Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/442)
  • Patent number: 6316658
    Abstract: N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3), wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1 is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or —CH═C(CO2R2)2, R2 being lower alkyl.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: November 13, 2001
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Hiroaki Takeuchi
  • Patent number: 6306179
    Abstract: The present invention relates to a new method for the synthesis of 2-hydroxyalkyl-para-phenylenediamines which are substituted or unsubstituted at the 5-position of the benzene ring, new 2-hydroxyalkyl-para-phenylenediamines which are substituted or unsubstituted at the 5-position of the benzene ring, their use for the oxidation dyeing of keratinous fibers, the dyeing compositions containing them, as well as the methods of dyeing using them.
    Type: Grant
    Filed: October 22, 1998
    Date of Patent: October 23, 2001
    Assignee: L'Oreal S.A.
    Inventors: Alain Genet, Alain Lagrange
  • Patent number: 6307045
    Abstract: The present invention provides a process for producing halogenated benzene compounds. In the process, an organometallic compound represented by the general formula [I]: wherein M represents an R13Sn group, an R13Si group, an R13Ge group, an (R2CO2)Hg group, a ClHg group or an (R3O)2B group wherein each R1 independently represents a C1-C8 alkyl group, R2 represents a C1-C3 alkyl group or a C1-C3 haloalkyl group, R3 represents a hydrogen atom or a C1-C3 alkyl group, n represents an integer of from 0 to 4, m represents an integer of from 0 to 1, each A independently represents a fluorine atom, a nitro group, a cyano group, a C1-C8 alkyl group, a C1-C8 alkoxy group or a C2-C8 acyloxy group, and Q represents an organic residue, is reacted in a solvent with a halide ion represented by the general formula X−, under light irradiation conditions in the presence of a semiconductor catalyst with a photocatalytic activity.
    Type: Grant
    Filed: June 30, 2000
    Date of Patent: October 23, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Komori, Kazuhiko Nishioka
  • Patent number: 6258956
    Abstract: A process for the synthesis of a compound of the formula wherein R1 is aryl, heteroaryl, substituted aryl or substituted heteroaryl and R2 is hydrogen, alkyl or aralkyl, or salt thereof.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: July 10, 2001
    Assignee: Ortho-McNeil Pharmaceutical, Inc.
    Inventors: Ahmed F. Abdel-Magid, Judith H. Cohen, Cynthia A. Maryanoff, Frank John Villani, Jr., Hua M. Zhong
  • Patent number: 6242634
    Abstract: Novel pyrimidin-4-one derivatives of formula [1] are provided, which are useful as active ingredients of herbicides, wherein R1 is hydrogen or alkyl; R2 is alkyl optionally substituted with halogen; R3 is alkyl optionally substituted with halogen, alkenyl, or alkynyl; and Q is substituted phenyl. Also provided are intermediates for their production and processes for producing these intermediates.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: June 5, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masayuki Enomoto, Hisayuki Hoshi, Yuzuru Sanemitsu
  • Patent number: 6242609
    Abstract: A method for manufacturing a color coupler used in a silver halide photographic light-sensitive material using an ammonium trihalide. Said method for manufacturing the color coupler comprising the following step: a step for halogenating a coupling position of a four equivalent coupler using a halogenating agent, wherein said halogenating agent is said ammonium trihalide.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: June 5, 2001
    Assignee: Konica Corporation
    Inventor: Fumio Ishii
  • Patent number: 6235939
    Abstract: Anilines which contain fluorine in a side chain are prepared by reacting chlorinated aromatic compounds with ammonia in the presence of a catalyst and optionally water at 200 to 280° C. Some of the trifluoromethoxy-anilines which may be prepared in this way are new compounds.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: May 22, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventor: Albrecht Marhold
  • Patent number: 6222074
    Abstract: The invention relates to a process for preparation of 4,6-diaminoresorcinol or salts thereof by reducing 4,6-bis(substituted)phenylazoresorcinol expressed by the formula [1] wherein, R denotes a halogen atom, an alkyl group having 1-5 carbon atoms, a hydroxycarbonyl group or an alkoxy group having 1-5 carbon atoms, n denotes 0 or any integer of 1-5, and two or more groups R may be same or different each other, for example, 4,6-bisphenylazoresorcinol, with hydrogen in the presence of a metal catalyst to obtain 4,6-diaminoresorcinol or salts thereof, characterized in that an aliphatic nitrile compound (for example, acetonitrile) is used as a solvent, or characterized in that the reduction is carried out by using at least one organic solvent selected from aliphatic nitrile compounds, aliphatic alcohols having 3-5 carbon atoms, dioxane and ethylene glycol monomethyl ether, etc. as a solvent and furthermore in the presence of a filter aid (for example, active carbon).
