Halogen, Bonded Directly To Carbon, Containing Patents (Class 564/442)
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Patent number: 5453542Abstract: The present invention is a method of preparing a 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt and resorcinol in the presence of a base and a reaction medium containing water and a water-miscible solvent at a temperature in the range of about -5.degree. C to about -60.degree. C. The present invention is also a method of preparing a 2-substituted 4,6-bisarylazoresorcinol comprising reacting an aryldiazonium salt with a 2-substituted resorcinol. The 4,6-bisarylazoresorcinol or 2-substituted 4,6-bisarylazoresorcinol can then be hydrogenated to a 4,6-diaminoresorcinol, which is a precursor to polybisbenzoxazoles (PBOs), polymers which are useful as insulators, solar arrays, and tear-resistant gloves.Type: GrantFiled: February 24, 1994Date of Patent: September 26, 1995Assignee: The Dow Chemical CompanyInventors: Ted A. Morgan, Bassam S. Nader, Paul Vosejpka, Weshi Wu, Andrew S. Kende
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Patent number: 5446186Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.Type: GrantFiled: November 9, 1993Date of Patent: August 29, 1995Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
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Process for producing (E)-alkoxyimino or hydroxyimino-acetamide compounds and intermediates therefor
Patent number: 5442063Abstract: The present invention relates to a process for producing (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides and a process for producing (E)-hydroxyiminoacetamide compounds useful as intermediates for producing them. The present invention also relates to an industrial process for producing (E)-methoxyiminoacetamide compounds useful as agricultural fungicides. This process is advantageous in terms of the cost, safety and the like.Type: GrantFiled: November 2, 1993Date of Patent: August 15, 1995Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kuniyoshi Nishida -
Patent number: 5426230Abstract: 4-Chloro-2-cyclopropylcarbonylaniline is prepared by condensation of 4-chloroaniline with 4-chlorobutyronitrile to form a 2-(4-chlorobutyryl)-4-chloroaniline, followed by ring closure of the 4-chlorobutyryl group to a cyclopropylcarbonyl moiety.Type: GrantFiled: June 10, 1994Date of Patent: June 20, 1995Assignee: Merck & Co., Inc.Inventors: Alan Douglas, Ioannis Houpis, Audrey Molina, Ralph P. Volante, Nobuyoshi Yasuda
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X-ray contrast compositions containing iodoaniline derivatives and pharmaceutically acceptable clays
Patent number: 5424056Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising an iodoaniline derivative as the x-ray producing agent in combination with a pharmaceutically acceptable clay in a pharmaceutically acceptable carrier; and methods for their use in diagnostic radiology of the gastrointestinal tract.Type: GrantFiled: April 29, 1994Date of Patent: June 13, 1995Assignee: Sterling Wintrhop Inc.Inventors: Stephen B. Ruddy, Gregory L. McIntire, Mary E. Roberts, Thomas J. Caulifield, Eugene R. Cooper -
Patent number: 5422114Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising an x-ray producing agent of the formula or a pharmaceutically acceptable salt thereof ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract, whereinZ is H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.sub.1 and R.sub.2 are independently H, C.sub.1 -C.sub.25 alkyl, cycloalkyl, acetyl or halo-lower-alkyl, wherein said C.sub.1 -C.sub.Type: GrantFiled: February 25, 1994Date of Patent: June 6, 1995Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Thomas J. Caulfield, Robert W. Lee, Edward J. Baker
