Halogen Containing Patents (Class 568/663)
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Patent number: 5756814Abstract: (1) CF.sub.2 .dbd.CFO(CF.sub.2).sub.n COOR is allowed to react with chlorine or bromine to obtain CF.sub.2 XCFXO(CF.sub.2).sub.n COOR', (2) which is allowed to react with a Grignard reagent MgBrC.sub.6 H.sub.3 (CH.sub.3).sub.2 to convert the terminal group to --COC.sub.6 H.sub.3 (CH.sub.3).sub.2, (3) followed by reaction with diethylaminosulfur trifluoride to convert --COC.sub.6 H.sub.3 (CH.sub.3).sub.2 to --CF.sub.2 C.sub.6 H.sub.3 (CH.sub.3).sub.2, (4) followed further by oxidation of the resulting methyl group and by esterification to convert the methyl group to --CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2 and (5) followed by dechlorination or debromination to obtain CF.sub.2 .dbd.CFO(CF.sub.2).sub.n CF.sub.2 C.sub.6 H.sub.3 (COOR).sub.2. The resulting bifunctional vinyl ether compound having an aromatic ring is a novel compound and can be used as a copolymer component for fluorine-containing elastomers.Type: GrantFiled: June 23, 1997Date of Patent: May 26, 1998Assignee: Nippon Mektron, LimitedInventors: Leng-Tain Lin, Kenji Iimura, Takehiro Sonoi
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Patent number: 5731477Abstract: This invention relates to a method for preparing difluoromethyl ethers, thiols and amines without using chlorofluorocarbon gases. The intermediates prepared by this method can be used to make certain compounds which act as PDE IV inhibitors which are useful for treating asthma and other diseases implicated with the PDE IV isozyme.Type: GrantFiled: January 31, 1995Date of Patent: March 24, 1998Assignee: SmithKline Beecham CorporationInventors: Joseph M. Karpinski, Siegfried B. Christensen, IV, Steven Dabbs
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Patent number: 5723682Abstract: The invention relates to difluorovinyl ethers of the general formula I ##STR1## in which R, A, X and m are as defined in claim 1, and to the use of these compounds as components of liquid-crystalline media, and to liquid-crystal and electro-optical display elements which contain the novel liquid-crystalline media.Type: GrantFiled: March 5, 1997Date of Patent: March 3, 1998Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Eike Poetsch, Werner Binder, Michael Kompter, Joachim Krause, Kazuaki Tarumi, Ekkehard Bartmann
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Patent number: 5616813Abstract: A novel bifunctional vinyl ether compound having an aromatic ring, represented by the following general formula: ##STR1## where X is a halogen atom and n is an integer of 1 to 5, effective as a copolymer component for fluorine-containing elastomers is produced by adding a chlorine atom or a bromine atom (Y) to CF.sub.2 .dbd.CFO(CF.sub.2)nCOOR, where R is a lower alkyl group, then subjecting the resulting CF.sub.2 YCFYO(CF.sub.2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene, reaction with SF.sub.4 to convert --CO-- to --CF.sub.2 --, and dechlorination or debromination, or by subjecting CF.sub.2 .dbd.CFO (CF.sub.2)nCOOR to hydrolysis and acid chloridation, followed by reaction with monohalogenobenzene and reaction with SF, to convert --CO-- to --CF.sub.2 --.Type: GrantFiled: October 31, 1995Date of Patent: April 1, 1997Assignee: Nippon Mektron LimitedInventors: Cherstokov V. Filippovich, Sterlin S. Rafailovich, S. Lev German, deceased, Lin Jeng-Tain, Satoru Saito, Haruyoshi Tatsu
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Patent number: 5574190Abstract: The present invention provides pharmaceutically active compounds formula I ##STR1## wherein R.sup.1 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), or --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl);R.sup.2 is --H, --OH, --O(C.sub.1 -C.sub.4 alkyl), --OCOC.sub.6 H.sub.5, --OCO(C.sub.1 -C.sub.6 alkyl), --OSO.sub.2 (C.sub.2 -C.sub.6 alkyl), or halo;R.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; andn is 2 or 3; and or a pharmaceutically acceptable salt thereof.Also provided are compounds of formula II ##STR2## wherein R.sup.1a is --H or --OR.sup.5 in which R.sup.5 is a hydroxy protecting group.R.sup.2a is --H, halo, or --OR.sup.6 in which R.sup.6 is a hydroxy protecting group; andR.sup.4 is --OH or --CHO;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 6, 1995Date of Patent: November 12, 1996Assignee: Eli Lilly and CompanyInventor: Alan D. Palkowitz
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Patent number: 5446186Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.Type: GrantFiled: November 9, 1993Date of Patent: August 29, 1995Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
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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: 5384415Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.Type: GrantFiled: May 28, 1993Date of Patent: January 24, 1995Assignee: Rhone-Poulenc ChimieInventors: Jean-Manuel Mas, Pascal Metivier
