Halogen Containing Patents (Class 568/649)
  • Patent number: 4959391
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: July 14, 1988
    Date of Patent: September 25, 1990
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin O. Kiesewetter, Ulrich G. P. Seippl
  • Patent number: 4956123
    Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4946865
    Abstract: A compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group and Y is a hydrogen atom, a halogen atom, a cyano group, a formyl group, an ethylene-dioxymethyl group, a hydroxyl group, a hydroxymethyl group or a group of either one of the formulas: --CH.dbd.N--OR.sup.1, --COOR.sup.2, --CONH--R.sup.2 and --CH(OR.sup.3).sub.2 in which R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group, a halo(C.sub.3 -C.sub.5)alkynyl group or a C.sub.1 -C.sub.3 alkyl group substituted with a phenyl group or a cyano group, R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or a C.sub.3 -C.sub.5 alkynyl group and R.sup.3 is a C.sub.1 -C.sub.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: August 7, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Shigeko Nakamura
  • Patent number: 4940807
    Abstract: 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: Grant
    Filed: June 12, 1989
    Date of Patent: July 10, 1990
    Assignee: Ethyl Corporation
    Inventor: Robert N. DePriest
  • Patent number: 4895987
    Abstract: Ruthenium-cobalt- or cobalt-containing catalysts which have been promoted with phosphonites or phosphinites effectively catalyze the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of these phosphonite- or phosphinite-promoted cobalt or ruthenium- cobalt catalysts to form the monomethyl ether of ethylene glycol. In a like manner acetaldehyde may be converted to the corresponding propylene glycol monoether. The process may advantageously be carried out with high yields and selectivities in the presence of a polar or non-polar organic solvent in combination with the catalyst system of this invention.The invention is also directed to the phosphonite- or phosphonite-promoted cobalt and ruthenium-cobalt catalyst system per se.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: January 23, 1990
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Robert E. Ledley
  • Patent number: 4891450
    Abstract: The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ -CH.sub.2 -Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: January 2, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robin A. E. Carr, Lyn Powell
  • Patent number: 4870064
    Abstract: A compound of the formula: ##STR1## wherein X is a halogen atom and Y is a C.sub.1 -C.sub.4 alkyl group, a C.sub.2 -C.sub.4 alkenyl group, a C.sub.1 -C.sub.3 alkoxy group, a C.sub.3 -C.sub.4 alkenyloxy group, a C.sub.3 -C.sub.4 alkynyloxy group, a C.sub.2 -C.sub.3 alkenyl group substituted with phenyl, a C.sub.3 -C.sub.4 alkenyloxy group substituted with halogen, a C.sub.1 -C.sub.3 alkoxy group substituted with one member selected from the group consisting of halogen, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkanoyl, cyano, hydroxycarbonyl, C.sub.1 -C.sub.3 alkylaminocarbonyl and phenyl, or a group of the formula: --CH.sub.2 O--R.sup.1, --CH.dbd.CH--R.sup.2, --CH.dbd.N--R.sup.3 or --CO--R.sup.4 in which R.sup.1 is a C.sub.1 -C.sub.3 alkyl group, a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, R.sup.2 is a cyano group, a methoxycarbonyl group or an acetyl group, R.sup.3 is a dimethylamino group or a phenyl group and R.sup.4 is a C.sub.1 -C.sub.
    Type: Grant
    Filed: July 29, 1987
    Date of Patent: September 26, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Shigeko Nakamura
  • Patent number: 4840971
    Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4816596
    Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: March 28, 1989
    Assignee: Rhone-Polenc Specialites Chimoues
    Inventor: Bernard Langlois
  • Patent number: 4804787
    Abstract: This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.
    Type: Grant
    Filed: October 9, 1985
    Date of Patent: February 14, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
  • Patent number: 4798906
    Abstract: Alkyl-, aryl- or alkylaryl-alkoxy halides are prepared by reacting the corresponding alcohol, phenol or alkyl phenol with ethylene oxide and/or propylene oxide in the presence of an amine catalyst to form an alkoxy alcohol, and directly reacting the latter with a halogenating agent in the continuing presence of the amine catalyst.Neutralization of the product and/or catalyst removal from the first stage is no longer necessary and reaction rates and yields are increased in the second stage.