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Patent number: 5414125Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.Type: GrantFiled: July 23, 1993Date of Patent: May 9, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5409503Abstract: The composition for oxidative dyeing of hair contains 0.01 to 5.0 percent by weight of at least one 5-aminophenol compound of the formula ##STR1## wherein R is an alkyl group having 1 to 4 carbon atoms, X is fluorine or OR.sup.1 and R.sup.1 is an alkyl group having 2 to 4 carbon atoms, a monohydroxyalkyl group with 2 to 4 carbon atoms or a dihydroxyalkyl group with 3 and 4 carbon atoms, and physiologically tolerated water-soluble salts thereof as coupler substance; and 0.1 to 6.1 percent by weight of a total amount of the coupler substance and at least one developer substance. The developer substance can be 1,4-diaminobenzene, 2,5-diaminotoluene, 2,5-diaminobenzyl alcohol, 2-(2'-hydroxyethyl)-1,4-diaminobenzene, 4-aminophenol, 4-amino-3-methylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-ethoxy-methylphenol and tetraaminophyrimidine and physiologically tolerated water-soluble salts thereof.Type: GrantFiled: October 21, 1993Date of Patent: April 25, 1995Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, Wolfgang R. Balzer, Helmut Keller
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Patent number: 5407936Abstract: A benzimidazole derivative having the following formula (I): ##STR1## or a pharmaceutically acceptable acid addition salt thereof, a process for preparing the same, an antiemetic agent containing the same as an active ingredient and an intermediate compound for preparing the same. The above novel benzimidazole derivative has a continuous 5-HT.sub.3 antagonistic activity, shows preventive and therapeutic effects against vomiting caused by cisplatin and has a low toxicity, and hence, is useful as an antiemetic agent against vomiting due to chemotherapeutic treatment with cisplatin etc.Type: GrantFiled: December 23, 1993Date of Patent: April 18, 1995Assignee: Kanebo Ltd.Inventors: Kenji Suzuki, Hiroshi Ohtaka, Akio Ozaki, Yasuo Morimoto, Takayuki Sukamoto
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Patent number: 5405998Abstract: There is provided an improved method for the production of o-aminophenyl ketones of formula I wherein R is C.sub.3 -C.sub.6 cycloalkyl or C.sub.1 -C.sub.6 haloalkyl. ##STR1## Compounds of formula I are key intermediates in the manufacture of sulfamoyl urea herbicides.Type: GrantFiled: November 30, 1993Date of Patent: April 11, 1995Assignee: American Cyanamid CompanyInventor: Albert A. Cevasco
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Patent number: 5401882Abstract: 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: November 24, 1993Date of Patent: March 28, 1995Assignee: Rhone-Poulenc ChimieInventor: Jean-Marc Ricca
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Patent number: 5401878Abstract: A fluorine-containing polyimide having a low dielectric constant, low water absorption and excellent heat resistance and moisture resistance and a precursor thereof such as a fluorine-containing polyamide-acid, can be prepared by reacting an acid anhydride with an aromatic diamine having perfluoroalkyl group.Type: GrantFiled: September 1, 1993Date of Patent: March 28, 1995Assignee: Hitachi Chemical Company, Ltd.Inventors: Masami Yusa, Shinji Takeda, Yasuo Miyadera
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Patent number: 5399767Abstract: A process for producing 3,5-difluoroaniline, which comprises reacting a benzonitrile compound of the formula (I): ##STR1## wherein each of X.sub.1, X.sub.2 and X.sub.3 is hydrogen, chlorine, bromine or a cyano group, provided that at least one of X.sub.1 to X.sub.3 is a cyano group, with a mineral acid for hydrolysis and decarboxylation to obtain an aniline compound of the formula (II): ##STR2## wherein each of X.sub.4, X.sub.5 and X.sub.6 is hydrogen, chlorine or bromine, provided that at least one of X.sub.4 to X.sub.6 is hydrogen, and in the case of a compound of the formula (II) wherein X.sub.4, X.sub.5 and X.sub.6 are not simultaneously hydrogen, reacting such a compound with hydrogen in a presence of a catalyst for reduction to obtain 3,5 -difluoroaniline.Type: GrantFiled: February 8, 1994Date of Patent: March 21, 1995Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Motohiko Hamaguchi