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Patent number: 5356560Abstract: 2-Fluoroperfluoroalkylcyclohexene derivatives of the formula I ##STR1## where R is an alkyl or alkenyl radical having up to 18 carbon atoms which is unsubstituted or substituted by CN or by at least one halogen and in which one or more non-adjacent CH.sub.2 groups may be replaced by a radical selected from the group consisting of --O--, --S--, --CO--, --O--CO--, --CO--O-- and --C.ident.C--,A.sup.1 and A.sup.2 are each, independently of one another,a) a 1,4-phenylene radical, in which one or two CH groups may be replaced by N,b) a 1,4-cyclohexylene radical, in which one or two non-adjacent CH.sub.2 groups may be replaced by --O-- or --S--,c) a 1,4-cyclohexenylene, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or naphthalene-2,6-diyl radical,where the radicals a) and b) may be monosubstituted or polysubstituted by halogen atoms, cyano groups and/or methyl groups,Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --C.ident.C--, --CH.dbd.CH--, --OCH.sub.Type: GrantFiled: August 20, 1993Date of Patent: October 18, 1994Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Herbert Plach
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Patent number: 5279764Abstract: The invention relates to dihalogenobenzene derivatives of the formula IR.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --(Z.sup.2 --A.sup.3).sub.n --R.sup.2wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and n are as defined in the specification.Type: GrantFiled: November 23, 1992Date of Patent: January 18, 1994Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Georg Weber, Ulrich Finkenzeller, Andreas Wachtler, Thomas Geelhaar, David Coates, Ian C. Sage, Simon Greenfield
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Patent number: 5210322Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.Type: GrantFiled: September 20, 1990Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson
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Patent number: 5196611Abstract: The preparation of an alkyl, alkenyl, or alkynyl chloride by the reaction of a corresponding alcohol with phosgene or thionyl chloride in the presence of a phosphine oxide acting as catalyst, wherein the catalyst used is an aliphatic, cycloaliphatic, or cyclic/aliphatic phosphine oxide.Type: GrantFiled: May 6, 1992Date of Patent: March 23, 1993Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Irene Troetsch-Schaller, Thomas Wettling, Thomas-Michael Kahl, Leopold Hupfer, Wolfgang Franzischka, Hermann Koehler
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Patent number: 5196569Abstract: Trifluorovinyl ethers containing selected functional groups, and homo- and copolymers prepared from them, are disclosed, as well as intermediates useful in the preparation of the ethers.Type: GrantFiled: October 10, 1991Date of Patent: March 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 5189204Abstract: 3-(2-Trifluoro-1-hydroxyethyl)propenyl benzyl ether or derivatives thereof having the formula ##STR1## wherein R is a substituted or not substituted phenyl group and a mark * shows an asymmetric carbon atom, and derivatives thereof are provided, which are useful as a material for preparing liquid crystal compound.Type: GrantFiled: June 25, 1991Date of Patent: February 23, 1993Assignee: Showa Shell Sekiyu Kabushiki KaishaInventors: Tomoya Kitazumo, Takashi Yamazaki, Hitoshi Iwatsubo
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Patent number: 5130462Abstract: Cyclobutane derivatives of the formulas ##STR1## wherein P is a hydroxy protecting group and X is a leaving group are useful intermediates in the preparation of antiviral compounds.Type: GrantFiled: February 19, 1991Date of Patent: July 14, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: William A. Slusarchyk, Robert Zahler
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Patent number: 5104987Abstract: This invention relates to a process for the alkoxylation of an active hydrogen-containing compound comprising contacting the active hydrogen-containing compound with an alkylene carbonate in the presence of a mixed metal oxide catalyst under conditions effective to alkoxylate the active hydrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: April 14, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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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
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Patent number: 4957986Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.Type: GrantFiled: December 15, 1989Date of Patent: September 18, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry N. Cripps
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Patent number: 4940807Abstract: Electron-rich aromatic compounds are selectively brominated in good yield in the presence of water using potassium tribromide as the brominating agent. In this way monobromination is favored and dibromination is suppressed as compared to the use of elemental bromine as the brominating agent.Type: GrantFiled: June 12, 1989Date of Patent: July 10, 1990Assignee: Ethyl CorporationInventor: Robert N. DePriest
