Halogen Containing Patents (Class 568/649)
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Patent number: 6635787Abstract: A 2,6-dichlorophenol compound of formula (1): wherein R represents a 3,3-dihalo-2-propenyl group or a benzyl group optionally substituted by halogen atom(s), can be produced by making a phenol compound of formula (2): wherein R has the same meaning mentioned above, react with sulfuryl chloride in the presence of a secondary amine in high yield. The obtained 2,6-dichlorophenol compound of formula (1) is useful as intermediate for producing dihalopropene compounds having insecticidal/acaricidal activity.Type: GrantFiled: December 17, 2002Date of Patent: October 21, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Sakaguchi, Sanshiro Matsuo
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Publication number: 20030098443Abstract: The invention relates to a liquid-crystalline medium with positive dielectric anisotropy and high optical anisotropy, characterized in that it contains one or more biphenyl derivatives comprising a terminal alkenyl group, and its use in electrooptical displays and projection systems, in particular reflective displays and displays based on a birefringence effect, such as OCB displays.Type: ApplicationFiled: June 26, 2002Publication date: May 29, 2003Applicant: Merck Patent GmbHInventors: Atsutaka Manabe, Volker Reiffenrath
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Publication number: 20030073847Abstract: The dihalopropene compounds of the general formula (I) have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.Type: ApplicationFiled: March 4, 2002Publication date: April 17, 2003Applicant: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Sanshiro Matsuo, Masaya Suzuki, Taro Hirose, Kazunori Tsushima, Kimitoshi Umeda
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Patent number: 6462242Abstract: Benzyl alcohols, particularly those which bear fluorine substituents or fluoroalkyl substituents on the benzyl ring, can be obtained by formylation of corresponding aryl bromides to form benzaldehydes and reduction of the latter using further formate, wherein the benzaldehydes formed do not have to be isolated.Type: GrantFiled: June 5, 2000Date of Patent: October 8, 2002Assignee: Bayer AktiengesellschaftInventors: Torsten Neugebauer, Albrecht Marhold
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Patent number: 6462240Abstract: 3-Substituted benzotrifluorides are selectively deprotonated and functionalized in the 2-position. The selectivity is achieved by equilibrating the mixture of lithiobenzotrifluorides initially formed in the presence of a primary or secondary amine catalyst.Type: GrantFiled: June 14, 2001Date of Patent: October 8, 2002Assignee: Dow AgroSciences LLCInventors: Michael Glenn Smith, Mark Andrew Pobanz, Gary A. Roth, Michael A. Gonzalez
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Patent number: 6448449Abstract: A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol, which is a useful intermediate in the synthesis of the widely used antibiotic Levofloxacin is provided. A process for the preparation of (R)-1-(2,3-difluoro-6-nitrophenoxy)-2-trimethylsiloxypropane is also described. The process includes the ring opening of (R)-propylene oxide with 2,3-difluoro-6-nitrophenyl trimethylsilyl ether in the presence of an optically active Co(salen) catalyst. The trimethylsilyl group of the reactant is transferred to the product aryloxy alcohol, which serves to protect the secondary alcohol in situ. Upon isolation, the trimethylsilyl group is removed and the resulting regioisomeric mixture purified to yield the desired (R)-1-(2,3-difluoro-6-nitrophenoxy)-propan-2-ol in high purity and yield.Type: GrantFiled: April 20, 2001Date of Patent: September 10, 2002Assignee: Rhodia ChiRex, Inc.Inventor: Jay Francis Larrow
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Patent number: 6355813Abstract: Invented is an improved process for preparing aromatic ring-fused cyclopentane derivatives. Preferred compounds prepared by this invention are indane carboxylates and cyclopentanopyridine derivatives. The most preferred compounds prepared by this invention are (+)(1S, 2R, 3S)-3-[2-(2-hydroxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof and (+)(1S, 2R, 3S)-3-(2-carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid and pharmaceutically acceptable salts thereof. Also invented are novel intermediates useful in preparing these compounds.Type: GrantFiled: June 29, 2000Date of Patent: March 12, 2002Assignee: SmithKline Beecham CorporationInventors: William Morrow Clark, Ivan Lantos, Robert John Mills, Lendon Norwood Pridgen, Ann Marie Tickner
