Nitrogen Or Sulfur In Phenolic Moiety Patents (Class 560/142)
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Patent number: 5124475Abstract: The invention encompasses methods for preparing in high purity and in high yield p-phenyl sulfonic acid acyl glycolates of the formula ##STR1## where R represents branched or straight chain alkyl having 6-12 carbon atoms by treating a phenyl ester or phenyl acyl glycolate of the formula ##STR2## where R represents branched or straight chain alkyl having 6-12 carbon atoms with a sulfonating agent to form intermediate sulfonation; transmuting the intermediate sulfonation products; and quenching the transmuted intermediate sulfonation products with a quenching reagent reactive with sulfur trioxide.Type: GrantFiled: March 1, 1991Date of Patent: June 23, 1992Assignee: Stepan CompanyInventors: Marshall J. Nepras, Peter F. Heid, Matthew I. Levinson, Randal J. Bernhardt, James A. Hartlage
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Patent number: 5116869Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.Type: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5101065Abstract: A process for the preparation of 2-(hydrogen, halogen or lower alkyl)-3-(hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, --OCH.sub.2 CH.sub.2 SCH.sub.3 or --OCH.sub.2 CH.sub.2 SC.sub.2 H.sub.5)-4-(alkythio or alkylsulfonyl)-acetophenones.Type: GrantFiled: February 4, 1991Date of Patent: March 31, 1992Assignee: Imperial Chemical Industries plcInventor: Richard W. Brown
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Patent number: 5100588Abstract: The process for the preparation of acyloxybenzenesulfonic acids of the general formula ##STR1## in which R denotes a (C.sub.1 -C.sub.17)-alkyl or (C.sub.2 -C.sub.17)-alkenyl radical, or alkali metal, alkaline earth metal or ammonium salts thereof, is carried out in the following stages: (a) sulfonation of phenol, (b) heat treatment of the phenolsulfonic acid formed as the intermediate product, (c) esterification of the phenolsulfonic acid and, if appropriate, (d) neutralization of the resulting (C.sub.2 -C.sub.18)-acyloxybenzenesulfonic acid. As a result of the incorporation of stage (b), the process affords products in which the proportion of the 1,4-isomer compared with the 1,2-isomer is markedly increased, as a result of which these products can be used, in particular, as perborate activators in detergents.Type: GrantFiled: February 9, 1988Date of Patent: March 31, 1992Assignee: Hoechst AktiengesellschaftInventors: Fritz-Feo Grabley, Gerd Reinhardt, Roland Steinl
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Patent number: 5089660Abstract: A comonomer composition of an aromatic polycyanate and an aromatic monocyanate substituted at each position ortho to the cyanate group, and a polytriazine copolymer derived therefrom.Type: GrantFiled: January 22, 1988Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Daniel J. Murray, Mitchell G. Dibbs, Philip C. Yang
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Patent number: 5089392Abstract: Fluorogenic substrates and compositions containing the same are useful for detecting enzymatic activity within intact cells. The fluorogenic substrates are lysosomotropic derivatives of 2,3-dicyano-hydroquinone (DCH). These derivatives may be employed for detecting lysosomal enzymatic activity within intact cells using fluorescent microscopy and cytometry.Type: GrantFiled: March 30, 1990Date of Patent: February 18, 1992Assignee: The United States of America as represented by of the Department of Health and Human ServicesInventors: Stephen P. F. Miller, Roscoe O. Brady
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Patent number: 5072025Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: July 26, 1990Date of Patent: December 10, 1991Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 5021197Abstract: A process for producing a sulfonium compound of the formula (III) ##STR1## which process comprises reacting a p-dialkylsulfoniophenol of the formula (I) ##STR2## and a carbonyl halogenide compound of the formula (II) ##STR3## in the presence of a secondary amine having a structure in which two secondary alkyl groups are linked to the nitrogen atom, wherein R.sup.1 and R.sup.2 are the same or different and are independently an alkyl group having 1 to 4 carbon atoms, X.sup.1 is a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms, Y.sup.- is a halogen anion, a perchlorate anion, an alkylsulfate anion, a hydrogensulfate anion or a p-toluenesulfonate anion, R is an alkyl group having 1 to 20 carbon atoms, a tert-butoxy group, a benzyloxy group, a p-methoxybenzyloxy group, a phenyl group or a 9-fluorenylmethoxy group, and X.sup.Type: GrantFiled: May 26, 1989Date of Patent: June 4, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mutsuhiko Takeda, Masamichi Mizukami, Yasumasa Norisue, Isao Hagiwara, Fumiya Zaima