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Patent number: 4929765Abstract: Phenylacetaldehydes of the general formula I ##STR1## where R.sup.1 to R.sup.5 are each independently of the others hydrogen, alkyl, alkoxy, halogen, haloalkyl, haloalkoxy or haloalkylthio, by catalytic rearrangement in the presence of a zeolite, are prepared by reacting an epoxy of the formula II or a phenylglycol of the formula III ##STR2## where Y and Z can be identical to or different from each other and are each hydroxyl, alkoxy, aryloxy or acyloxy, in the gas phase over a borosilicate zeolite catalyst at from 70.degree. to 200.degree. C. under reduced pressure.Type: GrantFiled: November 22, 1988Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Hubert Smuda, Wolfgang Hoelderich, Norbert Goetz, Hans-Gert Recker
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Patent number: 4918242Abstract: A process for producing the optically pure (+)- or (-)-isomer of a phenyl- or substituted-phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.Type: GrantFiled: June 12, 1989Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4902835Abstract: New chemical reactions of 1,1,2-trifluoro-1,3-butadiene provide simple access to a series of new fluorinated alkene derivatives. These derivatives provide a simple, general methodology for the stereocontrolled preparation of 2-fluoro-2-alkenoate esters and related monofluoroalkene derivatives which include fluoro analogs of known insecticides, pheromones or pharmaceuticals. A new method for the preparation of 1,1,2-trifluoro-1,3-butadiene is also provided.Type: GrantFiled: January 11, 1988Date of Patent: February 20, 1990Assignee: The University of RochesterInventors: Andrew S. Kende, Noritada Matsuo
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Patent number: 4900872Abstract: Improved process for the preparation of fluorohalogenated ethers by reaction of a fluorinated fluorooxycompound with a halogenated olefin, performed in liquid phase, in the presence of an inert solvent, at low temperature, the fluoroxycompound being continuously fed in form of solution in an inert solvent.Type: GrantFiled: May 26, 1989Date of Patent: February 13, 1990Assignee: Ausimont S.p.A.Inventors: Giorgio Guglielmo, Gian P. Gamberetto
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Patent number: 4891451Abstract: Vinyl ethers of the formula (I) ##STR1## where R.sup.1 to R.sup.3 are identical or different and are each hydrogen, a straight-chain or branched alkyl or alkenyl radical of not more than 12 carbon atoms, halogen-substituted alkyl, a cycloalkyl or cycloalkenyl radical of 5 to 8 carbon atoms, an aryl, alkylaryl, alkenylaryl, aralkyl or aralkenyl radical of 6 to 16 carbon atoms, halogen-substituted aryl or a heterocyclic radical and furthermore R.sup.1 and R.sup.2 or R.sup.1 and R.sup.3, together with the carbon atom to which they are bonded, may form a cycloalkane, cycloalkene or heterocyclic structure, and R.sup.4 is alkyl, alkylaryl or aralkyl, are prepared by a process in which an alcohol is eliminated from an acetal or ketal of the formula (II) ##STR2## where R.sup.1 to R.sup.4 have the above meanings, in the presence of borosilicate and/or iron silicate zeolites as catalysts.Type: GrantFiled: June 30, 1988Date of Patent: January 2, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer
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Patent number: 4855510Abstract: A compound having the formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is --CH.dbd.CH--X or --C.tbd.C--X where X is hydrogen or straight chain alkyl; R.sup.2 is halophenyl, Z is OR.sup.3 where R.sup.3 is H, alkyl, alkenyl or alkynyl; and acid addition salts and metal complexes thereof. These compounds have fungicidal and plant growth regulating properties. Intermediates for these compounds are also disclosed.Type: GrantFiled: November 14, 1986Date of Patent: August 8, 1989Assignee: Imperial Chemical Industries PLCInventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
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Patent number: 4847303Abstract: The present invention involves compounds having the structure: ##STR1## wherein: (a) --A.sup.1 is selected from the group consisting of --OH, --H, and --O.sub.2 CR;(b) --A.sup.2 is selected from the group consisting of unsubstituted or substituted, saturated or unsaturated, straight, branched and cyclic alkyl having from 1 to about 10 carbon atoms;(c)--A.sup.3 is selected from --C(CH.sub.3).sub.3, --Si(CH.sub.3).sub.3, and --CF.sub.3 ; and(d) --Y is selected from certain low molecular weight alkyl chains which terminate in specific unsaturated functional groups: ##STR2## and aldehydes in the form of their acetals; pharmaceutical compositions comprising such compounds; and methods for treating