Hydroxy, Bonded Directly To Carbon, Or Ether In A Substituent E (h Of -oh May Be Replaced By A Substituted Or Unsubstituted Ammonium Ion Or A Group Ia Or Iia Light Metal) Patents (Class 564/223)
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Patent number: 6187819Abstract: A composition for the upregulation of expression of cell antigens, without inducing shedding, which comprises a protein kinase C activator is provided by this invention. Further provided by this invention is a method of detecting and treating tumor cells comprising contacting tumor cells with an effective amount of a protein kinase C activator for the upregulation of expression of antigens of tumor cells, without inducing antigen shedding, and detecting the presence of said antigen or then further contacting said tumor cells with an effective amount of an antibody directed to said antigen.Type: GrantFiled: June 10, 1996Date of Patent: February 13, 2001Assignee: The Trustees of Columbia University in the City of New YorkInventors: Paul B. Fisher, Jorge A. Leon
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Patent number: 6169206Abstract: 4-(N,N-Dialkylamino)aniline compounds of the following general formula (I): wherein R1 represents an alkyl group, an aryl group or a heterocyclic group, R2 to R5 each represent a hydrogen atom or a substituent, and R2 and R3, R1 and R2, or R4 and R5 may form a ring together; a processing composition for color photography, which contains at least one of these compounds; and a color image-forming method wherein at least one of these aniline compounds is used.Type: GrantFiled: January 24, 2000Date of Patent: January 2, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Keizo Kimura, Shigeo Hirano, Hiroshi Kawamoto
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Patent number: 6069174Abstract: A composition for the upregulation of expression of cell antigens, without inducing shedding, which comprises a protein kinase C activator is provided by this invention. Further provided by this invention is a method of detecting and treating tumor cells comprising contacting tumor cells with an effective amount of a protein kinase C activator for the upregulation of expression of antigens of tumor cells, without inducing antigen shedding, and detecting the presence of said antigen or then further contacting said tumor cells with an effective amount of an antibody directed to said antigen.Type: GrantFiled: December 7, 1998Date of Patent: May 30, 2000Assignee: The Trustees of Columbia University in the City of New YorkInventors: Paul B. Fisher, Jorge A. Leon
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Patent number: 6028222Abstract: Novel stable paracetamol compositions for use in therapeutic chemistry and specifically galenic pharmacy are disclosed. The compositions contain a solution of paracetamol in an aqueous solvent combined with a buffer having a pH of 4 to 8, and a free radical capturing agent. A water-insoluble inert gas is carefully bubbled through the aqueous solvent to remove oxygen from the medium. Said compositions may also be combined with a centrally or peripherally acting analgesic agent, and are provided as injectable compositions for relieving pain.Type: GrantFiled: June 5, 1998Date of Patent: February 22, 2000Assignee: SCR PharmatopInventors: Francois Dietlin, Daniele Fredj
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Patent number: 6004565Abstract: The methods and compositions of the invention and the compounds used in the invention involve a novel immunosuppression mechanism, accelerated lymphocyte homing immunosuppression (ALH-immunosuppression). For example, the compound FTY720 specifically directs lymphocytes to the peripheral lymph nodes, mesenteric lymph nodes, and Peyer's patches. By reversibly sequestering lymphocytes in these tissues, the compounds can inhibit an immune response in a mammal. Understanding these mechanisms provides a novel immunosuppression therapy that can synergistically interact with other immunosuppressive compounds. Screening methods for identifying similar ALH-immunosuppression compounds are also described. The invention allows better treatments and therapies wherever an immunosuppression regimen is desired.Type: GrantFiled: September 23, 1997Date of Patent: December 21, 1999Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Kenji Chiba, Kunitomo Adachi
