Carbonyl Bonded Directly To Benzene Ring (i.e., Acetophenones) Patents (Class 568/335)
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Patent number: 5458806Abstract: Fluoromethyl ketones of the formula I ##STR1## are suitable as components of liquid-crystalline media wherein R is H, a substituted or unsubstituted alkyl or alkenyl radical having 1 to 15 carbon atoms,A.sup.1 and A.sup.2 are each, independently of one another, a(a) trans-1,4-cyclohexylene radicals and derivatives thereof in which, in addition, one or more non-adjacent CH.sub.2 groups is optionally replaced by --O-- and/or --S--,(b) 1,4-phenylene radicals and derivatives thereof in which, in addition, one or two CH groups is optionally replaced by N, or(c) radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,wherein radicals (a) and (b) are optionally substituted by one or two fluorine atoms,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.Type: GrantFiled: May 4, 1994Date of Patent: October 17, 1995Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ekkehard Bartmann, Herbert Plach
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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: 5371296Abstract: A 4,4-Dimethyl-1-phenylpentane-1,3-dione derivatives represented by the following formula (1): ##STR1## wherein all symbols are defined in the disclosure, is disclosed. An ultraviolet ray absorbent and a cosmetic comprising the derivative are also disclosed. The derivative of the present invention have excellent ultraviolet ray absorbing performance and superior light stability, and the ultraviolet ray absorbent and cosmetic comprising the derivative have excellent effect to prevent sunburn.Type: GrantFiled: March 17, 1992Date of Patent: December 6, 1994Assignee: Kao CorporationInventors: Masakazu Yamaguchi, Akira Kawamata, Genji Imokawa, Kouichi Niinaka
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Patent number: 5352761Abstract: This invention relates to naphthalene dicarboxylic acids or naphthalene dicarboxylic esters substituted with aroyl groups. More particularly, this invention relates to the following compounds: dialkyl 1-benzoyl-2,6-naphthalene dicarboxylate, 7-C1-C.sub.8 -alkoxycarbonyl-1-C1-Cs-alkoxy-l-aryl(1,3-H.sub.2 naphtho {1,2-c} furan-3-ones), and dialkyl 1-(2-naphthoyl)-2,6-naphthalene dicarboxylate. The compounds are useful in any polymer composition where dicarboxylic acids or dicarboxylic esters are used especially in poly(ethylene 2,6-naphthalene dicarboxylate) compositions where reduced fluorescence is desired.Type: GrantFiled: December 3, 1993Date of Patent: October 4, 1994Assignee: Eastman Chemical CompanyInventors: Allan S. Jones, Charles E. Sumner, Jr.
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Patent number: 5312930Abstract: This invention relates to optical elements capable of second harmonic generation and novel compositions for use in such optical elements comprising polar molecules placed in noncentrosymmetric configuration wherein such optical element has an electron donor moiety linked through a conjugated bonding moiety to an electron acceptor moiety which consists of a selected fluorinated sulfone, fluorinated ketone, fluorinated vinyl sulfone or fluorinated alkyl vinyl sulfone.Type: GrantFiled: December 31, 1992Date of Patent: May 17, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Lap T. Cheng, Andrew E. Feiring, Wilson Tam
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Patent number: 5281726Abstract: There are provided 4-Hydroxy-2'-nitrobutyrophenone and tetrahydro-2-(o-nitrophenyl)-2-furanol and mixtures thereof, important intermediates in the preparation of the crop-selective herbicidal agent 1-{[o-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidiny l)urea. Also provided is a method for the preparation of 4-halo-2'-nitrobutyrophenone, useful as an intermediate in the preparation of 1-{[o-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidiny l)urea.Type: GrantFiled: December 29, 1992Date of Patent: January 25, 1994Assignee: American Cyanamid CompanyInventor: David A. Cortes
