Fluorine Or Iodine Patents (Class 568/775)
  • Patent number: 5658927
    Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5658951
    Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5606084
    Abstract: The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Andrew J. Poss, George Shia
  • Patent number: 5416235
    Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: May 16, 1995
    Assignee: Octel Chemicals Limited
    Inventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
  • Patent number: 5397802
    Abstract: Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may be a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.
    Type: Grant
    Filed: February 22, 1993
    Date of Patent: March 14, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
  • Patent number: 5281742
    Abstract: Disclosed are fluorobenzene derivatives, which are important intermediates for producing herbicidal oxazolidinedione derivatives, and methods of producing them. The fluorobenzene derivatives include compounds of a formula (11): ##STR1## where X is a halogen atom, R.sup.3 is a nitro, amino or isocyanato group or R.sup.1 OCONH, and R.sup.1 is an alkyl or phenyl group. Via the intermediates of the invention, oxazolidinedione derivatives can be produced with high yield.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: January 25, 1994
    Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.
    Inventors: Kenji Hirai, Tomoyuki Yano, Mitsuo Yamashita, Emiko Ejiri, Tomoko Tateno, Kiyomi Aizawa
  • Patent number: 5276214
    Abstract: A biphenyl compound having the formula (I) is newly separated into its optical active compound, and useful as an optically separating agent: ##STR1## wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH.sub.3, CF.sub.3, OH, OCH.sub.3, NH.sub.2 and N(CH.sub.3).sub.2 and Z is an atom or atomic group selected from among Cl, Br, I, CH.sub.3 and OCH.sub.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: January 4, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Fumio Toda
  • Patent number: 5164502
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: November 17, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5149858
    Abstract: Phenolic compounds, notably admixtures of 2,4-dichlorophenol and 2,6-dichlorophenol, are selectively chlorinated at the ortho positions thereof, with gaseous chlorine and in a molten medium, in the presence of a selectivity-enhancing effective amount of an organic cation.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: September 22, 1992
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
  • Patent number: 5118874
    Abstract: Compounds of the formula ##STR1## in which, independently of one another, each R is OH or lower alkyl having 1-4 carbon atoms and each R' is hydrogen or lower alkyl having 1-4 carbon atoms, are prepared by the condensation of partially fluorinated aromatic hydrocarbons in the presence of hydrogen fluoride or by the reductive coupling of partially fluorinated aromatic compounds. The compounds are used as a starting material for the preparation of partially fluorinated polycondensates.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: June 2, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Appel, Gunter Siegemund
  • Patent number: 5116982
    Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.
    Type: Grant
    Filed: August 6, 1990
    Date of Patent: May 26, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5087764
    Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.
    Type: Grant
    Filed: May 12, 1989
    Date of Patent: February 11, 1992
    Assignee: Merck Patent Gesellschaft mit beschrankter Hafung
    Inventors: Volker Reiffenrath, Joachim Krause
  • Patent number: 5086178
    Abstract: Fluorinated diazabicycloalkane derivative of the following Formula I: ##STR1## wherein n represents 0, 1 or 2; R represents a quaternizing organic group; each R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, aryl, C.sub.1 -C.sub.6 alkyl-substituted aryl or aryl-substituted C.sub.1 -C.sub.6 alkyl and each X.sup.- independently represents a conterion or 2X.sup.- represents a single divalent counterion, are electrophilic fluorinating agents.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: February 4, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Ronald E. Banks
  • Patent number: 5053557
    Abstract: A process is disclosed for preparing 2-chloro-4-fluorophenol which comprises chlorinating 4-fluorophenol with a chlorinating agent in the presence of water. The process according to the present invention has advantages in that the chlorination can be carried out using inexpensive reagents without requiring the use of particular apparatus and under mild conditions, and the desired product can be obtained in good yields and with high selectivity. 2-Chloro-4-fluorophenol obtained in the present invention is useful as a starting material for producing various pharmaceutical agents and agricultural agents.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: October 1, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Kenji Hirai, Mitsuo Yamashita
  • Patent number: 5032592
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring a is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl, and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: July 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 5026929
    Abstract: A process is disclosed for making a highly fluorinated aromatic compound by contacting a perfluorocycloalkane, such as perfluorodecahydronaphthalene, with a complex of a metal from Groups IA and IIA of the Periodic Table and an organic electron acceptor. The reaction is carried out in an organic solvent and under reducing conditions which are relatively moderate. Best results are obtained using a perfluorocycloalkane having 2-4 condensed rings and a complex of either sodium or lithium and benzophenone thereby making a perfluorinated condensed ring aromatic compound such as perfluoronaphthalene or perfluorophenanthrene.