    Type: Grant
    Filed: July 29, 1987
    Date of Patent: January 17, 1989
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Philip K. G. Hodgson, Nevin J. Stewart
  • Patent number: 4760087
    Abstract: Phenol derivatives of the formula ##STR1## wherein A and B have the same or different meanings and each represent one of the groups --C.tbd.C--, cis--CH.dbd.CH-- or trans--CH.dbd.CH--, R.sub.1 is hydrogen, an optionally substituted alkyl or phenyl group or a cycloalkyl group, R.sub.2 is hydrogen, methyl or ethyl, R.sub.3 represents hydrogen, acetyl or propionyl, R.sub.4 has the same meaning as R.sub.3 or represents an alkyl group, R.sub.5 is a carboxylic or a hydroxy group or a functional derivative of such groups or R.sub.5 is a nitrile group and R.sub.6 is hydrogen, an alkyl group or the group OR.sub.4 which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds are prepared by reacting suitable acetylene compounds or metal derivatives thereof with alkyl or aryl halides or by means of Wittig reactions optionally followed by transforming the member R.sub.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: July 26, 1988
    Assignee: Gruenenthal GmbH
    Inventors: Oswald K. Zimmer, Werner P. Vollenberg, Gerriet K. H. Loschen, Werner Winter, Erwin Kiesewetter, Ulrich G. P. Seipp
  • Patent number: 4695657
    Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: September 22, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4678811
    Abstract: New substituted benzyl-type ethers of formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, C.sub.2-4 -alkynyloxy, halo-C.sub.2-4 -alkynyloxy, phenyl-C.sub.2-4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or one of these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 7, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4675421
    Abstract: Compound of the general formula ##STR1## wherein R represents an ether protecting group useful as intermediates.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: June 23, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Richard Barner, Josef Hubscher
  • Patent number: 4670604
    Abstract: 4-Acylresorcinol ethers of the formula ##STR1## in which R.sub.1 is lower alkyl, R.sub.2 is fluorinated lower alkyl, R.sub.3 is hydrogen, lower alkoxy, trifluoromethyl or halogen, alk is an alkylene or hydroxyalkylene radical which is uninterrupted or interrupted by oxygen, one of the radicals R.sub.4, R.sub.5 and R.sub.7 is a group of the formula --NH--C(.dbd.O)--R.sub.8, a radical R.sub.4 or R.sub.5 which differs from this is a radical R.sub.9 and a radical R.sub.7 which differs from this is a radical R.sub.10, R.sub.6 is hydrogen, lower alkyl, trifluoromethyl, halogen, carboxyl which is free, esterified or amidated, cyano or lower alkanoyl, R.sub.8 is carboxyl which is free, esterified or amidated or 5-tetrazolyl, R.sub.9 is hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl and R.sub.10 is hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, cyano or carboxyl which is free, esterified or amidated, and their salts have antiallergic and antiinflammatory properties.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: June 2, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Andreas Beck, Alfred Sallmann, Robert W. Lang, Paul Wenk
  • Patent number: 4663489
    Abstract: The cobalt carbonyl catalyst R.sup.5 CCo.sub.3 (CO).sub.9, desirably with Ru.sub.3 (CO).sub.12, wherein R.sup.5 is hydrogen; alkyl, preferably C.sub.1-5 lower alkyl; cycloalkyl or substituted cycloalkyl; cycloalkenyl, such as cyclohexenyl or cyclooctenyl; C.sub.1-12 alkoxy, such as methoxy or propoxy; aryl or alkyl-, cycloalkyl-, alkoxy-, halo-, or cyano-substituted aryl; cyano; or a silyl carbyne moiety of the formula R.sub.3.sup.6 Si, wherein R.sup.6 is alkyl or aryl, effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas; i.e., CO and H.sub.2, in the presence of this catalyst system to form the corresponding ethylene glycol monomethyl ether.The novel catalyst combination of R.sup.5 CCo.sub.3 (CO).sub.9 and Ru.sub.3 (CO).sub.12 is likewise claimed herein.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: May 5, 1987
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, Harry K. Myers, Jr., James E. Lyons
  • Patent number: 4650910
    Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: March 17, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
  • Patent number: 4650873
    Abstract: Processes for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide.
