method for the preparation of 1,1,1-trifluoro-2-propene compounds is presented.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: November 26, 1991
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Kenneth A. M. Kremer
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 5015780
    Abstract: Dihalobutyraldehydes of formula I ##STR1## wherein X and Y are each independently of the other Cl or Br, are obtainable at high rates of conversion and with excellent selectivities by catalytic dehalogenation with hydrogen by carrying out the reaction with appropriate .alpha.,.alpha.-dihalobutyraldehydes in an organic aprotic solvent. The dihalobutyraldehydes are intermediates for the synthesis of herbicidal acyl cyclohexanediones.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: May 14, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Steiner, Hans Tobler
  • Patent number: 5008462
    Abstract: A method for preparing a monochloroacetaldehyde trimer in a high yield is here disclosed which comprises the steps of dissolving, in an organic solvent, a solution containing monochloroacetaldehyde as the main component, and then trimerizing monochloroacetaldehyde in the presence of sulfuric acid. The thus prepared monochloroacetaldehyde trimer can be heated at 120.degree. C. under atmospheric pressure to obtain pure monochloroacetaldehyde.
    Type: Grant
    Filed: November 8, 1989
    Date of Patent: April 16, 1991
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Makoto Ishizuka, Takashi Wakasugi
  • Patent number: 4983776
    Abstract: The invention relates to the synthesis of functional fluoro derivatives and more particularly that of perfluorinated aldehydes of the type R.sub.F -CHO where R.sub.F denotes a linear or branched perfluoroalkyl radical.A perfluoroalkyl iodide R.sub.F I is reacted over the zinc-copper metal couple, in the presence of a radical initiator, with an amide RCONR.sub.1 R.sub.2, R denoting a hydrogen atom or a methyl or ethyl radical, and each of R.sub.1 and R.sub.2 denoting a C.sub.1 -C.sub.4 alkyl radical.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: January 8, 1991
    Assignee: Societe Atochem
    Inventors: Sylvie Benefice-Malouet, Hubert Blancou, Auguste Commeyras
  • Patent number: 4983775
    Abstract: Novel physiologically active substances Ks-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: January 8, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
  • Patent number: 4876370
    Abstract: 1,3,5-Nonatriene derivatives of formula: ##STR1## in which R.sub.1 and R.sub.2, together with the carbon atom to which they are linked, form a carbonyl group, or each of R.sub.1 and R.sub.2 denotes alkoxy or R.sub.1 and R.sub.2 together form an alkylenedioxy radical, which may be made by reaction of a butadiene derivative of formula: ##STR2## in which R is alkyl or phenyl, with a butanal ketoacetal of 10 formula: ##STR3## followed by reaction of the product with a halomethyltriphenylphosphonium halide, are useful intermediates e.g. for the production of phytol.
    Type: Grant
    Filed: September 19, 1988
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Sante
    Inventors: Lucette Duhamel, Pierre Duhamel
  • Patent number: 4806280
    Abstract: Compounds of formula ##STR1## in which n denotes an integer from 1 to 10 and X and Y, which are identical or different, each denote an electron-attracting group, are made by reacting a halogenating agent with a compound of formula ##STR2## in which R, X and Y are as hereinbefore defined, anionized by a base.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: February 21, 1989
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4733012
    Abstract: A process for the preparation of 4-chloromethylbenzaldehyde, 4-bromomethylbenzaldehyde and 4-iodomethylbenzaldehyde is disclosed. The desired 4-halomethylbenzaldehyde is prepared by reacting 4-hydroxymethylbenzaldehyde with the appropriate gaseous hydrogen halide and/or with the appropriate aqueous hydrohalic acid. The 4-halomethylbenzaldehydes produced by the disclosed process are useful as raw materials for pharmaceuticals and serve as starting materials for the preparation of conductive organic compounds.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: March 22, 1988
    Assignee: Wacker-Chemie GmbH
    Inventors: Hermann Braunling, Dieter Kippe
  • Patent number: 4691062
    Abstract: 4-chloro-butanals of the formula ##STR1## where R is hydrogen or a straight or branched chain alkyl group of 1 to 4 carbon atoms are produced by reacting the corresponding 1,1-dimethoxy-4-hydroxybutane at a temperature between -20.degree. and +80.degree. C. in the presence of triphenylphosphine with carbon tetrachloride and hydrolyzing the 1,1-dimethoxy-4-chloro-butane obtained in acid medium.
    Type: Grant
    Filed: October 22, 1986
    Date of Patent: September 1, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Juan Andrade, Gunter Prescher, Klaus Kohler
  • Patent number: 4628122
    Abstract: Chloral is removed from aqueous hydrochloric acid containing chloral in a stripping zone at superatmospheric pressure and concentrated in a rectifying zone at superatmospheric pressure. The method is particularly suited for the treatment of feed compositions originating from the oxychlorination of ethylene.