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Patent number: 5240568Abstract: A process for separating phenol obtained by the decomposition of cumene hydroperoxide from high boiling impurities, includes the following steps:a) feeding phenol rectification bottoms comprising phenol, acetophenone, cumylphenol, alpha-methylstyrene dimers and high boiler residues to a first phenol freeing distillation column A;b) feeding concentrated bottoms with substantially reduced phenol content from column A to a second residue concentration distillation column B;c) withdrawing a stream rich in compounds boiling between phenol and residue, particularly cumylphenol, from said column B from a point below the feed and returning at least a portion of said stream to said column A at a point above the feed;d) recovering overheads from column A comprising at least 95 weight percent phenol; ande) recovering acetophenone-rich overheads from column B comprising at least 70 weight percent acetophenone.Type: GrantFiled: August 29, 1991Date of Patent: August 31, 1993Assignee: Allied-Signal Inc.Inventors: Chong H. Chan, Lamberto Crescentini, Everett H. Hinton, Jr., Laszlo J. Balint, deceased
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Patent number: 5230874Abstract: The present invention relates to novel sunscreen agents which have the ability to absorb both UVA and UVB wavelength radiation. The sunscreen agents comprise a specific type of UVA-absorbing chromophore covalently bonded to a specific type of UVB-absorbing chromophore. The chromophore moieties are covalently bonded together such that the electron systems of these moieties are not directly coupled.The present invention further relates to sunscreen compositions containing the hereinbefore described type of sunscreen agents. Furthermore, the present invention relates to methods for protecting the skin of humans or lower animals from the effects of UVA and UVB wavelength radiation. This method comprises topically applying to the skin an effective coating of a sunscreen composition of the present invention.Type: GrantFiled: August 5, 1992Date of Patent: July 27, 1993Assignee: The Procter & Gamble CompanyInventors: Anthony D. Sabatelli, Josephine A. Spirnak
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Patent number: 5229107Abstract: The present invention relates to novel sunscreen agents which have the ability to absorb both UVA and UVB wavelength radiation. The sunscreen agents comprise a specific type of UVA-absorbing chromophore covalently bonded to a specific type of UVB-absorbing chromophore. The chromophore moieties are covalently bonded together such that the electron systems of these moieties are not directly coupled.The present invention further relates to sunscreen compositions containing the hereinbefore described type of sunscreen agents. Furthermore, the present invention relates to methods for protecting the skin of humans or lower animals from the effects of UVA and UVB wavelength radiation. This method comprises topically applying to the skin an effective coating of a sunscreen composition of the present invention.Type: GrantFiled: August 5, 1992Date of Patent: July 20, 1993Assignee: The Procter & Gamble CompanyInventors: Anthony D. Sabatelli, Josephine A. Spirnak
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Patent number: 5214131Abstract: A polyethylene glycol derivative of the formula ##STR1## wherein R represents a lower alkyl and n represents an optional positive integer which renders the average molecular weight of the polyethylene glycol moiety about 1,000 to 12,000, a peptide modified by said polyethylene glycol derivative and a method for production thereof. The polyethylene glycol derivative (I) is capable of modifying the guanidino groups in peptides. The peptides modified by the polyethylene glycol derivative (I) are extremely stable, are considerably delayed in biological clearance (i.e. the durability is extended) and exhibit their physiological activities effectively over the long period.Type: GrantFiled: November 26, 1991Date of Patent: May 25, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Akihiko Sano, Hiroo Maeda, Yoshiyuki Kai, Keiichi Ono