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Patent number: 5017610Abstract: A derivative of general formula: ##STR1## wherein Y is --SO.sub.2 -- or ##STR2## (i) R.sup.1 and R.sup.2, which may be the same or different, each represent, (1) --H, (2) C1-16 alkyl or (3) the formula: --X-- .circle.A --(R.sup.4).sub.n wherein X is a single-bond, --SO.sub.2 --, C1-4 alkylene, C1-4 alkylene substituted by ##STR3## -- .circle.A -- is carbocyclic or heterocyclic ring, n is 1.about.5, R.sup.4 is (1) --H or C1-8 alkyl, (2) C1-14 alkoxy, (3) C1-6 alkylthio, (4) --OH, halogen, --NO.sub.2 or trihalomethyl, (5) the formula: --NR.sup.41 R.sup.42 wherein R.sup.41 and R.sup.42 each represents halogen or C1-4 alkyl, (6) tetrazole, (7) --SO.sub.3 H or --CH.sub.2 OH, (8) the formula: --SO.sub.2 NR.sup.41 R.sup.42 (9) the formula: --Z.sup.41 --COOR.sup.43 wherein Z.sup.41 is single-bond, C1-4 alkylene or C2-4 alkenylene, R.sup.43 is --H, C1-4 alkyl or benzyl, (10) the formula: --CONR.sup.41 R.sup.42 (11) the formula: --COO--Z.sup.42 --COOR.sup.43 wherein Z.sup.42 is C1-4 alkylene, R.sup.Type: GrantFiled: June 12, 1989Date of Patent: May 21, 1991Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Katsuhiro Imaki, Yoshinobu Arai, Tadao Okegawa
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Patent number: 5017618Abstract: Compounds having the formula ##STR1## and their pharmaceutically acceptable acid addition salts, wherein --X-- is --O--, --CH.sub.2 -- or --; .dbd.Y is .dbd.O or a derivatized keto group which is hydrolyzable or enzymatically convertible to a keto group; R is alkyl having from 1 to 12 carbon atoms or aralkyl having from 7 to 20 carbon atoms; and Ar is the 3-aromatic or heterocyclic residue of a 1-alkylamino-2-propanol having an aromatic or heterocyclic substituent at the 3-position and having .beta.-adrenergic blocking properties; are useful as .beta.-adrenergic blocking agents and are of particular interest in the treatment of glaucoma or for lowering intraocular pressure.Type: GrantFiled: September 18, 1989Date of Patent: May 21, 1991Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 5013753Abstract: Compounds of formula ##STR1## (wherein R, R.sub.1, R.sub.2 and X have the meanings reported in the specification), the processes for their preparation and the pharmaceutical compositions containing them as active ingredient are described.The compounds of formula I are useful in the treatment of Parkinson's disease, renal failure, cardiac decompensation and hypertension.Type: GrantFiled: July 28, 1989Date of Patent: May 7, 1991Assignee: SimesInventors: Cesare Casagrande, Francesco Santangelo
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Patent number: 4985180Abstract: Phenyl esters of substituted acids are prepared by a two-step process in which a phenol derivative is first treated with an acid halide to yield a phenyl ester intermediate, and the intermediate is reacted with an appropriate nucleophile.Type: GrantFiled: June 6, 1989Date of Patent: January 15, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Harold E. Bellis, Donald J. Dumas, George C. Sonnichsen, Vinayakam Subramanyam
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Patent number: 4966915Abstract: An L-dopa derivative represented by formula (I) ##STR1## wherein one of R.sup.1 and R.sup.2 denotes a hydrogen atom and the other denotes a group of formula R--CO-- in which R denotes an alkyl, alkenyl, optionally substituted cycloalkyl, optionally substituted phenyl, optionally substituted aralkyl, lower alkoxy or optionally substituted aralkyloxy group,and its acid addition salt. The compounds are useful in the medical field, especially in the treatment of a series of diseases called Parkinson's disease or Parkinsonism.Type: GrantFiled: September 16, 1988Date of Patent: October 30, 1990Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Yoshimi Tsuchiya, Masahiro Hayashi, Hiroshi Takehana, Akihiro Hisaka, Yoshio Sawasaki, Masaki Ihara
