Nitrogen Or Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/72)
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Patent number: 4467101Abstract: Acylamido-3-cephem-4-carboxylic acid compounds of the formula ##STR1## in which the index n represents an integer of from 1 to 4,the index m represents 0 or 1,X represents oxygen, sulphur or an --NH-- group,W represents a --CO--, --CO--NHSO.sub.2 -- or --SO.sub.2 NH--CO-- group, orX-W together represent a --CO-- or --CO--NHSO.sub.2 -- group,A represents optionally substituted phenylene, thienylene or furylene,Y represents hydrogen, hydroxyl, formyloxy, amino or sulpho optionally present in salt form, andZ represents hydrogen, orY and Z together represent an oxo group or an .dbd.N--O--R.degree. group in which R.degree. represents hydrogen or optionally substituted lower alkyl,R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, halogen or a group of the formula --CH.sub.2 --R.sub.2 in which R.sub.2 is a free, esterified or etherified hydroxy or mercapto group or a quaternary ammonium group, andR.sub.Type: GrantFiled: September 20, 1982Date of Patent: August 21, 1984Assignee: Ciba-Geigy CorporationInventors: Karoly Kocsis, Peter Schneider, Bruno Fechtig, Riccardo Scartazzini
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Patent number: 4456618Abstract: Naphthenic and heterocyclic retinoic acid analogues such as (E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthaldehyde, methyl 6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthoate, 6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthoic acid, (E)-1-(5-carbethoxy-2-furanyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1- yl)-1,3-butadiene, (E)-1-(5-carboxy-2-furanyl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl) -1,3-butadiene, (E)-1-(5-carbethoxythien-2-yl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1- yl)-1,3-butadiene, and (E)-1-(5-carboxythien-2-yl)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl) -1,3-butadiene. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: October 15, 1982Date of Patent: June 26, 1984Assignee: SRI InternationalInventors: Marcia I. Dawson, Rebecca L. S. Chan
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Patent number: 4417053Abstract: A process for preparing substituted glyoxylic acid derivatives by oxidizing with a molecular oxygen containing gas an amide or ester of a hydroxy acid in the presence of a catalytic amount of a cobalt compound.Type: GrantFiled: November 12, 1981Date of Patent: November 22, 1983Assignee: Stamicarbon B.V.Inventors: Antonius Corvers, Cornelis W. van den Broek, Geertrudes H. Suverkropp
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Patent number: 4416889Abstract: N-allenyl-acetanilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl andR.sup.6 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl; or the grouping ##STR2## wherein R.sup.7 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical andAz represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.which possess fungicidal properties.Type: GrantFiled: September 20, 1982Date of Patent: November 22, 1983Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Winfried Lunkenheimer, Wilhelm Brandes
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Patent number: 4416826Abstract: Peresters of the formula: ##STR1## wherein R is an alkyl group; and ##STR2## light-absorbing chromophore group; and use thereof as photoinitiators are provided.Type: GrantFiled: October 29, 1980Date of Patent: November 22, 1983Inventor: Douglas C. Neckers
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Patent number: 4412856Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.Type: GrantFiled: May 22, 1981Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4405638Abstract: The invention provides 2-methoxyphenyl esters of N-substituted amino acids, which have mucolytic, antitussive and antiinflammatory activity.Type: GrantFiled: April 29, 1982Date of Patent: September 20, 1983Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.AInventors: Claudio Cavazza, Massimo Carloni, Maria T. Ramacci