    Type: Grant
    Filed: May 1, 1986
    Date of Patent: March 17, 1987
    Assignee: Riker Laboratories
    Inventor: Charles M. Leir
  • Patent number: 4629814
    Abstract: 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: Grant
    Filed: August 27, 1985
    Date of Patent: December 16, 1986
    Assignee: Rohm and Haas Company
    Inventor: Michael P. James
  • Patent number: 4621160
    Abstract: A process for the chlorination of aromatic derivatives. The aromatic derivative is reacted with chlorine gas in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: November 4, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4618729
    Abstract: The ruthenium-cobalt carbonyl metal cluster catalyst Co.sub.2 Ru(CO).sub.11 effectively catalyzes the dealkoxyhydroxymethylation of aldehyde acetals to form glycol monoethers. Methylal, for example, may be reacted with syngas, i.e., CO and H.sub.2, in the presence of this ruthenium-cobalt cluster catalyst to form the monomethyl ether of ethylene glycol.
    Type: Grant
    Filed: October 2, 1985
    Date of Patent: October 21, 1986
    Assignee: Sun Refining and Marketing Company
    Inventors: D. Michael Duggan, James E. Lyons, Harry K. Myers, Jr.
  • Patent number: 4618627
    Abstract: A catechol derivative represented by the formula ##STR1## The compounds of this invention are useful for the prophylaxis and treatment for various allergic diseases, ischemic heart diseases and inflammations caused by slow reacting substance of anaphylaxis (SRS-A), since the compounds inhibit very potently the formation and release of SRS-A.
    Type: Grant
    Filed: May 11, 1984
    Date of Patent: October 21, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Murase, Toshiyasu Mase, Hideki Arima, Kenichi Tomioka
  • Patent number: 4610996
    Abstract: Phenoxytriazolyl ketones and carbinols of the formula ##STR1## in which A represents the keto group or the CH(OH) grouping andR represents hydrogen, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkylcarbonyl, optionally substituted benzyl or optionally substituted phenoxymethyl,or addition products thereof with acids or metal salts, which possess fungicidal activity.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Kraatz, Karl H. Buchel, Paul Reinecke, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 4609735
    Abstract: Novel 1-aryloxy-4-amino-2-butanols of the formulaArO--CH.sub.2 --CHOH--CH.sub.2 --CH.sub.2 --NR.sup.1 R.sup.2wherein AR is 1-naphythyl, 2-naphthyl, indene-4(or 5-)yl, 3-(or 5-)chloro-2-pyridyl, phenyl, monosubstituted phenyl or di-substituted phenyl, R.sup.1 is lower alkyl, phenyl, phenylalkyl, 2-hydroxymethyl-2-propyl, adamantyl or lower-cycloalkyl, R.sup.2 is hydrogen or lower alkyl, wherein R.sup.1 and R.sup.2 together with the adjacent nitrogen form a heterocyclic residue and the pharmaceutically acceptable acid addition salts thereof having local anesthetic, beta-adrenergic blocking, antihypertensive and antiarrhythmic properties are disclosed. The compounds are prepared by reacting novel 1-aryloxy-4-chloro-2-butanols with amines. Methods for the preparation of the novel 1-aryloxy-4-chloro-2-butanol intermediates are also disclosed.
    Type: Grant
    Filed: September 11, 1984
    Date of Patent: September 2, 1986
    Assignee: A. H. Robins Company, Inc.
    Inventors: Carl D. Lunsford, Ying-Ho Chen
  • Patent number: 4605785
    Abstract: The invention relates to new 1,1-diphenylpropan-1-ol derivatives 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,R.sub.3 is halogen, trihalomethyl, alkyl having from one to 5 carbon atoms or alkoxy having from one to 5 carbon atoms,R.sub.4 is phenyl optionally substituted by one or more identical or different substituents selected from the group of halogen, trihalomethyl, alkyl, alkoxy, cyano, nitro, amino, alkylamino, dialkylamino, hydroxyl, carboxyl or substituted carboxyl; dialkylaminocarbonyl or alkoxycarbonyl containing from one to 4 carbon atoms in the alkyl and alkoxy moieties, respectively,n is 1, 2, 3, 4, or 5.According to another aspect of the invention there are provided processes for the preparation of the compounds of formula (I).
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: August 12, 1986
    Assignee: Richter Gedeon Vegyeszeti Gyar RT
    Inventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolcs Szeberenyi, Laszlo Szporny, Sandor Gorog, Istvan Hajdu
  • Patent number: 4605784
    Abstract: 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: Grant
    Filed: July 18, 1985
    Date of Patent: August 12, 1986
    Assignee: Eastman Kodak Company
    Inventors: Robert J. I. Eubanks, James G. Pacifici
  • Patent number: 4604243
    Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.