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Patent number: 4965400Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: August 2, 1988Date of Patent: October 23, 1990Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4959187Abstract: The invention provides novel bleaching compositions comprising peracid precursors with the general structure ##STR1## with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.Type: GrantFiled: October 14, 1988Date of Patent: September 25, 1990Assignee: The Clorox CompanyInventors: Ronald A. Fong, Sheldon N. Lewis, Richard J. Wiersema, Alfred G. Zielske
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Patent number: 4958046Abstract: Hydroxypropafenone glycerides of the formula I ##STR1## where R is n-propyl or 1,1-dimethylpropyl,x is 2 or 3,y is 12, 14, 16, 18 or 20, anda and b differ from one another and are 0 or 1,as well as the stereoisomers thereof and the preparation thereof are described. The compounds are suitable as active substances for antiarrhythmics.Type: GrantFiled: September 19, 1989Date of Patent: September 18, 1990Assignee: Knoll AGInventors: Joerg Rosenberg, Juergen Heberger, Hans-Heinrich Gruenhagen, Egon Brode, Gerda von Philipsborn
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Patent number: 4956474Abstract: The present invention relates to novel cephalosporin derivatives, processes for preparing thereof, compositions for preventing and/or treating infectious diseases which comprise the novel cephalosporin derivatives as active components, and the intermediate compounds in the synthesis of cephalosporin derivatives and processes for producing thereof.The present invention is based on the selection of groups containing a condensed heterocyclic ring, particularly a triazolopyrimidine ring or a thiadiazolopyrimidine ring, as substituents at the 3-position of the cephem skeleton, and of groups containing a catechol moiety, particularly a catechol carboxymethyloxyimino moiety or a catechol carboxyimino moiety, as substituents at the 7-position of the cephem skeleton.The compounds of the present invention containing the aforementioned substituents have a strong antibacterial activity against Gram-negative bacteria and also against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus.Type: GrantFiled: June 20, 1989Date of Patent: September 11, 1990Assignee: Mochida Pharmaceutical Co., Ltd.Inventors: Haruo Ohnishi, Hiroshi Kosuzume, Masahiro Mizota, Yasuo Suzuki, Ei Mochida
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Patent number: 4948812Abstract: Compounds of formula ##STR1## (the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are explained in the specification) may be prepared by conventional methods.Owing to their favorable activity profile the compounds may advantageously be used to treat certain heart and circulatory disorders.Type: GrantFiled: November 25, 1987Date of Patent: August 14, 1990Assignee: Boehringer Ingelheim KGInventors: Herbert Koppe, Franz Esser, Walter Kobinge, Christian Lillie
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Patent number: 4933329Abstract: Novel bis-S-alkylbenzene derivatives capable of inhibiting lipoxygenase, inparticular, 5-lipoxygenase are disclosed. It is expected that the compounds, which are hardly metabolized in vivo, are highly useful in the treatment and/or prevention of various diseases, including allergic diseases such as asthma, inflammation, myocardial infarction, nephritis, scabies and gout.Type: GrantFiled: December 6, 1988Date of Patent: June 12, 1990Assignee: Green Cross CorporationInventors: Youichiro Naito, Yasunari Yamaura, Masanori Sugiura, Chikara Fukaya, Kazumasa Yokoyama
