Halogen Containing Patents (Class 568/56)
  • Patent number: 6121496
    Abstract: The present invention relates to a process for the acylation of an aromatic thioether. In its preferred variant, the invention resides in a process for the condensation of acetic anhydride or acetyl chloride with thioanisole. The process for the acylation of an aromatic thioether according to the invention is characterised in that it consists in reacting said thioether with an acylating agent chosen from the group formed by the halides of carboxylic acids and the anhydrides of carboxylic acids, in the presence of an effective quantity of an acid zeolite.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: September 19, 2000
    Assignee: Rhodia Chemie
    Inventors: Laurent Gilbert, Michel Spagnol
  • Patent number: 6080790
    Abstract: Compounds of formula (1) ##STR1## are described wherein Y represents a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; R.sup.2 represents an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 is a monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen or sulphur atoms or a group --N(R.sup.4)-- where R.sup.4 is a hydrogen atom or an alkyl group; X is --O--, --S--, or --N(R.sup.5)--, where R.sup.5 is a hydrogen or an alkyl group; with the proviso that when X is --O-- then R.sup.3 is not a 3-cyanamino-6-pyridazinyl or a 3-chloro-6-pyridazinyl group; and the salts, solvates, hydrates and N-oxides thereof.The compounds are selective and potent inhibitors of phosphodiesterase IV and are useful for the prophylaxis and treatment of inflammatory diseases and the alleviation of conditions associated with central nervous malfunction.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: June 27, 2000
    Assignee: Celltech Therapeutics, Limited
    Inventors: Ewan Campbell Boyd, Michael Anthony William Eaton, Graham John Warrellow
  • Patent number: 5998667
    Abstract: The invention relates to new substituted biphenyloxazolines of the formula (I) ##STR1## in which R.sup.1 represents C.sub.1 -C.sub.6 -halogenoalkylthio andR.sup.2 represents hydrogen, orR.sup.1 and R.sup.2 together with the carbon atoms to which they are bonded form a halogen-substituted 5- or 6-membered heterocyclic ring,X represents hydrogen, halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: December 7, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold, Christoph Erdelen
  • Patent number: 5962483
    Abstract: Compounds of general formula (1) ##STR1## are described wherein Y is a halogen atom or a group --OR.sup.1, where R.sup.1 is an optionally substituted alkyl group; X is --O--, --S-- or --N(R.sup.7)--, where R.sup.7 is a hydrogen atom or an alkyl group; R.sup.2 is an optionally substituted cycloalkyl or cycloalkenyl group; R.sup.3 and R.sup.4, which may be the same or different, is each a hydrogen atom or an alkyl, --CO.sub.2 R.sup.8 (where R.sup.8 is a hydrogen atom or an alkyl, aryl, or aralkyl group), --CONR.sup.9 R.sup.10 (where R.sup.9 and R.sup.10 which may be the same or different is each a hydrogen atom or an alkyl, aryl or aralkyl group), --CSNR.sup.9 R.sup.10, --CN, --CH.sub.2 CN group; Z is --(CH.sub.2).sub.n -- (where n is zero or an integer 1, 2 or 3; R.sup.5 is an optionally substituted monocyclic or bicyclic aryl group optionally containing one or more heteroatoms selected from oxygen, sulphur or nitrogen atoms; R.sup.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: October 5, 1999
    Assignee: Celltech Therapeutics, Limited
    Inventors: Graham John Warrellow, Valerie Anne Cole, Rikki Peter Alexander
  • Patent number: 5942648
    Abstract: Naphthalene derivatives of the fomula I ##STR1## in which: R.sup.1 is an alkyl or alkenyl radical which is unsubstituted, monosubstituted by CH or CF.sub.3 or monosubstituted by halogen and has 1 to 15 carbon atoms, it also being possible for one or more CH.sub.2 groups in these radicals to be replaced, in each case independently of one another, by --O--, --S--, ##STR2## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a manner that oxygen atoms are not linked directly to one another, ##STR3## m is 0, 1 or 2, n is 0 or 1, wherem+n is 1 or 2,Z.sup.1 and Z.sup.2 are each, independently of one another, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or a single bond,L.sup.1 and L.sup.2 independently of one another, are H or F,x is an alkyl or alkoxy radical which is unsubstituted, monosubstituted by CN or CF.sub.3 or substituted bi halogen and has 1 to 15 carbon atoms, or is OH, CN, SCN, OCN, NCS or Q--Y,whereQ is a single bond, (CF.sub.2).sub.r or O(CF.sub.2).sub.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: August 24, 1999
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: David Coates, Mark Goulding, Simon Greenfield, Volker Reiffenrath, Reinhard Hittich, Herbert Plach
