Oxy Patents (Class 562/451)
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Patent number: 4644072Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.Type: GrantFiled: April 12, 1985Date of Patent: February 17, 1987Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 4622339Abstract: Norbornane- and norbornene-carboxylic acid amides of the formula ##STR1## in which ##STR2## represents the part structure ##STR3## A represents a ##STR4## or --CH.sub.2 --CH.sub.2 -- group, R.sup.1 and R.sup.2 each independently is hydrogen or an alkyl radical with 1-6 carbon atoms,R.sup.3 is alkyl or alkenyl which has 1-8 carbon atoms and is optionally substituted by halogen or alkyl with 1 or 2 carbon atoms, cycloalkyl or cycloalkeny wtih 3 to 7 carbon atoms, an aromatic radical which has 6 or 10 carbon atoms and and is optionally substituted by halogen, by alkyl with 1 or 2 carbon atoms or by halogenoalkyl with 1 or 2 carbon atoms, or is a five-membered or six-membered heteroaromatic radical,R.sup.4 is hydrogen or a hydroxyl group,R.sup.5 and R.sup.6 each independently is hydrogen or alkyl with 1 to 4 carbon atoms, andn is a number from 2 to 6,and, if R.sup.1 is hydrogen, also physiologically acceptable salts thereof, perform as thromboxan antagonists.Type: GrantFiled: January 11, 1985Date of Patent: November 11, 1986Assignee: Bayer AktiengesellschaftInventors: Folker Lieb, Hermann Oediger, Hans-Joachim Kabbe, Ulrich Niewohner, Elisabeth Perzborn, Friedel Seuter
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Patent number: 4596800Abstract: A compound of formula (I) ##STR1## or a pharmaceutically acceptable salt thereof, in which R.sup.1 is hydrogen, halogen, or trifluoromethyl;R.sup.2 is hydrogen or halogen;R.sup.3 is hydrogen or methyl;R.sup.4 is --O(CH.sub.2).sub.a CO.sub.2 H or an ester or amide derivative thereof, O(CH.sub.2).sub.b M or --CO.sub.2 H or an ester or amide derivative thereofwhereina is an integer from 1 to 6,b is an integer from 2 to 7, andM is hydroxy, C.sub.1-6 alkoxy or ##STR2## wherein R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-6 alkyl or ##STR3## together form a five or six membered ring; R.sup.5 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by carboxy or esters and amides thereof; or phenyl optionally substituted by C.sub.1-6 alkyl, halogen, alkoxy or trifluoromethyl;R.sup.8 is hydrogen or C.sub.1-6 alkyl or R.sup.8 together withR.sup.5 form a carbocyclic ring; andn is 1 or 2.Processes for preparing these compounds and their use in therapy is also described.Type: GrantFiled: July 19, 1985Date of Patent: June 24, 1986Assignee: Beecham Group p.l.c.Inventors: Anthony T. Ainsworth, Richard M. Hindley
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Patent number: 4595759Abstract: The 2-aryl-1-aminoalkylcyclohexane nitrile, carboxylic acid or amide and derivatives thereof and methods of preparing same.Type: GrantFiled: February 15, 1985Date of Patent: June 17, 1986Assignee: Pennwalt CorporationInventors: Thomas A. Davidson, Telfer L. Thomas
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Patent number: 4552569Abstract: Amide carboxylate salts of certain diamines are provided. These compounds give excellent results when tested in lubricants as, among other things, friction reducing additives.Type: GrantFiled: January 22, 1985Date of Patent: November 12, 1985Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4545995Abstract: The novel unsaturated arylalkyl ammonium salts described herein are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided, as well as pharmaceutical formulations containing such ammonium salts.Type: GrantFiled: July 12, 1983Date of Patent: October 8, 1985Assignee: Schering A.G.Inventors: William C. Lumma, Jr., Ronald A. Wohl
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Patent number: 4511482Abstract: Amide carboxylate salts of certain diamines are provided. These compounds give excellent results when tested in lubricants as, among other things, friction reducing additives.Type: GrantFiled: June 29, 1983Date of Patent: April 16, 1985Assignee: Mobil Oil CorporationInventor: Andrew G. Horodysky