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Patent number: 6309561Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: October 30, 2001Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 6248573Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) wherein R1 and R2 represent a lower alkyl group, etc., or R1 and R2 may form together an alkylene group, etc.; R3, R4 and R5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.Type: GrantFiled: December 10, 1998Date of Patent: June 19, 2001Assignee: Daicel Chemical Industries, Ltd.Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
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Patent number: 6235870Abstract: Process for the preparation of compounds of the formula wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein Ra represents hydrogen or a residue comprising one or more additional groups of the formula, from compounds wherein R2 represents hydrogen or a residue comprising one or more additional groups of the formula by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid; process for the preparation of epoxy compounds starting from the reaction to produce a compound of formula (III) which is converted to a compound of formula (A) that is dehydrohalogenated to form the epoxy rings of a diepoxy compound.Type: GrantFiled: September 29, 1999Date of Patent: May 22, 2001Assignee: Shell Oil CompanyInventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
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Patent number: 6172268Abstract: A method for producing an optically active 1-substituted 2-propanol of the following formula 1, which comprises reacting a hydroxy aromatic compound of the following formula 2 with an optically active propylene oxide in the presence of a catalyst: AOH Formula 2 CH3C*H(OH)CH2OA Formula 1 wherein A is a univalent aromatic group, and C* is an asymmetric carbon atom.Type: GrantFiled: January 28, 2000Date of Patent: January 9, 2001Assignee: Asahi Glass Company, LimitedInventors: Toshihiko Tohma, Tomoyuki Asai
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Patent number: 6156940Abstract: The present invention relates to a process for producing optically active halomethyl phenyl carbinols of the formula (1), comprising reducing halomethyl phenyl ketones of the formula (2) using an asymmetric reducing agent obtained from boranes and optically active .alpha.-phenyl-substituted-.beta.-amino alcohols of the formula (3) or optically active .alpha.-non-substituted-.beta.-amino alcohols of the formula (4).The present invention further relates to a process for producing optically active carbinols, comprising reacting a prochiral ketone with, an asymmetric reducing agent obtained from optically active .beta.-amino alcohols of the formula (5), a metal boron hydride and Lewis acid or lower dialkyl sulfuric acid. All of the formulas (1) to (5) are the same as shown in the specification.Type: GrantFiled: April 8, 1998Date of Patent: December 5, 2000Assignees: Sumika Fine Chemicals Company, Limited, Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Norio Kometani, Azusa Fujiwara, Yukio Yoneyoshi, Gohfu Suzukamo
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Patent number: 6068834Abstract: This invention relates to compositions, compounds and methods for lightening skin, using active compounds having the structure: ##STR1## wherein: (i) each X is, independently, selected from the group consisting of halo, alkyl, substituted alkyl, aryl, OR, OCOR, COR, CONRR COOR, CN, SR, SOR, SO.sub.2 R, SO.sub.3 R and NRR, wherein X is other than hydroxy, amino and thio, if this X is attached ortho to the phenol hydroxy;(ii) m is an integer from 0 to 4;(iii) each R' and each R" is, independently, selected from the group consisting of hydrogen, halo, alkyl, substituted alkyl, aryl, OR, OCOR, OCRROR, COR, CR(OR)OR, CONRR, COOR, CRROR, CN, SR, and NRR; wherein halo, when it appears, is other than geminal to a hydroxy, NH.sub.Type: GrantFiled: February 24, 1995Date of Patent: May 30, 2000Assignee: The Procter & Gamble CompanyInventors: Kalla Lynn Kvalnes, Mitchell Anthony DeLong, Barton James Bradbury, Curtis Bobby Motley, John David Carter
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Patent number: 6030547Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one caternary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: December 24, 1997Date of Patent: February 29, 2000Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 6013841Abstract: The 3- and 4-methylcatechols are converted to the corresponding benzaldehyde by first alkylating the hydroxyl groups to form an alkylated methylcatechol. The methyl group is then converted to a methyl dibromide group using 1,3-dibromo-5,5-dimethylhydantoin in the presence of a non-polar, non-reactive solvent such as carbon tetrachloride and heptane and a radical initiator having a ten hour half-life temperature in the range of 47.degree. to 55.degree. C. The dibromide is then hydrolyzed to form the aldehyde.Type: GrantFiled: July 30, 1998Date of Patent: January 11, 2000Assignee: Dakota Gasification CompanyInventor: Paul D. Pansegrau