  • Patent number: 5907063
    Abstract: Activated aromatic compounds are more economically ring brominated by reacting the compounds with a sulfoxide/HBr brominating agent while removing water from the reaction mixture. The water removal provides high conversions and yields when employing stoichiometric quantities of reactants.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: May 25, 1999
    Assignee: Albemarle Corporation
    Inventor: Kevin J. Theriot
  • Patent number: 5874656
    Abstract: o-Alkylfluorobenzenes are advantageously prepared by heating the corresponding chloroformates to from 70.degree. to 200.degree. C. in the liquid phase in the presence of hydrogen fluoride and in the presence of an inert diluent other than a halogenated alkane.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: February 23, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Michael-Harold Rock
  • Patent number: 5861540
    Abstract: Synthetic procedures to tetraalkyls, tetraacids and dianhydrides substituted 1,1,1-triaryl-2,2,2-trifluoroethanes which comprises: (1) 1,1-bis(dialkylaryl)-1-aryl-2,2,2 -trifluoroethane, (2) 1,1-bis(dicarboxyaryl)-1-aryl-2,2,2-trifluoroethane or (3) cyclic dianhydride or diamine of 1,1-bis(dialkylaryl)-1-aryl-2,2,2-trifluoroethanes. The synthesis of (1) is accomplished by the condensation reaction of an aryltrifluoromethyl ketone with a dialkylaryl compound. The synthesis of (2) is accomplished by oxidation of (1). The synthesis dianhydride of (3) is accomplished by the conversion of (2) to its corresponding cyclic dianhydride. The synthesis of the diamine is accomplished by the similar reaction of an aryltrifluoromethyl ketone with aniline or alkyl substituted or disubstituted anilines. Also, other derivatives of the above are formed by nucleophilic displacement reactions.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: January 19, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: William B. Alston, Roy F. Gratz
  • Patent number: 5820665
    Abstract: An object of the present invention is to provide a compound which imparts a sufficient water repellency and a suitable oil repellency to substrates such as a fiber, a paper, a wood material, a hide, a leather, a resin, a glass, a metal, etc. The compound of the present invention is a fluoroalkylcarboxylic acid of the general formula (I), and its derivative of the general formula (II) (e.g. fluoroalkyl alcohol, fluoroalkyl carboxylic acid chloride, fluoroalkylcarboxylic acid amide and fluoroalkylamine).
    Type: Grant
    Filed: May 28, 1997
    Date of Patent: October 13, 1998
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventor: Yoshiaki Kai
  • Patent number: 5808164
    Abstract: A process which can be used to produce an aromatic sulfide compound having the formula of (R.sub.4-n)(X.sub.n)(W)Ar--S--R' is provided. The process comprises contacting, in the presence of a surfactant, a halo-substituted aromatic compound in an aqueous solution with a salt of a mercaptan under conditions sufficient to produce the aromatic sulfide in which the halo-substituted aromatic compound and salt of mercaptan are each present in an amount effective to synthesize the aromatic sulfide wherein R is hydrogen or a hydrocarbyl radical, X is a halogen, n is a number from 0 to 3, W is a substituent, Ar is an aromatic ring, and R' is a hydrocarbyl radical.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: September 15, 1998
    Assignee: Phillipe Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5798396
    Abstract: The present invention is directed to sulfonium salt-containing compounds represented by a following general formula; ##STR1## wherein R.sub.1 is alkyl containing from 1 to 18 carbon atoms, hydroxy, alkoxy containing from 1 to 18 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or halogen, n is any of 0, 1, 2 or 3, however, each of R.sub.1 may be different from the others when n is 2 or more, R.sub.2 is alkyl containing from 1 to 6 carbon atoms, R.sub.3 and R.sub.4 are each independently hydrogen or alkyl containing from 1 to 6 carbon atoms, R.sub.5 and R.sub.6 are each independently hydrogen, alkyl containing from 1 to 6 carbon atoms, hydroxy, alkoxy containing from 1 to 6 carbon atoms, alkylcarbonyloxy containing from 1 to 18 carbon atoms or aromatic carbonyloxy, and R.sub.7 is alkyl containing from 4 to 20 carbon atoms or a group represented by a following formula; ##STR2## wherein R.sub.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: August 25, 1998
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Eiji Takahashi, Hiroo Muramoto
  • Patent number: 5760269
    Abstract: The invention provides the novel compound 4,4,4-trichlorobutyl methanesufonate, useful as an intermediate in the production of certain agricultural pesticides, and a process for its manufacture.