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5364413Abstract: 3-Substituted para-aminophenols, process for preparing them, their use for dyeing keratinous fibres and the intermediate compounds used in the process of preparation.3-Substituted para-aminophenols, of general formula: ##STR1## where X.dbd.H, halogen; Y.dbd.O--, --S--; R.dbd.alkyl, hydroxyalkyl, C.sub.1-4 aminoalkyl or C.sub.3 -C.sub.6 polyhydroxyalkyl;with the proviso that, when X.dbd.H, R is not methyl, and when X.dbd.H and Y.dbd.O, R is not ethyl;process #or preparing them, intermediate compounds of formula: ##STR2## where X.sup.1 .dbd.halogen, Y and R have the meaning stated above; with the proviso that, when Y.dbd.O, R is not methyl, and when R.dbd.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: November 12, 1992Date of Patent: November 15, 1994Assignee: L'OrealInventors: Alex Junino, Alain Genet, Gerard Lang
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Patent number: 5349104Abstract: Without added stabilizers, aminobenzotrifluorides have low thermal and storage stability.The present invention relates to preparations of a stabilized amionbenzotrifluoride, composed essentially ofa) an aminobenzotrifluoride of the formula (I), ##STR1## in which R.sup.1 and R.sup.2, independently of each other, are hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, substituted or unsubstituted aryl, halogen, CF.sub.3, nitro, amino, methoxy, hydroxyl or NR.sup.3 R.sup.4, where R.sup.3 and R.sup.4, independently of each other, are hydrogen or C.sub.1 -C.sub.5 -alkyl radicals, and the NH.sub.2 group can be located in the 2-, 3- or 4-position in relation to the CF.sub.3 group, andb) at least one base.Type: GrantFiled: May 4, 1993Date of Patent: September 20, 1994Assignee: Hoechst AktiengesellschaftInventors: Gilbert Billeb, Gunther Semler
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Patent number: 5349062Abstract: Compounds of formula I ##STR1## wherein X.sub.1 and X.sub.2 are each independently of the other O, S or Se, and R.sub.1 and R.sub.2 are each independently of the other a monovalent radical of an aliphatic or aromatic hydrocarbon of 1 to 20 carbon atoms which is unsubstituted or substituted by NH.sub.2, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl or C.sub.3 -C.sub.8 cycloalkyl. The compounds of formula I are able to form electrically conductive charge transfer complexes.Type: GrantFiled: June 28, 1993Date of Patent: September 20, 1994Assignee: Ciba-Geigy CorporationInventor: John Zambounis
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Patent number: 5340810Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl and C.sub.1-6 alkoxy;R.sup.2 represents a phenyl group substituted by a group selected from ##STR2## and optionally further substituted by one or two substituents selected from halogen atoms, C.sub.1-6 alkoxy, hydroxy, and C.sub.1-6 alkyl;R.sup.3 represents the group ##STR3## R.sup.4 and R.sup.5, which may be the same or different each independently represent a hydrogen atom or a halogen atom or a group selected from hydroxy, C.sub.1-6 alkoxy and C.sub.1-6 alkyl;R.sup.6 represents a hydrogen atom or a group selected from --NR.sup.9 R.sup.10 and a C.sub.1-6 alkyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkoxy, hydroxy, C.sub.1-6 acyloxy and --SO.sub.2 R.sup.11 ;R.sup.7, R.sup.8 and R.sup.Type: GrantFiled: September 17, 1992Date of Patent: August 23, 1994Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Malcolm Carter
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Patent number: 5330740Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract whereinZ=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.sub.1 and R.sub.2 are independently H, C.sub.1 -C.sub.25 alkyl, cycloalkyl acetyl, or halo-lower-alkyl, wherein said C.sub.1 -C.sub.25 alkyl, cycloalkyl, acetyl and halo-lower-alkyl are optionally substituted with, fiuoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy;n is 1-5;y is 1-4; andx is 1 or 2in a pharmaceutically acceptable carrier.Type: GrantFiled: March 1, 1993Date of Patent: July 19, 1994Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Thomas J. Caulfield
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Patent number: 5312999Abstract: Propoxybenzene derivatives represented by the following formula ##STR1## wherein Ra represents a nitro group, an amino group which may have a protecting group or an --NHCH.dbd.C(COO--C.sub.1-6 -Alkyl).sub.2 group, Rb represents a hydrogen atom, a protecting group for the hydroxyl group or a substituted sulfonyl group and Xa and Xb, which may be the same or different, each represents a halogen atom, and processes for preparation thereof are disclosed. These derivatives are useful in preparing antibacterial agents.Type: GrantFiled: March 2, 1992Date of Patent: May 17, 1994Assignee: Daiichi Seiyaku Co., Ltd.Inventors: Toshihiro Fujiwara, Tutomu Ebata