    Type: Grant
    Filed: February 8, 1990
    Date of Patent: June 25, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John A. Marsella, Guido P. Pez, Anne M. Coughlin
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4996377
    Abstract: Aliphatically substituted fluorobenzenes of the general formula I ##STR1## where R is an aliphatic or cycloaliphatic radical, n is 2, 3 or 4 and X is hydrogen, fluorine, chlorine or bromine, are prepared by diazotization of the corresponding aniline derivative of the general formula II ##STR2## in the presence of tetrafluoboric acid and decomposition of the resulting diazonium tetrafluoborate of the general formula III ##STR3## by a process in which the decomposition reaction is carried out simultaneously with the diazotization reaction, in the presence of elemental copper and/or copper(I) and/or copper(II) salts and at from -15.degree. to 80.degree. C.
    Type: Grant
    Filed: February 21, 1990
    Date of Patent: February 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochen Wild, Albrecht Harreus, Norbert Goetz
  • Patent number: 4940821
    Abstract: Fluorophenols are prepared by heating a chlorofluorobenzene with water in the presence of a copper salt at a pH of from 3.0 to 6.5.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: July 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, James A. Gall
  • Patent number: 4939172
    Abstract: Novel cyclopropane carboxylic acid esters of all possible stereoisomeric forms and mixtures thereof of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, fluorine, chlorine and bromine, R is selected from the group consisting of optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, optionally unsaturated cycloalkyl of 3 to 8 carbon atoms optionally substituted, optionally substituted aryl of 6 to 14 carbon atoms and optionally substituted heterocycle, Z is selected from the group consisting of hydrogen, --CH.sub.3, --CN and --C.tbd.CH and Y is selected from the group consisting of hydrogen, --OH, optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, --CN, --(CH.sub.2).sub.m --OAlk, --(CH.sub.2).sub.m --S--Alk, ##STR2## m is 0,1,2,3 or 4, Alk is alkyl of 1 to 12 carbon atoms, --Si(Alk').sub.3, Alk' is optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted, --O--Ar and --(CH.sub.2).sub.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: July 3, 1990
    Assignee: Roussel Uclaf
    Inventors: Joseph Cadiergue, Jacques Demassey, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4873329
    Abstract: A compound of the formula ##STR1## wherein X has the formula ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl; wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano, trifluoromethyl, alkylthio, alkylsulphinyl and alkylsulphonyl or each is hydrogen, alkyl, alkoxy or dialkylamino provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent; wherein R.sup.5 and R.sup.6, which may be the same or different, each is hydrogen, halogeno or alkyl; wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 is carbamoyl, alkyl, cycloalkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkanoyl, alkylcarbamoyl, dialkylcarbamoyl or aroyl; or wherein R.sup.
    Type: Grant
    Filed: February 21, 1985
    Date of Patent: October 10, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, John Oldfield, Howard Tucker
  • Patent number: 4855512
    Abstract: 2- and 3-fluorophenols are prepared by dehydrating 1,2-dihydroxy-3-fluorocyclohexa-3,5-diene under basic conditions and recovering the desired product, for example by fractional distillation.