    Type: Grant
    Filed: December 6, 1996
    Date of Patent: June 2, 1998
    Assignee: Zeneca Limited
    Inventors: Martin Charles Bowden, Trevor Robert Perrior
  • Patent number: 5756849
    Abstract: The invention relates to a process and a nucleophilic reagent which is useful for grafting a substituted difluoromethyl group onto a compound containing at least one electrophilic function, characterized in that it comprises:a) a fluorocarboxylic acid of formula Ew--CF.sub.2 --COOH where Ew represents an electron-withdrawing atom or group, at least partially salified with an organic or inorganic cation, andb) a polar aprotic solvent;and in that the content of releasable protons carried by its various components, including their impurities, is at most equal to half the initial molar concentration of the said fluorocarboxylic acid.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Jean-Manuel Mas, Laurent Saint-Jalmes
  • Patent number: 5731477
    Abstract: 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: Grant
    Filed: January 31, 1995
    Date of Patent: March 24, 1998
    Assignee: SmithKline Beecham Corporation
    Inventors: Joseph M. Karpinski, Siegfried B. Christensen, IV, Steven Dabbs
  • Patent number: 5639887
    Abstract: Compounds of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are herein described, A is a straight or branched (C.sub.2 -C.sub.12)alkyl or a phenyl moiety and B is a moiety of the formula: ##STR2## The compounds are effective in potentiating the activity of chemotherapeutic anti-cancer agents by increasing the sensitivity of multi-drug resistant cells to such chemotherapeutic agents.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: June 17, 1997
    Assignee: American Cyanamid Company
    Inventors: Dennis Powell, Rolf Paul, William A. Hallett, Dan M. Berger, Minu D. Dutia
  • Patent number: 5618981
    Abstract: A process which can be used to produce an aromatic sulfide compound having the formula of (R.sub.4-n)(X.sub.n)(W)Ar--S--R' is provided. The process comprises contacting, in the presence of a surfactant, a halo-substituted aromatic compound in an aqueous solution with a salt of a mercaptan under conditions sufficient to produce the aromatic sulfide in which the halo-substituted aromatic compound and salt of mercaptan are each present in an amount effective to synthesize the aromatic sulfide wherein R is hydrogen or a hydrocarbyl radical, X is a hlogen, n is a number from 0 to 3, W is a substituent, Ar is an aromatic ring, and R' is a hydrocarbyl radical.
    Type: Grant
    Filed: May 19, 1995
    Date of Patent: April 8, 1997
    Assignee: Phillips Petroleum Company
    Inventor: James E. Shaw
  • Patent number: 5600035
    Abstract: Photoreactive compounds are synthesized from 2,5- or 2,6-dintrobenzyl groups. Also disclosed are methods of synthesizing reactive monomers containing 2,5- or 2,6-dintrobenzyl groups.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: February 4, 1997
    Assignee: PPG Industries, Inc.