    Type: Grant
    Filed: July 25, 2000
    Date of Patent: April 24, 2001
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kenichi Tokunaga, Motohito Shiratori, Kazuhiko Akimoto, Hideo Suzuki, Isao Hashiba
  • Patent number: 6191309
    Abstract: The halogenation of a compound of formula (1) or formula (2′), wherein Q is an NH2 group optionally in the form of an addition salt, or an NHCOCH3 group, and X is a halogen atom, using a compound of formula X2, in a solvent selected from an anhydrous halogenated hydrocarbon, a mixture of water and a halogenated hydrocarbon and optionally the compound of formula (1) itself, gives a 2-amino or 2-acetamido trifluoromethylbenzene halogenated in the 5 position of the benzene ring.
    Type: Grant
    Filed: March 2, 1999
    Date of Patent: February 20, 2001
    Assignee: Rhodia Chimie
    Inventor: Michel Dury
  • Patent number: 6166273
    Abstract: A process is provided for increasing the fluorine content of benzene or pyridine rings which are optionally substituted with from 1 to 3 inert substituents. The process involves (a) contacting the ring with a metal fluoride composition comprising cupric fluoride (CuF.sub.2) at a temperature above 250.degree. C. sufficient to transfer F from cupric fluoride to the optionally substituted ring, thereby chemically reducing the metal fluoride composition; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate a metal fluoride composition comprising cupric fluoride; and (c) employing regenerated metal fluoride composition of (b) in (a).
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: December 26, 2000
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Munirpallam A. Subramanian
  • Patent number: 6156774
    Abstract: Mercapto amino acid derivatives of formula (I), wherein R is hydrogen, a salt-forming cation of a in vivo hydrolysable ester-forming group; R.sub.1 is selected from (a) and (b) in which A is a monocyclic aryl or heteroaryl ring and B is a monocyclic aryl, alicyclic or heterocyclic ring, C and D are independently --Z.sub.p --(CR.sub.8 CR.sub.9).sub.q -- or --(CR.sub.8 CR.sub.9).sub.q --Z.sub.p -- where p is 0 or 1, q is 0 to 3 provided that p+q in C is not 0, R.sub.8 and R.sub.9 are independently hydrogen or (C.sub.1-6)alkyl or together represent oxo and Z is O, NR.sub.10 or S(O).sub.x where R.sub.10 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl and x is 0-2, and wherein C and D are linked ortho to one another on each of the rings A and B in formula (b); R.sub.2 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl; R.sub.3 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms, (C.sub.3-7)cycloalkyl, fused aryl(C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: December 5, 2000
    Assignee: SmithKline Beecham P.L.C.
    Inventors: John Hargreaves Bateson, Desmond John Best, Brian Peter Clarke, Martin Leonard Gilpin, David Witty
  • Patent number: 6143208
    Abstract: An optical frequency conversion element has a wave-guiding layer which consists of a .chi..sup.(2) -active ferroelectric liquid crystal. The monomeric or polymeric liquid crystal material has a periodic structure which permits the so-called quasi phase matching of a guided laser beam. The period length of the structure is equal to twice the coherence length l.sub.c =.pi./.DELTA..beta. of the material, whereby .DELTA..beta.=.beta..sub.o (2.omega.)-2.beta..sub.o (.omega.), with .omega.=angular frequency of the fundamental wave, 0=zero-order mode and .beta.=propagation constant of the mode.