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Patent number: 4927956Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: June 2, 1989Date of Patent: May 22, 1990Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4883612Abstract: p-Acyloxybenzene sulfonates, well suited for detergency applications, are facilely and rapidly prepared by acylating an alkali or alkaline earth metal, or ammonium p-phenol sulfonate, with an anhydride of a straight or branched chain carboxylic acid having from 7 to 12 carbon atoms, in a polar aprotic solvent and in the presence of a catalytically effective amount of an alkali or alkaline earth metal salt of a straight or branched chain aliphatic carboxylic acid having from 7 to 12 carbon atoms.Type: GrantFiled: May 14, 1987Date of Patent: November 28, 1989Assignee: Rhone-Poulenc Chimie de BaseInventors: Jose Moyne, Camille Disdier
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Patent number: 4867916Abstract: Phenol sulphonate esters can be made in a known process by reacting an alkali metal phenol sulphonate salt with an acyl halide in a hydrocarbon solvent at elevated temperatures, but the use of anhydrous materials were strongly advocated because any residual water hydrolyses the acyl chloride in a competitive reaction. However, it becomes particularly difficult and expensive to dehydrate phenol sulphonate salts below about 2% w/w water on a commercial scale and the product obtained by reaction from such partly dehydrated salts can be comparatively impure or reduced in yield. Consequently, changes to the process such as omitting the solvent or using a different acylating agent have been proposed, but these alternatives introduce their own respective manufacturing problems such as entrainment of viscous acyl chloride and anhydride in the product or introduction of a cumbersome and hence expensive recovery process involving an extra distillation step amongst others.Type: GrantFiled: December 3, 1987Date of Patent: September 19, 1989Assignee: Interox Chemicals LimitedInventors: William R. Sanderson, John P. Sankey
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Patent number: 4857656Abstract: This invention is characterized by synthesizing an active ester represented by the general formula ##STR1## using an active esterifying agent consisting of a sulfonium salt represented by the general formula ##STR2## and further reacting the above-said active ester with a nucleophilic agent represented by the general formula H--B--Y to produce an ester or amide represented by the general formula (W)d.A--B--Y.Type: GrantFiled: March 9, 1987Date of Patent: August 15, 1989Assignee: Sanshin Kagaku Kogyo Co., Ltd.Inventor: Katsushige Kouge
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Patent number: 4851441Abstract: This invention relates to antiviral organic guanidine derivatives compositions; a process of producing the antiviral compositions; and a method for inhibiting viruses utilizing the compositions. More particularly, the compositions are tubastrines derived from marine coral Tubastrea aurea.Type: GrantFiled: January 28, 1988Date of Patent: July 25, 1989Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Tatsuo Higa, Ryuichi Sakai
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Patent number: 4835304Abstract: Esters having the general formula: ##STR1## where X is a halogen, n is 1-5, Y is an alkyl, ether, ester, or nitro substituent, m is 0-2, Z is an ester linkage --OCO-- or --CO.sub.2 --, R' is a haloalkyl group, and p is 1-3, constitute high density flotation fluids for inertial instruments such as gyroscopes and accelerometers. Synthetic methods are disclosed for production of such fluids from available starting materials.Type: GrantFiled: May 1, 1987Date of Patent: May 30, 1989Assignee: Charles Stark Draper LaboratoryInventor: John R. Williams
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Patent number: 4814110Abstract: The present invention provides a method of esterifying dihydroxybenzene starting materials to synthesize unsymmetrical diesters in high yield. Many of the resultant unsymmetrical diesters are useful in dry bleaching compositions. The method can be practiced by selectively monoacylating a dihydroxybenzene starting material with an acid anhydride to form an intermediate monoester having the structure ##STR1## which is then acylated to form a diester reaction product having the structure ##STR2## wherein R.sub.1 is greater than R.sub.3 (and both R.sub.1 and R.sub.3 are alkyl groups) and X is a substituent group which does not participate in the esterification (or which can have a protecting group thereon).Type: GrantFiled: July 9, 1986Date of Patent: March 21, 1989Assignee: The Clorox CompanyInventors: Ronald A. Fong, Richard R. Rowland