    Inventors: Charles F. Kahle, II, Neil D. McMurdie, Raphael O. Kollah, Daniel E. Rardon, Gregory J. McCollum
  • Patent number: 5557008
    Abstract: A one pot process for the perfluoroalkylation and/or perfluoroacyloxylation of organic substrates is provided. The process comprises contacting a substrate with a perfluoroalkanoic anhydride in the presence of an inorganic peroxygen compound at a temperature of greater than 10.degree. C. Substrates that can be perfluoroalkylated and/or perfluoroacyloxylated include alkylbenzenes, halogenated aromatic compounds, alkoxybenzenes, aryl benzenes, and aromatic and aliphatic disulphides. Preferably, the perfluoroalkanoic anhydride is trifluoroacetic anhydride and the inorganic peroxygen compound is sodium percarbonate.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: September 17, 1996
    Assignee: Solvay Interox Limited
    Inventors: Craig W. Jones, William R. Sanderson, John P. Sankey
  • Patent number: 5536754
    Abstract: Disclosed herein are partially fluorinated (co)polymers containing sulfonic acid or sulfonate salt groups, processes for making those polymers, and intermediates for those (co)polymers. The (co)polymers are useful as ion-exchange resins and (in the sulfonic acid form) acid catalysts.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: July 16, 1996
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 5534634
    Abstract: Process for preparing trifluoroethyl sulfur compounds from thiolates and 1-chloro-2,2,2-trifluoroethane. The invention relates to the preparation of trifluoroethyl sulfur compounds of the formula RSCH.sub.2 CF.sub.3 by reacting 1-chloro-2,2,2-trifluoroethane CH.sub.2 Cl--CF.sub.3 in a polar aprotic solvent with salts of thiols of the formula RSH, where R can be an alkyl or aryl radical or a heterocyclic radical.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: July 9, 1996
    Assignee: Hoechst AG
    Inventors: Wolfgang Appel, Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
  • Patent number: 5534557
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3): ##STR2## where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: July 9, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5498730
    Abstract: The present invention provides fluorinated alkyl compound derivatives represented by formula of: ##STR1## wherein: R is C.sub.2-4 lower alkyl, cyclohexyl or thiophene; phenyl substituted with hydrogen, C.sub.1-6 alkyl, haloalkyl, halogen or alkoxy; and,R.sub.f is fluorinated C.sub.1-3 lower alkyl.The fluorinated alkyl compound derivatives of the invention can be used as agrochemicals, drugs and intermediates therefor. The present invention also provides a novel process for preparing the fluorinated alkyl compound derivatives (I).
    Type: Grant
    Filed: July 26, 1994
    Date of Patent: March 12, 1996
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kwang-Yun Cho, Bum-Tae Kim, Young-Sup Kim, Yong-Ki Min, No-Kyun Park, In-Howa Jeong
  • Patent number: 5492917
    Abstract: Novel compounds of the general structural formula I: ##STR1## have endothelin antagonist activity and are therefore useful in treating cardiovascular disorders, such as hypertension, pulmonary hypertension, postischemic renal failure, vasospasm, cerebral and cardiac ischemia, myocardial infarction, endotoxic shock, inflammatory diseases including Raynaud's disease and asthma.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: February 20, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Ralph A. Rivero, Peter D. Williams, Daniel F. Veber
  • Patent number: 5478959
    Abstract: A method for preparing 1,4-(Z,Z)-disubstituted-1,4-disulfurated-1,3-butadienes is disclosed. The butadienes can be further elaborated to provide 3,6-unsymmetrically-substituted-1,2-dithiins. Also disclosed are butadienes prepared by the method of the invention. These butadienes are useful as intermediates in the synthesis of antibiotic 1,2-dithiins.