    Type: Grant
    Filed: February 12, 1997
    Date of Patent: November 7, 2000
    Assignee: Rolic AG
    Inventors: Richard Buchecker, Xin Hua Chen, Jurg Fufschilling, Rolf-Peter Herr, Martin Schadt, Klaus Schmitt
  • Patent number: 6118025
    Abstract: The invention concerns a method for preparing an optically active alcohol of formula (I) in which the carbon atom indicated by the symbol * can have the configuration (R) or (S) and X represents a non-substituted amino group or a mono- or di-(C.sub.1 -C.sub.4)alkylamino group optionally salified from corresponding ketones by catalytic hydrogenation in the presence of a rhodium complex.
    Type: Grant
    Filed: December 27, 1999
    Date of Patent: September 12, 2000
    Assignee: Sanofi-Synthelabo
    Inventors: Francine Agbossou, Marc Devocelle, Jean-Robert Dormoy, Andre Mortreux
  • Patent number: 6114584
    Abstract: Disclosed is a method of preparing brominated substituted anilines. A mixture in water is formed of a substituted aniline having the general formula ##STR1## where each R is independently selected from halogen, alkyl and haloalkyl from C.sub.1 to C.sub.12, aryl, alkaryl, and aralkyl from C.sub.6 to C.sub.12, R does not occupy all three 2, 4, and 6 positions, and n is 1 to 4. To the suspension is added about 1.0 to about 1.1 equivalents of bromine for each bromine atom to be substituted onto the aromatic ring of said substituted aniline. No acid is present during the reaction.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: September 5, 2000
    Assignee: Occidental Chemical Corporation
    Inventor: Sanjay Mandal
  • Patent number: 6069279
    Abstract: A method for the preparation of aromatic amines such as N-phenyl-p-phenylenediamine wherein an aromatic amine such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of a metal pentacyano ferrate(II) complex, includes subsequent catalytic reduction of the complex by hydrogenation in the presence of a metal catalyst having at least two Group VIII metals, preferably platinum in combination with ruthenium either together on a single carbon support or each metal separately on carbon supports.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: May 30, 2000
    Inventors: Mark W. Simon, Mohammad A. Khan
  • Patent number: 6040482
    Abstract: This invention relates to very specific oxyalkylene-substituted aminophenol compounds as intermediates for the production of poly(oxyalkylene)-substituted xanthene (or other type) colorants. Such an inventive intermediate compound is produced in a single step by reacting an oxyalkylene oxide having from 3 to 12 carbon atoms (branched or unbranched), glycidol, or a glycidyl directly with aminophenol without the use of a catalyst and at a relatively low temperature. Propylene oxide and m-aminophenol are the preferred reactants. The propylene oxide selectively reacts with the amine group on the m-aminophenol without propoxylating the phenolic hydroxyl group. Such a specific method thus does not require extra time- and cost-consuming steps of protecting the phenolic hydroxyl group from attack. After production, this intermediate may be reacted with suitable compounds to ultimately form any number of different colorants, including xanthenes, oxazines, coumarins, and the like.
    Type: Grant
    Filed: March 5, 1999
    Date of Patent: March 21, 2000
    Assignee: Milliken & Company
    Inventors: Philip G. Harris, Rajnish Batlaw
  • Patent number: 6040480
    Abstract: The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: February 11, 1999
    Date of Patent: March 21, 2000
    Assignee: Du Pont Pharmaceuticals Company
    Inventors: Michael E. Pierce, Cheng Y. Chen, Anusuya Choudhury, Lilian A. Radesca, Lushi Tan, Dalian Zhao
  • Patent number: 6015926
    Abstract: An efficient method for the preparation of key intermediate, in the synthesis of (-)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-ben zoxazin-2-one, a reverse transcriptase inhibitor is achieved using a chiral addition reaction to the 4-chloro-2-trifluoromethylketoaniline with an organozinc complex to give the desired alcohol. This instant method has broad applicability in the chiral addition to any prochiral ketone.
