Oxygen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/423)
  • Patent number: 5116987
    Abstract: The invention describes a method of synthesizing a compound of the formula ##STR1## in which X=O or NR,Z=an electron-attracting group,R=H, CN or NO.sub.2,R.sub.1 +R.sub.2 +N--C.dbd.X=a 5-membered or 6-membered heterocycle, andR.sub.3 =H, R.sub.4 =OH or R.sub.3 +R.sub.4 =a bond,said method involving intermediates of the formula ##STR2## in which R.sub.5 =H, Br or N(R.sub.1)CXR.sub.2. This method of synthesis does not involve the epoxide derivative of the chroman.The novel compounds of formula (IX) form a further subject of the invention.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: May 26, 1992
    Assignee: Sanofi
    Inventors: Georges Garcia, Daniel Mettefeu, Richard Roux
  • Patent number: 5105021
    Abstract: A higher yield of the difluorohalomethoxybenzene produced by the reaction of a metal phenolate with dibromodifluoromethane or bromochlorodifluoromethane can be obtained by conducting the addition of a metal alcoholate or a metal hydride as a reaction initiator to a solution or a suspension of an aprotic polar solvent containing the metal phenolate and dibromodifluoromethane or bromochlorodifluoromethane.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Hideyuki Akieda, Naoki Sato, Koichi Morinaga, Yoshinori Ide, Ryuichi Mita, Mitsumasa Umemoto
  • 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: 5093514
    Abstract: A process for dehydrating compounds of the formula ##STR1## where --R is --CH.dbd.CH.sub.2, --C.tbd.CH --C.tbd.N or ##STR2## in an aqueous solution thereof is disclosed. In the case where R is --CH.dbd.CH.sub.2 or --C.dbd.CH, the temperature is preferably at least 50.degree. C. and preferably 75.degree. to 100.degree. C. The base is at least 0.1N and preferably 1.0 to 8N. Preferred bases are NaOH, KOH and C.sub.5 OH. In the case where --R is C.tbd.N, the temperature preferably is 20.degree. to 50.degree. C.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: March 3, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alan D. Grund, Ronald J. Huss, Michael H. Reimer
  • Patent number: 5087743
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 23, 1990
    Date of Patent: February 11, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5084478
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##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 or each is hydrogen or 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, each is hydrogen, halogeno or alkylwherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --;and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: January 28, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 5068389
    Abstract: The invention relates to tertiary alcohols of the formula I ##STR1## wherein R.sup.1, A.sup.1, Z.sup.1, m, A.sup.2, Y, Q.sup.1, Q.sup.2, Q.sup.3 and Z.sup.2 have the meanings indicated in claim 1, and also to a process for the preparation of these compounds.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: November 26, 1991
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Rudolf Eidenschink, Joachim Krause, Hans-Adolf Kurmeier
  • Patent number: 5066822
    Abstract: Novel compounds which are 2,6-di-t-butylphenols substituted in the 4 position by an alkoxy or benzyloxy group or a benzylthio group, which alkoxy or benzyloxy group is directly substituted by a tetrazole ring, and which benzylthio group is directly substituted by carboxy or tetrazolyl are useful as inhibitors of leukotriene biosynthesis and as antiallergic agents. Synthetic intermediates for preparing such compounds are also described.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: November 19, 1991
    Assignee: Riker Laboratories, Inc
    Inventor: Mark A. Rustad
  • Patent number: 5043450
    Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R indicates a hydrogen atom or lower alkyl group, R.sup.1 indicates a lower alkyl group, R.sup.2 indicates a hydrogen atom, amino group or nitro group, X indicates a halogen atom, and Z indicates a halogen atom, piperazino group, N-methylpiperazino group, 3-methylpiperazino group, 3-hydroxypyrrolidino group, or pyrrolidino group of the following formula, ##STR2## (here, n is 0 or 1, R.sup.3 indicates a hydrogen atom or lower alkyl group, R.sup.4 indicates a hydrogen atom, lower alkyl group or substituted lower alkyl group and R.sup.5 indicates a hydrogen atom, lower alkyl group, acyl group or alkoxycarbonyl group), the hydrates and pharmaceutically acceptable salts thereof are useful as antibacterial agents.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: August 27, 1991
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
  • Patent number: 5041604
    Abstract: A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II)X--A--Y (II)wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) ##STR1## wherein R.sub.1 to R.sub.5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups,to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) ##STR2## and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.