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Patent number: 5990173Abstract: Novel 2,3,5-trimethyl-4-hydroxyanilide derivatives of general formula I, wherein, e.g., R.sub.1 is phenyl, R.sub.2 is H, R.sub.3 is C.sub.12 H.sub.25, and A is a sulphur atom, are disclosed. A method for preparing said derivatives, pharmaceutical compositions containing at least one of said compounds as active principle, and the use of such derivatives for treating hypercholesterolemia or atherosclerosis.Type: GrantFiled: May 27, 1998Date of Patent: November 23, 1999Assignee: Pierre Fabre MedicamentInventors: Jean-Fran.cedilla.ois Patoiseau, Jean-Marie Autin, Andre Delhon, Philippe Oms, Didier Junquero
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Patent number: 5981799Abstract: A method is provided for purifying a crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a hot aqueous solution of the crude APAP; and b) subsequently contacting the hot solution with an acid washed adsorbent carbon, e.g., an activated carbon, which acid washed carbon, prior to such contact, has been pretreated by contacting it with an aqueous solution of a reducing sulfite.Type: GrantFiled: March 15, 1994Date of Patent: November 9, 1999Assignee: BASF CorporationInventors: Olan Stanley Fruchey, Edward G. Zey, Larry O. Wheeler
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Patent number: 5948820Abstract: A benzene compound of the formula ##STR1## wherein each symbol is as defined in the specification; an optically active isomer or salt thereof, a medicinal composition containing the same, and an immunosuppressant containing the same as the active ingredient.The compound, optically active isomer or salt has an excellent immunosuppressive effect and is useful as an inhibitor for the rejection reaction occurring in organ or bone marrow transplantation, and as a preventive or remedy for articular rheumatism, atopic eczema (dermatitis), Beh.cedilla.Type: GrantFiled: February 20, 1997Date of Patent: September 7, 1999Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Tetsuro Fujita, Kunitomo Adachi, Toshiyuki Kohara, Masatoshi Kiuchi, Kenji Chiba, Koji Teshima, Tadashi Mishina
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Patent number: 5880158Abstract: The present invention is directed to a compound of the following formula: ##STR1## pharmaceutical compositions containing the same and the use thereof as an anticonvulsant.Type: GrantFiled: September 26, 1997Date of Patent: March 9, 1999Assignee: Research Corporation Tech., Inc.Inventor: Harold Kohn
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Patent number: 5872299Abstract: A synthesis is described for intermediates which are readily amenable to the large scale preparation of hydroxyethylurea-based chiral HIV protease inhibitors. The method includes forming a diastereoselective epoxide or cyanohydrin from a chiral alpha amino aldehyde.Type: GrantFiled: May 8, 1997Date of Patent: February 16, 1999Assignee: G. D. Searle & Co.Inventors: John S Ng, Claire A Przybyla, Richard A Mueller, Michael L Vazquez, Daniel P Getman, John J Freskos, Gary A DeCrescenzo, Deborah E Bertenshaw, Robert M Heintz, Suhong Zhang, Chin Liu, Scott A Laneman
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Patent number: 5866611Abstract: Compounds of formula I, and their pharmaceutically acceptable salts, ##STR1## in which R.sup.1 and R.sup.2 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, phenylalkyl or alkenyl; or NR.sup.1 R.sup.2 is a heterocyclic group; A is trimethylene optionally substituted by alkyl and the phenyl ring is optionally substituted by substituents such as halogeno, alkenyl, amino, cyano, ureido, alkyl, carbamoylalkyl, alkanoylamino, alkoxycarbonyl, N-alkyl-alkanoylamino, alkanoyl and amines thereof; are inhibitors of squalene synthese and hence useful in treating diseases in which a lowering of cholesterol is desirable. As well as the use of these compounds in medicine, novel compounds, processes for their preparation and pharmaceutical compositions are also referred to.Type: GrantFiled: May 19, 1994Date of Patent: February 2, 1999Assignee: Zeneca LimitedInventors: George Robert Brown, Murdoch Allan Eakin, Peter John Harrison, deceased, Keith Blakeney Mallion