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Patent number: 6005063Abstract: Process for the preparation of compound of the formula: ##STR1## wherein R.sub.c represents a residue comprising one or more additional groups of the formula: ##STR2## by heating a compound of the formula (A) ##STR3## at a temperature in the range of from 120 to 220.degree. C. in the presence of hydrogen halide addition salt of tertiary amine;process for the preparation of epoxy compounds starting from the reaction of a polyphenol compound and glycidol; andepoxy resins obtained by this process showing a significantly lower content of intermingled clorine and being substantially free of usual build-up products.Type: GrantFiled: February 6, 1998Date of Patent: December 21, 1999Assignee: Shell Oil CompanyInventors: Johannes Adrianus Van Doorn, Jozef Jacobus Titus Smits, Eric Johannes Vos
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Patent number: 6001954Abstract: Process for the preparation of compounds of the formula ##STR1## wherein Hal represents chlorine, bromine or iodine and preferably chlorine, wherein R.sub.a represents hydrogen or a residue comprising one or more additional groups of the formula, ##STR2## from compounds ##STR3## wherein R.sub.2 represents hydrogen or a residue comprising one or more additional groups of the formula ##STR4## by reaction with gaseous hydrogen halide in the presence of a catalytic amount of an organic acid. Epoxy resins are prepared via the reaction of a compound of formula (A) in the presence of a basic compound.Type: GrantFiled: February 6, 1998Date of Patent: December 14, 1999Assignee: Shell Oil CompanyInventors: Jozef Jacobus Titus Smits, Judith Johanna Berendina Walhof
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Patent number: 5972241Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: November 6, 1997Date of Patent: October 26, 1999Assignee: 3M Innovative Properties CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5936102Abstract: The present invention is drawn to a process for preparing a 2,2,3,3-tetrafluoro-1,4-benzodioxane, by cyclocondensing a o-(2-bromo-tetrafluoroethoxy)-phenol in the presence of an acid binder.Type: GrantFiled: July 23, 1998Date of Patent: August 10, 1999Assignee: Bayer AktiengesellschaftInventors: Vera Yakovlevna Popkova, Albrecht Marhold
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Patent number: 5928562Abstract: A process for controlling the cone tilt angle of a tilted smectic liquid crystal composition comprises the step of combining (a) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound comprising (i) an aliphatic fluorocarbon terminal portion comprising a terminal fluoroalkyl or fluoroether group and an alkylene group having at least two carbon atoms and containing at least one catenary ether oxygen atom, (ii) an aliphatic hydrocarbon terminal portion, and (iii) a central core connecting the terminal portions; and (b) at least one liquid crystal composition comprising at least one smectic or latent smectic liquid crystal compound; with the provisos that at least one of the compositions (a) and (b) comprises at least one chiral liquid crystal compound and that the combining of compositions (a) and (b) provides an optically active, tilted chiral smectic liquid crystal composition.Type: GrantFiled: March 27, 1997Date of Patent: July 27, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: John F. Kistner, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad
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Patent number: 5872137Abstract: The dihalopropene compounds of the general formula ?I! have excellent insecticidal/acaricidal activity, so that they are satisfactorily effective for the control of noxious insects, mites and ticks.Type: GrantFiled: August 26, 1997Date of Patent: February 16, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Masaya Suzuki, Kazunori Tsushima, Kimitoshi Umeda
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Patent number: 5702637Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion containing at least one methylene group and optionally containing at least one catenary ether oxygen atom; (b) a saturated, chiral or achiral, hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.Type: GrantFiled: April 19, 1995Date of Patent: December 30, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 5508461Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-[(2-phenyl-1-methylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.Type: GrantFiled: June 2, 1994Date of Patent: April 16, 1996Assignee: Daicel Chemical Industries, Ltd.Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