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Patent number: 5313001Abstract: Process for the preparation of .alpha.-fluorostyrene from fluoroolefins: ##STR1## Z=hydrogen, fluorine, chlorine X=iodine, bromine, chlorine.A halogenated aromatic (I) is reacted with a fluorine-substituted ethylene (II) in the presence of a palladium catalyst to give an .alpha.-fluorostyrene (III), it being possible for R to be a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 -alkyl group, a C.sub.1 -C.sub.5 -alkoxy group, an amino, alkylamino or dialkylamino group, an aryl radical or a fused aryl or heteroaryl ring, a hydroxyl or hydroxyalkyl group, a trifluoromethyl or perfluoroalkyl group or a nitro group.Type: GrantFiled: November 17, 1992Date of Patent: May 17, 1994Assignee: Hoechst AktiengesellschaftInventors: Walter Heitz, Arno Knebelkamp
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Patent number: 5310537Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinZ=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R.sub.1 and R.sub.2 are independently H, C.sub.1 -C.sub.25 alkyl, cycloalkyl, acetyl or halo-lower-alkyl, wherein said C.sub.1 -C.sub.25 alkyl, cycloalkyl, acetyl and halo-lower-alkyl are optionally substituted with fluoro-lower-alkyl, aryl, lower-alkoxy, hydroxy, carboxy, lower-alkoxy carbonyl or lower-alkoxy-carbonyloxy,n is 1-4;y is 1-4; andx is 1 or 2.Type: GrantFiled: March 1, 1993Date of Patent: May 10, 1994Assignee: Sterling Winthrop Inc.Inventors: Carl R. Illig, Thomas J. Caulfield
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Patent number: 5308829Abstract: There are disclosed novel benzofuran derivatives of the formula: ##STR1## Also disclosed are a herbicidal composition containing the above benzofuran derivative as an active ingredient and a method for exterminating undesired weeds by the application of a herbicidally effective amount of the above benzofuran derivative to an area where the undesired weeds grow or will grow.Type: GrantFiled: March 18, 1993Date of Patent: May 3, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Susumu Takemura, Masayuki Enomoto, Toru Uekawa, Masaharu Sakaki, Ryo Sato, Eiki Nagano
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Patent number: 5300692Abstract: Disclosed is a process for producing 4-amino-3-fluorobenzotrifluoride which comprises reacting 3,4-difluorobenzotrifluoride with anhydrous ammonia (liquid ammonia or gaseous ammonia) under pressure.Type: GrantFiled: November 19, 1992Date of Patent: April 5, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Toshiaki Taki, Noritada Matsuo
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Patent number: 5270309Abstract: 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, other than carboxy or C.sub.1-6 alkoxycarbonyl, are novel compounds, as also are compounds of formula II ##STR1## wherein R.sup.2 represents carboxy or a group convertible thereto in vivo, R.sup.6 is hydrogen and R.sup.5 and R.sup.7 represent C.sub.1-6 alkyl or halogen, provided that R.sup.5 and R.sup.7 are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.Type: GrantFiled: July 20, 1992Date of Patent: December 14, 1993Assignee: Merck Sharp & Dohme LimitedInventor: Paul Leeson
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Patent number: 5264502Abstract: An epoxy resin composition useful as a molded article is cured with a combination of curing agents including diamino-alpha-alkylstilbenes and other curing agents wherein the epoxy resin and/or the other curing agent can contain rodlike mesogenic moieties.Type: GrantFiled: April 10, 1991Date of Patent: November 23, 1993Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5260428Abstract: A process for the detection of substances with hydrolase activity in a sample by mixing the sample with a hydrolase substrate and an oxidising agent, and the evaluating the resultant colour intensity, wherein, as hydrolase substrate, there is used at least one compound of the formula ##STR1## in which R.sup.1 is hydrogen or an alkoxy radical,R.sup.2 is hydrogen or halogen, an amino group or an alkoxy or aralkoxy radical,R.sup.3, R.sup.4, R.sup.5, R.sup.6, which can be the same or different, are hydrogen, halogen, carboxyl, a carbamoyl group, sulpho, an amino groups alkyl, an alkoxy radical, aralkoxy, alkylcarbonyl or alkoxycarbonyl, andX is a glycosyl, phosphate or acyl residue. Optionally R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.4 and R.sup.5, and R.sup.5 and R.sup.6 can be joined to form a ring system. At least one of R.sup.1 and R.sup.2 must be hydrogen and at least one of R.sup.1, R.sup.2 and R.sup.3 must not be hydrogen. Compounds in which X is .beta.