Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/442)
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Patent number: 6316658Abstract: 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: GrantFiled: April 11, 2000Date of Patent: November 13, 2001Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yasuo Yoshida, Hiroaki Takeuchi
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Patent number: 6306179Abstract: 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: GrantFiled: October 22, 1998Date of Patent: October 23, 2001Assignee: L'Oreal S.A.Inventors: Alain Genet, Alain Lagrange
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Patent number: 6307045Abstract: 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: GrantFiled: June 30, 2000Date of Patent: October 23, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Komori, Kazuhiko Nishioka
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Patent number: 6258956Abstract: 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: GrantFiled: March 21, 2000Date of Patent: July 10, 2001Assignee: Ortho-McNeil Pharmaceutical, Inc.Inventors: Ahmed F. Abdel-Magid, Judith H. Cohen, Cynthia A. Maryanoff, Frank John Villani, Jr., Hua M. Zhong
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Patent number: 6242634Abstract: 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: GrantFiled: May 31, 2000Date of Patent: June 5, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Masayuki Enomoto, Hisayuki Hoshi, Yuzuru Sanemitsu
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Patent number: 6242609Abstract: 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: GrantFiled: April 7, 1999Date of Patent: June 5, 2001Assignee: Konica CorporationInventor: Fumio Ishii
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Patent number: 6235939Abstract: 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: GrantFiled: March 8, 2000Date of Patent: May 22, 2001Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 6222074Abstract: 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: GrantFiled: July 25, 2000Date of Patent: April 24, 2001Assignee: Nissan Chemical Industries, Ltd.Inventors: Kenichi Tokunaga, Motohito Shiratori, Kazuhiko Akimoto, Hideo Suzuki, Isao Hashiba
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Patent number: 6191309Abstract: 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: GrantFiled: March 2, 1999Date of Patent: February 20, 2001Assignee: Rhodia ChimieInventor: Michel Dury
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Patent number: 6166273Abstract: 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: GrantFiled: July 27, 1999Date of Patent: December 26, 2000Assignee: E.I. du Pont de Nemours and CompanyInventor: Munirpallam A. Subramanian
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Patent number: 6156774Abstract: 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: GrantFiled: April 7, 1999Date of Patent: December 5, 2000Assignee: SmithKline Beecham P.L.C.Inventors: John Hargreaves Bateson, Desmond John Best, Brian Peter Clarke, Martin Leonard Gilpin, David Witty
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Patent number: 6143208Abstract: 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: GrantFiled: February 12, 1997Date of Patent: November 7, 2000Assignee: Rolic AGInventors: Richard Buchecker, Xin Hua Chen, Jurg Fufschilling, Rolf-Peter Herr, Martin Schadt, Klaus Schmitt
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Patent number: 6118025Abstract: 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: GrantFiled: December 27, 1999Date of Patent: September 12, 2000Assignee: Sanofi-SynthelaboInventors: Francine Agbossou, Marc Devocelle, Jean-Robert Dormoy, Andre Mortreux
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Patent number: 6114584Abstract: 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: GrantFiled: September 29, 1999Date of Patent: September 5, 2000Assignee: Occidental Chemical CorporationInventor: Sanjay Mandal
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Patent number: 6069279Abstract: 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: GrantFiled: June 14, 1999Date of Patent: May 30, 2000Inventors: Mark W. Simon, Mohammad A. Khan
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Patent number: 6040482Abstract: 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: GrantFiled: March 5, 1999Date of Patent: March 21, 2000Assignee: Milliken & CompanyInventors: Philip G. Harris, Rajnish Batlaw
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Patent number: 6040480Abstract: 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: GrantFiled: February 11, 1999Date of Patent: March 21, 2000Assignee: Du Pont Pharmaceuticals CompanyInventors: Michael E. Pierce, Cheng Y. Chen, Anusuya Choudhury, Lilian A. Radesca, Lushi Tan, Dalian Zhao
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Patent number: 6015926Abstract: 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: GrantFiled: May 11, 1998Date of Patent: January 18, 2000Assignee: Merck & Co., Inc.Inventors: Cheng Yi Chen, Lushi Tan, Richard D. Tillyer
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Patent number: 6013838Abstract: 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: GrantFiled: January 26, 1999Date of Patent: January 11, 2000Assignee: Alliedsignal Inc.Inventor: Michael Van Der Puy
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Patent number: 5986140Abstract: 7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine.Type: GrantFiled: March 19, 1997Date of Patent: November 16, 1999Assignee: Clariant Finance (BVI) LimitedInventor: John C. Saukaitis
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Patent number: 5965735Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.Type: GrantFiled: May 23, 1995Date of Patent: October 12, 1999Assignee: Schering CorporationInventors: Henry J. Doran, Donal J. Coveney
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Patent number: 5962740Abstract: 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: GrantFiled: April 28, 1998Date of Patent: October 5, 1999Assignee: Nissan Chemical Industries, Ltd.Inventors: Kazuhiko Akimoto, Kenichi Tokunaga, Isao Hashiba, Hideo Suzuki, Yasuo Katsumura, Kazuo Osaki, Hideo Kawashita, Satoshi Yamazaki
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Patent number: 5932726Abstract: 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: GrantFiled: April 11, 1997Date of Patent: August 3, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Michael Ernest Pierce, Anusuya Choudhury, Rodney Lawrence Parsons, Jr., Lilian Alicia Radesca
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Patent number: 5900509Abstract: 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: GrantFiled: January 16, 1998Date of Patent: May 4, 1999Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Albrecht Marhold, Guido Steffan
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Patent number: 5874656Abstract: 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: GrantFiled: October 7, 1997Date of Patent: February 23, 1999Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Michael-Harold Rock