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Patent number: 5856575Abstract: This invention provides a process for the manufacture of N-acetyl amino phenol, which process comprises reacting an appropriate phenol and an amide in the presence of a heteropoly acid or its alkali metal salt catalyst.Type: GrantFiled: January 22, 1997Date of Patent: January 5, 1999Assignee: Council of Scientific Industrial ResearchInventors: Sarada Gopinathan, Changaramponnath Gopinathan, Joseph Kuruvilla, Sanjeevani Amrit Pardhy, Paul Ratnasamy
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Patent number: 5786509Abstract: A method and compositions for authenticating a document or article comprises applying a mixture of a carrier, a leuco dye and an activator to a surface of a document or article, wherein the leuco dye and activator react in response to a rubbing force applied to the surface to change color and wherein the activator is at least one selected from the group consisting of amidophenol, anilides with hydroxyl groups and benzoamides with hydroxyl groups and authenticating the document or article by applying a rubbing force to the surface to effect a color change.Type: GrantFiled: September 27, 1996Date of Patent: July 28, 1998Assignee: Nocopi Technologies, Inc.Inventors: Blake Quenten Belding, JoAnn Silknitter, Kevin Bruce Stevenson, Terry William Stovold
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Patent number: 5770772Abstract: Disclosed are intermediates for the preparation of novel aminocoumaran derivatives of the general formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are a hydrogen atom, an acyl group, an alkoxycarbonyl group, an aliphatic group or aromatic group; R.sup.3, R.sup.4 and R.sup.5 are an optionally acylated hydroxyl, optionally substituted amino group, alkoxy group or aliphatic group, or two of R.sup.3, R.sup.4 and R.sup.5 may be linked together to form a carbocyclic group; R.sup.6 and R.sup.7 are an aliphatic group and at least one of them has a methylene group at the .alpha.-position; R.sup.8 and R.sup.9 are a hydrogen atom or an aliphatic group or aromatic group, or a salt thereof is useful for medicines for preventing and treating various diseases such as arterial sclerosis, hepatopathy, cerebrovascular diseases and the like.Type: GrantFiled: September 17, 1996Date of Patent: June 23, 1998Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Aono, Shigenori Ohkawa, Takayuki Doi
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Patent number: 5733935Abstract: A hydroxylamine derivatives of formula (I): ##STR1## wherein R represents ##STR2## in which R.sup.1 and R.sup.2 represents alkyl group, alkenyl group, alkynyl group, cycloalkyl group, haloalkyl group, haloalkynyl group, alkoxy - alkyl group, phenoxy - alkyl group, alkylthio - alkyl group, alkylsulfonyl - alkyl group, alkylamino - alkyl group, phenyl group, benzyl group, phenethyl group, cinnamyl group, pyridyl group, furyl group, thienyl group, X represents CO.sub.2, CO or SO.sub.2, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 represent a hydrogen atom or a lower alkyl group, and n represents 0 or 1, and fungicides contain said compound as an active ingredient.The compounds of the present invention have excellent effects for controlling wood-rot fungi, plant diseases and fungi of humans and animals, and are useful as industrial, agricultural and medical fungicides.Type: GrantFiled: June 17, 1996Date of Patent: March 31, 1998Assignee: Nihon Nohyaku Co., Ltd.Inventors: Nobuharu Andoh, Tsutomu Nishiguchi, Katsutoshi Endo
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Patent number: 5734063Abstract: The present invention provides a method for preparation of a compound of the formula (I) useful as a fog restrainer for a silver halide light-sensitive material, especially for a heat-developing light-sensitive material and a synthetic intermediate for the fog restrainer. The method makes it possible to obtain the fog restrainer in good yield and in short steps. ##STR1## wherein, R.sup.1 is alkyl, cycloalkyl, or aryl, R.sup.2 and R.sup.3 are hydrogen atom or alkyl, R.sup.4 is hydrogen atom or acyl, and R.sup.1 and R.sup.4 may be bonded together to form 5- or 6-membered ring.Type: GrantFiled: October 24, 1996Date of Patent: March 31, 1998Assignee: Fuji Photo Film Co.,Ltd.Inventors: Katsuyoshi Yamakawa, Tadahisa Sato