-galactosyl are new.Type: GrantFiled: January 29, 1993Date of Patent: November 9, 1993Assignee: Boehringer Mannheim GmbHInventors: Rupert Herrmann, Hans-Joachim Guder, Werner Guthlein, Manfred Kuhr, Johann Berger, Harvey Buck
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Patent number: 5254685Abstract: A tricyclic compound represented by the general formula (1) and salts thereof. ##STR1## A method for producing the tricyclic compound and salts thereof, and an antimicrobial agent containing the tricyclic compound and salts thereof as an active ingredient are also disclosed.Type: GrantFiled: August 7, 1991Date of Patent: October 19, 1993Assignees: Wakunaga Seiyaku Kabushiki Kaisha, Fujisawa Pharmaceutical Co., Ltd.Inventors: Masaharu Yokomoto, Akira Yazaki, Norihiro Hayashi, Shunso Hatono, Satoshi Inoue, Yasuhiro Kuramoto
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Patent number: 5250708Abstract: A poly(oxyalkylene) substituted xanthene colorant is providing having the following structure: ##STR1## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of from 3 to 400 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol;R.sub.1 and R.sub.2 are independently selected from H, C1-C8 alkyl, aryl and Y, provided that if either R.sub.1 or R.sub.2 are Y, the other is not H;R.sub.3 and R.sub.4 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I;X is selected from H, SO.sub.3 --, CO.sub.2 -- and COOR.sub.5, where R.sub.5 is C1-C4 alkyl or aryl; andeach Z is independently selected from SO.sub.3 --, CO.sub.2 --, COOR.sub.6, Cl, and OH, where R.sub.6 is C1-C4 alkyl or aryl, and n is 0, 1, 2 or 3.The colorant is synthesized using a novel poly(oxyalkylene) substituted aminophenol intermediate.Type: GrantFiled: August 13, 1991Date of Patent: October 5, 1993Assignee: Milliken Research CorporationInventor: Carey N. Barry, Jr.
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Patent number: 5250735Abstract: Novel 2-(N-substituted-aminoalkyl)-5-(E)-alkylidene cyclopentanones, 2-(N-substituted-aminoalkyl)-5-(E)-arylalkylidene cyclopentanones, and derivatives thereof having the formula ##STR1## wherein x is methylene or ethylene; R.sub.1 is dimethylamino, diethylamino, 1-pyrrolidinyl, 1-piperidinyl, 4-morpholinyl, anilino or substituted anilino; R.sub.2 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; R.sub.3 is hydrogen, straight or branched alkyl of 1 to 9 carbon atoms, aryl or arylalkyl; and R.sub.4 is hydrogen, methyl, ethyl, allyl, benzyl, substituted benzyl, cyclopentyl, substituted cyclopentyl, cyclopenten-1-yl, or substituted cyclopenten-1-yl; and wherein aryl is phenyl or phenyl substituted with one or more methoxyl, hydroxyl, methylenedioxy, chloro, bromo, fluoro, ethoxycarbonylmethoxy, benzoxy, alkyl group, or their combination, possess anti-inflammatory, analgesic and anticancer properties.Type: GrantFiled: April 3, 1992Date of Patent: October 5, 1993Assignee: University of PittsburghInventors: Lan K. Wong, Hai-Tao Chen, Zhi-Zhong Ji
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Patent number: 5238818Abstract: This amount of an oxidative substance or a peroxidase-like substance can be determined by using a combined color former comprising 4-aminoantipyrine or a derivative thereof, etc., as a main color former and a p-fluoroaniline derivative or a salt thereof as a color producing component.Type: GrantFiled: November 26, 1991Date of Patent: August 24, 1993Assignee: Wako Pure Chemicals Co., Ltd.Inventors: Kazunari Hashizume, Haruhiko Sugiyama, Mutsuhiro Date
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Patent number: 5230666Abstract: A prepolymer of the formula ##STR1## where LG is a linking group, and copolymers thereof; polymers prepared therefrom, and a reaction injection molding process employing the same.Type: GrantFiled: November 24, 1992Date of Patent: July 27, 1993Assignee: Dayco Products, Inc.Inventor: Charles M. Lewis