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Patent number: 4385004Abstract: New compounds of the formula (VIIIa) are disclosed ##STR1## wherein R.sup.1 is hydrogen, methyl or ethyl;R.sup.2 is hydrogen, fluoro, or alkyl having 1 to 4 carbon atoms;R.sup.3 is hydrogen, phenyl, alkoxy having 1 to 6 carbon atoms; phenoxy, thenoyl, or benzoyl; orR.sup.2 and R.sup.3 together with the phenyl group to which they are attached form a naphthyl group which is unsubstituted or substituted by C.sub.1 to C.sub.4 alkyl or C.sub.1 to C.sub.4 alkoxy;R.sup.10 is phenylaminocarbonyl, 1-phenyl-5-tetrazolyl, a group --SO.sub.2 OMe, wherein Me is a metal atom selected from the group which consists of sodium or potassium, or a group --SO.sub.2 R.sup.6 in which R.sup.6 is alkyl having 1 to 4 carbon atoms, 4-methylphenyl, amino, C.sub.1 to C.sub.4 alkoxycarbonyl-amino, or benzoylamino, or R.sup.10 is a group ##STR2## in which R.sup.7 is cycloalkyl having 5 to 6 carbon atoms, and R is vinyl. The compounds are intermediates useful in the preparation of arylacetic acids having antiinflammatory compounds.Type: GrantFiled: March 23, 1981Date of Patent: May 24, 1983Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Endre Palosi, Dezso Korbonits, Pal Kiss, Csaba Gonczy, Gergely Heja, Judit Cser nee Kun, Rudolf Szebeni, Maria Szomor nee Wundele, Ida Szvoboda nee Kanzel
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Patent number: 4381305Abstract: New derivatives of 1,2-ethylenediamine and salts thereof endowed with vascular antispasmodic and antiallergic activity; processes for preparing them, some new intermediates useful in their preparation and pharmaceutical compositions containing them.Type: GrantFiled: June 5, 1981Date of Patent: April 26, 1983Assignee: Simes S.p.A.Inventors: Cesare Casagrande, Giorgio Ferrari
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Patent number: 4380464Abstract: Disclosure is made of certain optionally substituted N,N-diacylaminoperfluoroalkanesulfonanilides and agriculturally acceptable salts thereof which are useful as herbicides and plant growth regulators.Type: GrantFiled: February 4, 1982Date of Patent: April 19, 1983Assignee: Minnesota Mining and Manufacturing CompanyInventor: Ezzat A. Mikhail
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Patent number: 4363920Abstract: N-[2-(2-thenoyl)thiopropionyl]-glycine is prepared, according to a process which is especially advantageous for the purity and the stability of the product, by means of N-acylation of glycine with an activated derivative of 2-(2-thenoyl)thiopropionic acid.Type: GrantFiled: May 26, 1981Date of Patent: December 14, 1982Assignee: B.T.B. Industria Chimica S.p.A.Inventor: Renzo Viscardi
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Patent number: 4352935Abstract: Para-acetamidophenol .alpha.-methyl-4(2'-thienyl-carbonyl) phenyl acetate, having anti-inflammatory activity, is provided, along with a process for its preparation by reacting .alpha.-methyl-4(2'-thienyl-carbonyl) phenyl acetic acid or a reactive species thereof with p-acetamidophenol in an aprotic organic solvent and, when the reactive species is an acid halide, the reaction is carried out also in the presence of a hydrohalic binding compound.Type: GrantFiled: November 23, 1981Date of Patent: October 5, 1982Inventors: Eduardo Guzman Llansa, Pablo Arino Maestrojuan, Enrique Melendez Andreu
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Patent number: 4347373Abstract: This invention relates to a series of compounds having therapeutic activity, consisting of the derivatives obtained by reacting 4-methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole with non-steroidal, traditional, antiinflammatory agents. The derivatives are carboxamides of formula ##STR1## wherein R.sub.1 =H; --CH.sub.3 ; --C.sub.2 H.sub.5 ; and ##STR2## of the antiinflammatory agents, i.e. the acylic radical of the antiinflammatory acid, or ##STR3## of the antiinflammatory acid and the corresponding physiologically acceptable salts on the imidazole ring.Type: GrantFiled: March 9, 1981Date of Patent: August 31, 1982Inventor: Franco Turconi
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Patent number: 4344893Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: February 25, 1980Date of Patent: August 17, 1982Assignee: The Boots Company LimitedInventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
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Patent number: 4344954Abstract: This disclosure describes certain novel 2,3-disubstituted-2,3,5,6,7,8-hexahydro-thiazolo[3,2-][1,3]diazepin-3-ols which are useful as diuretic agents.Type: GrantFiled: July 9, 1980Date of Patent: August 17, 1982Assignee: American Cyanamid CompanyInventors: Andrew S. Tomcufcik, William B. Wright, Jr., Joseph W. Marsico, Jr.