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Patent number: 4486598Abstract: Novel compounds of the following general formula: ##STR1##Type: GrantFiled: February 22, 1982Date of Patent: December 4, 1984Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4478849Abstract: The compounds of the formula (II): ##STR1## and their pharmaceutically acceptable salts wherein R.sub.1 is a hydrogen, fluorine or chlorine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R.sub.2 is a hydrogen, fluorine or chlorine atom or a hydroxyl group; R.sub.3 is a hydrogen or chlorine atom or a hydroxyl group; R.sub.4 is a carboxylic acid group or a salt, ester or amide thereof; R.sub.5 is a hydrogen, chlorine or fluorine atom or a methyl, methoxyl or hydroxyl group or a carboxylic acid group or a salt, ester or amide thereof; R.sub.6 is a hydrogen atom or a methyl, or propyl group; X is an oxygen atom or a bond; and Y is an alkylene group of up to 6 carbon atoms or a bond have been found to possess anti-obesity and/or antihyperglycaemic activity.Type: GrantFiled: March 10, 1983Date of Patent: October 23, 1984Assignee: Beecham Group LimitedInventors: Anthony T. Ainsworth, David G. Smith
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Patent number: 4464396Abstract: A novel compound of 4-[N-(hydroxybenzyl)aminomethyl]-cyclohexane-1-carboxylic acid represented by the general formula (I): ##STR1## wherein n is an integer of 1 to 3, or a salt or an ester thereof which has specific pharmacological activities, a method for preparing the derivative and a pharmacological composition in dosage unit form comprising the derivative as an active ingredient are disclosed herein.Type: GrantFiled: November 10, 1982Date of Patent: August 7, 1984Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Yutaka Mukaida, Sakuo Noda, Hidetoshi Kobayashi
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Patent number: 4450173Abstract: A short-acting .beta.-blocking compound of the formula ##STR1## wherein Ar may be substituted or unsubstituted aromatic, Y may be a straight or branched carbon chain or aralkyl, R may be lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, and x is an integer from 1 to about 3; or a pharmaceutically acceptable salt thereof.Type: GrantFiled: June 21, 1982Date of Patent: May 22, 1984Assignee: American Hospital Supply CorporationInventors: Paul W. Erhardt, Robert J. Borgman
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Patent number: 4447428Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: July 15, 1983Date of Patent: May 8, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton
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Patent number: 4442305Abstract: Novel polybenzamide compounds useful for in vitro or in vivo chelation are described. The compounds have the formula ##STR1## Polyamines are reacted with 2,3-dimethoxy benzoyl chloride unsubstituted or substituted with SO.sub.3 H, SO.sub.3 M, NO.sub.2, CO.sub.2 H or CO.sub.2 M as desired is reacted with a polyamine in an inert solvent then demethylated with BBr.sub.3 or BCl.sub.3 in an inert solvent. Where compounds symmetrically substituted on the terminal N's are desired, the polyamine is first reductively alkylated by reaction with an aldehyde or ketone and the resulting Schiff base is hydrogenated.Type: GrantFiled: August 24, 1981Date of Patent: April 10, 1984Assignee: The United States of America as represented by the United States Department of EnergyInventors: Frederick L. Weitl, Kenneth N. Raymond