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Patent number: 5491261Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.Type: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5466435Abstract: Disclosed are contrast agents of the formula ##STR1## wherein Z is H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, alkoxycarbonyl, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R is C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl; each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy;(CR.sub.1 R.sub.2).sub.p --(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H or lower-alkyl, optionally substituted with halo;x is 1-4;n is 1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkyl;in an aqueous, pharmaceutically acceptable carrier comprising a cellulose derivative.Type: GrantFiled: April 4, 1994Date of Patent: November 14, 1995Assignee: Sterling Winthrop Inc.Inventors: Edward J. Baker, Edward R Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef, John L. Toner, Robert W. Lee
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Patent number: 5463083Abstract: 2,5-Diaryl tetrahydrofurans, 2,5-diaryl tetrahydrothiophenes, 1,3-diaryl cyclopentanes are disclosed that reduce the chemotaxis and respiratory burst leading to the formation of damaging oxygen radicals of polymorphonuclear leukocytes during an inflammatory or immune response. The compounds exhibit this biological activity by acting as PAF receptor antagonists, by inhibiting the enzyme 5-lipoxygenase, or by exhibiting dual activity, i,e., by acting as both a PAF receptor antagonist and inhibitor of 5-lipoxygenase. Also disclosed is a method to treat disorders mediated by PAF and/or leukotrienes that includes administering an effective amount of one or more of the above-identified compounds or a pharmaceutically acceptable salt thereof, optionally in a pharmaceutically acceptable carrier, to a patient in need of such therapy.Type: GrantFiled: January 6, 1994Date of Patent: October 31, 1995Assignee: Cytomed, Inc.Inventors: Tesfaye Biftu, Xiong Cai, Sajjet Hussion, Gurmit Grewal, T. Y. Shen
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Patent number: 5463088Abstract: A process for preparing perfluoroalkoxy(alkylthio)benzenes from perfluorochloroalkoxy(alkylthio)-benzenes by reaction with hydrogen fluoride in the gas phase and in the presence of a catalyst.Type: GrantFiled: April 26, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold, Karl-Rudolf Gassen
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Patent number: 5463138Abstract: Difluoromethoxyarenes and difluoromethylthioarenes of the general formula (I),Ar--Q--CHF.sub.2 (I)in whichAr represents optionally substituted aryl, andQ represents oxygen or sulphur,(which can be used as intermediates for preparing biologically active products) are obtained in very good yields and in a high degree of purity by reacting hydroxyarenes or mercaptoarenes of the general formulaAr--Q--H (II)with chlorodifluoromethane (ClCHF.sub.2) in the presence of an aqueous alkali metal hydroxide or alkaline earth metal hydroxide at temperatures of between 20.degree. C. and 120.degree. C.Type: GrantFiled: May 18, 1994Date of Patent: October 31, 1995Assignee: Bayer AktiengesellschaftInventor: Klaus-Helmut Muller
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Patent number: 5440051Abstract: Aryl ethers are chlorinated in the .alpha.-position by a process in which they are metered into a reaction vessel at the same time as chlorine, the reaction being carried out at temperatures in the range from 60.degree. to 150.degree. C.Type: GrantFiled: March 22, 1994Date of Patent: August 8, 1995Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Klaus Jelich
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Patent number: 5437812Abstract: Fluorine-containing liquid crystal compounds are provided. The compounds comprise a fluorocarbon terminal portion having at least one catenary ether oxygen and a hydrocarbon terminal portion, the terminal portion being connected by a central core, the compounds having smectic mesophases or having latent smectic mesophases.Type: GrantFiled: April 16, 1993Date of Patent: August 1, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventors: Eugene P. Janulis, Gilbert C. Johnson, Patricia M. Savu, Terence D. Spawn, Marc D. Radcliffe
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Patent number: 5420359Abstract: Normally liquid chlorofluoroether compositions consisting or consisting essentially of one or a selected mixture of perhalogenated chlorofluoroether compounds are provided by direct fluorination of the corresponding chloroether or chlorofluoroether precursors. The compositions are useful, for example, as heat transfer agents, blood substitutes, and solvents.Type: GrantFiled: October 7, 1993Date of Patent: May 30, 1995Assignees: Minnesota Mining and Manufacturing Company, HemaGen/PFCInventors: George G. I. Moore, Richard M. Flynn, Robert J. Kaufman, Thomas J. Richard