inflammation by administering such compounds.Type: GrantFiled: November 23, 1987Date of Patent: July 11, 1989Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4831183Abstract: A process for the telomerization of a conjugated alkadiene with an organic hydroxy compound to produce an organo-oxyalkadiene is disclosed. A palladium catalyst having an ionic ligand is employed in a substantially oxygen-free environment in the presence of an aprotic polar solvent so that the reaction products may be separated from the catalyst by solvent extraction with a hydrocarbon solvent.Type: GrantFiled: October 17, 1988Date of Patent: May 16, 1989Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4792637Abstract: A process for the synthesis of vinyl ethers of formula ##STR1## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or a primary, secondary or tertiary alkyl group,R.sub.3 is a hydrogen, a primary alkyl, phenyl, or substituted phenyl group, orR.sub.2 and R.sub.3, taken together, represent a polymethylene chain containing from 3 to 10 carbon atoms wherein one or more hydrogens can be replaced by methyl or ethyl groups, andR is a primary, secondary or tertiary alkyl group, which comprises reacting a suitably selected dioxolane derivative of formula II ##STR2## wherein R.sub.1, R.sub.2, and R.sub.3 are as defined above, andR.sub.4, R.sub.5, R.sub.6, and R.sub.7, each independently, represent hydrogen or an alkyl group, with a boric acid ester of formula IIIB(OR).sub.3 IIIwhereinR is as defined above, in the vapor phase, at a temperature comprised between 100.degree. and 400.degree. C., and in the presence of an acidic heterogeneous catalyst.Type: GrantFiled: July 17, 1987Date of Patent: December 20, 1988Assignee: Enichem Anic SpAInventors: Giuseppe Messina, Mario D. Moretti, Salvatore R. Sanna, Giovanni Soma, Pier G. Cabras
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Patent number: 4742077Abstract: Compounds of formula I ##STR1## wherein R.sub.1 represents a group of formula ##STR2## whereby R.sub.4 and R.sub.5 are the same or different and represent hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl and X represents oxygen, sulfur, imino, lower alkylimino, --(CH.sub.2)--, --(S.CH.sub.2)-- or --(O.CH.sub.2)--,R.sub.2 represents hydrogen or lower alkyl,R.sub.3 represents a group of formula ##STR3## whereby R.sub.6, R.sub.7 and R.sub.8 are the same or different and represent hydrogen or alkyl or R.sub.6 together with R.sub.7 or R.sub.7 together with R.sub.8 represent --(CH.sub.2).sub.m -- wherein m is 3 to 6,R.sub.9 represents alkyl, alkenyl, trialkylsilyl or alkyl substituted by hydroxy, lower alkoxy, lower halogenalkyl or aryl andn stands for 1, 2 or 3,which possess pharmaceutical in particular antimycotic activity as well as activity against phytopathogenic fungi.Type: GrantFiled: September 8, 1986Date of Patent: May 3, 1988Assignee: Sandoz Ltd.Inventor: Anton Stutz
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Patent number: 4708966Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.Type: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4705801Abstract: There is described a process for producing fungicidally active 4-phenylpyrrole derivatives of the formula I ##STR1## wherein R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and n is 0, 1 or 2, which process comprises reacting a 3-trifluoromethyl-4-phenylpyrrole of the formula II ##STR2## wherein R.sub.n is as defined under the formula I, and R.sub.1 is hydrogen or an acyl group, at elevated temperature and elevated pressure, with ammonia. Important intermediates and the production thereof are also described.Type: GrantFiled: October 7, 1985Date of Patent: November 10, 1987Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4690948Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.Type: GrantFiled: December 1, 1986Date of Patent: September 1, 1987Assignee: International Minerals & Chemical Corp.Inventor: Jing-Jong Lu
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Patent number: 4634466Abstract: A compound having the formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is --CH.dbd.CH--X or --C.tbd.C--X where X is hydrogen or straight chain alkyl; R.sup.2 is halophenyl, Z is OR.sup.3 where R.sup.3 is H, alkyl, alkenyl or aklynyl; and acid addition salts and metal complexes thereof. The compounds are characterized by their fungicidal and plant growth activity.Type: GrantFiled: May 31, 1983Date of Patent: January 6, 1987Assignee: Imperial Chemical Industries PLCInventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
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Patent number: 4629814Abstract: This process relates to the preparation of unsubstituted or substituted bis-bromoalkyl ethers by reacting unsubstituted or substituted 1,3-dioxolane or unsubstituted or substituted 1,3-dioxane with thionyl bromide. The bis-bromoalkyl ethers made by this process can be used in preparing biologically active compounds.Type: GrantFiled: August 27, 1985Date of Patent: December 16, 1986Assignee: Rohm and Haas CompanyInventor: Michael P. James