    Type: Grant
    Filed: May 11, 1998
    Date of Patent: January 18, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Cheng Yi Chen, Lushi Tan, Richard D. Tillyer
  • Patent number: 6013838
    Abstract: Novel trifluoromethylated intermediates are provided which are useful in synthesizing trifluoromethylated organic compounds. Specifically, compounds of the formula CF.sub.3 CR are provided, wherein R is (Cl).dbd.CHCH.sub.2 SO.sub.2 Ph, (Cl).dbd.CHCH.sub.2 CH.sub.2 C(.dbd.O)CH.sub.3, (Cl).dbd.CHCH.sub.2 CH(COCH.sub.3).sub.2, (Cl).dbd.CHCH.sub.2 NR'R" or H.dbd.CHCH.dbd.NR'; R' and R" are the same or different and are selected from the group consisting of hydrogen, unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, unsubstituted or substituted C.sub.3 to C.sub.7 cycloalkyl, unsubstituted or substituted C.sub.2 to C.sub.12 alkenyl, a benzyl group unsubstituted or substituted with R'", or a phenyl group unsubstituted or substituted with R'"; or R' and R" taken together form a five- or six-membered ring; and R'" is an unsubstituted or substituted C.sub.1 to C.sub.6 straight chain or branched alkyl, an unsubstituted or substituted C.sub.1 to C.sub.
    Type: Grant
    Filed: January 26, 1999
    Date of Patent: January 11, 2000
    Assignee: Alliedsignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5986140
    Abstract: 7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: November 16, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventor: John C. Saukaitis
  • Patent number: 5965735
    Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: October 12, 1999
    Assignee: Schering Corporation
    Inventors: Henry J. Doran, Donal J. Coveney
  • Patent number: 5962740
    Abstract: A process for producing 4,6-bisphenylazoresorcinol of formula ?2! wherein R represents halogen atom, C.sub.1-5 alkyl group, hydroxycarbonyl or C.sub.1-5 alkoxy group, n represents 0 or an integer of 1 to 5, and two or more Rs are the same or different from each other, which comprises reacting resorcinol with a benzenediazonium salt of formula ?1! wherein R and n are the same as defined in the above formula ?1!, and X represents Cl, Br, OSO.sub.3 H or OPO.sub.3 H.sub.
    Type: Grant
    Filed: April 28, 1998
    Date of Patent: October 5, 1999
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kazuhiko Akimoto, Kenichi Tokunaga, Isao Hashiba, Hideo Suzuki, Yasuo Katsumura, Kazuo Osaki, Hideo Kawashita, Satoshi Yamazaki
  • Patent number: 5932726
    Abstract: The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: August 3, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Michael Ernest Pierce, Anusuya Choudhury, Rodney Lawrence Parsons, Jr., Lilian Alicia Radesca
  • Patent number: 5900509
    Abstract: p-Haloalkoxyanilines are obtained from the corresponding nitrobenzenes by catalytic hydroxylation in the presence of an aqueous acidic reaction medium with the formation of a corresponding aminophenol and reaction of this aminophenol with a halogenated olefin in the presence of water and a catalytic amount of base.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: May 4, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Albrecht Marhold, Guido Steffan
  • Patent number: 5874656
    Abstract: o-Alkylfluorobenzenes are advantageously prepared by heating the corresponding chloroformates to from 70.degree. to 200.degree. C. in the liquid phase in the presence of hydrogen fluoride and in the presence of an inert diluent other than a halogenated alkane.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: February 23, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Michael-Harold Rock
  • Patent number: 5856576
    Abstract: There are provided aryne intermediates of formula I, useful in the manufacture of herbicidal compounds. ##STR1## Also provided is a method to prepare the formula I intermediates via the palladium catalyzed coupling of an o-halonitrobenzene or o-haloaniline with 3-butyne-1-ol.