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5362835Abstract: A process for the production of a material having an increased molecular weight relative to the diepoxide starting material the material being either a hydroxy-terminated or an epoxy-terminated material comprisinga) reacting a diepoxide with a dihydroxy compound, in the presence, as catalyst, of a triflate salt of a metal of Group IIA, IIB, IIIA, IIIB, or VIIIA of the Periodic Table of Elements (according to the IUPAC 1970 convention);b) de-activating the triflate salt catalyst; andc) optionally advancing the material produced in step b), with an aromatic diol or phenol.Type: GrantFiled: December 9, 1991Date of Patent: November 8, 1994Assignee: Ciba-Geigy CorporationInventors: William M. Rolfe, Michael R. Thoseby, Bryan Dobinson
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Patent number: 5348727Abstract: A compound of the formula: ##STR1## wherein Z.dbd.H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, alkoxycarbonyl, cyano, wherein thealkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.dbd.C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl; each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p -(CR.sub.3 .dbd.CR.sub.4).sub.m Q, or (CR.sub.1 R.sub.2).sub.p --C.tbd.C-Q;R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H, or lower-alkyl, optionally substituted with halo;x is 1-4;n is [1-5]1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, these compounds are useful as X-ray contrast agents or aryl-lower alkyl.Type: GrantFiled: March 11, 1993Date of Patent: September 20, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef
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Patent number: 5310538Abstract: R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, ##STR2## or halo-lower-alkyl, each of which may be optionally substituted with halo, fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy, (CR.sub.1 R.sub.2).sub.p --(CR.sub.3 =CR.sub.4).sub.m Q ,or (CR.sub.1 R.sub.2).sub.p --C.tbd.C--Q;R.sub.1, R.sub.2 and R.sub.3 and R.sub.4 are independently H, or lower-alkyl, optionally substituted with halo;x is 1-4;n is 1-4;m is 1-15;p is 1-20; andQ is H, lower-alkyl, lower-alkenyl, lower-alkynyl, lower-alkylene, aryl, or aryl-lower alkylThese compounds are combined in a polymer for use as an X-ray contrast agent.Type: GrantFiled: March 11, 1993Date of Patent: May 10, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Carl R. Illig, Thomas J. Caulfield, Brent D. Douty, Kurt A. Josef
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Patent number: 5290958Abstract: A phase transfer catalytic process for the preparation of epoxide and halohydrin intermediates, which can be subsequently and directly reacted with isopropylamine to produce beta-adrenergic antagonists such as atenolol, propanolol and their derivatives. In the process disclosed in the present invention, quaternary ammonium salts of high alkyl groups or tertiary ammonium salts of lower alkyl groups are used as catalyst in the phase transfer catalytic oxygenated-alkylation reaction between an aromatic alcohol such as p-hydroxyphenyl acetamide (for the production of atenolol) or .alpha.-naphthol (for the production of propranolol) and epichlorohydrin to yield epoxide and halohydrin intermediates. The quaternary ammonium salts of high alkyl groups are represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are C.sub.1 to C.sub.20 alkyl groups and at least one of the R.sub.1, R.sub.2, R.sub.3, or R.sub.4 is a C.sub.9 to C.sub.20 alkyl group, and X is a halide group.Type: GrantFiled: August 18, 1993Date of Patent: March 1, 1994Assignee: Industrial Technology Research InstituteInventors: Shyue-Ming Jang, Tian-Shy Shieh
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Patent number: 5248447Abstract: 2,3-difluorohydroquinone compounds of the formula I ##STR1## in which R.sup.1 and R.sup.2, in each case independently of one another, are alkyl having 1 to 15 C atoms or alkenyl having 3 to 15 C atoms which are unsubstituted, monosubstituted by cyano or at least monosubstituted by fluorine or chlorine, it also being possible for one CH.sub.2 group in these radicals to be replaced by --O--, --CO--, --CO--O--, --O--CO-- or --O--CO--O--,A.sup.1, A.sup.2 and A.sup.3, in each case independently of one another, are(a) trans-1,4-cyclohexylene, in which, in addition, one or two non-adjacent CH.sub.Type: GrantFiled: April 21, 1992Date of Patent: September 28, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