    Type: Grant
    Filed: March 25, 1988
    Date of Patent: August 8, 1989
    Assignee: Shell Oil Company
    Inventor: George Ryback
  • Patent number: 4828764
    Abstract: N-fluoro-N-perfluoromethyl sulfonamide compounds are provided as fluorinating agents for the fluorination of organic compounds by either the direct electrophilic fluorination of organic compounds or by the fluorination of organic compound carbanions.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: May 9, 1989
    Assignee: Research Corporation
    Inventor: Darryl D. DesMarteau
  • Patent number: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4708966
    Abstract: 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: Grant
    Filed: June 27, 1986
    Date of Patent: November 24, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
  • Patent number: 4691057
    Abstract: The reaction of alkali metal with aromatic hydroxy compounds is promoted by inclusion of an alcohol in the reaction mixture. The alkali metal aryloxide formed can be reacted with phosphonitrilic chloride polymers to make polyaryloxyphosphazenes.
    Type: Grant
    Filed: September 19, 1984
    Date of Patent: September 1, 1987
    Assignee: Ethyl Corporation
    Inventor: Allan A. Eisenbraun
  • Patent number: 4656311
    Abstract: A process for preparing hydroxylated aromatic compounds optionally bearing at least one trifluoromethyl, trifluoromethoxy or trifluoromethylthio group. A chloroformate or fluoroformate, optionally bearing at least one trihalomethyl-, trihalomethoxy- or trihalomethylthiophenyl group, is reacted with liquid hydrofluoric acid.The aromatic compounds obtained are useful as synthesis intermediates in the pharmaceutical or the plant-protection industry.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: April 7, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4620042
    Abstract: 2-Chloro-4-fluorophenol is obtained with good yield by direct chlorination of 4-fluorophenol with chlorine gas at 0.degree.-185.degree. C. in the absence of catalyst. In a combination of these reactants, the selectivity to the substitution chlorination reaction at the 2-position of 4-fluorophenol is uncommonly high and reaches about 99% under optimum conditions. 4-Fluorophenol is subjected to the reaction as either pure liquid or solution in a suitable organic solvent such as carbon tetrachloride or acetic acid.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: October 28, 1986
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Ysunobu Nishimura, Katumi Kanesaki
  • Patent number: 4607128
    Abstract: Novel compounds of the general formula ##STR1## in which X is hydrogen or chlorine, and each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently is hydrogen, methyl or ethyl, are useful intermediates in the preparation of the corresponding phenols. They may be prepared by treating a compound of the formula ##STR2## in which Hal is chlorine or fluorine, with a compound of the formulaHO--CHR.sup.1 --CR.sup.2 .dbd.CR.sup.3 R.sup.4in the presence of a base.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: August 19, 1986
    Assignee: Shell Oil Company
    Inventors: Paul H. Briner, Ronald F. Mason
  • Patent number: 4599462
    Abstract: Novel composites or solid solutions made from heretofore immiscible chemical components and methods for making such composites or solid solutions. A wall of a deposition cell is cooled to a temperature within the range of about -273.degree. C. to about -20.degree. C. A solid host component and one or more guest components are vaporized and codeposited onto the cold wall of the deposition cell so as to form a solid solution. The resultant solid solutions are stable at room temperature and often at much higher temperatures. The present invention also provides methods for modifying the surface structure of solid materials.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: July 8, 1986
    Assignee: University of Utah
    Inventor: Josef Michl
  • Patent number: 4524032
    Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: June 18, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
  • Patent number: 4523041
    Abstract: A method of efficiently purifying crude 4-fluorophenol containing phenol as impurity. Phthalic acid or its anhydride, or a suitable derivative of phthalic acid, and a dehydrating agent such as sulfuric acid or a metal chloride are mixed with the crude 4-fluorophenol, and the mixture is kept in a liquid state usually with moderate heating to 30.degree.-180.degree. C. until completion of condensation reaction between phenol and the phthal-compound. After that pure 4-fluorophenol can easily be recovered by distillation or recrystallization.