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Patent number: 5681860Abstract: A composition for the upregulation of expression of cell antigens, without inducing shedding, which comprises a protein kinase C activator is provided by this invention. Further provided by this invention is a method of detecting and treating tumor cells comprising contacting tumor cells with an effective amount of a protein kinase C activator for the upregulation of expression of antigens of tumor cells, without inducing antigen shedding, and detecting the presence of said antigen or then further contacting said tumor cells with an effective amount of an antibody directed to said antigen.Type: GrantFiled: September 21, 1993Date of Patent: October 28, 1997Assignee: The Trustees of Columbia University in the City of New YorkInventors: Paul B. Fisher, Jorge A. Leon
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Patent number: 5663442Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## characterized in that the radical X in sulphones of the formulaX--(CH.sub.2 --CH.sub.2 --O).sub.m --(CH.sub.2).sub.n --SO.sub.2 --CH.sub.2 --CH.sub.2 OH (2)is replaced by ##STR2## or a compound of the formula ##STR3## is added to the sulphone of the formulaCH.sub.2 =CH--SO.sub.2 --CH.sub.2 --CH.sub.2 --OH (3),the substituents having the meanings given in the description.Type: GrantFiled: May 31, 1995Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Wolfgang Harms, Udo-Winfried Hendricks, Karl-Josef Herd, Klaus Kunde
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Patent number: 5536876Abstract: Fiber-reactive formazan dyes are prepared by diazotizing a protectively formylated hydroxyphenylenediamine, coupling with a hydrazone compound, metallizing, eliminating the protective group, and reacting with a halotriazine and optionally thereafter with an amine or a hydroxy compound via novel aminophenol intermediates.Type: GrantFiled: October 31, 1994Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5510389Abstract: Improved concentrated liquid pharmaceutical compositions containing acetaminophen wherein said acetaminophen is formed by adding a Beckman rearrangement catalyst to 4-hydroxyacetophenone oxime.Type: GrantFiled: March 2, 1994Date of Patent: April 23, 1996Assignee: The Procter & Gamble CompanyInventor: Dadi J. Dhabhar
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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: 5434118Abstract: A catalytically active gel product is described consisting of a silica matrix which is amorphous to x-rays with uniform porosity, monomodal pore distribution and high surface area, within which one or more metal oxides possessing catalytic activity are dispersed. A process for preparing this catalytic gel is also described.Type: GrantFiled: October 12, 1993Date of Patent: July 18, 1995Assignees: Eniricerche S.p.A., Snamprogetti SpAInventors: Angela Carati, Enrico Davini, Mario G. Clerici, Giuseppe Bellussi
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Patent number: 5410027Abstract: Fiber-reactive formazan dyes are prepared by diazotizing a protectively formylated hydroxyphenylenediamine, coupling with a hydrazone compound, metallizing, eliminating the protective group, and reacting with a halotriazine and optionally thereafter with an amine or a hydroxy compound via novel aminophenol intermediates.Type: GrantFiled: June 11, 1993Date of Patent: April 25, 1995Assignee: BASF AktiengesellschaftInventors: Claus Marschner, Manfred Patsch
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Patent number: 5399760Abstract: A method is provided for purifying crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a solution of the crude APAP; and b) subsequently contacting the solution with substoichiometric quantifies of an acetylating agent for a sufficient period of time to convert said color bodies or their precursors to substantially non-color bodies/stable, colorless substances; said quantities of acetylating agent provided is such that substantially none of the APAP is converted to other compounds.Type: GrantFiled: August 11, 1993Date of Patent: March 21, 1995Assignee: Hoechst Celanese CorporationInventors: Edward G. Zey, Olan S. Fruchey, Thomas H. Shockley, Joe S. Trevino, B. Frank Wood, Daniel D. Lindley