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Patent number: 5242996Abstract: A modified epoxy resin or compound of the formula: ##STR1## wherein A is the backbone reside of a glycidyl ether epoxy resin with removal of the glycidyloxy groups; R.sup.1 and R.sup.2 are independently a hydrogen atom or C.sub.1 -C.sub.12 alkyl; R.sup.3 is a glycidyl group; and n is an integer of greater than 1. A method for producing the modified epoxy resin is also disclosed.Type: GrantFiled: May 22, 1991Date of Patent: September 7, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki, Ryuzo Mizuguchi
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Patent number: 5196610Abstract: A compound of formula: ##STR1## wherein W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Z represents a fluoroalkyl group of up to two carbon atoms; Y represents a substituted aryl group where such substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; and either X' is hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and aryloxy, or X and X' together represent a second bond between the adjacent carbon atoms. The compounds have useful insecticidal properties.Type: GrantFiled: July 31, 1986Date of Patent: March 23, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Alan J. Whittle, Robin A. E. Carr
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Patent number: 5189225Abstract: A monoalkylether of dihydric phenol compound is produced by bringing a feed gas comprising a mixture gas of a dihydric phenol compound with a monohydric alcohol compound into contact with an active catalyst component comprising at least one member selected from phosphorus compounds, and mixtures and reaction products of phosphorus compounds with boron compounds and carried on an inert solid carrier consisting of, for example, .alpha.-alumina, .gamma.-alumina, activated carbon or titania grains, and preferably having a pore volume of 0.1 ml/g or more and a specific surface area of 1 m.sup.2 /g or more, at a temperature of 200.degree. C. to 400.degree. C., and collecting the resultant reaction product from the reaction mixture.Type: GrantFiled: September 28, 1990Date of Patent: February 23, 1993Assignee: Ube Industries, Ltd.Inventors: Shinichi Furusaki, Masaoki Matsuda, Muneki Saito, Yasushi Shiomi, Yasuo Nakamura, Michio Tobita
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Patent number: 5117010Abstract: The present invention relates to the preparation of di-secondary alcohols comprising the reaction of an alcohol and a diglycidyl ether of a dihydric phenol in the presence of a catalyst of the formula (IV):MX (IV)wherein M is a metal from Groups IB to VIIIB or a metal or metalloid from Groups IIA to VA of the Periodic Chart of Elements or an ammonium ion and X is an anion selected from the group consisting of BF.sub.4.sup.-, PF.sub.6.sup.-, AsF.sub.6.sup.-, SbF.sub.6.sup.-, AlF.sub.4.sup.-, TiF.sub.6.sup.2-, SiF.sub.6.sup.2-, and ZrF.sub.6.sup.2- to produce the di-secondary alcohol, which can then be subjected to glycidylation to produce a glycidyl ether, orthe reaction of an alcohol, glycol or polyol and epichlorohydrin in the presence of the foregoing catalyst, followed by ring closure employing an alkali to produce a mono- or polyglycidyl ether. The monoglycidyl ether can be further reacted with a dihydric phenol to produce a di-secondary alcohol which is then glycidylized to produce a glycidyl ether.Type: GrantFiled: August 15, 1991Date of Patent: May 26, 1992Assignee: Ciba-Geigy CorporationInventor: Chi-Wen F. Cheng
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Patent number: 5105021Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.Type: GrantFiled: April 12, 1990Date of Patent: April 14, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
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Patent number: 5082978Abstract: Mono-, di- and triphenols are selectively monomethylated by reaction with para-dimethoxybenzene in the presence of a catalytically effective amount of an acid catalyst.Type: GrantFiled: May 9, 1991Date of Patent: January 21, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Christian Allandrieu
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Patent number: 5068451Abstract: A method of producing 3-phenoxy propanal derivatives of 3-phenoxy propanal derivatives of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are --H, --CH.sub.3 or a halogen radical, which comprises oxidizing allyl phenoxy ether derivatives of the formula ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above, in an alcohol as a solvent in the presence of a palladium salt, an oxidant, optionally an alkali metal salt of an onganic acid, and/or an acid at a temperature of 5.degree. C. -100.degree. C.Type: GrantFiled: May 4, 1990Date of Patent: November 26, 1991Assignee: National Science CouncilInventors: Ivan J. B. Lin, S. J. Jong