    Type: Grant
    Filed: June 20, 1990
    Date of Patent: August 20, 1991
    Assignee: Sanko Kaihatsu Kagaku Kenkyusho
    Inventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
  • Patent number: 5026726
    Abstract: A compound of the chemical formula ##STR1## wherein n is 1 or 2, X is NH and O, and R.sub.1 and R.sub.2 are H, (C.sub.1 -C.sub.12) alkyl, (C.sub.2 -C.sub.12)alkenyl, (C.sub.2 -C.sub.12)alkynyl, (C.sub.2 -C.sub.12)acyl, (C.sub.6 -C.sub.12)aryl or (C.sub.7 -C.sub.21)alkylaryl, salts thereof and a composition thereof. In vivo and in vitro methods of inhibiting the growth of a virus relying on the effect of the above compound. In vitro and in vivo methods of inhibiting the growth of the HIV-1 virus comprising administering a compound of the formula ##STR2## wherein n is 1 or 2, X is NH or O, and R.sub.1 and R.sub.2 are independently of one another H, (C.sub.1 -C.sub.12)alkyl, (C.sub.2 -C.sub.12)alkenyl, (C.sub.2 -C.sub.12)alkynyl, (C.sub.2 -C.sub.12)acyl, (C.sub.6 -C.sub.12)aryl or (C.sub.7 -C.sub.21)alkylaryl, R.sup.3 is C.dbd.N or COR.sup.5, wherein R.sup.5 is selected from the group consisting of H, (C.sub.1 -C.sub.12) alkyl, alenyl or alkynyl, HO, NH.sub.2 and (C.sub.2 -C.sub.12) alkoxy, and R.sup.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: June 25, 1991
    Assignee: The University of New Mexico
    Inventors: David L. Jagt, Robert E. Royer
  • Patent number: 5017721
    Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 21, 1991
    Assignee: Enichim ANIC S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
  • Patent number: 5002960
    Abstract: Compounds of the formulas: ##STR1## wherein Het is an oxazole or oxazine moiety; X is O, S or SO, n is an integer from 3 to 9, Y is an aliphatic bridge; and the various R groups represent hydrogen or various substituents as described herein, are useful as antiviral agents, especially against picornaviruses. N-(Chloroalkyl)amide intermediates for the compounds of Formula I are also active as antiviral agents. Related compounds outside the scope of the above formulas are also disclosed. Also disclosed are novel intermediates, N-halo-alkyl-4-(isoxazol-5-yl)alkoxybenzamides, also useful as antiviral agents.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: March 26, 1991
    Assignee: Sterling Drug, Inc.
    Inventor: Guy D. Diana
  • Patent number: 5003101
    Abstract: X is hydrogen, halogen, cyano, nitro, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted haloalkyl,n is 1, 2, 3 or 4,Y is substituted or unsubstituted alkylene, alkenylene, alkynylene, O, S(O), unsubstituted or alkyl-substituted N, oxycarbonyl, carbonyloxy, carbonyloxyalkylene, oxycarbonylalkylene, oxyalkylene, thioalkylene, azo, carbonylamino, aminocarbonyl, ##STR2## methylenoxy or methylenethio and Z is hydrogen, alkyl, cycloalkyl, aryl, aralkyl, aralkenyl, aralkoxy, aryloxy, aryloxyalkyl, hetaryl, alkoxy, alkoxyalkyl, alkylthio, or haloalkyl, these radicals being unsubstituted or substituted by halogen, cyano, nitro, alkyl, alkenyl, haloalkenyl, alkoxy, haloalkyl, alkoxycarbonyl or unsubstituted or substituted phenyl,and fungicides containing these compounds.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: March 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Siegbert Brand, Franz Schuetz, Bernd Wenderoth, Hubert Sauter, Eberhard Ammermann, Gissela Lorenz
  • Patent number: 5001256
    Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexanediones are described.
    Type: Grant
    Filed: July 31, 1989
    Date of Patent: March 19, 1991
    Assignee: ICI Americas Inc.
    Inventors: William J. Michaely, Jeff K. Curtis
  • Patent number: 5001266
    Abstract: Novel aniline compounds that are useful in preparing N-aroyl N'-phenyl ureas having alkyl substituents in the 2-, 3-, 5- and 6-positions and haloalkoxy in the 4-position of the N'-phenyl which are more active and have a broader spectrum of effectiveness than the known benzoylurea insecticides.