    Type: Grant
    Filed: May 25, 1984
    Date of Patent: June 11, 1985
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Haruo Suzuki, Shouzou Kaneda
  • Patent number: 4510338
    Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 9, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4508926
    Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 2, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4504689
    Abstract: This invention relates to a process for preparing phenates substituted by halogen groups of the corresponding phenols which comprises reacting a halo-substituted benzene with a powdered base having a particle size of less than 4 mm in the presence of an aprotic polar solvent.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: March 12, 1985
    Inventor: Serge Veracini
  • Patent number: 4478760
    Abstract: The process for making a fluorinated product comprising reacting a perfluoroalkyl iodide and an olefin in the presence of a finely divided zinc and an acidic solvent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 23, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
  • Patent number: 4476328
    Abstract: A novel trifluoropropyl derivative of mono-substituted benzene represented by the general formula: ##STR1## wherein R is halogen atom, hydroxy, trifluoromethyl, n-octyl, n-dodecyl, or phenoxy group not substituted or mono-substituted by 3,3,3-trifluoropropyl group, and n is an integer of 1, 2 or 3, with the proviso that the total number of 3,3,3-trifluoropropyl group of the derivative of mono-substituted benzene is at most 3, and a process for producing the derivative of mono-substituted benzene.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: October 9, 1984
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Masaaki Takahashi, Takashi Yamauchi
  • Patent number: 4467121
    Abstract: Fluorinated bisphenols having a fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are prepared at atmospheric pressure or at low pressures from a phenol reactant and a fluorinated aldehyde compound in the presence of gaseous hydrogen chloride or gaseous hydrogen bromide catalyst. The fluorinated bisphenols having the fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are produced in excellent yields and are used for making flame-retardant polycarbonates and polyester-carbonate copolymers.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: August 21, 1984
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4454158
    Abstract: 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: Grant
    Filed: June 1, 1981
    Date of Patent: June 12, 1984
    Assignee: Merrell Toraude et Compagnie
    Inventor: Philippe Bey
  • Patent number: 4366330
    Abstract: An intermediate useful in the production of liquid crystal esters has a molecular structure ##STR1## in which of the groups R' and R" one is fluorine and the other is hydrogen, and in which R is an alkyl group having more than one carbon atom, an aryl substituted alkyl group or a cyclohexyl substituted alkyl group.These compounds may be prepared from the corresponding alkoxy compounds ##STR2## where R'" is a protective alkyl group such as methyl. These compounds may be used in the production of liquid crystal esters by a conventional esterification with carboxylic acids, or acid derivative, eg chloride, eg containing the radical ##STR3## where X is an alkyl group and ##STR4## is a benzene or cyclohexane ring.
    Type: Grant
    Filed: September 30, 1980
    Date of Patent: December 28, 1982
    Assignees: BCH Chemicals Limited, The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern Ireland
    Inventors: George W. Gray, David Lacey, John A. Jenner, Martin G. Pellatt
  • Patent number: 4365098
    Abstract: Fluorinated bisphenols having a fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are prepared at atmospheric pressure or at low pressures from a phenol reactant and a fluorinated aldehyde compound in the presence of gaseous hydrogen chloride or gaseous hydrogen bromide catalyst. The fluroinated bisphenols having the fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are produced in excellent yields and are used for making flame-retardant polycarbonates and polyester-carbonate copolymers.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: December 21, 1982
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4365099
    Abstract: A method of improving the performance of cationic exchange catalysts used in the production of bisphenols from phenolic compounds and carbonyl compounds by pretreating the phenolic compound with a chelating resin to remove metallic impurities.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: December 21, 1982
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Ashok K. Mendiratta
  • Patent number: 4262152
    Abstract: A process for preparing trifluoromethylphenyl nitro phenylethers which comprises treating a trifluoromethylhalobenzene with a base in a cosolvent system to afford a trifluoromethyl phenolate which may be isolated as its free phenol or reacted with an appropriately substituted halobenzene to afford a diphenylether herbicide or a precursor thereto.