    Type: Grant
    Filed: January 29, 1998
    Date of Patent: January 5, 1999
    Assignee: American Cyanamid Company
    Inventors: Philip M. Harrington, Kenneth A. M. Kremer
  • Patent number: 5840983
    Abstract: 2-Trifluoromethoxy-aniline, which can be used as an intermediate for example for preparing pharmaceuticals and agrochemicals, is obtained in very good yields and high purity by nitrating in a first step 1,2-dichlorotrifluoromethoxy-benzene at temperatures between -20.degree. C. and +80.degree. C. and catalytically hydrogenating the resulting nitration products (exclusively 1,2-dichloro-5-nitro-4-trifluoromethoxy-benzene and 1,2-dichloro-3-nitro-4-trifluoromethoxy-benzene) in a 2nd step, it being possible to isolate the aniline intermediates corresponding to the two nitrobenzene derivatives; the nitrobenzene and aniline derivatives mentioned, being novel compounds, are also part of the subject matter of the invention.
    Type: Grant
    Filed: July 18, 1997
    Date of Patent: November 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold
  • Patent number: 5801201
    Abstract: 1-phenyl-2-dimethylaminomethyl-cyclohexan-1-ol compounds, methods of preparing them and the use of these compounds in drugs are described.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: September 1, 1998
    Assignee: Gruenenthal GmbH
    Inventors: Ivars Graudums, Werner Winter, Ernst Frankus, Wolfgagn Werner Alfred Strassburger, Elmar Josef Friderichs
  • Patent number: 5741476
    Abstract: The invention relates to polyhydric phenol compounds of the general formula ##STR1## wherein R is a hydrogen atom or a saccharide moiety;A and B are hydrogen atoms or form together a C--C bond;R.sub.1 is a hydroxy group and R.sub.2 is a hydrogen atom, orR.sub.1 and R.sub.2 form together an oxygen atom;Z is a hydroxy group, an amino group, a carboxy group or a N-(carboxymethyl)carbamoyl group;X* is a radioactive halogen isotope; andm and n are 0 or 1, with the proviso, that m is 1 if n is 0, and that m is 0 if n is 1.The radiolabelled phenol compounds can be used for diagnosis and therapy.
    Type: Grant
    Filed: June 20, 1995
    Date of Patent: April 21, 1998
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: John Janine Rene Mertens
  • Patent number: 5712418
    Abstract: The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting groupAA is an amino acid residue andX is H or a protecting group useful,and the first amino and peptide have a free amino group and a blocked carboxy end.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: January 27, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
  • Patent number: 5683998
    Abstract: Novel tricyclic triazolo derivatives and pharmaceutically acceptable salts thereof, which are useful as anti-inflammation agents, anti-allergy agents or anti-PAF agents as well as processes for producing the same are disclosed. The triazolo derivatives of the present invention are represented by the formula (I): ##STR1## ?wherein R.sup.1 represents hydrogen, lower alkyl or C.sub.3 -C.sub.5 cycloalkyl; R.sup.2 and R.sup.3 respectively represent hydrogen, lower alkyl, lower alkoxy or halogen; W represents C.dbd.O or CR.sup.4 R.sup.5 (wherein R.sup.4 and R.sup.5 respectively represents hydrogen or lower alkyl); A represents C.sub.1 -C.sub.5 straight or branched saturated or unsaturated alkylene which may contain one or more hetero atoms; l represents 0 to 2, n represents 1 to 3, . . . represents single bond or double bond; Y represents N or C; Z represents C(B)Ar.sup.1 Ar.sup.2 (wherein B represents hydrogen, hydroxy or methoxy, Ar.sup.1 and Ar.sup.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: November 4, 1997
    Assignee: Toray Industries, Inc.