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Patent number: 4605784Abstract: Disclosed is a process for the preparation of ether-containing chlorides by reacting an ether-alcohol, ether-glycol or ether-polyglycol with a chlorinating agent such as thionyl chloride in the presence of a catalytic amount of a quaternary ammonium salt, the reaction being conducted at a temperature of about 25.degree. C. to about 90.degree. C.Type: GrantFiled: July 18, 1985Date of Patent: August 12, 1986Assignee: Eastman Kodak CompanyInventors: Robert J. I. Eubanks, James G. Pacifici
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Patent number: 4554112Abstract: Fluorovinyl compounds having the formulaTLCF.dbd.CF.sub.2are prepared by reacting compounds having the formula ##STR1## for a time and at a temperature sufficient to form the vinyl compound: whereX=Cl, Br or I;Z=F, Cl, Br, OH, NRR', OA, or SA;R and R' are independently selected from the group consisting of hydrogen, an alkyl having one or more than one carbon atom, and aryl;A=Alkali metal, alkali earth metal, quaternary nitrogen, or R;L=oxygen or sulfur; andT=an alkyl or aryl radical which does not interfere with the reaction.Type: GrantFiled: April 30, 1981Date of Patent: November 19, 1985Assignee: The Dow Chemical CompanyInventors: Bobby R. Ezzell, William P. Carl, William A. Mod
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Patent number: 4431845Abstract: A method for the preparation of hydroxyl-terminated poly(haloalkylene ethers) is disclosed wherein a catalyst system comprising a fluorinated acid and a polyvalent tin compound is utilized.Type: GrantFiled: March 5, 1982Date of Patent: February 14, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventors: Chung I. Young, Loren L. Barber, Jr.
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Patent number: 4412958Abstract: 5-Phenyl-2S-pentanol is synthesized stereospecifically from S ethyl lactate. The method provides easily purified 5-phenyl-2S-pentanol useful in the synthesis of central nervous system active (CNS) agents such as levonantradol.Type: GrantFiled: August 5, 1982Date of Patent: November 1, 1983Assignee: Pfizer Inc.Inventors: Berkeley W. Cue, Jr., Bernard S. Moore
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4360698Abstract: A process to form glycol ethers by reacting an organic compound (A) having at least one aliphatic hydroxyl group with an oxirane compound (B) under reaction conditions in the presence of a catalytic amount of a polymeric material that is substantially insoluble in the reaction mixture, said polymeric material having a plurality of pendant sulfonate moieties with divalent metal counterions. Preferential formation of the mono adduct of glycol ethers is noted.Type: GrantFiled: July 22, 1981Date of Patent: November 23, 1982Assignee: The Dow Chemical CompanyInventor: James H. Sedon
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4326055Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.Type: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4297366Abstract: 2,2-Dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is fluoroalkyl,R.sup.2 is an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, andR.sup.3 is a radical customary in the alcohol component of pyrethroidswhich possess arthropodicidal properties. New intermediates therefor are also shown.Type: GrantFiled: April 23, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: 4263212Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.Type: GrantFiled: February 14, 1980Date of Patent: April 21, 1981Assignee: Rikagaku KenkyushoInventors: Pangbu Hong, Hiroshi Yamazaki
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Patent number: 4237055Abstract: A method of synthesizing 1RS,4SR,5RS-4-(4,8-dimethyl-5-hydroxy-7-nonen-1-yl)-4-methyl-3,8-dioxabicy clo [3.2.1]octane-1-acetic acid. The acid is a derivative of the natural product zoapatanol, one of the active ingredients in the zoapatle plant, and is active as a utero-evacuant agent.Type: GrantFiled: June 18, 1979Date of Patent: December 2, 1980Assignee: Ortho Pharmaceutical CorporationInventors: Zoltan G. Hajos, Michael P. Wachter
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Patent number: 4171318Abstract: 9-Substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.Type: GrantFiled: August 24, 1978Date of Patent: October 16, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4171456Abstract: The title compound can be made by reacting ethylene glycol with hexabromo-p-xylene in the presence of anhydrous potassium carbonate. The compound is useful as a fire retardant for plastics, and can be used to form a polyester of the linear type. Fibers made from such polyesters are useful for making fire retardant textiles, carpets, drapes, and garments.Type: GrantFiled: October 3, 1977Date of Patent: October 16, 1979Assignee: Ethyl CorporationInventors: David R. Brackenridge, Lawrence C. Mitchell