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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: 5393923Abstract: The present invention is a novel compound which is a 3,5-di-t-butyl-4-hydroxyphenylmethylhydroxylamine or derivative thereof and a pharmaceutically acceptable acid addition or base salt thereof, pharmaceutical composition and methods of use therefor. The invention compounds are now found to have activity as inhibitors of one or both of cyclooxygenase and 5-lipoxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like.Type: GrantFiled: October 12, 1993Date of Patent: February 28, 1995Assignee: Warner-Lambert CompanyInventors: Thomas Capiris, David T. Connor, Jagadish C. Sircar
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Patent number: 5387716Abstract: The present invention relates to compounds of the general formula I ##STR1## wherein R.sup.1 denotes formyl or (C.sub.1 -C.sub.3)-alkylcarbonyl,R.sup.2 denotes the group CH.sub.2 --CH(A)--B, wherein A represents hydroxyl and B represents hydrogen or methyl, or A represents hydrogen and B represents hydroxymethyl, or the group COO--CH(X)--CH.sub.2 --D, wherein X represents hydrogen or methyl and D represents chlorine or bromine, or X represents hydrogen and D represents chloromethyl or bromomethyl, andR.sup.3 denotes (C.sub.1 -C.sub.4)-alkyl,processes for their preparation and their use.Type: GrantFiled: May 3, 1994Date of Patent: February 7, 1995Assignee: Cassella AktiengesellschaftInventors: Willi Steckelberg, Peter Koch
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Patent number: 5344979Abstract: A method is provided for purifying a crude N-acetyl-para-aminophenol (APAP) containing color bodies or their precursors, the method comprising: a) forming a wet crude APAP; and b) subsequently drying said crude APAP in the presence of a sufficient amount of an acetylating agent for a sufficient period of time to convert said color bodies or their precursors to substantially non-color bodies.Type: GrantFiled: April 29, 1993Date of Patent: September 6, 1994Assignee: Hoechst Celanese CorporationInventors: Edward G. Zey, George A. Blay
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Patent number: 5338884Abstract: Acylamides or amine acylate salts of arylalkanolamines are prepared by reacting an arylisonitrosoalkanone with hydrogen and a carboxylic acid, carboxylic acid anhydride or carboxylic acid ester or mixture thereof in the presence of a transition metal catalyst; optionally the product is converted to the corresponding arylalkanolamine hydrochloride salt by reaction of the acylamide or amine acylate salt of the arylalkanolamine with hydrogen chloride in a C.sub.1 -C.sub.3 alkyl alcohol.Type: GrantFiled: October 2, 1992Date of Patent: August 16, 1994Assignee: Hoechst CelaneseInventors: Ahmed M. Tafesh, Olan S. Fruchey, Charles B. Hilton
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Patent number: 5276192Abstract: A process for preparing phenoxyethanamines from phenols and 2-oxazolines in quantitative yields was discovered. Phosphoric acid hydrolyzes the amide intermediate from the phenol/2-oxazoline reaction without cleaving the amide at the ether linkage and without undesired aromatic ring substitution. Thus, yield to the desired phenoxyethanamines is often 98% or better, requiring no subsequent purification. In contrast, sulfuric and hydrochloric acids give these undesired side reactions. Phenoxyethanamines are useful in thermosetting resins, pharmaceuticals and as surfactants.Type: GrantFiled: April 22, 1991Date of Patent: January 4, 1994Assignee: Texaco Chemical CompanyInventors: Wei-Yang Su, George P. Speranza
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Patent number: 5221769Abstract: p-Aminophenyl acetate is isomerized to p-acetylaminophenol in the presence of an acid such as acetic acid or phosphoric acid.Type: GrantFiled: December 27, 1990Date of Patent: June 22, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Hideyuki Akieda, Naoki Sato, Ryuichi Mita, Mitsumasa Umemoto