    Type: Grant
    Filed: October 5, 1994
    Date of Patent: December 26, 1995
    Assignee: The Research Foundation of State University of New York
    Inventors: Eric Block, Chuangxing Guo
  • Patent number: 5475143
    Abstract: Disclosed herein are partially fluorinated (co)polymers containing sulfonic acid or sulfonate salt groups, processes for making those polymers, and intermediates for those (co)polymers. The (co)polymers are useful as ion-exchange resins and (in the sulfonic acid form) acid catalysts.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: December 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 5463138
    Abstract: 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: Grant
    Filed: May 18, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus-Helmut Muller
  • Patent number: 5463088
    Abstract: 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: Grant
    Filed: April 26, 1994
    Date of Patent: October 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Albrecht Marhold, Karl-Rudolf Gassen
  • Patent number: 5449801
    Abstract: A process for the selective high yield halogenation R--CH.sub.3 wherein R is ##STR1## Si(Cl).sub.m (CH.sub.3).sub.n, wherein m is 1 to 3, n is 1 to 3 and m+n is 3; phenyl; or phenyl substituted with Cl, Br, F, OR.sup.1, SR.sup.1 or NO.sub.2 ; R.sup.1 is C.sub.1 -C.sub.3 alkyl; and X is chlorine or bromine; under reactive distillation conditions which continuously and selectively separate the mono, di, or trihalogenated product from the reaction zone and which does not require recycling of the starting materials is disclosed.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: September 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Chris S. Barnum, Charles T. Blaisdell
  • Patent number: 5446186
    Abstract: 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: Grant
    Filed: November 9, 1993
    Date of Patent: August 29, 1995
    Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
  • Patent number: 5426232
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, or phenyl or benzyl which is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or di(C.sub.1 -C.sub.6 alkyl)amino.The compounds are suitable as .pi.-acceptors and electrical semiconductors, and they can be used for antistatic finishing of objects.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: June 20, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: John Zambounis
  • Patent number: 5393885
    Abstract: Compounds of the formula ##STR1## in which R.sub.1 is halogen, C.sub.1 -C.sub.3 alkyl, halo-C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, halo-C.sub.1 -C.sub.3 alkoxy or cyano and/or two substituents R.sub.1 which are bonded to adjacent C atoms of the phenyl ring together are --O--CH.sub.2 --O--; R.sub.2 is hydrogen, halogen or methyl;R.sub.3 is fluorine, chlorine, bromine or C.sub.1 -C.sub.3 alkyl; R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl;either R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --COCO--R.sub.8,--CO--R.sub.9 or S(O).sub.m --N(R.sub.10)--COO--R.sub.11 andR.sub.6 is C.sub.1 -C.sub.6 alkyl, halo-C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.5 alkynyl, halo-C.sub.3 -C.sub.5 alkynyl, C.sub.1 -C.sub.3 alkoxy-C.sub.1 -C.sub.3 alkyl, C.sub.3 -C.sub.6 cycloalkyl, unsubstituted or substituted phenyl; or R.sub.5 and R.sub.6 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.3 alkyl; R.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: February 28, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 5393776
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • Patent number: 5382686
    Abstract: Nitrodiphenyl(thio) ethers in which the nitro group is in the ortho- or para-position with respect to the ether oxygen or ether sulphur can be prepared from halonitrobenzones in which the nitro group is in the ortho- or para-position with respect to the halogen and, alkali metal (thio)phenolates in liquid ammonia, the reaction being carried out under pressure and at a temperature from -30.degree. C. to +140.degree. C. and the ammonia being separated off after the reaction is completed.
    Type: Grant
    Filed: June 2, 1993
    Date of Patent: January 17, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ferdinand Hagedorn, Helmut Fiege
  • Patent number: 5380923
    Abstract: Polymeric triarylsulfonium salts are provided having a repeating structural unit with the formula: ##STR1## where R represents a substituted or unsubstituted aryl group, X.sup.- represents a non-nucleophilic anion, n represents an integer greater than or equal to 0 and p represents an integer greater than or equal to 2 and may be prepared by combining (a) an arylbis(p-fluorophenyl)substituted sulfonium salt with a bis(trimethylsilylated)dithiol in a polar aprotic solvent.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: January 10, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Bradford B. Wright, Omar Farooq, Robert J. DeVoe
  • Patent number: 5354511
    Abstract: Compounds having non-linear optical activity of the general formula ##STR1## wherein D and A are electron donor and acceptor groups, respectively, R.sup.1 and R.sup.2 are aromatic bridging groups, X and Y are preferably groups capable of partaking in polymerization reactions are suitable for use in polymer-based light modulator devices.