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Patent number: 5166375Abstract: The antioxidant is safe for human health, has excellent antioxidation activity and is suitably utilized for preventing oxidation of unsaturated fatty acids, esters of unsaturated fatty acids and various kinds of products comprising these acids and esters. The oxidation resistant polyunsaturated oil is made by giving strong antioxidation activity to polyunsaturated oils, such as polyunsaturated fatty acids, esters of polyunsaturated fatty acids and polyunsaturated fats.The antioxidant comprises musizin and tocopherol as the effective components. The oxidation resistant polyunsaturated oil and fat of the invention is characterized in that an antioxidant comprising musizin as the effective component is added to a polyunsaturated oil.Type: GrantFiled: August 8, 1991Date of Patent: November 24, 1992Assignees: Nippon Oil and Fats Company, Limited, Nagaoka Perfumery Company, LimitedInventors: Hiromu Kameoka, Kiyoshi Furukawa, Hiroshi Kihara, Atsuyoshi Nishina
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Patent number: 5164112Abstract: .alpha.-hydroxyketone derivatives represented by the general formula (I) which are novel optically active compounds; liquid crystal compositions, such as chiral smectic or chiral nematic compositions, containing the derivatives; and liquid crystal devices using the compositions. ##STR1## wherein A and B are independently a radical represented by the general formula (II): ##STR2## wherein R.sup.2 is an aliphatic hydrocarbon having 1 to 16 carbon atoms, which may contain --O-- and may be substituted by a cyano group and/or a halogen atom, ##STR3## are independently a single bond, ##STR4## etc., X and Y are independently a single bond, or --CH.sub.2 CH.sub.2 --, etc., or an aliphatic hydrocarbon having 1 to 16 carbon atoms; R.sup.1 is an alkyl group, a phenyl group, or a cyclohexyl group; n is 0 or 1; and the asterisk (*) indicates an asymmetric carbon atom.Type: GrantFiled: July 17, 1990Date of Patent: November 17, 1992Assignee: Chisso CorporationInventors: Shinichi Saito, Hiromichi Inoue, Kouji Ohno
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Patent number: 5142092Abstract: Fluorine-containing acetophenones, optionally halogenated on the CH.sub.3 group, of the formula ##STR1## in which X represents hydrogen, chlorine or bromine and the radicals R.sub.1 to R.sub.5 have the following meaning,a) R.sub.1 and R.sub.4 denote fluorine, R.sub.2 and R.sub.5 denote chlorine and R.sub.3 denotes CF.sub.3, orb) R.sub.1, R.sub.3 and R.sub.4 denote fluorine and R.sub.2 and R.sub.5 denote hydrogen, orc) R.sub.1, R.sub.4 and R.sub.5 denote hydrogen, R.sub.2 denotes chlorine and R.sub.3 denotes CF.sub.3, ord) R.sub.1, R.sub.4 and R.sub.5 denote hydrogen, R.sub.2 denotes chlorine and R.sub.3 denotes OCF.sub.3, ore) R.sub.1, R.sub.4 and R.sub.5 denote hydrogen and R.sub.2 and R.sub.3 denote CF.sub.3, orf) R.sub.1 denotes chlorine, R.sub.2 denotes CF.sub.3 and R.sub.3, R.sub.4 and R.sub.5 denote hydrogen, org) R.sub.1 denotes chlorine, R.sub.2, R.sub.3 and R.sub.4 denote hydrogen and R.sub.5 denotes CF.sub.3, orh) R.sub.1 denotes chlorine, R.sub.2, R.sub.4 and R.sub.5 denote hydrogen and R.sub.Type: GrantFiled: July 30, 1991Date of Patent: August 25, 1992Assignee: Bayer AktiengesellschaftInventors: Ernst Kysela, Bernd Baasner, Klaus Schaller
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Patent number: 5120876Abstract: This invention relates to optical elements capable of second harmonic generation and novel compositions for use in such optical elements comprising polar molecules placed in noncentrosymmetric configuration wherein such optical element has an electron donor moiety linked through a conjugated bonding moiety to an electron acceptor moiety which consists of a selected fluorinated sulfone, fluorinated ketone, fluorinated vinyl sulfone or fluorinated alkyl vinyl sulfone.Type: GrantFiled: February 28, 1990Date of Patent: June 9, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Lap T. Cheng, Andrew E. Feiring, Wilson Tam