    Type: Grant
    Filed: May 19, 1988
    Date of Patent: March 19, 1991
    Assignee: The Dow Chemical Company
    Inventors: Raymond H. Rigterink, Barat Bisabri-Ershadi
  • Patent number: 4999448
    Abstract: A method of preparing a compound of Formula XII ##STR1## wherein R.sub.1 and R.sub.2 together represent the fragment --Ch.sub.2 CH.sub.2 --;each R.sup.4 independently represents C.sub.1 -C.sub.4 alkyl optionally substituted with 1 to 2 C.sub.1 -C.sub.4 alkoxy groups; andX, X', Y, Y', Z, and Z' each, independently represent H, F, Cl, Br, I, CN, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenoxy, C.sub.1 -C.sub.4 alkylthio, phenylthio, or C.sub.1 -C.sub.4 dialkylamino, wherein each alkyl, alkoxy, and alkylthio group is optionally substituted with one or more compatible groups selected from C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, F, Cl, Br, CN, and phenyl and wherein each phenyl group is optionally substituted with up to 3 groups selected from F, Cl, Br, CN, CF.sub.3, C.sub.1 -C.sub.4 alkyl, and C.sub.1 -C.sub.4 alkoxy.
    Type: Grant
    Filed: April 12, 1990
    Date of Patent: March 12, 1991
    Assignee: The Dow Chemical Company
    Inventors: Michael G. Smith, James M. Renga, Brian K. Riley, Patricia G. Ray, Charles Marlowe
  • 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: 4996347
    Abstract: The present invention relates, by way of novel industrial products, to osides selected from the group consisting of:(i) the .beta.-.eta.-phenylthioxylosides of the formula: ##STR1## in which: R represents a hydrogen atom, a halogen atom, a nitro group or a cyano group,A represents the sulfur atom or the oxygen atom,B represents a CH.sub.2, CHOH or CO group andY represents the hydrogen atom or an acyl group; and(ii) epimers thereof when B is CHOH.These products are useful in therapy as antithrombotics.
    Type: Grant
    Filed: June 27, 1989
    Date of Patent: February 26, 1991
    Assignee: Fournier Innovation et Synergie
    Inventors: Soth Samreth, Francois Bellamy, Jean Millet
  • Patent number: 4978769
    Abstract: Aromatic, ring-fluorinated compounds are particularly advantageously prepared by nucleophilic exchange in the course of reaction wih potassium fluoride in the presence of phase transfer catalysts and, if desired, solvents by carrying out the reaction in the additional presence of metal salts.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst Kysela, Rudolf Braden
  • Patent number: 4971995
    Abstract: Pharmaceutical or veterinary preparations containing (a) at least one compound with the formula: ##STR1## where:R.sub.o represents a C.sub.3 -C.sub.6 alkyl group or a benzyl group with the formula: ##STR2##in which R.sub.3 =H, a halogen, a C.sub.1 -C.sub.4 alkyl, a C.sub.1 -C.sub.4 alkoxy, CF.sub.3, NO.sub.2 or a CN group; andR.sub.2 represents:a C.sub.1 -C.sub.4 alkoxy group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (CHOH, H), (O, H), (CH.sub.2, H) or (CO, H);and OH group, in which case the pair (X, R.sub.1)=(O, OH), (O, C.sub.1 -C.sub.4 alkoxy), (O, H) or (CH.sub.2, H), with the reservation that when (X, R.sub.1)=(O, OH), R.sub.o is different from a C.sub.3 -C.sub.6 alkyl or a benzyl group; ora CN or C.sub.1 -C.sub.4 alkyl-NH group, in which case the pair (X, R.sub.1)=(O, H) or (CH.sub.2, H), together with (b) a carrier or vehicle which is physiologically acceptable and appropriate for the compound used.
    Type: Grant
    Filed: January 26, 1989
    Date of Patent: November 20, 1990
    Assignee: Delande S.A.
    Inventors: Alain R. Schoofs, Michel Langlois, Christian R. Jeanpetit, Maryse F. Masson
  • Patent number: 4966726
    Abstract: The new compounds produced from a molecular structural element with two chirality centers and at least one mesogenic structural element are defined by the general formula (I) ##STR1## in which the symbols have the following meaning: Y.sup.1 =H, (C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, MC denoting the molecular radical of a mesogenic carboxylic acid after splitting off a COOH group,Y.sup.2 =(C.sub.1 -C.sub.10)alkyl, MC--CH.sub.2 or MC--CO, it being possible for Y.sup.1 and Y.sup.2 to jointly represent a MC--CH group, which is then part of a dioxolane ring,X=COOR.sup.1, CONH.sub.2, CONR.sup.2 R.sup.3 or C.tbd.N,R.sup.1 =(C.sub.1 -C.sub.10)alkyl or MC--CH.sub.2, andR.sup.2, R.sup.3 =H and (C.sub.1 -C.sub.4)alkyl or, independently of each other, (C.sub.1 -C.sub.4)alkyl.Said esters preferably find application as dopants in twistable liquid crystal phases in which they produce temperature compensation and twisting.