    Inventors: Katsuhiro Shibayama, Tetsuya Makino, Takayuki Imaoka, Tetsuya Katou, Masayuki Kaneko
  • Patent number: 5663448
    Abstract: Compounds of general formula (I), stereosiomers and pharmaceutically acceptable salts thereof, wherein each of Z and Z' are independently H or F; Q is (a), CH(OH), (b); X is H, Br, Cl, F or CF.sub.3 ; Y is H, Br, Cl, F, OH, OR.sub.5, OC(O)R.sub.4, N.sub.3, CN, NO.sub.2, SO.sub.3 H, CO.sub.2 R.sub.4, NH.sub.2, NHR.sub.9, NR.sub.9 R'.sub.9, C(R.sub.6)(R.sub.7)(V'R.sub.8) or C(O)R.sub.7, provided that when both Z and Z' are F, then Y is H or F; V and V' are each independently CH.sub.2 or O; R.sub.1 is H or CH.sub.3 ; R.sub.2, R.sub.9 and R'.sub.9 are each independently (C.sub.1-6)alkyl, or R.sub.2 and V--R.sub.3 taken together with the carbon atom to which they are attached form a 3-6 membered ring; R.sub.3, R.sub.6, R.sub.7 and R.sub.8 are each independently H, (C.sub.1-6)alkyl, or (C.sub.3-6)cycloalkyl; R.sub.4 is H, (C.sub.1-10)alkyl, (C.sub.0-4)alkylene aryl or (C.sub.3-8)cycloalkyl; and R.sub.5 is (C.sub.1-10)alkyl, benzyl, phenethyl or (C.sub.
    Type: Grant
    Filed: November 21, 1995
    Date of Patent: September 2, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Jean-Noel Collard, Jean-Marie Hornsperger, Daniel Schirlin
  • Patent number: 5645610
    Abstract: The new coupler compounds of the invention are 4-amino-2 -(2'-hydroxyethyl)-amino-5-methoxytoluene and/or 4-amino-2-(2'-hydroxyethyl)amino-5-chlorotoluene. The invention also includes an oxidation hair dye composition including an effective amount, advantageously from 0.01 to 5 percent by weight, of the above-mentioned new coupler compounds together with one or more known developer compounds and optionally certain direct dyes.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: July 8, 1997
    Inventors: Wolfgang R. Balzer, Anke Frank, Alexa Weinges
  • Patent number: 5644056
    Abstract: A method of preparing 7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4 benzoxazine. The method includes the steps of reacting 2,3,4-trifluoroaniline or trifluoronitrobenzene with hydroxyacetone or a derivative thereof under reducing conditions to yield N-(3-hydroxy-2-propyl)-2,3,4 trifluoroaniline. The N-(3-hydroxy-2-propyl)-2,3,4-trifluoroaniline is treated with a base to yield the above-mentioned benzoxazine.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 1, 1997
    Assignee: Hoechst Celanese Corporation
    Inventor: John C. Saukaitis
  • Patent number: 5639915
    Abstract: Industrial process for the efficient production of aniline derivatives which are important intermediates for the manufacture of oxazolidinedione derivatives and tetrahydrophthalimide derivatives which are useful as active ingredients of herbicides. The process starts from 2,4-dihalo-5-aminophenol or bis(2,4-dihalo-5-aminophenyl)carbonate and selectively cycloalkylates or alkynylates the hydroxy group without protecting the amino group, whereby aniline derivatives having the cycloalkyloxy group or alkynyloxy group can be produced in high yield.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: June 17, 1997
    Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.