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Patent number: 4429152Abstract: The 3-substituted 2,4,6-trihalogenated benzamides having the formula I ##STR1## wherein Hal is chlorine, bromine, or iodine andZ is a carboxyl group or the group ##STR2## wherein P is 1 and L is 0 or 1, with the proviso that L is 0 when K is 0; K is 0, 2, 3, or 4;M is 0, 1, 2 or 3;N is 0 or 1;X is a hydrogen atom;Y is a hydrogen atom or a lower alkyl group of 1-4 carbon atoms, or when either M or N is other than 0, a hydroxy group, a C.sub.1-6 alkoxy group or a C.sub.1-4 acyloxy group, or when N is 1 and M is other than 0, X and Y together represent an additional carbon-carbon bond;or P and L are each 0; p1 K is 0, 2, 3 or 4;M is 0, 1, 2 or 3;N is 0 or 1;X is a hydrogen atom;Y is a hydrogen atom, a lower alkyl group of 1-4 carbon atoms, a hydroxy group, a C.sub.1-6 alkoxy group, a C.sub.Type: GrantFiled: December 22, 1981Date of Patent: January 31, 1984Assignee: Schering, AktiengesellschaftInventors: Heinz Gries, Wolfgang Mutzel
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Patent number: 4414396Abstract: Polyhalophthalimidoalkyl-functional carbonates may be employed as fire retardant additives to polymers. Examples of such carbonates are 2-(tetrabromophthalimido)ethyl 2,4,6-tribromophenyl carbonate, 2-(tetrabromophthalimido)ethyl pentabromophenyl carbonate and bis[2-(tetrabromophthalimido)ethyl] carbonate.Polyhalophthalimidoalkyl haloformates, N-(hydroxyalkyl)-polyhalophthalimides, and 2-(hydroxyalkylcarbamyl)-polyhalobenzoic acids are useful as intermediates in the preparation of the carbonates.Type: GrantFiled: January 7, 1982Date of Patent: November 8, 1983Assignee: PPG Industries, Inc.Inventor: Nicodemus E. Boyer
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Patent number: 4409240Abstract: A novel derivative of dihydroxybenzoic acid represented by the formula (I) ##STR1## wherein R represents ##STR2## or a salt or an ester thereof which has specific pharmacological activities, a method for preparing thereof and a pharmaceutical composition comprising thereof as an active ingredient are provided.Type: GrantFiled: February 16, 1982Date of Patent: October 11, 1983Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Hitoshi Takita, Yutaka Mukaida, Sakuo Noda, Hidetoshi Kobayashi
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Patent number: 4396627Abstract: Compounds having the formula: ##STR1## where R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, Y and X are as defined hereinbelow, are useful for the reduction of abnormally high blood glucose and lipid levels in the treatment of obesity or hyperglycaemia.Type: GrantFiled: March 15, 1982Date of Patent: August 2, 1983Assignee: Beecham Group LimitedInventors: Anthony T. Ainsworth, David G. Smith
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Patent number: 4390476Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup..sym. is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.Type: GrantFiled: November 5, 1981Date of Patent: June 28, 1983Assignee: Ciba-Geigy CorporationInventor: Michael Marky
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Patent number: 4389416Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo; R.sub.1 is carboxy, carboxyloweralkyl, aminocarbonyl, hydroxymethyl, anilinomethyl, or aminomethyl; A is oxygen, CH.sub.2, Sulfur or a single bond; X is oxygen, CH.sub.2, sulfur or sulfoxide; and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof.The compounds are effective as diuretic agents.Type: GrantFiled: October 9, 1981Date of Patent: June 21, 1983Assignee: Abbott LaboratoriesInventor: Jacob J. Plattner
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Patent number: 4385066Abstract: Compounds of formula (II): ##STR1## or a pharmaceutically acceptable salt, lower alkyl or aralkyl ester or amide thereof, wherein R.sup.1 and R.sup.2, which may be the same or different, are each of a hydrogen atom or a methyl group, n is 1, 2 or 3, and Z is a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group, or a halogen or hydrogen atom are useful in treating obesity and/or hyperglycaemia and/or inflammation in mammals.Type: GrantFiled: May 13, 1981Date of Patent: May 24, 1983Assignee: Beecham Group LimitedInventors: Anthony T. Ainsworth, David G. Smith