    Type: Grant
    Filed: July 18, 1988
    Date of Patent: October 30, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Manel Gunaratne
  • Patent number: 4960950
    Abstract: Disclosed is a novel process for effecting an ether interchange reaction by heating together in the presence of a basic catalyst, a nitroaromatic ether or thioether and an organic compound containing at least one hydroxyl or mercapto group. The novelty resides particularly in carrying out the interchange in an inert solvent while sparging the heated reactants thereby to remove at least a portion of solvent along with an evolving alcohol or thiol.The process is particularly adapted to the capping of organic polyols with nitroaromatic ether groups. The capped products are useful as intermediates for the preparation of high molecular weight polyamines which in turn find utility in various polymer applications.
    Type: Grant
    Filed: March 28, 1988
    Date of Patent: October 2, 1990
    Assignee: The Dow Chemical Company
    Inventor: Visweswara R. Durvasula
  • Patent number: 4956488
    Abstract: The present invention discloses an optically active cyanobiphenyl compound represented by the following general formula: ##STR1## wherein, R is ##STR2## X is hydrogen atom or chlorine atom: when X is hydrogen atom, R.sub.1 is normal alkyl having from 1 to 11 carbon atoms and when X is chlorine atom, R.sub.1 is hydrogen atom or normal alkyl having from 1 to 11 carbon atoms; n is 3 to 5; Y is --CH.sub.2 --or --CO--; and * represents an asymmetric carbon atom.
    Type: Grant
    Filed: April 5, 1988
    Date of Patent: September 11, 1990
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Masaki Kimura
  • Patent number: 4950802
    Abstract: A novel method for the preparation of aryl trifluoromethyl ethers which comprises reacting a phenol, a perhalomethane, and an antimony pentahalide. For example, 4-nitrophenol may be reacted with an excess over stoichiometry of both carbon tetrachloride and antimony trifluoride with a catalytic amount of antimony pentachloride to form 4-nitrophenyl trifluoromethyl ether.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: August 21, 1990
    Assignee: The Dow Chemical Company
    Inventor: Bassam S. Nader
  • 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: 4931209
    Abstract: A new family of liquid crystalline or potential liquid crystalline compounds is made relatively cheaply generally by reducing an acid chlorine derivative alkyl or alkoxy benzene or its analogues of an alkyl cyclohexanoic acid to an alkanol derivative, converting the alkanol derivative to a halide such as the bromide or chloride and reacting said halide with a cyano phenol, cyanodiphenol and related compound to form a compound having the formula of equation 1.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: June 5, 1990
    Assignee: Crystaloid Electronics, Inc.
    Inventors: Joseph P. Ferrato, Julie C. Ferrato
  • Patent number: 4925590
    Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: May 15, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
  • Patent number: 4914244
    Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.
    Type: Grant
    Filed: January 14, 1987
    Date of Patent: April 3, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Albrecht Marhold
  • Patent number: 4913838
    Abstract: An optically active liquid crystal compound having specific features suitable to a display mode utilizing ferroelectric chiral smectic phases and particularly having a large spontaneous polarization value, and a chiral liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 represents an alkyl group of 2 to 18 carbon atoms; R.sup.2 represents an alkyl group or alkoxy group each of 1 to 20 carbon atoms, hydrogen atom, a halogen atom or cyano group; A represents --COO-- or --OCO--; B and C each represent a single bond, ##STR2## wherein X represents hydrogen atom, a halogen atom or cyano group; and l, m and n each represent 0 or 1.