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Patent number: 4788316Abstract: A process for preparing sulphonated aromatic esters of the group consisting of substituted or unsubstituted sulphonato-phenyl carboxylates and sulphonato-phenyl carbonates is disclosed, comprising the steps of:(1) preparing the unsulphonated aromatic ester;(2) sulphonating said unsulphonated aromatic ester; and(3) neutralizing the acid-sulphonated aromatic ester in a non-aqueous organic solvent with an alkali metal, earth alkali metal or ammonium carboxylate in an amount in excess over the amount needed to neutralize the sulphonic acid group(s) and any free or complexed SO.sub.3 present in the product mixture from the sulphonation reaction.Preferred neutralizing agent is sodium acetate; preferred solvents are acetic acid or glyme and diglyme.Type: GrantFiled: December 16, 1986Date of Patent: November 29, 1988Assignee: Lever Brothers CompanyInventors: David W. Thornthwaite, David W. Roberts, Stephen A. Madison
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Patent number: 4785004Abstract: Novel asymmetric thioethers of the formula ##STR1## in which the general symbols have the following meanings: R.sup.0 represents hydrogen or C.sub.1-7 -alkanoyl,R.sup.1 represents C.sub.1-3 -alkyl which may be substituted by one or more halogen atoms having an atomic number of at most 17,R.sup.2 represents an aliphatic radical having from 5 to 15 carbon atoms,A represents ethylene, a single bond or vinylene,B.sup.1 represents C.sub.1-7 -alkylene or phenylene,B.sup.2 represents a single bond, ethylene or phenylene, andM represents an aromatic radical of the partial formula ##STR2## in which the symbols have the following meanings: R.sup.3 represents hydrogen or C.sub.1-4 -alkyl,X represents NH, O, S or if R.sup.4 represents hydrogen, a single bond,one of the symbols R.sup.4 and R.sup.5 represents hydrogen and the other represents the group --CO--R.sup.6, orR.sup.4 and R.sup.5 together represent the radical --CO--C(R.sup.6).dbd.C(R.sup.7)--or--CO--C(R.sup.7).dbd.C(R.sup.6)--orR.sup.4 R.sup.Type: GrantFiled: December 15, 1986Date of Patent: November 15, 1988Assignee: Ciba-Geigy CorporationInventors: Andreas Von Sprecher, Werner Breitenstein, Andreas Beck, Robert W. Lang, Konrad Oertle
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Patent number: 4781866Abstract: An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): ##STR1## with H.sub.2 O.sub.2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.Type: GrantFiled: November 24, 1986Date of Patent: November 1, 1988Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, James N. Plampin, Robin C. Stanzione
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Patent number: 4778629Abstract: A process for the preparation of acyloxybenzenesulfonic acids and salts thereof, of the formula ##STR1## in which R is C.sub.1 -C.sub.17 -alkyl or C.sub.2 -C.sub.17 -alkenyl and M is an alkali or alkaline earth metal, ammonium or hydrogen, including the stages of (a) sulfonation of phenol, if appropriate (b) thermal treatment of the sulfonated phenol, (c) esterification of the sulfonated phenol and if appropriate (d) neutralization of the ester, wherein the sulfonation of the phenol is carried out with sulfuric acid or oleum and the water of reaction is removed during or after stage (b) by distillation and/or by reaction with a dehydrating agent.Type: GrantFiled: October 23, 1986Date of Patent: October 18, 1988Assignee: Hoechst AktiengesellschaftInventors: Fritz-Feo Grabley, Gerd Reinhardt, Georg Bader, Walter Rupp
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Patent number: 4772744Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a substituted alkoxy group,and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: April 27, 1987Date of Patent: September 20, 1988Assignee: Rohm and Haas CompanyInventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