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Patent number: 4370495Abstract: A process for the preparation of 2-[4-(4-chlorobenzoylaminoethyl)-phenoxy]-2-methylpropionic acid of the formula ##STR1## which process comprises reacting N-(4-chlorobenzoyl)-tyramine with acetone and chloroform in a mole ratio of 1:20-100:2-10, in the presence of 3 to 4 moles of alkali per mole of chloroform, at a temperature of from about 10.degree. to 40.degree. C.Type: GrantFiled: April 17, 1979Date of Patent: January 25, 1983Assignee: Boehringer Mannheim GmbHInventor: Peter Beyer
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Patent number: 4347177Abstract: A radioimmunoassay procedure has been discovered for bupropion [(.+-.)-2-t-butylamino-3-chloropropiophenone], an antidepressant compound, in biological fluids. Novel compounds of formula ##STR1## wherein either R.sub.2 is oxygen and R.sub.1 is (CH.sub.2).sub.n --O--(CO).sub.m --(CH.sub.2).sub.p --COOH where n is an integer from 0 to 5, m is 0 or 1, and p is an integer from 1 to 4; or R.sub.1 is hydrogen and R.sub.2 is N--O--(CH.sub.2).sub.q --COOH where q is an integer from 1 to 3, and novel methods of making them and novel intermediates useful therein are disclosed. Novel immunogens for raising bupropion specific antisera, and novel methods of making them are disclosed comprising conjugates of the novel compounds and suitable carrier material. The drug is added to the antisera together with novel radiolabeled competitor of formula ##STR2## wherein R' is a suitable radioisotope as described above and R.sub.3 is hydrogen, R.sub.4 is Cl, and R.sub.5 is oxygen, orR' is hydrogen and either(a) R.sub.3 is H and R.Type: GrantFiled: April 14, 1980Date of Patent: August 31, 1982Assignee: Burroughs Wellcome Co.Inventor: Arthur P. Phillips
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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Patent number: 4338333Abstract: The compounds of formula (II): ##STR1## in which R.sub.1 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R.sub.2 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl group; R.sub.3 is a hydrogen, chlorine or bromine atom or a hydroxyl group, R.sub.4 is a hydrogen atom or a methyl group; R.sub.5 is a hydrogen atom or a methyl group; R.sub.6 is a hydrogen, fluorine or chlorine atom or a methyl, methoxyl or hydroxy group; X is an oxygen atom or a bond; Y is an alkylene group of up to 6 carbon atoms or a bond; and Z is an alkylene, alkenylene or alkynylene group of up to 10 carbon atoms, have been found to possess anti-obesity and/or anti-hyperglycaemic activity.Type: GrantFiled: June 9, 1980Date of Patent: July 6, 1982Assignee: Beecham Group LimitedInventors: Anthony T. Ainsworth, David G. Smith
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Patent number: 4329358Abstract: Compounds of formula (III): ##STR1## and esters, amides and pharmaceutically acceptable salts thereof, wherein A.sup.1 is hydrogen or methyl;A.sup.2 is hydrogen or methyl; andn is 1, 2 or 3have anti-obesity activity. Methods for their preparation pharmaceutical formulations of the compounds and their use in medicine are described.Type: GrantFiled: October 24, 1980Date of Patent: May 11, 1982Assignee: Beecham Group LimitedInventors: Anthony T. Ainsworth, David G. Smith
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Patent number: 4323691Abstract: Described are compounds of the formula ##STR1## wherein ##STR2## wherein Z is hydrogen or loweralkyl, R.sub.5 and R.sub.6 may be the same or different and are hydrogen, loweralkyl or together are alkylene of 4 or 5 carbon atoms,R.sub.2 is hydrogen, halo, haloloweralkyl, loweralkyl, loweralkoxy, loweralkylthio or ##STR3## wherein R.sub.5 and R.sub.6 are previously defined, R.sub.3 is hydroxy, alkoxy, branched alkoxy, adamantyloxy, morpholino, amino or amino substituted by loweralkyl or alkylene of 4 or 5 carbon atoms,R.sub.4 is hydrogen or loweralkyl, andX.sub.1 and X.sub.2 are hydrogen, loweralkyl, halo or when substituted on adjacent carbon atoms of the benzene ring form a 1,3-butadienylene linkage, Y is oxygen or sulfur, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents in increasing urinary excretion.Type: GrantFiled: December 1, 1980Date of Patent: April 6, 1982Assignee: Abbott LaboratoriesInventors: Carroll W. Ours, Cheuk M. Lee