    Type: Grant
    Filed: March 18, 1988
    Date of Patent: April 3, 1990
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Takashi Inukai, Hiromichi Inoue, Shinichi Saito, Kouji Ohno
  • Patent number: 4908388
    Abstract: Derivatives of carbonyl-group containing behavior modifying compounds, in which said carbonyl group has been converted to a photolabile group which regenerates the carbonyl group on exposure to radiation, are of value in various methods for the control of animal, and in particular insect, species.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: March 13, 1990
    Assignee: National Research Development Corporation
    Inventors: John A. Pickett, Ewen D. M. Macaulay
  • Patent number: 4892963
    Abstract: Compounds of the following formula have pharmaceutical properties: ##STR1## in which X is R.sup.1 (HO)C.dbd.C(CN)--, R.sup.1 (CO)--CH(CN)-- or ##STR2## R.sup.1 and R.sup.2 are each hydrogen or C.sub.1-6 alkyl, R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, hydroxy, halogen, nitro, cyano, carboxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halo-substituted C.sub.1-4 alkyl, halo-substituted C.sub.1-4 alkoxy, halo-substituted C.sub.1-4 alkylthio, C.sub.2-5 alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, R'R"N- where R' and R" are each hydrogen or C.sub.1-4 alkyl R'"CONH-- where R'" is C.sub.1-4 alkyl, R.sup.6, R.sup.7 and R.sup.8 are each C.sub.1-6 alkyl, halo-substituted C.sub.1-6 alkyl or optionally substituted phenyl, or R.sup.6 and R.sup.7, together with the carbon atom to which they are attached, form a cycloalkyl group containing 3 to 7 carbon atoms, or R.sup.6, R.sup.7 and R.sup.
    Type: Grant
    Filed: August 7, 1987
    Date of Patent: January 9, 1990
    Assignee: Lilly Industries Limited
    Inventors: Peter T. Gallagher, Terence A. Hicks, Graham W. Mullier
  • Patent number: 4886622
    Abstract: An optically liquid crystalline compound having an extremely large spontaneous polarization value and a chiral smectic liquid crystal composition containing the compound are provided, the compound being expressed by the formula ##STR1## wherein m represents an integer of 2 to 18; l represents an integer of 0 to 12; n represents 0 or 1; R represents an alkyl group or an alkoxy group each of 2 to 20 carbon atoms, a halogen atom or cyano group; and A and B each represent a single bond, ##STR2## wherein X represents hydrogen atom, a halogen atom or cyano group, and a chiral smectic liquid crystal composition containing at least one kind of the above compound.
    Type: Grant
    Filed: August 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Chisso Corporation
    Inventors: Kazutoshi Miyazawa, Takashi Inukai, Hiromichi Inoue, Shinichi Saito, Kouji Ohno
  • Patent number: 4886891
    Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.
    Type: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4879061
    Abstract: A method of making liquid crystalline compounds of the formula ##STR1## where A represents a cyclohexane ring, n has values of 1, 2 or 3, R1 is an alkyl radical, R2 is an alkyl, alkoxy, or alkylcyclohexyl or cyanide radical, and X1 is lower alkyl and X2, X3 and X4 is alkyl and preferably methyl, ethyl or propyl, hydrogen, halogen and preferably fluorine or cyanide and to the compound.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: November 7, 1989
    Assignee: Crystaloid Electronics Co.
    Inventors: Joseph P. Ferrato, Julie C. Ferrato
  • Patent number: 4876376
    Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent 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: December 15, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialistes Chimiques
    Inventors: Michael Desbois, Camille Disdier
  • 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: 4871470
    Abstract: Cyclohexane derivatives of formula I ##STR1## wherein R is an alkyl group which has 1-12 C atoms and in which one or two non-adjacent CH.sub.2 groups can also be replaced by O, --CO--O-- or --OCO--,A.sup.1 and A.sup.2 each independently of one another are trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene, and one of the groups A.sup.1 and A.sup.2 can also be a single bond,X is --CN, halogen, OH, --COOR.sup.1, --OOCR.sup.1, --COR.sup.1, --OR.sup.1 or R.sup.1 andR.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by O, but excluding direct links between two O atoms,with the proviso that, in the case of X=CN, A.sup.2 is trans-1,4-cyclohexylene or fluorine-substituted, 1,4-phenylene, are suitable as components of liquid-crystalline phases.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: October 3, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Joachim Krause, Rudolf Eidenschink, Georg Weber
  • Patent number: 4867904
    Abstract: Bicyclooctane derivatives of the Formula I ##STR1## wherein R.sup.1, R.sup.2, A.sup.1, A.sup.2 and Z have the meanings indicated in claim 1, are suitable for use as components of liquid-crystal phases for field effect and/or bistability effect displays.