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Patent number: 5091586Abstract: A novel dialkyl peroxide is represented by a general formula (I): ##STR1## This peroxide is produced by particular methods and used as a photolysis type or pyrolysis type radical forming agent.Type: GrantFiled: July 11, 1990Date of Patent: February 25, 1992Assignee: Nippon Oil and Fats Company, LimitedInventors: Yoshiki Higuchi, Shuji Suyama
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Patent number: 5068449Abstract: Fluorinated benzoyl compounds of the formula: ##STR1## wherein Q is a lower alkyl group, a halogen atom, --CH.sub.2 CO.sub.2 R.sup.1 wherein R.sup.1 is a lower alkyl group, or ##STR2## wherein each of R.sup.2 and R.sup.3 is a lower alkyl group.Type: GrantFiled: February 7, 1990Date of Patent: November 26, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki
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Patent number: 5011931Abstract: A process to prepare compounds of formula I ##STR1## in which n=0, 1 or 2 comprising the cyclisation of compounds of formula II ##STR2## in which n=0, 1 or 2. The cyclisation may be effected in the presence of an organic or inorganic base or thermally at a temperature in the range 40.degree.-160.degree. C.Compounds of formula II and certain analogues thereof are disclosed as cardiovascular agents.Type: GrantFiled: June 23, 1989Date of Patent: April 30, 1991Assignee: The Boots Company PLCInventors: Lachlan MacLean, David L. Roberts, Kenneth Barron, Kenneth J. Nichol, Albert E. Harrison
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Patent number: 4956123Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).Type: GrantFiled: September 14, 1988Date of Patent: September 11, 1990Assignee: Nippon Oils & Fats Company, Ltd.Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
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Patent number: 4929741Abstract: Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula--C(R.sup.14)(R.sup.15)OR.sup.16' (f'):exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.Type: GrantFiled: March 17, 1988Date of Patent: May 29, 1990Assignee: Hoffman-La Roche Inc.Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
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Patent number: 4894483Abstract: Vinylglyoxal derivatives of the general formula I ##STR1## where R is straight-chain or branched alkyl or alkenyl, cycloalkyl or unsubstituted or substituted phenyl, are prepared by a process in which bicyclo[2.2.1]hept-5-enecarbaldehyde of the formula V ##STR2## is either (a) subjected to autocondensation with formation of a compound of the formula VII ##STR3## or (b) reacted with a compound of the general formula IIR-CH.dbd.O (II)where R has the above meanings, with formation of a mixture of the compounds of the general formulae VIII (a) and (b) ##STR4## where R is as defined above, in the presence of a catalyst, and the compound of the formula VII or the compounds of the formulae VIII (a) and (b) is or are oxidized to the corresponding dicarbonyl compounds, after which gas-phase pyrolysis is carried out at from 500.degree. to 700.degree. C. and under reduced pressure, in particular less than 10.sup.-1 mbar, and, if desired, the resulting compound of the general formula I is further purified.Type: GrantFiled: October 28, 1987Date of Patent: January 16, 1990Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Hans-Dieter Martin, Roland Kramme, Ralf T. Weimann
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Patent number: 4870109Abstract: A series of 1,3-propanediones having a perfluoroalkyl group or a perfluorocycloalkyl group on one carbonyl, and a 3,5-disubstituted phenyl group on the other, are useful when administered to animals for the control of ectoparasites.Type: GrantFiled: November 20, 1987Date of Patent: September 26, 1989Assignee: Eli Lilly and CompanyInventors: Rudolph J. Boisvenue, Gary D. Crouse
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Patent number: 4855460Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.Type: GrantFiled: July 11, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Marc Tordeux, Claude Wakselman, Catherine Francese