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Patent number: 4339591Abstract: There are produced carboxylic acid cyanides, e.g., acyl cyanides by reacting a carboxylic acid halide with an alkali cyanide or hydrogen cyanide in the presence of a copper (I) salt and a carboxylic acid nitrile. Especially advantageous are glutaric acid dinitrile and 2-methyl glutaric acid dinitrile.Type: GrantFiled: March 23, 1981Date of Patent: July 13, 1982Assignee: Degussa AktiengesellschaftInventors: Axel Kleemann, Bernd Lehmann, Herbert Klenk
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Patent number: 4337268Abstract: N-Oximinoalkyl-anilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen, alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl or optionally substituted aralkyl andR.sup.7 represents furyl, tetrahydrofuryl, thiophenyl, or tetrahydrothiophenyl; isoxazolyl which is optionally substituted in alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl or cycloalkyl; or the grouping --CH.sub.2 Az, --CH.sub.2 --OR.sup.8, --.sub.CH.sub.2 --SR.sup.8, --OR.sup.8, --SR.sup.8, --CH.sub.2 --OSO.sub.2 R.sup.8, --COOR.sup.8 or ##STR2## wherein R.sup.8 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical andAz represents pyrazol-1-yl, 1,2,4-thiazol-1-yl or imidazol-1-yl,which possess fungicidal activity.Type: GrantFiled: May 15, 1980Date of Patent: June 29, 1982Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Wilhelm Brandes
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Patent number: 4335098Abstract: This invention relates to acylated furanyl acrylic acids, salts, esters and amides, to acylated thienyl acrylic acids, salts, esters and amides, and to their use as hypolipidemic agents, and to the processes for producing said compounds.Type: GrantFiled: May 26, 1981Date of Patent: June 15, 1982Assignee: Merrell Dow Pharmaceuticals Inc.Inventor: Roger A. Parker
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Patent number: 4331592Abstract: What is disclosed is a method of making a carboxylic acid amide, including a peptide, by reacting a compound having a free amino group with a compound having a free carboxy group in the presence of an anhydride of an alkane-phosphonic acid.Type: GrantFiled: January 16, 1980Date of Patent: May 25, 1982Assignee: Hoechst AktiengesellschaftInventors: Hans Wissmann, Hans-Jerg Kleiner
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Patent number: 4328237Abstract: Pyrethroid type insecticides are described having the formula: ##STR1## Compounds of general formula I are endowed with a high insecticide and acaricide activity.Type: GrantFiled: February 26, 1979Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Francesco Corda, Franco Gozzo, Augusto Menconi, Angelo Longoni
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Patent number: 4316907Abstract: Thiophene carboxamides are described of general formula I ##STR1## in which the amide function is in the 2- or 3-position on the thiophene ring, R.sub.1 to R.sub.5 inclusive are hydrogen atoms or lower alkyl groups, X is --CH.sub.2 --, --O-- or --NR.sub.6 -- where R.sub.6 is hydrogen or a lower alkyl group, n is a number from 0 to 3 and Ar is an optionally substituted phenyl groupand their physiologically acceptable salts.The compounds have been found to lower blood pressure in animals and to exhibit a blocking action at .beta.-adrenoreceptors and their use is indicated for the treatment of cardiovascular disorders such as hypertension and angina. Some of the compounds also exhibit a blocking action on .alpha.-adrenoreceptors and their use is indicated for the treatment of hypertention.Type: GrantFiled: June 27, 1980Date of Patent: February 23, 1982Assignee: Glaxo Group LimitedInventors: Alexander W. Oxford, John Bradshaw, Ian H. Coates
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Patent number: 4315020Abstract: Certain phenyl amines have been prepared wherein the "methyl" carbon is substituted with a polyfluoroalkyl radical. The compounds form acid addition salts, exist in resolvable stereoisomeric forms, and are useful for treating hypertension. Formulations for human and veterinary medicine are described, as well as methods of use.Type: GrantFiled: October 15, 1980Date of Patent: February 9, 1982Assignee: Science Union et CieInventors: Charles E. Malen, Pierre Roger, Michel Laubie