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Patent number: 4318923Abstract: Benzaminoethylphenoxycyclohexylacetic acid derivatives having the formula ##STR1## wherein R.sup.1 represents hydrogen atom, a halogen atom, hydroxyl group, a lower alkyl group or a lower alkoxy group; n is 1 or 2; and R.sup.2 represents hydrogen atom, a lower alkyl group which can have a substituent of phenyl group, a lower alkoxycarbonyl group, 3,3,5-trimethylcyclohexyloxycarbonyl group or a heterocyclic group; hexadecyl group; phenyl group which can have a substituent of a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or a halogen atom; a cyclohexyl group or .alpha.-[4-(4-chlorobenzaminoethyl) phenoxy]-.alpha.-cyclohexylacetoxycyclohexyl group a antihyperlipidemic compositions thereof.Type: GrantFiled: March 13, 1981Date of Patent: March 9, 1982Assignee: Kaken Chemical Co., Ltd.Inventors: Yasuhiko Hamazaki, Nobuo Ishiyama, Toshiyuki Yamamoto, Kenji Seri, Reiko Sato
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Patent number: 4316860Abstract: Phosphonium compounds of the formula(R).sub.3 P.sup..sym. --CH.sub.2 --X--CH.dbd.CH--R.sub.1 --Y.sup..crclbar.in which R is preferably alkyl having 1 to 4 C atoms, cyclohexyl or phenyl, R.sub.1 is a substituted or unsubstituted aromatic radical, especially a phenyl radical, X is phenylene, 4,4'-biphenylene or 1,4- or 2,6-naphthylene and Y.sup..crclbar. is SO.sub.3.sup..crclbar., SO.sub.2.sup..crclbar. or COO.sup..crclbar., a process for their preparation and a process for the preparation of asymetrically substituted fluorescent brightening agents of the formulaZ--CH.dbd.CH--X--CH.dbd.CH--R.sub.1 Y.sup..crclbar. M.sup..sym.in which R.sub.1, X and Y.sup..crclbar. are as defined above, M.sup.61 is a cation and Z is preferably a substituted or unsubstituted phenyl or 2-phenyl-triazol-4-yl radical, by reacting a bis-phosphonium compound of the formula ##STR1## in which Q.sup..crclbar. is an anion, with an aldehyde of the formula M.sup..sym. Y.sup..crclbar. --R.sub.Type: GrantFiled: May 15, 1980Date of Patent: February 23, 1982Assignee: Ciba-Geigy CorporationInventor: Michael Marky
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Patent number: 4311846Abstract: This disclosure describes novel 4-[(monosubstituted-alkyl)amino]benzoic acids and analogs which are useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: August 11, 1980Date of Patent: January 19, 1982Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4309443Abstract: A compound of the formula (I): ##STR1## or a pharmaceutically acceptable ester, amide or salt thereof wherein R.sub.1 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R.sub.2 is a hydrogen, fluorine, chlorine or bromine atom or a hydroxyl group; R.sub.3 is a hydrogen, chlorine or bromine atom or a hydroxyl group; R.sub.4 is a hydrogen, chlorine or fluorine atom or a methyl, methoxyl or hydroxyl group or a carboxylic acid group or a salt, ester or amide thereof; R.sub.5 is a hydrogen atom or a methyl group; R.sub.6 is a hydrogen atom or a methyl group; R.sub.7 is a hydrogen atom or a methyl or ethyl group; R.sub.Type: GrantFiled: September 3, 1980Date of Patent: January 5, 1982Assignee: Beecham Group LimitedInventors: David G. Smith, Anthony T. Ainsworth
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Patent number: 4306075Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4306076Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: December 15, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4298603Abstract: Compounds of the formula ##STR1## or pharmaceutically acceptable acid addition salts thereof (for example, a chloride) are useful as local anesthetics. In the compound of the formula (I), R is hydrogen or C.sub.1 -C.sub.14 alkyl, ALK is C.sub.1 -C.sub.4 alkylene, R.sub.1 and R.sub.2 may be the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl or R.sub.1 and R.sub.2 taken together form a 5 to 7 atom ring which contains 1 to 2 nitrogen atoms.Type: GrantFiled: December 6, 1979Date of Patent: November 3, 1981Assignee: Industrial Technology Research InstituteInventors: Ching-Te Chang, Tsung-Tsan Su