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Patent number: 4839323Abstract: Insoluble complex oxidation catalysts comprising chromium salts bound on an insoluble polymer supports having pendant pyridine groups, that are useful in oxidation reactions such as Tetralin.RTM. to .alpha.-tetralone, ethylbenzene to acetophenone, and 2-methyl-5-ethylpyridine to 2-methyl-5-acetylpyridine. Also disclosed are processes for accomplishing such oxidations utilizing such catalysts.Type: GrantFiled: November 2, 1987Date of Patent: June 13, 1989Assignee: Reilly Tar & Chemical CorporationInventors: Gerald L. Goe, Thomas D. Bailey, James R. Beadle
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Patent number: 4836896Abstract: Meta- and para-diisopropylbenzenes cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be readily removed from p-diispropylbenzene by azeotropic distillation using acetophenone. The acetophenone - m-diisopropylbenzene azeotrope can be separated by solvent extraction with propylene glycol to remove the acetophenone and the propylene glycol - acetophenone mixture is readily separated from each other by rectification.Type: GrantFiled: January 9, 1989Date of Patent: June 6, 1989Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 4804760Abstract: A process for the preparation of a compound of the formula ##STR1## in which Y is a nitrile group, an ester group COOR.sup.1 or an acid amide CONR.sup.2 R.sup.3,R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sup.3 may also be phenyl, andX.sup.2, X.sup.3, X.sup.4 and X.sup.5 each independently is hydrogen, halogen, nitro, cyano, alkyl having 1-3 carbon atoms, alkoxy having 1-3 carbon atoms, alkylmercapto having 1-3 carbon atoms, alkyl-sulphonyl having 1-3 carbon atoms, or a phenylsulphonyl group which is optionally substituted in the aryl radical,comprising reacting an aminoacrylate of the formulain whichX.sup.1 is halogen, a nitro group, an alkoxy, alkoxy, alkylmercapto or alkylsulphonyl group having 1-3 carbon atoms in each case, or an arylsulphonyl group,W is hydrogen or a --CH.sub.2 CH.sub.2 Z radical,Z is a nitrile group, an ester group COOR.sup.4 or an acid amide group CONR.sup.5 R.sup.6, andR.sup.4, R.sup.5 and R.sup.6 each independently is hydrogen or C.Type: GrantFiled: April 28, 1987Date of Patent: February 14, 1989Assignee: Bayer AktiengesellschaftInventors: Michael Schriewer, Klaus Grohe
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Patent number: 4782156Abstract: Compounds of the structure ##STR1## wherein R is alkyl with 1-3 carbon atoms, 2-fluoroethyl, phenyl or cyclopropyl, X is halogen, and X.sup.1 and X.sup.2 each independently is hydrogen or halogen. The compounds are useful as intermediates for quinoline antibacterial compounds.Type: GrantFiled: March 24, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventor: Klaus Grohe
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Patent number: 4772714Abstract: Disclosed is a process for the preparation of alpha-aryl and alpha-heteroaryl ketones useful as intermediates in the synthesis of various pharmaceutical and agricultural chemicals, which process operates according to the following reaction scheme: ##STR1##Type: GrantFiled: July 7, 1986Date of Patent: September 20, 1988Assignee: Agency of Industrial Science & TechnologyInventors: Masato Tanaka, Toshiyasu Sakakura
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Patent number: 4739098Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where n is 0-5 and A is H, lower alkyl, or --COOH or ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or a pharmaceutically acceptable salt.Type: GrantFiled: September 22, 1986Date of Patent: April 19, 1988Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 4720591Abstract: Chloro-olefins which contain a group of the formula ##STR1## where Y is chlorine or hydrogen, which are prepared by a process in which a trichloromethyl compound which contains a group of the general formula ##STR2## where X is hydrogen or an organic radical, is reduced with a chromium(II) salt in an aqueous medium.Type: GrantFiled: December 12, 1986Date of Patent: January 19, 1988Assignee: BASF AktiengesellschaftInventors: Eberhard Steckhan, Reinhard Wolf, Hermann Puetter