    Type: Grant
    Filed: November 27, 1992
    Date of Patent: October 11, 1994
    Assignee: AlliedSignal Inc.
    Inventors: Chengjiu Wu, Jianhui Shan, Ajay Nahata
  • Patent number: 5350878
    Abstract: This invention provides 1) novel reactive fluorinated compounds derived from a specified class of telomers or cotelomers of fluoroolefins; and 2) stable products and stable polymers thereof obtained by reaction or polycondensation of the novel reactive fluorinated compounds with specified classes of hydrogenated aliphatic, alicyclic, aromatic reactive compounds, telechelic oligomers and block polymers wherein said stable products and polymers contain hetero atoms such as oxygen, sulfur or nitrogen and are characterized by high thermal and chemical resistance.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: September 27, 1994
    Assignee: Dow Corning Corporation
    Inventor: Gerardo Caporiccio
  • Patent number: 5321046
    Abstract: Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.
    Type: Grant
    Filed: October 27, 1992
    Date of Patent: June 14, 1994
    Assignee: Bristol-Myers Squibb Company
    Inventors: Sing-Yuen Sit, John J. Wright, Jeff A. Field
  • Patent number: 5302757
    Abstract: A composition of matter including an onium salt and a method of forming images. The onium salt has a chromophore which absorbs ultraviolet radiation, an S, Se, As, N or P atom which is free of substituents exhibiting a higher energy occupied molecular orbital than the chromophore; an insulating group which links the chromophore to the S, Se, As, N or P atom of the salt and substantially prevents .pi. resonance from the chromophore through the S, Se, As, N or P atom; and an anion. The onium salt is capable of forming a Bronsted acid upon exposure to ultraviolet radiation in the presence of a proton source. In the method of forming images, the onium salt is exposed to ultraviolet radiation in the presence of a proton source, to convert said onium salt to a Bronsted acid.
    Type: Grant
    Filed: September 14, 1992
    Date of Patent: April 12, 1994
    Assignee: Eastman Kodak Company
    Inventor: Franklin D. Saeva
  • Patent number: 5288742
    Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: February 22, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Philip N. Edwards, David Waterson
  • Patent number: 5281730
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, or phenyl or benzyl which is unsubstituted or substituted by F, Cl, Br, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or di(C.sub.1 -C.sub.6 alkyl)amino.The compounds are suitable as .pi.-acceptors and electrical semiconductors, and they can be used for antistatic finishing of objects.
    Type: Grant
    Filed: April 15, 1993
    Date of Patent: January 25, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: John Zambounis
  • Patent number: 5231221
    Abstract: Compounds of the formula ##STR1## can advantageously be prepared by reacting compounds the formula II ##STR2## in which the substituents R.sup.1 -R.sup.4 have the meanings given, with the anhydride of the formula III ##STR3## in the presence of dimethyl sulfoxide and the acid corresponding to the anhydride of the formula III.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: July 27, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Winfried Hertzsch, Gerhard Jahne
  • Patent number: 5223643
    Abstract: The present invention relates to a multi-step process for the preparation of 1,1-difluoroalkanesulphenyl chlorides of the general formula (I):R--CH.sub.2 --CF.sub.2 --S--ClThe process comprises the following steps:(1) R.sup.1 --SH+R--CH.dbd.CF.sub.2 .fwdarw.R.sup.1 --S--CF.sub.2 --CH.sub.2 --R(2) R.sup.1 --S--CF.sub.2 --CH.sub.2 --R+chlorine agent.fwdarw.Cl--S--CF.sub.2 --CH.sub.2 --RStep (1) is carried out in a base at 0.degree. C.-250.degree. C., optionally in the presence of a solvent and/or a phase transfer catalyst. Step (2) is carried out at -78.degree. C.-100.degree. C., optionally in a solvent and optionally after the product of step (1) has been isolated. The final products are intermediates for organic syntheses.