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Patent number: 4279836Abstract: 2-Chloro-4-N-(.beta.-diethylaminoethyl)aminocarbonyl-5-methoxybenzhydroxami c acid of the formula, ##STR1## or its metal salt, a process for their preparation and a process for preparing metoclopramide of the formula, ##STR2## using the above described 2-chloro-4-N-(.beta.-diethylaminoethyl)aminocarbonyl-5-methoxybenzhydroxam ic acid or its metal salt.Type: GrantFiled: May 14, 1979Date of Patent: July 21, 1981Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Joji Nishikido, Yohei Fukuoka, Nobuhiro Tamura
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Patent number: 4277420Abstract: Preparation of novel prochiral olefinic compounds which can be asymmetrically hydrogenated to enantiomers, which are converted to ephedrine and pseudoephedrine by described procedures.Type: GrantFiled: September 24, 1979Date of Patent: July 7, 1981Assignee: Monsanto CompanyInventor: Karl E. Koenig
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Patent number: 4267333Abstract: 2-Trifluoromethyl cinchoninic acids can be prepared in high yields by reaction of an alkali metal 2-aminophenylglyoxylate and 1,1,1-trifluoroacetone in the presence of a weak acid and a metal salt of a weak acid. Preferably reaction is effected by first hydrolyzing isatin, or a substituted isatin, in the presence of an alkali metal hydroxide to produce the alkali metal 2-aminophenylglyoxylate, and then reacting this intermediate product with 1,1,1-trifluoroacetone without isolating it from the reaction medium.Type: GrantFiled: September 26, 1979Date of Patent: May 12, 1981Assignee: Union Carbide Agricultural Products Company, Inc.Inventor: Hsiang-Wei Tsao
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Patent number: 4264572Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1-4 alkyl, C.sub.1-4 alkyl substituted by OH or C.sub.1-2 alkoxy; R.sub.2, R.sub.3 and R.sub.4 are independently each hydrogen or C.sub.1-4 alkyl; Z is --A--NHCH.sub.3 or when R.sub.1 is hydroxy or alkoxy substituted alkyl and/or when R.sub.3 is lower alkyl, Z can also be hydroxy-C.sub.2-5 -alkylamino;R.sub.5 is C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by OH; n is 1, 2 or 3; and A is: ##STR2## wherein R.sub.7 is H or C.sub.1-4 alkyl; R.sub.8 is H, C.sub.1-4 alkyl or C.sub.1-4 alkyl substituted by OH or C.sub.1-2 alkoxy; or together R.sub.7 and R.sub.8 form a propylene or hydroxypropylene ring; and m is 0 or 1;or an ester thereof with a C.sub.1 -C.sub.4 alkanol or a physiologically acceptable salt thereof with a base, are valuable as X-ray contrast media.Type: GrantFiled: November 30, 1979Date of Patent: April 28, 1981Assignee: Schering AktiengesellschaftInventors: Erich Klieger, Wolfgang Mutzel
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Patent number: 4239635Abstract: Carboxylic acid terminated diamides and alkali metal, ammonium or amine salts thereof are provided which are derived from the reaction of organic polycarboxylic acids and polyoxyalkylene diamines. The diamides have lubricating properties and are especially useful in aqueous metal working fluids.Type: GrantFiled: June 11, 1979Date of Patent: December 16, 1980Assignee: Cincinnati Milacron Inc.Inventor: Walter E. Rieder
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Patent number: 4235792Abstract: Immune lysis of sensitized liposomes containing a marker is employed in an assay method wherein an antigenic material to be determined is reacted with a specific antiserum and the degree of inhibition of the antiserum is detected by the extent of release of a marker when the antiserum reacts with liposomes containing a sensitizer specific to the antiserum.Type: GrantFiled: April 14, 1977Date of Patent: November 25, 1980Assignee: The Governing Council of the University of TorontoInventors: Jen C. Hsia, Chou-Tok Tan