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Patent number: 4761495Abstract: The present invention is directed to a composition and method relating to the preparation of aspartyl peptides having the general formula: ##STR1## where the radical-NHR represents an amino acid or peptide group. In the method, a .beta.-monoester of aspartic acid having the general formula: ##STR2## where R.sub.1 represents a hydrocarbon-containing radical, is reacted with a .beta.-dicarbonyl compound, preferably ethylacetoacetate to protect the aspartyl amino group and form an enamine. The enamine is then coupld to an amino acid or peptide, following which any protecting groups are removed to yield .alpha.-aspartyl peptides without any .beta.-isomer. In its composition aspects, the present invention is directed to novel enamines resulting from reaction of the .beta.-monoester of aspartic acid with a .beta.-dicarbonyl compound.Type: GrantFiled: January 11, 1985Date of Patent: August 2, 1988Assignee: Isochem S.A.Inventors: Didier Wirth, Dominique Gibert, Annie Boutin
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Patent number: 4745212Abstract: Isocyanates containing ester and/or amide groups are produced by reacting (a) an isocyanatocarboxylic acid chloride with (b) an organic compound containing a silylated alcoholic group and/or silylated phenolic hydroxyl group and/or silylated amino group which compound contains no other group which is reactive with isocyanate and chlorocarbonyl groups under the reaction conditions. The reaction of (a) with (b) is carried out at a temperature of from -20.degree. to 150.degree. C. This process makes it possible to produce the desired isocyanates with a high degree of selectivity.Type: GrantFiled: October 8, 1987Date of Patent: May 17, 1988Assignee: Bayer AktiengesellschaftInventors: Werner Mormann, Edith Hissmann
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Patent number: 4739097Abstract: Compounds of the general formula I ##STR1## in which R is a hydrogen or halogen atom, a cyanide or an alkyl group having 1-4 carbon atoms andR.sub.1 is a hydrogen or halogen atom, nitro, alkyl, alkoxy, aryl, aryloxy, acyl or alkoxycarbonyl group,are prepared by esterifying two adjacent OH groups to give the cyclic carbonate, esterifying the free OH group with (meth)acrylic acid and selectively hydrolyzing the carbonate. The compounds are free of polyunsaturated impurities and can be used for preparing purely linear polymers.Type: GrantFiled: August 13, 1986Date of Patent: April 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Juergen Sander, Arnold Schneller
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Patent number: 4735740Abstract: Novel sulfonated phenyl esters of dicarboxylic acids are useful as diperoxyacid precursors in bleaching and laundering applications when combined with a source of peroxide. These diperoxyacid precursors can be produced by reacting a dicarboxylic acid, a phenol sulfonate, and a lower alkyl acid anhydride in an alkyl hydrocarbon solvent and removing a carboxylic acid byproduct through distillation. The diperoxyacid precursors have the structure: ##STR1## wherein n is an integer from about 4 to about 18 and M is an alkali metal, an alkaline earth metal, or ammonium. The diperoxyacid precursors have a high perhydrolysis profile coupled with a relatively low-to-moderate hydrolysis profile.Type: GrantFiled: October 3, 1986Date of Patent: April 5, 1988Assignee: The Clorox CompanyInventor: Alfred G. Zielske
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Patent number: 4725602Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.Type: GrantFiled: October 24, 1985Date of Patent: February 16, 1988Assignee: McNeilab, Inc.Inventor: John R. Carson
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Patent number: 4721805Abstract: A process is provided for making acyloxy benzene sulfonates by the steps of sulfonating with SO.sub.3, digesting the sulfonation adduct, and neutralizing. The sulfonation adduct can spontaneously rearrange. Unless the rearrangement is controlled as taught in the sulfonating and digesting steps, product yields of acyloxy benzene sulfonate drop to unusable levels and the color of the product is poor and the content of by-products is excessive in the product.Type: GrantFiled: November 28, 1986Date of Patent: January 26, 1988Assignee: Stepan CompanyInventor: Marvin Nussbaum