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Patent number: 4709107Abstract: A method for preparing nitrones from mixtures of arylhydroxylamines and alkylhydroxylamines containing zinc oxide solids is provided which does not require filtration of the mixture prior to reaction. This is accomplished by introducing a dilute acid solution to the mixture so as to solubilize the zinc oxide powder. The hydroxylamines within solution may be reacted with an aldehyde to produce a nitrone where the dilute acid dissolves the zinc oxide.Type: GrantFiled: October 11, 1985Date of Patent: November 24, 1987Assignee: General Electric CompanyInventors: Paul R. West, Gary C. Davis
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Patent number: 4676604Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen or straight-chain alkyl; R.sup.2 is --CN, --R, --COR, --COOR or when R.sup.2 is positioned on an aromatic ring R.sup.2 also can be --OR, --OOCR or --F; R is alkyl; A is a group with 1 to 4 six-membered rings, these rings being linked directly with one another and with ring B in each case via a single covalent bond or being linked at one or two positions also via --COO--, --OOC-- or --CH.sub.2 CH.sub.Type: GrantFiled: March 5, 1984Date of Patent: June 30, 1987Assignee: Hoffmann-La Roche Inc.Inventor: Martin Petrzilka
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Patent number: 4623736Abstract: In preparing arylalkanoic acids, e.g. ibuprofen or naproxen, via the conversion of the selected .alpha.-haloketal derivative of a 1-haloethyl aryl ketone to the haloalkyl ester of the arylalkanoic acid using a zinc salt catalyst the improvement comprising reacting a ring-substituted 6-membered ring ketal of the selected 1-haloethyl C.sub.6 -C.sub.12 -aryl ketone with a soluble zinc carboxylate salt to form the corresponding 3-haloalkyl arylalkanoic acid ester. The ester is converted to the alkali metal salt of the acid with base in an aqueous/water insoluble organic liquid mixture and the crude salt is converted to the corresponding acid in an aqueous/water insoluble solvent mixture for the acid, the organic solution of the acid is washed with a pH 7.0 to 8.Type: GrantFiled: July 9, 1982Date of Patent: November 18, 1986Assignee: The Upjohn CompanyInventors: Jerry A. Walker, Sanjay I. Amin
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Patent number: 4623749Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide with a substituted or unsubstituted prenyl ester having the structure: ##STR2## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: August 17, 1984Date of Patent: November 18, 1986Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4616027Abstract: Compounds of the general formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from one to three substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and n is zero or an integer from 1 to 5; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing them.Type: GrantFiled: July 25, 1983Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4612322Abstract: A compound of the formula: ##STR1## (wherein Az is imidazolyl or triazolyl;R is C.sub.1 -C.sub.5 alkyl or phenyl optionally substituted by 1 to 3 members selected from halogen, C.sub.1 -C.sub.5 alkyl, and C.sub.1 -C.sub.5 alkoxy;X.sup.1 and X.sup.2 each is hydrogen, halogen, C.sub.1 -C.sub.5 alkyl, or C.sub.1 -C.sub.5 alkoxy;Y is C.dbd.O, C.dbd.S, S.dbd.O, or R.sup.1 --C--R.sup.2 ; andR.sup.1 and R.sup.2 each is hydrogen, C.sub.1 -C.sub.3 alkyl or, taken together may form C.sub.4 -C.sub.6 alkylene)or its acid addition salt being useful as an antimycotic agent is prepared by reacting a corresponding diol with a cyclizing agent.Type: GrantFiled: July 20, 1984Date of Patent: September 16, 1986Assignee: Shionogi & Co., Ltd.Inventors: Masaru Ogata, Hiroshi Matsumoto, Shiro Kida, Katsuya Tawara
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Patent number: 4609668Abstract: The invention provides novel .alpha.-(ethynyl substituted phenyl)-.alpha.-hydrocarbyl-1H-azole-ethanols wherein the azole group is 1,2,4-triazol-1-yl or imidazol-1-yl, the ethynyl group is unsubstituted or substituted and the phenyl group may bear an additional substituent and ethers thereof, which are useful as fungicides.Type: GrantFiled: August 24, 1984Date of Patent: September 2, 1986Assignee: Sandoz Ltd.Inventors: Fritz Schaub, Rupert Schneider