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Patent number: 4233054Abstract: New phenoxy-alkanecarboxylic acid derivatives which have a herbicidal action and which are effective in regulating plant growth are described. They correspond to the formula ##STR1## in which A is the cyano group, a carboxylic acid, a salt, ester, thioester or amide thereof,Q is a mono- to trisubstituted phenyl or pyrid-2-yl radical,R.sub.3 is hydrogen, halogen, cyano, nitro, alkyl or carbamoyl,R.sub.4 is alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzyl, andX, Y and Z are each oxygen or sulfur.They can be used as selective herbicides in cereal and rice crops, or for reducing the vegetative growth, for example in soya-bean crops, and also for defoliation and desiccation in cotton or potato crops shortly before the harvesting thereof.Type: GrantFiled: March 12, 1979Date of Patent: November 11, 1980Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
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Patent number: 4225577Abstract: This invention relates to compounds of the formula (I): ##STR1## in which: n is an integer from 1 to 5 inclusive,R.sub.1 represents a hydrogen atom or a C.sub.1-4 alkanoyl group,R.sub.2 represents a hydrogen atom, a C.sub.1-4 alkanoyl group, or a C.sub.1-4 alkyl group,R.sub.3 represents a hydrogen atom, a group of the formula ##STR2## or of the formula --CONHR.sub.6, in which: R.sub.4 represents a hydrogen atom or a C.sub.1-4 alkanoyl group,R.sub.5 represents a hydrogen atom or a C.sub.1-4 alkanoyl group, or a C.sub.1-4 alkyl group,R.sub.6 represents a hydrogen atom or a C.sub.1-4 alkyl group,R.sub.7 represents a hydrogen atom or a methyl group, and their C.sub.1-4 alkyl esters and their salts with pharmaceutically acceptable bases.Said compounds are useful as X-ray contrast media.Type: GrantFiled: May 29, 1979Date of Patent: September 30, 1980Assignee: Guerbet S.A.Inventors: Guy Tilly, M. Jean-Charles Hardouin, Jean Lautrou
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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: 4220659Abstract: Racemic and optically active compounds of the formula ##STR1## wherein R.sub.1 is --COOR.sub.6, where R.sub.6 is hydrogen or alkyl of 1 to 4 carbon atoms; --OCO--R.sub.9, where R.sub.9 is alkyl of 1 to 6 carbon atoms, phenyl (alkyl of 1 to 4 carbon atoms) or phenyl; --Q--CO--NR.sub.7 R.sub.8, where Q is a single bond, oxygen, --NH--, --CH2-- or --CH.sub.2 --NH--, and R.sub.7 and R.sub.8, taken together with the nitrogen, are pyrrolidino, piperidino or morpholino; cyano-phenyl; carboxyl-phenyl; cyano-phenoxy; or carboxyl-phenoxy;R.sub.2 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoyl of 2 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, amino, nitro or, together with R.sub.1, 3,4-methylenedioxy;R.sub.3 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or, together with R.sub.2 in the ortho-position, --CH.dbd.CH--CH.dbd.CH-- or --(CH.sub.2).sub.n -- where n is an integer from 3 to 5;R.sub.Type: GrantFiled: July 14, 1978Date of Patent: September 2, 1980Assignee: Boehringer Ingelheim GmbHInventors: Herbert Koppe, Werner Kummer, Helmut Stahle, Gojko Muacevic
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Patent number: 4220753Abstract: Alkyl alkoxymethylbenzoates and essentially linear polyester ethers and copolyester ethers therefrom.Type: GrantFiled: December 18, 1978Date of Patent: September 2, 1980Assignee: Standard Oil Company (Indiana)Inventors: Steven A. Cerefice, Edward E. Paschke