    Type: Grant
    Filed: May 2, 1979
    Date of Patent: April 14, 1981
    Assignee: Rohm and Haas Company
    Inventor: Wayne O. Johnson
  • Patent number: 4259510
    Abstract: A process for preparing trifluoromethylphenyl nitro phenylethers which comprises treating a trifluoromethylhalobenzene with a base in a cosolvent system to afford a trifluoromethyl phenolate which may be isolated as its free phenol or reacted with an appropriately substituted halobenzene to afford a diphenylether herbicide or a precursor thereto.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: March 31, 1981
    Assignee: Rohm and Haas Company
    Inventor: Wayne O. Johnson
  • Patent number: 4225731
    Abstract: A process for the preparation of a trifluoromethylphenol or the corresponding alkoxy compound which comprises contacting a halogenobenzotrifluoride of the formula ##STR1## in which X denotes halogen,R.sup.1, R.sup.2 and R.sup.3 denote hydrogen, trifluoromethyl or a substituent which promotes the replacement of X by a hydroxyl group andY denotes hydrogen, a halogen or alkoxy, at least one of the substituents R.sup.1, R.sup.2 and R.sup.3 representing a trifluoromethyl group and at least one of them representing a substituent which promotes the replacement of the radical X by a hydroxyl group,with an excess aqueous alkali metal hydroxide in an alcoholic solution in the presence of a quaternary onium salt.
    Type: Grant
    Filed: July 13, 1978
    Date of Patent: September 30, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Erich Klauke
  • Patent number: 4192669
    Abstract: Ethers, such as 2-[[4-[4-(trifluoromethoxy)phenoxy]phenoxy]]propanoic acid, methyl ester, useful for control of weeds.
    Type: Grant
    Filed: December 22, 1977
    Date of Patent: March 11, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John B. Adams, Jr., Joel B. Wommack, Jr.
  • Patent number: 4182918
    Abstract: A process has been invented for the preparation of dihydric substituted phenols which comprises reacting a solution, which is essentially anhydrous and free from hydrogen peroxide, of a percarboxylic acid in an inert organic solvent with a monohydric substituted phenol, which is derived from benzene, naphthalene or anthracene and still contains at least one free hydrogen atom in the aromatic nucleus, at temperatures from about -20.degree. C. to about 120.degree. C.The dihydric substituted phenols obtained according to the invention are known, important industrial intermediate products used in the fields of photography, dyestuffs and plastics, as well as in the scent and flavoring areas.
    Type: Grant
    Filed: December 5, 1977
    Date of Patent: January 8, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hermann Seifert, Helmut Waldmann, Wulf Schwerdtel, Wolfgang Swodenk
  • Patent number: 4168388
    Abstract: Trifluoromethylphenols are prepared by hydrogenation of the corresponding trifluoromethylbenzylethers.
    Type: Grant
    Filed: March 23, 1978
    Date of Patent: September 18, 1979
    Assignee: Eli Lilly and Company
    Inventors: Edward R. Lavagnino, Bryan B. Molloy, Paul Pranc
  • Patent number: 4152529
    Abstract: Halogenated alkyl substituted phenols may be dealkylated by treating a compound such as 5-t-butyl-2-fluorophenol with a diealkylation catalyst such as an acid acting compound at dealkylation conditions whereby the t-butyl substituent is removed and the resulting compound comprising 2-fluorophenol is recovered.
    Type: Grant
    Filed: November 16, 1977
    Date of Patent: May 1, 1979
    Assignee: UOP Inc.
    Inventors: Nils J. Christensen, Joseph Levy
  • Patent number: 4124643
    Abstract: 3-Fluorosalicylaldehyde may be prepared in a more economical manner by alkylating o-fluorophenol with an allyl halide such as allyl chloride, thereafter rearranging the resultant o-fluorophenyl allyl ether to form allyl-o-fluorophenol. The latter compound is then isomerized to form propenyl-o-fluorophenol. Thereafter this compound is subjected to ozonolysis at a subambient temperature to form the desired compound, namely, 3-fluorosalicylaldehyde.
    Type: Grant
    Filed: August 3, 1977
    Date of Patent: November 7, 1978
    Assignee: UOP Inc.
    Inventors: Michael Martan, Dusan J. Engel