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Patent number: 5214194Abstract: A process for the preparation of 5-substituted 2-aminophenols via nitrones, comprises two reactions. First, a nitrone is reacted with a trihaloacetyl halide to regiospecifically convert the nitrone to a 5-substituted-2-aminophenol derivative (I). Subsequently, the derivative is hydrolyzed to form the 5-substituted-2-aminophenol. The product is useful as a chemical intermediate, e.g. for the preparation of couplers used in photographic chemistry.Type: GrantFiled: September 24, 1991Date of Patent: May 25, 1993Assignee: Eastman Kodak CompanyInventors: Ping-Wah Tang, Jeffrey R. Neff, Frank T. Melia, Donald J. Schuster
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Patent number: 5155269Abstract: A process for removing impurities from an aqueous feed mixture comprising a reaction solution produced by catalytic hydrogenation of nitrobenzene in an acid aqueous medium. An aqueous feed mixture comprising the reaction solution is contacted with an extractant comprising aniline for extraction from the feed mixture of 4,4'-diaminodiphenylether, thereby providing a primary raffinate that contains p-aminophenol and is contaminated with aniline. The primary raffinate is contacted at a pH of between about 5.5 and about 8.0 with a purifying solvent, the purifying solvent comprising an organic solvent effective for extraction of aniline from the primary raffinate, thereby producing a purified raffinate comprising p-aminophenol.Also described is a unified process for the preparation of N-acetyl-p-aminophenol in which p-aminophenol contained in the aforesaid purified raffinate is acetylated without prior separation of solid p-aminophenol from the raffinate.Type: GrantFiled: May 24, 1989Date of Patent: October 13, 1992Assignee: MallinckrodtInventors: Thomas J. Dunn, Vojko B. Jovanovic
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Patent number: 5155273Abstract: N-acetyl-para-aminophenol is prepared by contacting 4-hydroxyacetophenone oxime with a Beckmann rearrangement catalyst in an alkyl alkanoate reaction solvent. An integrated process is disclosed wherein 4-hydroxyacetophenone is reacted with a hydroxylamine salt and a base to obtain 4-hydroxyacetophenone oxime, the oxime product is extracted from the resulting reaction mixture with a substantially water-immiscible solvent, and the mixture of oxime and substantially water-immiscible solvent is contacted with a Beckmann rearrangement catalyst to produce N-acetyl-para-aminophenol. Novel Beckamnn rearrangement catalysts are used to limit by-product formation in the ester solvent.Type: GrantFiled: July 20, 1990Date of Patent: October 13, 1992Assignee: Hoechst Celanese CorporationInventors: John R. Fritch, O. Stanley Fruchey, Theodore Horlenko, Daniel A. Aguilar, Charles B. Hilton, Phillip S. Snyder, William J. Seeliger
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Patent number: 5145483Abstract: 5-Substituted ortho-aminophenols of formula: ##STR1## in which: R.sub.1 denotes a hydrogen atom, an alkyl radical having 1 to 4 carbon atoms or a hydroxyalkyl radical having 1 to 4 carbon atoms; andR.sub.2 denotes, independently of R.sub.1, an alkyl radical having 1 to 4 carbon atoms, an alkoxy radical having 1 to 4 carbon atoms or a benzyl radical;the addition salts with an acid and the phenates, anddyeing composition containing a compound of formula (I) or a salt or a phenate of such a compound.The 5-substituted ortho-aminophenols enable hair to be dyed in a rich spectrum of hues having good durability.Type: GrantFiled: October 27, 1989Date of Patent: September 8, 1992Assignee: L'OrealInventors: Alex Junino, Herve Andrean, Gerard Lang
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Patent number: 5107022Abstract: The invention relates to a process for the preparation of compounds of formula ##STR1## wherein R is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl or unsubstituted or substituted phenyl, X is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, and Y is unsubstituted or substituted C.sub.1 -C.sub.4 alkyl, which process comprises subjecting compounds of formula ##STR2## wherein R, X and Y are as defined for formula I, to catalytic hydrogenation in the alkaline pH range.The compounds obtained by the process of this invention are suitable intermediates for the synthesis of dyes.Type: GrantFiled: August 24, 1990Date of Patent: April 21, 1992Assignee: Ciba-Geigy CorporationInventor: Amaury P. de Besset