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Patent number: 4214094Abstract: The present invention relates to new substituted-phenyl substituted-alkyl ethers and pharmaceutically acceptable salts thereof, which have hypolipidemic activity, and to processes for the preparation thereof, the compound having the following formula ##STR1## wherein R.sub.1 is lower alkyl, cycloalkyl, aryl, ar(lower)alkyl, a heterocyclic group or a group represented by the formula: ##STR2## wherein R.sub.3 and R.sub.4 are each hydrogen or lower alkyl,R.sub.5 is carboxy, esterified carboxy or hydroxymethyl and A is lower alkylene;R.sub.2 is hydrogen, lower alkyl, cycloalkyl, aryl, ar(lower)alkyl, a heterocyclic group or a group represented by the formula: ##STR3## and R.sub.6 is hydrogen, hydroxy or lower alkoxy; in which the aryl or the ar(lower)alkyl for R.sub.1 and R.sub.2 may be substituted with halogen, hydroxy or lower alkoxy, and when R.sub.1 and R.sub.2 are both lower alkyl, R.sub.1 and R.sub.2 may be linked together.Type: GrantFiled: March 30, 1977Date of Patent: July 22, 1980Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Yoshihisa Saito
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Patent number: 4209459Abstract: Novel L-leucyl-4-hydroxyanilide derivatives of the formula, ##STR1## wherein R represents a carboxyl group or a sulfo group or an acid addition salt thereof, which are useful for assay of leucine-aminopeptidase activity.Type: GrantFiled: May 4, 1979Date of Patent: June 24, 1980Assignees: Nitto Boseki Co., Ltd., Iatron Laboratories, Inc.Inventors: Takeshi Nagasawa, Katsumasa Kuroiwa, Tadami Akatsuka, Osamu Kodama, Mitoshi Shimamoto
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Patent number: 4199597Abstract: Omega-[4-(polyfluoro-2-hydroxy-2-propyl)-2,3,6-substituted-phenoxy and phenylthio]alkanoic acids and compounds related thereto having antihypertensive activity are preparable by reaction of the appropriate 2,3,6-substituted-4-(polyfluoro-2-hydroxy-2-propyl)phenol or thiophenol with an alkyl ester of a bromoalkanoic acid, followed by hydrolysis to the free acid.Type: GrantFiled: May 4, 1979Date of Patent: April 22, 1980Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4191765Abstract: Compounds of formula I ##STR1## wherein R.sup.1 and R.sup.1' are identical or different and represent hydrogen, an alkyl radical or alkoxy radical having 1-4 carbon atoms, the allyl group, a halogen atom or the nitro group, R.sup.2 represents an acrylic acid radical or an acrylic acid nitrile radical of the formulae ##STR2## wherein R.sup.5 represents hydrogen, an alkyl radical having 1-5 carbon atoms, an aryl radical or aryl-lower alkyl radical either unsubstituted or substituted by lower alkyl or alkoxy, R.sup.6 represents hydrogen or an alkyl radical having 1-8 carbon atoms, R.sup.7 represents hydrogen, a lower alkyl radical or an aryl-lower alkyl radical, R.sup.3 and R.sup.4 represent together with the nitrogen atom a heterocyclic ring with 5-7 members being optionally substituted by C.sub.1 -C.sub.4 alkyl, in which ring one carbon atom may be replaced by one oxygen atom, sulfur atom or one further nitrogen atom, the latter may be substituted, or wherein R.sup.3 represents hydrogen and R.sup.Type: GrantFiled: August 10, 1978Date of Patent: March 4, 1980Assignee: Hoechst AktiengesellschaftInventors: Werner Fritsch, Ulrich Stache, Ernst Lindner
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Patent number: 4183954Abstract: This invention relates to compounds having the general formula: ##STR1## in which R.sub.1 is a hydrogen atom or a lower alkyl radical and n is zero or an integer from 1 to 4, and their salts with therapeutically acceptable organic or inorganic bases.Said compounds possess, in particular, choleretic, antiatherosclerotic, hypocholesterolemic and antiphlogistic activities.Type: GrantFiled: April 12, 1978Date of Patent: January 15, 1980Assignee: Seuref A.G.Inventor: Aldo Bertelli
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Patent number: RE30885Abstract: Carboxylic acid terminated diamides and alkali metal, ammonium or amine salts thereof are provided which are derived from the reaction of organic polycarboxylic acids and polyoxyalkylene diamines. The diamides have lubricating properties and are especially useful in aqueous metal working fluids.Type: GrantFiled: March 13, 1981Date of Patent: March 23, 1982Assignee: Cincinnati Milacron Inc.Inventor: Walter E. Rieder