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Patent number: 5230710Abstract: New substituted 2,6-diaminotoluenes of the general formula I ##STR1## wherein R is a hydrogen atom and R.sup.1 is a radical of the formula Ia--CH.sub.2 --CH(A)--B (Ia)or R and R.sup.1 are independent from each other and are represented by the formula Ia and if A in formula Ia represents a hydrogen atom, B is a hydroxyl group or HO--CH.sub.2 -- group; if A denotes a methyl group, B is a hydroxyl group; with the proviso that formula I is not N-(2-hydroxyethyl)-2,6-toluylenediamine; processes for their preparation and coloring compositions for keratin fibers which contain them. The dyeings produced with the coloring compositions are stable, bright and intense in color. They have improved properties with respect to attack by perspiration, acid rain, detergents, sunlight, UV radiation, seawater and the like.Type: GrantFiled: September 30, 1992Date of Patent: July 27, 1993Assignee: Hans Schwarzkopf GmbHInventors: Mustafa Akram, Winfried Seidel, Wolfgang Schlenther
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Patent number: 5224965Abstract: The composition for the oxidative dyeing of hair contains at least one coupler substance of the formula ##STR1## where R is a straight-chain or branched C.sub.1 - to C.sub.4 -alkyl group and X is fluorine or bromine, and new 5-halogen-2,4-diaminoalkylbenzenes.The coupler substances of formula (I) are obtainable by simple chemical reactions, easily soluble in water and have a good shelf stability particularly as constituents of the hair dye composition described here.In addition to the multitude of color shades, the dye results which can be achieved with the hair dye composition according to the invention are distinguished particularly by the intensity of color of the red tones and good uniformity of color of the blue tones.Type: GrantFiled: April 7, 1992Date of Patent: July 6, 1993Assignee: Wella AktiengesellschaftInventors: Thomas Clausen, Alexa Weinges, Wolfgang R. Balzer
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Patent number: 5225607Abstract: This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.Type: GrantFiled: December 30, 1987Date of Patent: July 6, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr, Alan J. Whittle
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Patent number: 5221750Abstract: 2-aryl-4-isoxazolin-3-1-derivatives of formula (I), useful as intermediates for positive working compounds in silver halide photographic materials ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl having from 1 to 6 carbon atoms or a substituted or unsubstituted aryl having from 6 to 24 carbon atoms; and R.sup.2, R.sup.3, and R.sup.4, are the same or different, each having up to 20 carbon atoms and each represents hydrogen, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted acyl, a substituted or unsubstituted alkoxycarbonyl, a substituted or unsubstituted aryloxycarbonyl, halogen, nitro, a substituted or unsubstituted carbamoyl, a substituted or unsubstituted sulfamoyl, a substituted or unsubstituted sulfonyl, cyano, or trifluoromethyl, with the proviso that at least one of said R.sup.2 and R.sup.3 is cyano, a substituted or unsubstituted sulfonyl, trifluoromethyl, or nitro.Type: GrantFiled: January 13, 1992Date of Patent: June 22, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Koki Nakamura, Shigeru Nakamura
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Patent number: 5212173Abstract: Pharmacologically active compounds corresponding to the formula I ##STR1## in which n represents 2-5,m represents 2-6,R.sup.1 denotes hydrogen or lower alkyl,R.sup.2 represents an OR.sup.4 group in which R.sup.4 denotes lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.2 represents a ##STR2## group in which R.sup.5 and R.sup.6 independently of one another each denote hydrogen, lower alkyl or a phenyl or phenyl-lower alkyl group which is optionally substituted in the phenyl ring, orR.sup.5 and R.sup.6, together with the nitrogen atom to which they are bonded, represent a saturated 5- or 6-membered heterocycle,R.sup.3 represents a saturated monocyclic or bicyclic hydrocarbon group which is derived from terpenes and has 10 or 11 carbon atoms, andZ represents oxygen or, if R.sup.3 is a dihydronopyl group, Z may also represent sulfur,and salts thereof.Type: GrantFiled: December 19, 1991Date of Patent: May 18, 1993Assignee: Kali-Chemie Pharma GmbHInventors: Herman Kraehling, Samuel David, Insa Hell, Ulf Preuschoff, Ivan Ban, Marie-Odile Christen