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Patent number: 4708966Abstract: The present invention relates to novel specifically-substituted phenyl compounds, especially substituted di-tert-butyl phenol derivatives, which are effective as anti-inflammatory, analgesic and/or antipyretic agents. These phenyl compounds are substituted with a low molecular weight alkyl chain which terminates in a specific unsaturated functional group. These unsaturated functionalities are --C.tbd.CH, C.dbd.CH.sub.2, C.dbd.C.dbd.CH.sub.2, and aldehydes in the form of their acetals.The present invention further relates to pharmaceutical compositions which contain an anti-inflammatory agent of the present invention and a pharmaceutically-acceptable carrier.Finally, the present invention relates to methods for treating diseases characterized by inflammation, such as rheumatoid arthritis and osteoarthritis, in humans or lower animals.Type: GrantFiled: June 27, 1986Date of Patent: November 24, 1987Assignee: The Procter & Gamble CompanyInventors: Maurice E. Loomans, Randall S. Matthews, Joseph A. Miller
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Patent number: 4705649Abstract: Acyloxybenzenesulfonic acids and their alkali metal and alkaline earth metal salts are prepared by sulfonation of phenol in the presence of a small amount of a complexing agent for the sulfonating agent SO.sub.3 or chlorosulfonic acid, followed by esterification and, if required, neutralization to give the alkali metal or alkaline earth metal salt.Type: GrantFiled: November 7, 1986Date of Patent: November 10, 1987Assignee: BASF AktiengesellschaftInventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
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Patent number: 4704236Abstract: Sulphophenyl esters can be made amongst other routes by reacting an acyl halide with a phenol sulphonate salt, but it has been suggested in the prior art that there are substantial problems or disadvantages associated with carrying out the reaction in the presence of an organic solvent such as gelation of the reaction medium or excessive reaction times.In the present invention, the process employs as organic solvent high boiling point primarily aliphatic hydrocarbons which forms with linear acyl halide a reaction medium in which products of high and/or improved purity and/or yield are obtainable without gelation and in reasonable reaction periods, especially between C.sub.6 -C.sub.10 linear acyl chlorides and sodium phenol sulphonate.Type: GrantFiled: September 24, 1986Date of Patent: November 3, 1987Assignee: Interox Chemicals Ltd.Inventors: John P. Sankey, William R. Sanderson
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Patent number: 4695657Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.Type: GrantFiled: December 17, 1985Date of Patent: September 22, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4695589Abstract: Alpha-(aminoalkyl)-4-hydroxy-3-(alkylthio)benzenemethanols useful as intermediates and as antihypertensive agents are prepared by reduction of the corresponding aminoalkyl 4-hydroxy-3-(alkylthio)phenyl ketones.Type: GrantFiled: May 27, 1983Date of Patent: September 22, 1987Assignee: Sterling Drug Inc.Inventor: Richard E. Philion
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Patent number: 4693850Abstract: Novel synthetic steps and intermediates leading to guanidines such as the anti-diabetic compound linogliride.Type: GrantFiled: November 26, 1986Date of Patent: September 15, 1987Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, James N. Plampin, Robin C. Stanzione
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Patent number: 4693848Abstract: Alkali metal and alkaline earth metal salts of acyloxybenzenesulfonic acids of the formula I ##STR1## where R is a saturated or unsaturated alkyl radical of 1 to 17 carbon atoms or is phenyl which is unsubstituted or monosubstituted or disubstituted by alkyl of 1 to 3 carbon atoms, halogen, methoxy or nitro, are prepared by neutralization, by a method in which a liquid acyloxybenzenesulfonic acid of the formula I and an aqueous solution of an alkali metal or alkaline earth metal hydroxide, carbonate or bicarbonate are combined in water, at from 0.degree. to 60.degree. C. and while mixing thoroughly, so that the pH is kept at from 2.5 to 7.0, and, if desired, the resulting salt is isolated from the aqueous solution in a conventional manner.Type: GrantFiled: April 2, 1986Date of Patent: September 15, 1987Assignee: Basf AktiengesellschaftInventors: Wolf-Dieter Balzer, Hans-Heinrich Bechtolsheimer, Karl-Heinz Beyer, Rolf Fikentscher, Johannes Perner, Rudi Widder, Helmut Wolf