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Patent number: 4312663Abstract: Cyclicacylaminoperfluoroalanesulfonanilides and agriculturally acceptable salts thereof are useful as herbicides and plant growth regulators.Type: GrantFiled: September 18, 1980Date of Patent: January 26, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: Ezzat A. Mikhail
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Patent number: 4304941Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a clay.Type: GrantFiled: August 1, 1980Date of Patent: December 8, 1981Assignee: Hoechst Roussel Pharmaceuticals, Inc.Inventors: Thomas B. K. Lee, Gregory M. Jobin
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Patent number: 4296092Abstract: Benzene and 2-thiophene carbothioic and 2-aminoalkyl ester acid salts having the formula: ##STR1## wherein R is 2-thiophene, benzene or substituted benzene; n is 2 and 3 and X.sup.- is a chlorine or bromine radical and methods of using the compounds and compositions are disclosed.Type: GrantFiled: November 19, 1979Date of Patent: October 20, 1981Assignee: A. H. Robins Company, Inc.Inventor: Harry R. Munson, Jr.
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Patent number: 4293555Abstract: Disclosed are 6- and 6,6-disubstituted-2-substituted-oxapen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from hydrogen, alkyl, alkoxyl, aralkyl, aryl, heterocyclyl and heterocyclylalkyl; R is selected from hydrogen, --OR, --SR, --NR.sub.2, alkyl, aryl, aralkyl, heterocyclyl, or heterocyclylalkyl. Such compounds and their pharmaceutically acceptable salt, and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.Type: GrantFiled: October 10, 1979Date of Patent: October 6, 1981Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Frank P. DiNinno
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4278680Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy,Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, andR.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical,or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.Type: GrantFiled: December 10, 1979Date of Patent: July 14, 1981Assignee: Boehringer Mannheim GmbHInventors: Manfred Hubner, Hans Kuhnle, Ernst-Christian Witte, Ruth Heerdt, Rudi Weyer, Volker Hitzel
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Patent number: 4278802Abstract: Novel .alpha.-thio-alkanoic acid derivatives and a process for their preparation. These novel compounds can be easily converted to useful medicines.Type: GrantFiled: June 4, 1980Date of Patent: July 14, 1981Assignee: Sagami Chemical Research CenterInventors: Genichi Tsuchihashi, Katsuyuki Ogura, Shuichi Mitamura
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Patent number: 4271171Abstract: Aroylureas of the formula ##STR1## where A denotes a phenyl, thienyl or pyridyl-3 radical which is mono- or polysubstituted by halogen, linear or branched alkyl of 1 to 4 carbon atoms, or linear or branched alkoxy of 1 to 4 carbon atoms, R denotes linear or branched alkyl of 1 to 4 carbon atoms or linear or branched alkoxy of 1 to 4 carbon atoms, and n denotes one of the integers 0,1 and 2, which have an insecticidal and acarididal action, and a process for combating insects and mites with these active ingredients.Type: GrantFiled: May 2, 1980Date of Patent: June 2, 1981Assignee: BASF AktiengesellschaftInventors: Annegrit Baumann, Karl Kiehs, Heinrich Adolphi, Karl-Heinz Koenig
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Patent number: 4268442Abstract: There are disclosed processes for preparing an aromatic acetic acid by the reaction of an aromatic aldehyde with a combination of a trihalomethane and an alkanethiol, and by the reaction of an alcohol derivative (2,2,2-trihalo-1-arylethanol) with an alkanethiol, in the presence of a base in a mixed medium of water and an aprotic polar solvent.Type: GrantFiled: November 13, 1979Date of Patent: May 19, 1981Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Tamotsu Fujimoto, Minoru Suda, Daiei Tunemoto