    Type: Grant
    Filed: April 23, 1987
    Date of Patent: September 19, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Joachim Krause, Volker Reiffenrath, Bernhard Scheuble, Georg Weber
  • Patent number: 4857539
    Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Philip M. Carabateas
  • Patent number: 4845119
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##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 of each is hydrogen or 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 substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 4, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 4844836
    Abstract: The present invention discloses an optically active cyanobiphenyl compound represented by the following formula and nematic liquid crystal composition comprising thereof. ##STR1## wherein, m is 2 or 3; n is 2 when m is 2 and n is one when m is 3; and * represents an asymmetric carbon atom.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: July 4, 1989
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Norio Kurosawa
  • Patent number: 4837364
    Abstract: A process for the preparation of (pentafluoroethoxy)- and (pentafluoroethylthio)benzene derivatives either from phenol, thiophenol or from halobenzene. A halobenzene is reacted with trifluoroethanol or a phenol or a thiophenol is reacted with a compound of the formula CF.sub.3 --CH.sub.2 --O--R'. The product is chlorinated and the chlorinated product is fluorinated in liquid hydrofluoric acid in the presence of a Lewis acid.The compounds obtained by the process of the present invention are used as synthesis intermediates in the phytosanitary, pharmaceutical and veterinary industries, and are used in lubricants.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: June 6, 1989
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Bernard Langlois
  • Patent number: 4824989
    Abstract: A (trifluoromethyl)naphthalene which has been prepared by reacting a halonaphthalene with a trifluoroacetate salt in the presence of cuprous iodide and a dipolar aprotic solvent is recovered by (1) replacing the dipolar aprotic solvent in the final reaction mixture with an alkane containing 6-12 carbons, (2) heating the resultant slurry to a temperature sufficient to dissolve the organic ingredients, (3) allowing the inorganic ingredients of the slurry to settle, (4) decanting the organic layer, and (5) cooling to precipitate the (trifluoromethyl)naphthalene.
    Type: Grant
    Filed: March 3, 1987
    Date of Patent: April 25, 1989
    Assignee: Ethyl Corporation
    Inventor: Gary D. Heidebrecht
  • Patent number: 4824988
    Abstract: In a process for preparing a (trifluoromethyl)napthalene by reacting a halonapthalene with a trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent and separating out the inorganic ingredients of the final reaction mixture in the recovery of the product, the cuprous iodide is recovered by washing the separated inorganic ingredients with an alcohol and a carboxylic acid and then with water to purify the cuprous iodide.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: April 25, 1989
    Assignee: Ethyl Corporation
    Inventors: Ronny W. Lin, Venkataraman Ramachandran
  • Patent number: 4785131
    Abstract: 6-Alkoxy-5-halo-1-cyanonaphthalenes, useful as pharmaceutical intermediates, are prepared by (1) reacting a 6-alkoxytetralone with cyanide ion and a Lewis acid in a nitroalkane or nitroarene solvent to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) intimately mixing the resultant solution with an aqueous base selected from alkali metal, alkaline earth metal, and tetraalkylammonium hydroxides, alkoxides, carbonates, and bicarbonates to aromatize the 6-alkoxy-1-cyano-3,4-dihydronaphthalene, and (3) halogenating the resultant 6-alkoxy-1-cyanonaphthalene while still in the nitroalkane or nitroarene solvent.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: November 15, 1988
    Assignee: Ethyl Corporation
    Inventor: Venkataraman Ramachandran
  • Patent number: 4767879
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;m is an integer chosen from 3 to 5.
    Type: Grant
    Filed: December 17, 1986
    Date of Patent: August 30, 1988
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Lynette A. Garson, Graham J. Bird, Lindsay E. Cross, Graeme J. Farquharson
  • Patent number: 4766243
    Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: August 23, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Michael J. Fifolt
  • Patent number: 4764635
    Abstract: A hydroaromatic compound is aromatized by heating it at about 100.degree.-300.degree. C. in the presence of a hydrogen acceptor. In a preferred embodiment of the invention, the hydroaromatic compound is a dihydronaphthalene bearing an electron-withdrawing substitutent, e.g., a cyanodihydronaphthalene.
    Type: Grant
    Filed: August 14, 1986
    Date of Patent: August 16, 1988
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, David M. Mohr
  • Patent number: 4762943
    Abstract: A dihydroaromatic compound is aromatized by intimately contacting it with a base selected from alkali metal, alkaline earth metal, and tetraalkylammonium hydroxides, alkoxides, carbonates, and bicarbonates in the presence of a hydrogen acceptor. In a preferred embodiment of the invention, the dihydroaromatic compound is a dihydronaphthalene bearing an electron-withdrawing substituent, e.g., a cyanodihydronaphthalene.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: August 9, 1988
    Assignee: Ethyl Corporation
    Inventors: Venkataraman Ramachandran, John R. Maloney