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Patent number: 5023380Abstract: Compounds have a structure represented by Formula I:CF.sub.2 =CF-X-R-(X-CF=CF.sub.2).sub.mwherein R represents an unsubstituted or inertly substituted hydrocarbyl group; each X is independently selected from the group consisting of groups having at least one non-carbon atom between R and --CF=CF.sub.2 ; and m is an integer of from 1 to about 3. Polymers formed from such compounds are also prepared. The compounds are preferably prepared by a method by a process comprising the steps of:(a) forming a salt having anion corresponding to a compound of Formula II:HX--R--(XH).sub.m ;wherein X, R and m are as defined for Formula I;(b) reacting the salt with a 1,2-dihalo-1,1,2, 2-tetrafluoroethane wherein the halo groups are iodine, bromine, chlorine or mixtures thereof, at least one halo group being bromine or iodine, to form a compound of Formula III:Z-CF.sub.2 CF.sub.2 -X-R-(X-CF.sub.2 CF.sub.2 - Z).sub.Type: GrantFiled: June 9, 1989Date of Patent: June 11, 1991Assignee: The Dow Chemical CompanyInventors: David A. Babb, Bobby R. Ezzell, Katherine S. Clement
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Patent number: 4997989Abstract: Novel tert-butylalkynols of the formula (I) ##STR1## where Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, aryl, aryloxy or benzyl and m is an integer from 1 to 3, and the individual groups Y may be identical or different when m>1, and a process for their preparation are described.Type: GrantFiled: January 4, 1989Date of Patent: March 5, 1991Assignee: BASF AktiengesellschaftInventors: Hubert Smuda, Wolfgang Rohr
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Patent number: 4973736Abstract: Diethers of m- or p-hydroxyphenol, as well as the monoethers, are prepared by reacting m- or p-tert.-butoxyphenol of the formula II ##STR1## with a halogen compound in the presence of a hydroxide, carbonate and/or bicarbonate of an alkali metal or alkaline earth metal and an organic solvent which is inert under the reaction conditions, at from 20.degree. C. to 150.degree. C., and, if desired, reacting the resulting diether with a dilute aqueous inorganic acid at from 30.degree. to 100.degree. C. to give the monoether.The end products which can be prepared by the process according to the invention are useful starting materials for the preparation of dyes, drugs and crop protection agents.Type: GrantFiled: August 15, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Werner Hoffmann, Heinz-Guenter Oeser, Wolfgang Rohr, Juergen Varwig
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Patent number: 4973764Abstract: There are disclosed novel compositions of matter comprising monoalkylphenols prepared by selectively alkylating the olefin component of a thermally cracked sulfur-containing petroleum distillate derived from residua. The monoalkylphenols have certain ortho to para ratios and may be used to prepare a number of useful derivatives such as ethoxylated and propoxylated surfactants, sulfoalkylated products, sulfurized antioxidants, overbased phenates, dithiophosphate derivatives, formaldehyde reaction products and similar methylene bridged products which are useful demulsifiers.Type: GrantFiled: November 13, 1989Date of Patent: November 27, 1990Assignee: Exxon Research and Engineering CompanyInventors: Alexis A. Oswald, Ram N. Bhatia, Edmund J. Mozeleski, Darrell W. Brownawell, Thomas L. Ashcraft
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Patent number: 4968836Abstract: The invention relates to a process for the preparation of cyclopropanecarbaldehydes of formula ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl, which comprises (a) reacting a tetrahydrofuran of formula ##STR2## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 -cycloalkyl that is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, nitro or cyano, with a halogenating agent to form a 1,2,4-trihalobutyl ether of formula ##STR3## in which X is halogen and R.sub.2 is unsubstituted or halo-substituted C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.6 cycloalkyl that is unsubstituted or substituted by halogen C.sub.1 -C.sub.4 alkyl or by C.sub.1 -C.sub.4 alkoxy, or phenyl or benzyl each of which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.Type: GrantFiled: January 30, 1990Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Hans-Ruedi Kanel, John G. Dingwall
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Patent number: 4960884Abstract: Pesticidal mono-, di-, and tri-2-fluoroethyl ethers of the formula R.sup.1 R.sup.2.sub.m Ar(OCH.sub.2 CH.sub.2 F).sub.n, compositions thereof and their insecticidal, acaricidal and nematicidal uses are described and claimed.Type: GrantFiled: August 28, 1989Date of Patent: October 2, 1990Assignee: FMC CorporationInventors: David M. Roush, Donald A. Shaw, Michael L. Jones, Jun H. Chang