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 4582843Abstract: Triazolyl-alkanones or triazolyl-alkanols of the formula ##STR1## in which R.sup.1 is alkyl, cycloalkyl, aryl or substituted aryl, andR.sup.2 is hydrogen, alkyl, cycloalkyl, aryl or substituted aryl, orR.sup.1 and R.sup.2 are joined to form an aliphatic ring, andA is a keto group or a CH(OH) group,or a salt thereof which possess fungicidal, microbicidal and plant-growth regulating properties.Type: GrantFiled: August 10, 1981Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Helmut Timmler, Wolfgang Kramer, Karl H. Buchel, Helmut Kaspers, Wilhelm Brandes
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Patent number: 4560791Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: November 14, 1983Date of Patent: December 24, 1985Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4559110Abstract: Distillation of the heavy waste stream from the manufacture of phenol via the cumene process provides an overhead stream containing phenol, acetophenone and 2-phenyl propionaldehyde. Extraction of the overhead stream with aqueous caustic removes the phenol and subsequent distillation of the remaining two components in the presence of a catalytic amount of caustic provides a substantially pure acetophenone distillate.Type: GrantFiled: July 11, 1983Date of Patent: December 17, 1985Assignee: The Dow Chemical CompanyInventors: Loren L. Swearingen, Alfred W. Heinsohn, Craig W. Snook, Wallace E. Embrey, Garnet E. McConchie
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Patent number: 4550173Abstract: Ditriazolylvinyl phenyl ketones of the formula I ##STR1## where R is halogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, trifluoromethyl, cyano, nitro, phenyl or phenoxy, and n is an integer from 0 to 5, and the two triazole rings can, as desired, be bonded in the 1-position or 4-position to the vinyl group, their preparation and their use as nitrification inhibitors.Type: GrantFiled: January 17, 1984Date of Patent: October 29, 1985Assignee: BASF AktiengesellschaftInventors: Alfred Ruland, Wolfgang Reuther, Ernst-Heinrich Pommer, Eberhard Ammermann
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4499013Abstract: Certain fatty acids, esters and alcohol derivatives useful as electrical tree and water tree resistant compounds in polymer compositions are disclosed.Type: GrantFiled: August 17, 1983Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventors: Anthony Barlow, Irwin S. Schlossman, Robert E. Borgerding
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Patent number: 4496388Abstract: Compounds, having fungicidal and plant growth regulatory properties, of the formula (I): ##STR1## and stereoisomers thereof, wherein Z is --CH.dbd. or .dbd.N--; R.sup.1 is alkyl, cycloalkyl, alkenyl, alkynyl, optionally substituted aryl especially phenyl, or aralkyl; R.sup.2 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, optionally-substituted aryl especially phenyl or aralkyl; R.sup.3 and R.sup.4, which may be the same or different, are alkyl, alkenyl, alkynyl, aryl, aralkyl, or together form a bridging group linking X and Y; R.sup.5 is hydrogen, alkyl or aryl; R.sup.6 is hydrogen, alkyl, alkenyl, alkynyl or acyl; and X and Y, which may be the same or different, are oxygen or sulphur; and acid salts and metal complexes thereof.Type: GrantFiled: July 27, 1982Date of Patent: January 29, 1985Assignee: Imperial Chemical Industries PLCInventor: John M. Clough
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Patent number: 4486355Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.Type: GrantFiled: April 25, 1983Date of Patent: December 4, 1984Assignee: Imperial Chemical Industries PLCInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4486605Abstract: A method for producing an aromatic carbonyl compound represented by the formula (B)-1 or (B)-2: ##STR1## comprising decomposing a hydroperoxide represented by the formula (A)-1 or (A)-2: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in the specification, in an inert gas atmosphere in the presence of an aqueous layer containing an iron salt, a copper salt and an acid is disclosed. Novel m-(2-hydroxy-2-propyl)acetophenone and m-isopropenylacetophenone which are useful as an intermediate for the preparation of medicines are also disclosed. A method for producing m-isopropenylacetophenone comprising dehydrating m-(2-hydroxy-2-propyl)acetophenone in the presence of an acid catalyst is further disclosed.Type: GrantFiled: January 7, 1983Date of Patent: December 4, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Haruhisa Harada, Hiroshi Maki