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Patent number: 5207798Abstract: Process for dyeing keratinous fibres, in particular human keratinous fibres such as hair, characterized in that there is applied to these fibres a composition containing, in a suitable dyeing mixture, at least one indole-based coupler, of the formula: ##STR1## in which R.sub.1 designates a hydrogen atom or a C.sub.1 -C.sub.4 alkyl radical; R.sub.2 and R.sub.3, which may be identical or different, designate a hydrogen atom, a C.sub.1 -C.sub.4 lower alkyl radical, a carboxyl radical or an alkoxycarbonyl radical; X designates a hydrogen atom, a C.sub.1 -C.sub.4 lower alkyl radical, a C.sub.1 -C.sub.18 alkoxy radical, a halogen atom, a C.sub.2 -C.sub.20 acyloxy radical or an acetylamino group; the OH group occupying the 6- or 7- positions of the aromatic ring; as well as the salts of these compounds;one oxidation dye precursor;one oxidising agent;the pH of the composition applied to the fibres being less than 7.Type: GrantFiled: March 7, 1991Date of Patent: May 4, 1993Assignee: L'OrealInventors: Jean Cotteret, Marie P. Audousset
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Patent number: 5199955Abstract: 1,5-diamino-2,4-bis(2,2,2-trifluoroethoxy) benzene is a novel m-phenylenediamine coupler and oxidative dye compositions containing same. Stronger dyeing intensity is afforded by use of the novel coupler of the invention.Type: GrantFiled: June 15, 1992Date of Patent: April 6, 1993Assignee: Clairol Inc.Inventors: Yuh-Guo Pan, Mu-Ill Lim, Alexander C. Chan
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Patent number: 5196583Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.Type: GrantFiled: December 4, 1990Date of Patent: March 23, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Kei Aoki
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Patent number: 5196569Abstract: Trifluorovinyl ethers containing selected functional groups, and homo- and copolymers prepared from them, are disclosed, as well as intermediates useful in the preparation of the ethers.Type: GrantFiled: October 10, 1991Date of Patent: March 23, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 5196586Abstract: Disclosed herein are polydiphenyldiacetylenes having the following repeating unit (III): ##STR1## (wherein R.sup.1 denotes a hydrogen atom or a methoxy group; R.sup.2 denotes a hydrogen atom, a methoxy group or a methylamino group; R.sup.3 denotes a hydrogen atom or a trifluoromethyl group; and R.sup.4 denotes a hydrogen atom or a trifluoromethyl group; provided that R.sup.1 is not a hydrogen atom when R.sup.2 is hydrogen atom, and R.sup.3 is not a hydrogen atom when R.sup.4 is hydrogen atom).Type: GrantFiled: August 9, 1991Date of Patent: March 23, 1993Assignees: Toda Kogyo Corp., The Agency of Industrial Science and TechnologyInventors: Hiro Matsuda, Shuji Okada, Hachiro Nakanishi, Masao Kato, Minoru Ohsugi, Shigeru Takaragi, Nanao Horiishi
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Patent number: 5196593Abstract: Novel halogenated trifluoromethylbenzenes have the structural formula ##STR1## wherein X is halogen, preferably Cl, F or Br, and R is a group selected from the group consisting of --COOH, --C(O)NH.sub.2 and --CN. These compounds are intermediates for pesticidal trifluoromethyl diphenyl ethers and are converted thereto by replacing the fluorine para to the trifluoromethyl with substituted phenoxy group in aromatic nucleophilic substitution.Type: GrantFiled: October 31, 1988Date of Patent: March 23, 1993Assignee: Occidental Chemical CorporationInventors: Karl W. Seper, James J. Maul, Henry C. Lin
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Patent number: 5194567Abstract: A prepolymer of the formula ##STR1## where LG is a linking group, and copolymers thereof; polymers prepared therefrom, and a reaction injection molding process employing the same.Type: GrantFiled: April 8, 1991Date of Patent: March 16, 1993Assignee: Dayco Products, Inc.Inventor: Charles M. Lewis