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Patent number: 4259508Abstract: This invention relates in the free form or in salts or esters form, new N,S-diacyl-L-cysteines in which at least one of the acetylating radicals is 2-thenoyl radical and particularly N-acetyl, S-2-thenoyl cysteine and its esters. A process for manufacturing those new cysteines is claimed, as their utilization in therapeutic and cosmetological grounds.Type: GrantFiled: November 3, 1978Date of Patent: March 31, 1981Inventor: Jean Blum
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Patent number: 4254043Abstract: A process is disclosed for the single step acylation of heterocyclic aryl compounds of the formula: ##STR1## wherein X is the radical selected from the group --N.dbd., --NH--, --O-- and --S-- and Y is the radical selected from the group --CH-- and --CH.dbd.CH-- by treatment with a compound of the formula ##STR2## wherein R is C.sub.1 to C.sub.12 alkylene; Z is selected from the group hydrogen, cyano, halo, C.sub.1 to C.sub.6 alkoxy, C.sub.1 to C.sub.6 alkoxy carbonyl, unsubstituted or substituted phenyl, the substituents selected from the group C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 alkoxy, cyano, halo and trifluoromethyl; and n' is the integer 1 or 2.Type: GrantFiled: April 11, 1980Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: George S. Kuta
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Patent number: 4250183Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.Type: GrantFiled: December 15, 1978Date of Patent: February 10, 1981Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4242519Abstract: Novel .alpha.-thio-alkanoic acid derivatives and a process for their preparation. These novel compounds can be easily converted to useful medicines.Type: GrantFiled: March 13, 1979Date of Patent: December 30, 1980Assignee: Sagami Chemical Research CenterInventors: Genichi Tsuchihashi, Katsuyuki Ogura, Shuichi Mitamura
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Patent number: 4241079Abstract: 2-Imino substituted isothioureidobenzene products useful as anthelmintics and fungicides are disclosed. The products may be prepared by several different methods including treating a 2-iminothioureidobenzene with a base and either an organic halide, a diester of sulfuric acid or a diester of sulfurous acid or treating a 2-aminoisothioureidobenzene with an appropriately substituted aldehyde.Type: GrantFiled: May 4, 1978Date of Patent: December 23, 1980Assignee: Rohm and Haas CompanyInventors: Edward E. Kilbourn, W. David Weir
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Patent number: 4240979Abstract: Aroylureas of the formula ##STR1## where A denotes a phenyl, thienyl or pyridyl-3 radical which is mono- or polysubstituted by halogen, linear or branched alkyl of 1 to 4 carbon atoms, or linear or branched alkoxy of 1 to 4 carbon atoms, R denotes linear or branched alkyl of 1 to 4 carbon atoms or linear or branched alkoxy of 1 to 4 carbon atoms, and n denotes one of the integers 0, 1 and 2, which have an insecticidal and acarididal action, and a process for combating insects and mites with these active ingredients.Type: GrantFiled: August 30, 1979Date of Patent: December 23, 1980Assignee: BASF AktiengesellschaftInventors: Annegrit Baumann, Karl Kiehs, Heinrich Adolphi, Karl-Heinz Koenig
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Patent number: 4230872Abstract: Novel 9-substituted or unsubstituted thienyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives, useful as antitumor agents as well as processes for their preparation and novel intermediates are disclosed.Type: GrantFiled: May 11, 1978Date of Patent: October 28, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Klaus, Beverly A. Pawson
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Patent number: 4223039Abstract: There are provided compounds of the general formula ##STR1## in which Ar represents a phenyl group which is unsubstituted or substituted by a halogen atom or a lower alkyl group, or represents a thienyl group, R.sub.1 represents a hydrogen or halogen atom or, when the Ar--CO-- grouping is in the meta-position with respect to the nitrogen atom, a lower alkyl group, R.sub.2 represents a hydrogen atom, or a lower alkyl or an acyl group, and R.sub.3 represents a hydrogen atom, a lower alkyl or a phenyl group and a physiologically acceptable salt thereof.The compounds of the general formula I and their salts have therapeutic utility, especially as analgesics.Type: GrantFiled: March 14, 1979Date of Patent: September 16, 1980Assignee: Metabio JoullieInventors: Francis E. E. Rose, Christian J. M. Warolin, Pierre Muller, Paul M. P. Fabiani, Bernard Gaudilliere