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Patent number: 5073173Abstract: The present invention concerns the aminophenols (I) as novel couplers ##STR1## wherein R.sub.1 and R.sub.2 may be the same or different and are hydrogen, alkyl and hydroxyalkyl of from 1 to about 6 carbons in the alkyl moiety, or R.sub.1 and R.sub.2 can also form, together with the nitrogen atom to which they are attached, a morpholine, piperidine or pyrrolidine ring, and R.sub.3 and R.sub.4 are hydrogen, alkyl, acyl and hydroxyalkyl having from 1 to about 6 carbons, and oxidative hair dye compositions containing same along with at least one primary dye intermediate in aqueous or hydroalcoholic media.Type: GrantFiled: October 23, 1990Date of Patent: December 17, 1991Assignee: Clairol IncorporatedInventors: Yuh-Guo Pan, Alexander Chan, Lana Hochman
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Patent number: 5068392Abstract: 2-Chloro and 2,6-dichloroanilines, optionally substituted in the 3-, 5-, and/or 6-position are prepared from the corresponding anilides by selective bromination, chlorination, reduction and hydrolysis. The selectivity of the process for introducing chlorines ortho to the amino group is very high.Type: GrantFiled: January 24, 1991Date of Patent: November 26, 1991Assignee: DowElancoInventors: Lennon H. McKendry, Mark W. Zettler
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Patent number: 5006660Abstract: The present invention relates to a process for producing an alkoxybenzene compound or an aryloxybenzene compound by reacting a halogenobenzene compound with an alcohol or a phenol compound in the presence of copper or a copper compound, an amine, and a base. According to the disclosure, an alkoxybenzene compound and an aryloxybenzene compound can be produced under moderate conditions in good yield with high selectivity.Type: GrantFiled: June 28, 1989Date of Patent: April 9, 1991Assignee: Fuji Photo Film Co., Ltd.Inventor: Katsuyoshi Yamakawa
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Patent number: 4999457Abstract: A novel process for the preparation of 3-chloro-4-hydroxyacetanilide in high yields is disclosed which involves reacting N-acetyl-para-aminophenol (APAP) with sulfuryl chloride (SO.sub.2 Cl.sub.2) as the chlorine source and liquid SO.sub.2 as the reaction medium.Type: GrantFiled: February 8, 1990Date of Patent: March 12, 1991Assignee: Hoechst Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4994613Abstract: A novel process is disclosed for the preparation of 4-hydroxyacetopheone oxime by reaction of 4-hydroxyacetophenone with a hydroxylamine in caustic wherein the mother liquor obtained after crystallization of the oxime together with the wash water is recycled back and reused. This invention illustrates the criticality of maintaining the reactants in certain critical mol ratios in order to obtain 4-hydroxyacetopheone oxime of acceptable color.Type: GrantFiled: January 29, 1990Date of Patent: February 19, 1991Assignee: Hoechst Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4980366Abstract: Novel 4'-hydroxybenzylamine derivatives of the formula ##STR1## pharmaceutical compositions and methods of use thereof are the present invention. Utility is for the treatment of arthritis, asthma, Raynaud's disease, inflammatory bowel disorders, trigeminal or herpetic neuralgia, inflammatory eye disorders, psoriasis, dental pain, and headaches, particularly vascular headache, succh as migraine, cluster, mixed vascular syndromes, as well as nonvascular, tension headaches.Type: GrantFiled: March 16, 1989Date of Patent: December 25, 1990Assignee: Warner-Lambert Co.Inventors: Graham Johnson, Michael F. Rafferty