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Patent number: 5856576Abstract: 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: GrantFiled: January 29, 1998Date of Patent: January 5, 1999Assignee: American Cyanamid CompanyInventors: Philip M. Harrington, Kenneth A. M. Kremer
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Patent number: 5840983Abstract: 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: GrantFiled: July 18, 1997Date of Patent: November 24, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Albrecht Marhold
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Patent number: 5801201Abstract: 1-phenyl-2-dimethylaminomethyl-cyclohexan-1-ol compounds, methods of preparing them and the use of these compounds in drugs are described.Type: GrantFiled: December 19, 1996Date of Patent: September 1, 1998Assignee: Gruenenthal GmbHInventors: Ivars Graudums, Werner Winter, Ernst Frankus, Wolfgagn Werner Alfred Strassburger, Elmar Josef Friderichs
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Patent number: 5741476Abstract: 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: GrantFiled: June 20, 1995Date of Patent: April 21, 1998Assignee: Mallinckrodt Medical, Inc.Inventor: John Janine Rene Mertens
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Patent number: 5712418Abstract: 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: GrantFiled: August 2, 1994Date of Patent: January 27, 1998Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
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Patent number: 5683998Abstract: 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: GrantFiled: May 2, 1995Date of Patent: November 4, 1997Assignee: Toray Industries, Inc.Inventors: Katsuhiro Shibayama, Tetsuya Makino, Takayuki Imaoka, Tetsuya Katou, Masayuki Kaneko
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Patent number: 5663448Abstract: 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: GrantFiled: November 21, 1995Date of Patent: September 2, 1997Assignee: Merrell Pharmaceuticals Inc.Inventors: Jean-Noel Collard, Jean-Marie Hornsperger, Daniel Schirlin
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Patent number: 5645610Abstract: 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: GrantFiled: May 26, 1995Date of Patent: July 8, 1997Inventors: Wolfgang R. Balzer, Anke Frank, Alexa Weinges
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Patent number: 5644056Abstract: 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: GrantFiled: June 7, 1995Date of Patent: July 1, 1997Assignee: Hoechst Celanese CorporationInventor: John C. Saukaitis
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Patent number: 5639915Abstract: 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: GrantFiled: March 10, 1995Date of Patent: June 17, 1997Assignees: Sagami Chemical Research Center, Kaken Pharmaceutical Co., Ltd.Inventors: Kenji Hirai, Emiko Ejiri, Tomoyuki Yano, Kiyomi Aizawa
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Patent number: 5637256Abstract: 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: GrantFiled: May 26, 1995Date of Patent: June 10, 1997Assignee: University Research CorporationInventors: David M. Walba, Maria B. Ros, James A. Rego, Teresa Sierra
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Patent number: 5616810Abstract: 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: GrantFiled: March 28, 1995Date of Patent: April 1, 1997Assignee: Rhone-Poulenc ChimieInventor: Jean-Marc Ricca
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Patent number: 5599996Abstract: 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: GrantFiled: May 4, 1995Date of Patent: February 4, 1997Assignee: American Cyanamid CompanyInventors: Michael E. Condon, Philip M. Harrington
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Patent number: 5599814Abstract: 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: GrantFiled: April 24, 1995Date of Patent: February 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Thomas M. Bare, Richard B. Sparks
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Patent number: 5597922Abstract: 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: GrantFiled: July 29, 1994Date of Patent: January 28, 1997Assignees: 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 CaliforniaInventors: Sui X. Cai, John F. W. Keana, Eckard Weber
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Patent number: 5585522Abstract: 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: GrantFiled: May 10, 1995Date of Patent: December 17, 1996Assignee: The United States of America as represented by the Secretary of the NavyInventors: John D. Stenger-Smith, William P. Norris, Andrew P. Chafin
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Patent number: 5567846Abstract: 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: GrantFiled: June 6, 1995Date of Patent: October 22, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Zhenyu Yang
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Patent number: 5565612Abstract: 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: GrantFiled: May 5, 1995Date of Patent: October 15, 1996Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Thomas Schach
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Patent number: 5550291Abstract: 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: GrantFiled: May 4, 1995Date of Patent: August 27, 1996Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
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Patent number: 5542953Abstract: 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: GrantFiled: October 22, 1993Date of Patent: August 6, 1996Assignee: Wella AGInventors: Wolfgang R. Balzer, Thomas Clausen, Anke Frank, Alexa Weinges
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Patent number: 5503640Abstract: 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: GrantFiled: May 26, 1994Date of Patent: April 2, 1996Assignee: L'OrealInventors: Alex Junino, Alain Genet, Gerard Lang
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Patent number: 5491261Abstract: 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: GrantFiled: July 1, 1994Date of Patent: February 13, 1996Assignee: Ciba-Geigy CorporationInventors: Marlon Haniff, Robert Falk, Ted Deisenroth, Karl F. Mueller
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Patent number: 5486609Abstract: 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: GrantFiled: March 24, 1995Date of Patent: January 23, 1996Assignee: BASF AktiengesellschaftInventors: Robert Reinhardt, Helmut Reichelt, Roland Merger
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Patent number: 5484953Abstract: 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: GrantFiled: June 3, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
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Patent number: 5484931Abstract: Process for preparing a key intermediate, 2-methyl-3-trifluoromethylaniline (MTA) of Flunixin, as well as novel intermediates thereof are described.Type: GrantFiled: June 15, 1994Date of Patent: January 16, 1996Assignee: Schering CorporationInventors: Henry J. Doran, Donal J. Coveney