    Type: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4600787
    Abstract: Aromatic compounds which contain perfluorinated side-chains bonded via a heteroatom are prepared by treating aromatic compounds, which contain side-chains which are perhalogenated, but only partially fluorinated, and bonded via heteroatom, with a catalyst capable of transferring halogen atoms.
    Type: Grant
    Filed: April 23, 1984
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Erich Klauke
  • Patent number: 4595763
    Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: June 17, 1986
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4582905
    Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen; Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: April 15, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventor: Makiko Sakai
  • Patent number: 4579981
    Abstract: An improved process for the preparation of 2-chloro-1,3-dimethoxybenzene involving the reaction of [2,6-dimethoxyphenyl]lithium with chlorinating agents is disclosed. 2-Chloro-1,3-dimethoxybenzene is useful as a starting material for the synthesis of pharmacologically valuable 1,2-benzisoxazoloxyacetic acids.
    Type: Grant
    Filed: August 13, 1984
    Date of Patent: April 1, 1986
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Gregory M. Shutske, Thomas B. K. Lee, Gregory M. Jobin
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4568497
    Abstract: Preparation of monoethers of dihydroxybenzenes from an alkenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: February 4, 1986
    Assignee: The Dow Chemical Company
    Inventors: Abel Mendoza, Eric W. Otterbacher
  • Patent number: 4560811
    Abstract: Novel methods for making chlorohydrins are provided using a Lewis acid catalyst with an olefin and peroxy compound or where an enantiomer is desired, a Lewis acid catalyst in combination with a chiral alcohol, particularly glycol, and a combination of a peroxy compound and alkenol. In certain situations, an epoxide may be employed.
    Type: Grant
    Filed: January 18, 1984
    Date of Patent: December 24, 1985
    Assignee: Massachusetts Institute of Technology
    Inventors: Karl B. Sharpless, Roy A. Johnson
  • Patent number: 4558129
    Abstract: Novel compounds of the general formula: ##STR1## and the pharmaceutically acceptable esters and acid addition salts thereof, wherein:R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each independently hydrogen, lower alkyl, lower alkoxy, trifluoromethyl, halo, lower alkylthio, lower alkyl sulfinyl, lower alkyl sulfonyl; orR.sup.2 and R.sup.3 together form --OCH.sub.2 O--; andR.sup.10 and R.sup.11 are each independently hydrogen or lower alkyl.These compounds combine .beta.-blockade and calcium entry blockade properties in the same compound and therefore are useful in therapy in the treatment of cardiovascular diseases, including hypertension, arrhythmias and variant and exercise induced angina.
    Type: Grant
    Filed: May 18, 1983
    Date of Patent: December 10, 1985
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Robin D. Clark, Arthur M. Strosberg
  • Patent number: 4543430
    Abstract: Process for the preparation of addition products of epoxides and hydroxylated compounds, characterized by the fact that it comprises the reaction of an epoxide and a hydroxylated compound in the homogeneous liquid phase, in the presence, as catalyst, of a salt of trifluoromethanesulphonic acid.
    Type: Grant
    Filed: November 7, 1983
    Date of Patent: September 24, 1985
    Assignee: BP Chimie Societe Anonyme
    Inventors: Daniel Falgoux, Danielle Simoulin, Michel Pascal-Mousselard
  • 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: 4518795
    Abstract: The di-ester of beta-pentabromophenoxyethanol and succinic acid, bis(beta-pentabromophenoxyethyl) succinate, is prepared by mono-ethoxylating pentabromophenol with ethylene oxide, then esterifying the resulting pentabromophenoxyethanol with succinic acid. The di-ester is a flame retardant for ABS.
    Type: Grant
    Filed: December 2, 1982
    Date of Patent: May 21, 1985
    Assignee: Borg-Warner Chemicals, Inc.
    Inventor: Yuval Halpern
  • Patent number: 4518788
    Abstract: Aromatic polyvinylethers and active hydrogen compound reaction products thereof have been found to provide fast heat curable molding compositions when used with various heat activated curing catalysts, for example, diaryliodonium salts in combination with aromatic polyvinylether soluble copper compounds, or dialkylhydroxyarylsulfonium salts in combination with certain organic oxidants.