    Inventors: Kenji Hirai, Emiko Ejiri, Tomoyuki Yano, Kiyomi Aizawa
  • Patent number: 5637256
    Abstract: This invention provides chiral nonracemic compound of formula: ##STR1## wherein n and m are 0 or 1, but one of n or m must be 1; k=0 or 1; B=COO or OOC; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are either H, an electron donor or an electron acceptor where at least one of the groups X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is an electron acceptor and at least one of these groups is an electron donor and when one of X.sub.1 or X.sub.3 is an electron donor, the other is an electro a acceptor and when one of X.sub.2 or X.sub.4 is an electron donor, the other is an electron acceptor; and R.sub.1 and R.sub.2 can be various substituted and unsubstituted alkanes and monoalkenes. Compounds provided include those where one of R.sub.1 or R.sub.2 is a chiral non-racemic tail group, particularly a group selected from --O--C.sup.* H(CH.sub.3)R.sub.c, --O--C.sup.* H(CH.sub.3)COOR.sub.d, and --O--CH.sub.2 C.sup.* HF--C.sup.* HF--R.sub.2 in which the .sup.* indicates an asymmetric carbon enriched in one stereoconfiguration where R.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: June 10, 1997
    Assignee: University Research Corporation
    Inventors: David M. Walba, Maria B. Ros, James A. Rego, Teresa Sierra
  • Patent number: 5616810
    Abstract: The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula ( I ) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which:R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups;R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG);R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect;with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect.A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation.
    Type: Grant
    Filed: March 28, 1995
    Date of Patent: April 1, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventor: Jean-Marc Ricca
  • Patent number: 5599996
    Abstract: The present invention provides 1-{[2-(cyclopropylcarbonyl)-4-fluorophenyl]sulfamoyl}-3-(4,6-dimethoxy-2-p yrimidinyl)urea which has the structural formula I ##STR1## Further provided are compositions and methods comprising that compound for the control of undesirable plant species.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: February 4, 1997
    Assignee: American Cyanamid Company
    Inventors: Michael E. Condon, Philip M. Harrington
  • Patent number: 5599814
    Abstract: The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Thomas M. Bare, Richard B. Sparks
  • Patent number: 5597922
    Abstract: Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: January 28, 1997
    Assignees: State of Oregon, Acting by and through the Oregon State Board of Higher Education, Acting for and on Behalf of the Oregon Health Sciences University and the University of Oregon, Acea Pharmaceuticals, Inc., The Regents of the University of California
    Inventors: Sui X. Cai, John F. W. Keana, Eckard Weber
  • Patent number: 5585522
    Abstract: Novel amino substituted bishalomethyl benzene compounds, which are precurs to phenylene polymers are disclosed having non-linear optical properties, and which can be converted to electrically conductive polymers. Such polymers are produced by reacting a novel amino substituted bishalomethyl benzene compound with a dialkyl sulfide to make a bis-cycloalkylene sulfonium salt of 2,5,N,N-tetramethylaniline hydrochloride, which is 2,5-(N,N-dimethyl)aniline hydrochloride dimethylene bis-(tetramethylene sulfonium chloride) and reacting this sulfonium salt with alkali metal hydroxide to form a cycloalkylene sulfonium salt precursor polymer, and then heating the precursor polymer under conditions to produce the amino substituted phenylene vinylene polymer, such as poly(2-(N,N-dimethylamino) phenylene vinylene). The polymers can also be made directly by treatment of the bis chlormethyl dimethyl aminobenzene hydrochloride derivative with alkali metal alkoxide.
    Type: Grant
    Filed: May 10, 1995
    Date of Patent: December 17, 1996
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: John D. Stenger-Smith, William P. Norris, Andrew P. Chafin
  • Patent number: 5567846
    Abstract: Novel diamines 1,2-bis(3-aminophenyl)perfluorocyclobutane 1,2-bis(3 or 4-aminophenyl)perfluorocyclobutene, cyclopenetene; and cyclohexene and the correspnding dintro compounds, from which they are made.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 22, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Zhenyu Yang
  • Patent number: 5565612
    Abstract: The present invention relates to substituted 2-chloro-3,4,5-trifluorobenzenes of the formula ##STR1## in which R is NO.sub.2, NH.sub.2, CN or Cl, and to a process for the preparation of substituted 2-chloro-3,4,5-trifluorobenzenes of the formula given above, in which R is NO.sub.2, NH.sub.2, CN, Cl or Br, which involves reacting 2,3,4-trifluorochlorobenzene with a nitrating agent in the presence or absence of a water-insoluble solvent at from -10.degree. C. to 50.degree. C., reducing 2-chloro-3,4,5-trifluoronitrobenzene or a mixture which contains 2-chloro-3,4,5-trifluoronitrobenzene and 5-chloro-2,3,4-trifluoronitrobenzene, in the presence of an organic solvent, isolating 2-chloro-3,4,5-trifluoroaniline or a mixture which contains 2-chloro-3,4,5-trifluoroaniline and 5-chloro-2,3,4-trifluoroaniline, diazotizing this product, if desired, and exchanging the diazotized group for a chloride atom, bromide atom or cyanide radical.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: October 15, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Thomas Schach
  • Patent number: 5550291
    Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: August 27, 1996
    Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.
    Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
  • Patent number: 5542953
    Abstract: The composition for the oxidative dyeing of hair contains at least one coupler of the general formula ##STR1## where R is a straight-chain or branched C.sub.1 - to C.sub.4 -alkyl group, X is chlorine or fluorine, and R.sup.1 is a straight-chain or branched C.sub.1 - to C.sub.4 -alkyl group or a straight-chain or branched C.sub.2 - to C.sub.4 -hydroxyalkyl group. The 5-halogen-2,4-bis(alkylamino)-1-alkylbenzenes of the formula (I) are novel. The couplers of the general formula (I) may be obtained through simple chemical reactions, are easily soluble in water and have an outstanding shelf stability, in particular as a constituent of the hair dye composition described here. The dyeing results which can be achieved with the hair dye composition according to the invention are particularly distinguished by the color intensity of the red hues, in addition to the multitude of shades, and by a good purity of color with respect to blue hues.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: August 6, 1996
    Assignee: Wella AG
    Inventors: Wolfgang R. Balzer, Thomas Clausen, Anke Frank, Alexa Weinges
  • Patent number: 5503640
    Abstract: 3-Substituted para-aminophenols of general formula: ##STR1## where X=H, halogen; Y=O--, --S--; R=alkyl, hydroxyalkyl, C.sub.1-4 aminoalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl;with the proviso that, when X=H, R is not methyl, and when X=H and Y=O, R is not ethyl;process for preparing them, intermediate compounds of formula: ##STR2## where X.sub.1 =halogen, Y and R have the meaning stated above; with the proviso that, when Y=O, R is not methyl, and when R=aminoalkyl, X.sub.1 can also denote hydrogen;dyeing compositions containing one or more compounds of formula (I), and a process For dyeing human hair.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: April 2, 1996
    Assignee: L'Oreal
    Inventors: Alex Junino, Alain Genet, Gerard Lang
  • Patent number: 5491261
    Abstract: Di-, tri- and poly-perfluoroalkyl-substituted alcohols and acids and derivatives thereof are described which are prepared from perfluoroalkyl iodides and di-, tri- or polyallyl alcohols or acids. These compounds contain two or more perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkenyl groups and one or two alcohol or acid groups or derivatized alcohol or acid functions. They can be reacted with isocyanates, epoxy compounds, anhydrides, acids or acid derivatives to prepare a great variety of oil- and water-repellent compositions which are useful for oil- and water-repellent treatment of textiles, glass, paper, leather and other substrates.
    Type: Grant
    Filed: July 1, 1994
    Date of Patent: February 13, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
  • Patent number: 5486609
    Abstract: A process for preparing carbocyclic m-aminohydroxyaromatics comprises reacting the corresponding o-- or m-halohydroxyaromatics or metal salts thereof with primary or secondary amines in the presence of a base and in the presence or absence of a diluent.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: January 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Robert Reinhardt, Helmut Reichelt, Roland Merger
  • Patent number: 5484953
    Abstract: Novel o-phenylenediamines of the formula containing fluoroalkyl(ene) groups ##STR1## in which the symbols used have the meaning given in the description, processes for their preparation and their use as intermediates.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: January 16, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
  • Patent number: 5484931
    Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.
    Type: Grant
    Filed: June 15, 1994
    Date of Patent: January 16, 1996
    Assignee: Schering Corporation
    Inventors: Henry J. Doran, Donal J. Coveney