    Type: Grant
    Filed: November 1, 1985
    Date of Patent: December 9, 1986
    Assignee: PPG Industries, Inc.
    Inventors: Frederick J. Kuntz, Henry W. Schussler
  • Patent number: 4577028
    Abstract: Novel 5-haloalkyl-pyridines suitable for producing pesticidal compositions, particularly insecticides, and corresponding to the formula ##STR1## wherein R is a C.sub.2 -C.sub.10 -alkyl group which is uniformly or nonuniformly substituted by 1 to 21 halogen atoms, and X is halogen;processes for producing them, as well as to the novel starting products and intermediates used or intermediately produced or formed in the production processes.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: March 18, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Eginhard Steiner
  • Patent number: 4469896
    Abstract: Chloropyridines of the formula ##STR1## wherein either R is chlorine and R' is methyl or trifluoromethyl, or R is methyl, trichloromethyl or trifluoromethyl and R' is chlorine, or R and R' are methyl, can be obtained by a novel, simple process by the addition of trichloroacetaldehyde to methacrylonitrile or .alpha.-trifluoromethacrylonitrile, 2,2-dichloropropionaldehyde, pentachloropropionaldehyde or 2,2-dichloro-3,3,3-trifluoropropionaldehyde to acrylonitrile, or 2,2-dichloropropionaldehyde to methacrylonitrile, in the presence of a catalyst, in particular copper powder or copper(I) chloride, and cyclizing the open-chain intermediate obtained.The chloropyridines of the formula (I) are known per se and are suitable for the production of different compounds, in particular of insecticides and herbicides.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: September 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Eginhard Steiner, Pierre Martin
  • Patent number: 4375563
    Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.
    Type: Grant
    Filed: March 30, 1982
    Date of Patent: March 1, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4315764
    Abstract: 1-Allyl-triazole derivatives of the formula ##STR1## in which R represents hydrogen, alkyl or optionally substituted aralkyl,R.sup.1 represents optionally substituted alkyl, cycloalkyl or optionally substituted aryl,R.sup.2 represents alkyl andR.sup.3 represents alkyl, cycloalkyl, optionally substituted cycloalkenyl, alkenyl or optionally substituted aryl, orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkenyl or cycloalkylX represent the group ##STR2## or the keto group, R.sup.4 represents hydrogen, alkyl, optionally substituted aralkyl, acyl or optionally substituted carbamoyl andR.sup.5 represents hydrogen, alkyl or optionally substituted aralkyl,or acid addition salts or metal salt complexes thereof are characterized by fungicidal and plant growth regulatory activity.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: February 16, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4311563
    Abstract: The invention relates to a process for the isolation of chloroacetaldehyde which is obtained as a by-product during the synthesis of acetaldehyde from ethylene and air in an aqueous palladium/cupric chloride solution by the 2-stage process. The mixture to be worked-up to chloroacetaldehyde is taken from the acetaldehyde distillation column and transferred to a distillation and extraction system, where it is fractionally condensed. The chloroacetaldehyde-containing fraction is extracted with water and the aqueous extract is subjected to purification distillation.
    Type: Grant
    Filed: March 31, 1981
    Date of Patent: January 19, 1982
    Assignee: Wacker-Chemie GmbH
    Inventors: Werner Opavsky, Josef Reisner, Alois Maier
  • Patent number: 4305876
    Abstract: A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: December 15, 1981
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Richard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
  • Patent number: 4288635
    Abstract: A method for the preparation of (E)-4-bromo-2-methylbut-2-en-1-al comprises brominating 3,4-epoxy-3-methyl-1-butene with cupric bromide in the presence of lithium carbonate.
    Type: Grant
    Filed: May 23, 1980
    Date of Patent: September 8, 1981
    Assignee: J. T. Baker Chemical Co.
    Inventor: Gary M. Gray
  • Patent number: 4283536
    Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII).
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: August 11, 1981
    Assignee: University of Vermont
    Inventor: Martin E. Kuehne
  • Patent number: 4267330
    Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: May 12, 1981
    Assignee: Omnium Chimique Societe Anonyme
    Inventor: Martin E. Kuehne
  • Patent number: 4263269
    Abstract: Method of removing organic contaminants from aqueous hydrochloric acid comprising countercurrently contacting the aqueous acid containing the contaminants and steam at superatmospheric pressures, and recovering said aqueous acid substantially free from organic contaminants. The invention is particularly adapted for the removal of chloral from aqueous hydrochloric acid.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: April 21, 1981
    Assignee: The Dow Chemical Company
    Inventors: John C. Little, Charles R. Youngson, Jr.
  • Patent number: 4220774
    Abstract: The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.
    Type: Grant
    Filed: October 26, 1978
    Date of Patent: September 2, 1980
    Assignee: Omnium Chimique
    Inventor: Martin E. Kuehne
  • Patent number: 4215044
    Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.
    Type: Grant
    Filed: April 23, 1979
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William J. Middleton