    Type: Grant
    Filed: January 20, 1983
    Date of Patent: May 21, 1985
    Assignee: General Electric Company
    Inventor: James V. Crivello
  • Patent number: 4514409
    Abstract: 5-Aryloxy-5-azolyl-3,3-dimethylpent-1-en-4-ones and -ols of the formula ##STR1## in which Ar is an optionally substituted aryl group,Az is a 1,2,4-triazol-1-yl, 1,2,4-triazol-4-yl or imidazol-1-yl group, andB is a keto group of a CH(OH) grouping,or addition products thereof with physiologically acceptable acids or metal salts are suitable for use as plant protection agents, and can be employed with particularly good success for combating those fungi which cause powdery mildew diseases, thus for combating Erysiphe species, Sphaerotheca species and Podosphaera species, and for combating diseases of rice.
    Type: Grant
    Filed: July 14, 1982
    Date of Patent: April 30, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Manfred Jautelat, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4504685
    Abstract: Hydroxyl compounds are oxyalkylated by contacting them with an alkylene oxide, such as ethylene oxide or propylene oxide, in the presence of a perfluorocarbon polymer containing pendant sulfonic acid groups.
    Type: Grant
    Filed: August 19, 1980
    Date of Patent: March 12, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4493846
    Abstract: A compound of the formula ##STR1## wherein X.sup.1 is a free or esterified carboxyl group, a hydroxymethyl group, a cyano group, a group of the formula: ##STR2## (R.sup.a and R.sup.b are each independently a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.7 cycloalkyl group, a benzyl group, a phenyl group, a phenyl group substituted with a halogen atom or a C.sub.1 -C.sub.4 alkyl group, or, when taken together with the adjacent nitrogen atom to which they are attached, they represent a 5 to 7-membered saturated heterocyclic group) or a group of the formula: ##STR3## (R.sup.a and R.sup.b are each as defined above), Y is an ethylene group or a vinylene group, R.sup.1 is a hydrogen atom, a hydroxyl group or a protected hydroxyl group, R.sup.2 is a hydrogen atom or R.sub.1 and R.sub.2, when taken together, means a single linkage to form a double bond between the carbon atoms which they are linked, R.sup.3 is a hydroxyl group or a protected hydroxyl group, R.sup.4 is a hydrogen atom or a C.sub.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: January 15, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Keiichi Ono, Akihiko Sugie, Hajime Kawakami, Shunsuke Sami, Atsuyuki Kojima, Junki Katsube
  • Patent number: 4489212
    Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: December 18, 1984
    Assignee: Shell Oil Company
    Inventor: Thomas H. Johnson
  • Patent number: 4487953
    Abstract: Compounds of Formula (I) ##STR1## wherein the 9-bromine atom can be in the .alpha.- or .beta.-position,R.sub.1 is CH.sub.2 OH or C(O)OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is C(O)NHR.sub.3 wherein R.sub.3 is an acid residue or R.sub.2 ; andA is --CH.sub.2 --CH.sub.2 -- or cis --CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 --, trans --CH.dbd.CH--, or --C.tbd.C--;W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position; D and E together are a direct bond; orD is straight-chain, branched, or cyclic alkylene of 1-10 carbon atoms, optionally substituted by fluorine atoms; andE is oxygen, sulfur, a direct bond --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 are different from each other and each is hydrogen, chlorine, or C.sub.1 -C.sub.4 -alkyl;R.sub.4 is a free or functionally modified hydroxy group;R.sub.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: December 11, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger
  • Patent number: 4479901
    Abstract: Process for fluorinating an organic carbanion, which process comprises contacting and reacting, in a dry inert atmosphere, the compound of the formula selected from ##STR1## wherein ##STR2## is the carbanion, M is a counter ion, and X is a halide and a selected N-flouro-N-alkylsulfonamide.
    Type: Grant
    Filed: August 15, 1983
    Date of Patent: October 30, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William E. Barnette
  • Patent number: 4454339
    Abstract: 9-Fluoroprostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is the residue ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 and A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C,W is a free or functionally modified hydroxymethylene group wherein the OH-group can be in the .alpha.- or .beta.-position,D and E jointly are a direct bond orD is straight-chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen or sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine, or alkyl,R.sub.4 is a free or functionally modified hydroxy group, andR.sub.5 is hydrogen, an optionally substituted aliphatic group, e.g.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: June 12, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4443625
    Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein X is H or ##STR2## R is H or C.sub.1 -C.sub.8 alkyl; R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: April 17, 1984
    Assignee: The Dow Chemical Co.
    Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
  • Patent number: 4435601
    Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.
    Type: Grant
    Filed: July 7, 1981
    Date of Patent: March 6, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Karel Formanek, Daniel Michelet, Dominique Petre