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Patent number: 4221815Abstract: Acyl-aminoalkyl-benzoic acid and derivates thereof show a blood sugar lowering effect upon oral administration and can be used as orally applicable hypoglycemiants.Type: GrantFiled: January 2, 1976Date of Patent: September 9, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Karl Geisen, Werner Pfaff
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Patent number: 4209638Abstract: Disclosed is a process for increasing the proportion of a desired enantiomer of a 2-arylpropionic acid which comprises heating at a temperature of at least 80.degree. C. a mixture comprising an inert liquid organic diluent and a salt of the 2-arylpropionic acid with an enantiomer of a chiral organic nitrogenous base, the base and the diluent being such that the salt of the racemic acid has a solubility of 0.1 to 10% w/v in the diluent at the operating temperature and in which process a proportion of the salt is undissolved in the diluent, whereby a proportion of one optical isomer of the acid component of the salt is converted into its enantiomer, and collecting the salt of which the acid component has an increased proportion of that enantiomer.Type: GrantFiled: September 25, 1978Date of Patent: June 24, 1980Assignee: The Boots Company LimitedInventors: John S. Nicholson, James G. Tantum
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Patent number: 4207341Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein A is an aryl radical optionally substituted by halogen, trifluoromethyl, alkyl, alkoxy, alkenyloxy, alkoxyalkoxy, alkyl-substituted amino or aryloxy, or a heterocyclic ring system optionally substituted by halogen, alkyl or alkoxy,Y is a valency bond or an optionally branched alkylene radical containing up to 3 carbon atoms, andR.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical,or a physiologically compatible salt or ester thereof, exhibit marked hypoglycaemic and hypolipidaemic activity.Type: GrantFiled: July 1, 1976Date of Patent: June 10, 1980Assignee: Boehringer-Mannheim GmbHInventors: Manfred Hubner, Hans Kuhnle, Ernst-Christian Witte, Ruth Heerdt, Rudi Weyer, Volker Hitzel
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Patent number: 4201715Abstract: Process for the anilidization of carboxylic acid esters of the general formula R.sub.1 COOR.sub.2, wherein R.sub.1 is a cycloaliphatic or substituted cycloaliphatic radical with 3-8 C-atoms, preferably 5-6 C-atoms, an aromatic or substituted aromatic radical, preferably a heterocyclic or substituted heterocyclic radical, more particularly an oxygen-containing heterocyclic radical, with 4-5 C-atoms, and R.sub.2 is a hydrocarbon radical with up to 4 C-atoms, preferably 1-2 C-atoms, wherein such esters are reacted in the presence of aniline with equimolar amounts of magnesium dianilide and/or aluminum trianilide in the fluid phase. The products obtained are used as intermediates or directly as pesticides.Type: GrantFiled: November 20, 1978Date of Patent: May 6, 1980Assignee: Wacker-Chemie GmbHInventors: Wolfgang Deinhammer, Hellmuth Spes
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Patent number: 4198519Abstract: 4-(Thien-2-oyl- and thien-3-oylphenyl)pentan-2-ones and 4-(thien-2-oyl- and thien-3-oylphenyl)butan-2-ones, the corresponding pentan-2-ols and butan-2-ols, and esters of the latter alkanols are anti-inflammatory agents. The compounds, of which 4-[4-(2-thienoyl)phenyl]pentan-2-one is a representative embodiment, can be prepared by acylation of the corresponding 4-phenylpentan-2-one, 4-phenylbutan-2-one, or an ester of the corresponding pentan-2-ol or butan-2-ol, with a thienylcarboxylic acid, or by acylation of a 4-(4-carboxyphenyl)pentan-2-one, 4-(4-carboxyphenyl)butan-2-one or an ester of the corresponding pentan-2-ol or butan-2-ol with thiophene, optionally in either case with