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Patent number: 4973752Abstract: A novel process is disclosed for the prevention of the formation of chlorinated by-products during the Beckmann rearrangement of 4-hydroxyacetophenone oxime to APAP utilizing thionyl chloride as catalyst, by the addition of an inorganic iodide such as potassium iodide to the Beckmann rearrangement reactor.Type: GrantFiled: April 24, 1989Date of Patent: November 27, 1990Inventor: Olan S. Fruchey
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Patent number: 4954652Abstract: N-acetyl-para-aminophenol is prepared by subjecting 4-hydroxyacetophenone oxime to a Beckmann rearrangement in the presence of a thionyl chloride catalyst and an alkyl alkanoate as the reaction solvent. An integrated process is disclosed wherein 4-hydroxyacetophenone is reacted with a hydroxyl amine salt and a base to obtain the ketoxime of the ketone, e.g., 4-hydroxyacetophenone oxime, extracting the ketoxime product from the reaction with alkanoate ester and subjecting the ketoxime dissolved in the ester to a Beckmann rearrangement in the presence of a thionyl chloride catalyst.Type: GrantFiled: July 12, 1988Date of Patent: September 4, 1990Assignee: Hoechst Celanese CorporationInventors: John R. Fritch, Olan S Fruchey, Theodore Horlenko
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Patent number: 4954653Abstract: The invention discloses a catalyst on the basis of silicon and titanium having the form of microspheres and constituted by oligomeric silica and by titanium-silica-lite crystals having an oligomeric silica/titanium-silicalite molar ratio comprised within the range of from 0.05 to 0.11, wherein the crystals of titanium-silicalite are encaged by means of Si-O-Si bridges.Type: GrantFiled: June 7, 1989Date of Patent: September 4, 1990Assignee: Enichem Sintesi S.p.A.Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
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Patent number: 4943591Abstract: The invention provides compounds of the general formula (I) ##STR1## wherein X represents a C.sub.1-6 alkylene, C.sub.2-6 alkenylene or C.sub.2-6 alkynylene chain andY represents a bond, or a C.sub.1-4 alkylene, C.sub.2-4 alkenylene or C.sub.2-4 alkynylene chain with the proviso that the sum total of carbon atoms in X and Y is not more than 8;Ar represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms or the groups C.sub.1-3 alkyl, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, C.sub.1-3 alkoxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom, or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O-- or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.Type: GrantFiled: October 14, 1986Date of Patent: July 24, 1990Assignee: Glaxo Group LimitedInventors: Ian F. Skidmore, Lawrence H. C. Lunts, Harry Finch, Alan Naylor, Ian B. Campbell
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Patent number: 4933496Abstract: A process for preparing a stable 4-hydroxyacetophenone oil by mixing 4-hydroxyacetophenone with an aqueous hydroxylamine salt in the absence of added caustic, at a temperature of 50.degree.-100.degree. C., for about 10-60 minutes and then cooling the same is disclosed.Type: GrantFiled: May 3, 1989Date of Patent: June 12, 1990Assignee: Hoechst Celanese CorporationInventor: Olan S. Fruchey
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Patent number: 4883787Abstract: A process for preparing 2-acyl-3,4-dialkoxyanilines is described. The 2-acyl-3,4-dialkoxyanilines are useful intermediates in the preparation of 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones. The substituted quinazolinones are active as cardiotonic agents.Type: GrantFiled: June 20, 1988Date of Patent: November 28, 1989Assignee: Ortho Pharmaceutical CorporationInventors: Richard A. Conley, Donald L. Barton
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Patent number: 4872902Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.Type: GrantFiled: February 8, 1988Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4855499Abstract: A novel process for the prevention of the formation of chlorinated by-products during the Beckmann rearrangement of 4-hydroxyacetophenone oxime to APAP by the addition of an inorganic iodide such as potassium iodide to the Beckmann rearrangement reactor is disclosed.Type: GrantFiled: November 6, 1987Date of Patent: August 8, 1989Assignee: Hoechst Celanese CorporationInventor: Olan S. Fruchey