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Patent number: 4692279Abstract: A process is provided for making acyloxy benzene sulfonates by the steps of sulfonating with SO.sub.3, digesting the sulfonation adduct, and neutralizing. The sulfonation adduct can spontaneously rearrange. Unless the rearrangement is controlled as taught in the sulfonating and digesting steps, product yields of acyloxy benzene sulfonate drop to unusable levels and the color of the product is poor and the content of by-products is excessive in the product.Type: GrantFiled: April 15, 1985Date of Patent: September 8, 1987Assignee: Stepan CompanyInventor: Marvin Nussbaum
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Patent number: 4692546Abstract: Acyloxy aromatic carboxylic acids, e.g., 4-acetoxybenzoic acid, are prepared by oxidizing with oxygen an acyloxy aromatic ketone, e.g., 4-acetoxyacetophenone in the presence of manganese cations and a lower-carboxylic acid anhydride as catalyst and a co-reductant or promoter. The acyloxy aromatic ketone may be prepared by acylating a hydroxy aromatic ketone, e.g., 4-hydroxyacetophenone, which has the effect of "masking" the hydroxyl group of the ketone in a manner necessary to effect the subsequent transition-metal catalyzed oxidation of the ketone to the acyloxy aromatic carboxylic acid.Type: GrantFiled: September 25, 1985Date of Patent: September 8, 1987Assignee: Celanese CorporationInventor: Kenneth G. Davenport
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Patent number: 4665216Abstract: A process is provided for producing N-acyl-acyloxy aromatic amine, such as 4-acetoxyacetanilide by reacting a hydroxy-aromatic ketoxime with a carboxylic acid anhydride, e.g. acetic anhydride, in the presence of phosphoric or oxalic acid as a Beckmann rearrangement catalyst. Preferably the ketoxime is prepared by reacting a hydroxy aromatic ketone such as 4-hydroxyacetophone with a hydroxyl amine salt, and the ketone is obtained by the Fries rearrangement of a phenolic ester, e.g. phenyl acetate or the Friedel-Crafts acylation of a phenolic compound, e.g. phenol, with an acylating agent, e.g. acetic acid.Type: GrantFiled: March 12, 1985Date of Patent: May 12, 1987Assignee: Celanese CorporationInventors: Theodore Horlenko, James H. George
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Patent number: 4609758Abstract: This invention provides a group of hydroxycycloalkanephenoxyethylamine antidepressant derivatives of the following structural formula: ##STR1## in which R.sub.1 is hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2 is alkyl of 1 to 6 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, hydroxyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 7 carbon atoms, halo or trifluoromethyl;R.sub.5 is hydrogen, alkyl of 1 to 6 carbon atoms or alkanoyl of 2 to 7 carbon atoms;and n is one of the integers 0, 1, 2 or 3;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 9, 1985Date of Patent: September 2, 1986Assignee: American Home Products CorporationInventor: George E. M. Husbands
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Patent number: 4605667Abstract: Pesticidal water-soluble aminoacid sulfenylated carbamates useful as broad spectrum insecticides and miticides, particularly useful as systemic insecticides.Type: GrantFiled: March 29, 1985Date of Patent: August 12, 1986Assignee: Union Carbide CorporationInventors: Chennupati K. Rao, Themistocles D. D'Silva
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Patent number: 4588533Abstract: Alkali metal salts and alkaline earth metal salts of acyloxybenzenesulfonate are prepared by sulfonating an aryl ester of an organic acid with gaseous sulfur trioxide to produce a sulfonation reaction mixture containing acyloxybenzenesulfonic acid, neutralizing the sulfonation reaction mixture with alkali metal hydroxide or alkaline earth metal hydroxide to produce an alkali metal salt or alkaline earth metal salt of an acyloxybenzenesulfonic acid and thereafter recovering from the reaction mixture the acyloxybenzenesulfonic acid salt product thus formed.Type: GrantFiled: May 18, 1984Date of Patent: May 13, 1986Assignee: Ethyl CorporationInventor: C. Bernard Berry, Jr.