subsequent reduction of the resultant alkanone and with optional esterification of the resultant alkanol.Type: GrantFiled: October 18, 1978Date of Patent: April 15, 1980Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4197309Abstract: The invention provides certain 4-keto-phenoxyacetic acids and their oximes of the formula: ##STR1## in which A is selected from oxygen and sulphur,Z is selected from oxygen and the group NOH, andX.sub.1 and X.sub.2 are radicals independently selected from hydrogen, halogen and methyl, with the proviso that the benzene nucleus is never substituted by two halogen atoms in ortho-position with respect of one another, and pharmaceutically acceptable alkaline and amine addition salts thereof.Type: GrantFiled: May 30, 1978Date of Patent: April 8, 1980Assignee: Albert Roland S.A.Inventors: Germaine Thuillier, nee Nachmias, Jean E. Thuillier, Jacqueline S. Laforest, nee Boutillier du Retail, Bernard J. M. Cariou, Pierre A. R. Bessin, Jacqueline S. Bonnet, nee Roux
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Patent number: 4197310Abstract: This disclosure describes new compounds and compositions of matter useful as anti-inflammatory agents and as inhibitors of the progressive joint deterioration characteristic of arthritic disease and the methods of meliorating inflammation and of inhibiting joint deterioration in mammals therewith, the novel active ingredients of said compositions of matter being certain substituted cis-2-[2(or 3)-thenoyl]-3-hydroxy-2-alkenenitriles and/or the pharmacologically acceptable cationic salts thereof.Type: GrantFiled: April 30, 1979Date of Patent: April 8, 1980Assignee: American Cyanamid CompanyInventors: John W. Hanifin, Jr., David N. Ridge
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Patent number: 4189436Abstract: This disclosure describes new compounds and compositions of matter useful as anti-inflammatory agents and as inhibitors of the progressive joint deterioration characteristic of arthritic disease and the methods of meliorating inflammation and of inhibiting joint deterioration in mammals therewith, the active ingredients of said compositions of matter being .beta.-oxo-3-thiophenepropionitrile, .beta.-amino-2-thiopheneacrylonitrile, and/or .beta.-amino-3-thiopheneacrylonitrile.Type: GrantFiled: August 24, 1978Date of Patent: February 19, 1980Assignee: American Cyanamid CompanyInventors: John W. Hanifin, David N. Ridge
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Patent number: 4183859Abstract: Compounds of formula: ##STR1## wherein R is hydroxyl, lower alkoxy having 1 to 4 carbon atoms or amino and R.sup.1 is hydrogen or lower alkyl having 1 to 4 carbon atoms, are useful as medicines such as antipyretics, analgesics and antiinflammatory agents.Type: GrantFiled: April 4, 1978Date of Patent: January 15, 1980Assignee: Takeda Chemical Industries, Ltd.Inventors: Tetsuya Aono, Yasuhiko Kawano
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Patent number: 4182775Abstract: Benzoic acids of the general formula I ##STR1## in which R, R.sup.1, R.sup.2 and Y have the meanings as mentioned in the following, and which in the form of the free compounds or in the form of the physiologically tolerated salts and esters possess valuable pharmacological properties, processes for preparing them, pharmaceutical preparations containing them, and their use as or in medicaments.Type: GrantFiled: September 1, 1977Date of Patent: January 8, 1980Assignee: Hoechst AktiengesellschaftInventors: Rudi Weyer, Volker Hitzel, Ernold Granzer
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Patent number: 4180510Abstract: A method for preparing thienylacetic acid and its derivatives is disclosed, wherein a glyoxylic ester is made to react with hydrazine, and after with potash. Advantageously, the glyoxylic ester is prepared by condensation of a monoester monochloride of oxalic acid upon a thiophenic derivative, in the presence of titanium chloride.The so obtained products are useful as organic synthesis intermediaries for various products of pharmaceutical type.Type: GrantFiled: January 12, 1978Date of Patent: December 25, 1979Assignee: Produits Chimiques Auxiliaires et de Synthese, P.C.A.S.Inventors: Yves Le Guen, Georges Thiault