    Type: Grant
    Filed: November 7, 1991
    Date of Patent: June 29, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Bohm, Albrecht Marhold, Dietmar Bielefeldt
  • Patent number: 5220048
    Abstract: Benzocyclobutene-1,2-dichlorides, -bromides and -iodides which are substituted in the benzene ring are accessible in good yields and short reaction times by reacting substituted 1,2-(dichloromethyl or dibromomethyl)-benzenes with NaI in acetonitrile as the solvent. They can be used together with dienophils, for example 1,4-quinones, in Diels-Alder reactions.
    Type: Grant
    Filed: May 24, 1989
    Date of Patent: June 15, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Marcus Baumann, Walter Fischer, Vratislav Kvita, Carl W. Mayer
  • Patent number: 5166446
    Abstract: Polyarylene sulfide having a much reduced content of impurities is prepared by reacting an aromatic polyhalide with an alkali metal sulfide in the presence of a polar organic solvent and subjecting the resulting polyarylene sulfide subsequently to an acid treatment, filtration through a screen having a mesh size of 50-100 .mu., and washing with, successively, the same solvent as used in the preparation of the polymer, water, an organic or inorganic acid, and water. The resulting polyarylene sulfide has a sodium content of less than 20 ppm.
    Type: Grant
    Filed: July 2, 1991
    Date of Patent: November 24, 1992
    Assignee: Akzo N.V.
    Inventors: Willem M. Barentsen, Petrus F. Beuker, Johannes M. L. Penninger
  • Patent number: 5123953
    Abstract: Compounds of formula: ##STR1## in which: n=0, 1, 2f=0, 1Ar is an optionally substituted phenyl or pyridyl groupU a chlorine or bromine atomV a bromine or chlorine or iodine atomB is C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 cycloalkyl, which are optionally substituted by 1 to 6 halogen atoms, phenyl or pyridyl or oxidized pyridyl, which are optionally substituted.Use of these compounds as herbicides which are selective but especially antigraminaceous at preemergence.
    Type: Grant
    Filed: April 10, 1990
    Date of Patent: June 23, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philipe Desbordes, Michel Euvrard, Francois De Reinach Hirtzbach, Christopher Pearson
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5087724
    Abstract: A process for producing a 4-benzoyl-5-hydroxylpyrazole of the formula III: ##STR1## which comprises reacting carbon monoxide and a 5-hydroxypyrazole of the formula II: ##STR2## with a substituted benzene of the formula I: ##STR3## in the presence of a base and a catalyst of Group VIII of the Periodic Table.
    Type: Grant
    Filed: May 7, 1990
    Date of Patent: February 11, 1992
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Norio Tanaka, Takuya Kakuta, Eiichi Oya, Masatoshi Baba
  • Patent number: 5082945
    Abstract: The present invention relates to a process for the preparation of perhaloalkylthioethers by bringing a perhaloalkyl halide, preferably a bromide or an iodide, into contact with a disulphide in the presence of zinc and of sulphur dioxide or of a dithionite or of a hydroxymethanesulphinate or of a formate anion and sulphur dioxide.
    Type: Grant
    Filed: December 12, 1989
    Date of Patent: January 21, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Claude Wakselman, Marc Tordeux, Bernard Langlois, Jean-Louis Clavel, Roland Nantermet
  • Patent number: 5055235
    Abstract: A process is disclosed for preparing a mixture of brominated, non-condensed ring polyaromatics, which process features multiple bromination temperatures and multiple catalyst additions for brominating the precursor non-condensed ring polyaromatic. The mixture has an average bromine number of about 6 to about 8 bromine atoms per molecule, a low melting point range, and a low amount of light end impurities.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: October 8, 1991
    Assignee: Ethyl Corporation
    Inventors: David R. Brackenridge, William T. Murray
  • Patent number: RE34423
    Abstract: A process for producing a 4-benzoyl-5-hydroxylpyrazole of the formula III: ##STR1## which comprises reacting carbon monoxide and a 5-hydroxypyrazole of the formula II: ##STR2## with a substituted benzene of the formula I: ##STR3## in the presence of a base and a catalyst of Group VIII of the Periodic Table.
    Type: Grant
    Filed: May 20, 1992
    Date of Patent: October 26, 1993
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Norio Tanaka, Takuya Kakuta, Eiichi Oya, Masatoshi Baba