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Patent number: 5186716Abstract: N.sup.1 -Trifluoroalkyl substituted 2-nitro-p-phenylenediamines, compositions containing same, and their use as direct dyes for keratinous fibers are disclosed.Type: GrantFiled: September 13, 1991Date of Patent: February 16, 1993Assignee: Clairol IncorporatedInventors: Mu-Ill Lim, Yuh-Guo Pan
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Patent number: 5169955Abstract: A process for producing a 2-hydroxyquinoxaline which may be substituted with one or more substituents selected from the group consisting of halogen, lower alkyl and lower alkoxy, which comprises reacting o-phenylenediamine which may be substituted with one or more substituents selected from the group consisting of halogen, lower alkyl and lower alkoxy with glyoxylic acid in a lower aliphatic alcohol solvent without using a catalyst is disclosed. By the process according to the present invention, the 2-hydroxyquinoxaline derivatives can be obtained at a high purity and a high yield without using any catalyst.Type: GrantFiled: February 21, 1991Date of Patent: December 8, 1992Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hisabumi Kobayashi, Hiroshi Maruyama, Shuji Kawata, Sadahiko Noda
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Patent number: 5166438Abstract: A charge transporting material comprising a 1,3-pentadiene derivative having formula (I):A--CH.dbd.CH--CH.dbd.CH--CH.sub.2 --A (I)wherein A represents a 9-anthryl group which may have a substituent, a N-substituted carbazolyl group which may have a substituent, a N-substituted phenothiazinyl group which may have a substituent or ##STR1## in which Ar represents an arylene group which may have a substituent, R.sup.1 and R.sup.2 each represent an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aryl group which may have a substituent; an electrophotographic photoconductor comprising an electroconductive support and a photoconductive layer formed thereon, which comprises as an effective component at least one of the 1,3-pentadiene derivatives of the above formula (I); and novel 1,3-pentadiene derivatives of the formula (I), provided that in the formula (I), R.sup.1 and R.sup.2 cannot be a methyl group at the same time, are disclosed.Type: GrantFiled: August 23, 1991Date of Patent: November 24, 1992Assignees: Ricoh Company, Ltd., Hodogaya Chemical Co., Ltd.Inventors: Mitsuru Hashimoto, Masaomi Sasaki, Tomoyuki Shimada, Nobuo Suzuki, Takayuki Sakai, Susumu Suzuka
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Patent number: 5166181Abstract: Halogenoalkylphenyl-alcohols, ketones and their hydrates of formula I, ##STR1## wherein R.sub.1 to R.sub.8 are as defined in the description, are useful as acetylcholinesterase inhibitors.Type: GrantFiled: August 15, 1990Date of Patent: November 24, 1992Assignee: Sandoz Ltd.Inventor: Sylvain Cottens
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Patent number: RE34300Abstract: New chloro-meta-phenylenediamines, their use as couplers in the oxidation dyeing of keratinous fibres, dyeing compositions for hair containing these compounds and dyeing process using the said compositions.The invention relates to the compounds of formula: ##STR1## in which Z and Z' denote, independently of one another, an alkyl radical having from 1 to 4 carbon atoms or a hydroxyalkyl radical having from 2 to 4 carbon atoms, andR.sub.1 and R.sub.2 denote, independently of one another, a hydrogen atom, an alkyl radical having from 1 to 4 carbon atoms or a mono- or polyhydroxyalkyl radical having 2 or 3 carbon atoms, to their addition salts with an acid, and to their use by way of couplers for the oxidation dyeing of keratinous fibres, especially human hair.These compounds, when they are combined with paraphenylenediamines, surprisingly give beige to light brown hues or purple hues of greater of lesser redness, depending on the substitution of the 5-amino group of the chlorobenzene.Type: GrantFiled: August 13, 1990Date of Patent: July 6, 1993Assignee: L'OrealInventors: Alex Junino, Jean J. Vandenbossche, Herve Borowiak, Gerard Lang