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Patent number: 4474810Abstract: Arylglyoxals which are new compounds, active as hypoglycemic agents.Type: GrantFiled: January 27, 1983Date of Patent: October 2, 1984Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Vern G. DeVries
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Patent number: 4472415Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.8 alkyl, unsubstituted benzyl or benzyl substituted with halogen methyl, ethyl, propyl, butyl, nitro, trifluoromethyl, cyano, methoxy, ethoxy, phenyl or methylenedioxy; R.sup.2 is hydrogen or C.sub.1 -C.sub.8 alkyl; Y is hydrogen, halogen, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, unsubstituted amino or methyl- or ethyl-substituted amino, and n is 1 or 2; each of the groups Y being the same or different when n is 2 and Y being other than hydrogen or halogen when R.sup.1 and R.sup.2 are both hydrogen; or a fungicidal acid salt or metal complex of said compound. Fungicidal compositions containing these compounds and methods of using the same to combat plant fungal diseases are also disclosed.Type: GrantFiled: November 18, 1981Date of Patent: September 18, 1984Assignee: Imperial Chemical Industries PLCInventors: Paul A. Worthington, Margaret C. Shephard
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Patent number: 4457859Abstract: 2,2-azimidazole derivatives of the formula: ##STR1## wherein R and R.sup.1 are H, a C.sub.1 -C.sub.12 alkyl, a C.sub.1 -C.sub.12 alkoxy; NO.sub.2 ; R.sup.2 is hydrogen, a C.sub.1 -C.sub.3 alkyl; n, m=1 to 3, but where n-m=1, R=R.sup.1 =R.sup.2 =H is excluded, are disclosed as well as a method for preparing these compounds by oxidation of a compound of the formula ##STR2## wherein R, R.sup.1, R.sup.2, n and m are as identified above, except for the compound, wherein R=R.sup.2 =R.sup.2 =H, n=m=1. A liquid-crystal or mesomorphic material containing the 2,2'-azoimidazole compounds and electrooptical device comprised of such mesomorphic material are disclosed. The electrooptical devices are useful for systems of electronic representation and processing of information. The compounds therein have two spectrally spaced absorption bands in the visible part of their spectrum such that their position insures the contrast required for the human eye to be able to readily recognize the difference in color.Type: GrantFiled: March 23, 1982Date of Patent: July 3, 1984Inventors: Alexandr V. Ivaschenko, Valentina T. Lazareva, Elena K. Prudnikova, Vladimir G. Rumyantsev, Tamara S. Pljusnina, Viktor A. Nefedov, Lev M. Blinov, Viktor V. Titov, Vladimir P. Sevostyanov, Vadim M. Shoshin
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Patent number: 4454158Abstract: Compounds of the formula ##STR1## wherein: R is phenyl, phenyl monosubstituted, disubstituted, or trisubstituted by (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.8)alkoxy, hydroxy, chlorine, bromine, iodine, fluorine, trifluoromethyl, nitro, (C.sub.1 -C.sub.6)alkylcarbonyl, benzoyl, or phenyl; 1-, or 2-naphthyl; 1-, 2-, or 3-indenyl; 1-, 2-, or 9-fluorenyl; 1-, 2-, or 3-piperidinyl; 2- or 3-pyrrolyl; 2- or 3-thienyl; 2- or 3-furanyl; 2- or 3- indolyl; 2- or 3-thianaphthenyl; or 2- or 3-benzofuranyl;R.sub.1 is hydrogen, (C.sub.1 -C.sub.8)alkyl, benzyl, or phenethyl;X and Y independently, are hydrogen, fluorine, chlorine, or bromine; andA is a divalent radical of the formula: ##STR2## wherein R.sub.2 is hydrogen, methyl, or ethyl, and m and n, independently, are an integer from 0 to 4, provided that m+n cannot be greater than 4; --(CH.sub.2).sub.p --D--(CH.sub.2).sub.Type: GrantFiled: June 1, 1981Date of Patent: June 12, 1984Assignee: Merrell Toraude et CompagnieInventor: Philippe Bey