Ortho Fused Rings In Acid Moiety Patents (Class 560/56)
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Patent number: 4414405Abstract: Process for preparing esters of 2-(6'-methoxy-2'-naphtyl)-propionic acid via rearrangement of new ketals of 2-halo-1-(6'-methoxy-2'-naphtyl)-propan-1-one in the presence of a Lewis acid.The esters thus obtained are useful as intermediate products for preparing Naproxen.The process involves the preparation of the following new compounds:ketals of 2-halo-1-(6'-methoxy-2'-naphtyl)-propan-1-oneesters of 2-(5'-bromo-6'-methoxy-2'-naphtyl)-propionic acid1-(5'-bromo-6'-methoxy-2'-naphtyl)-propan-1-one2-halo-(5'-bromo-6'-methoxy-2'-naphtyl)-propan-1-one.Type: GrantFiled: February 20, 1981Date of Patent: November 8, 1983Assignee: Blaschim S.p.A.Inventors: Claudio Giordano, Aldo Belli, Fulvio Uggeri, Giovanni Villa
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Patent number: 4410716Abstract: Novel compounds, dibenzo[a,d]cycloheptene derivatives, of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a halogen atom or a lower alkyl group, R.sub.2 and R.sub.3 each represent a hydrogen atom or a lower alkyl group, and Z represents a group of the formula ##STR2## These novel compounds are useful as non-steroidal anti-inflammatory agents free from gastrointestinal lesions. The compounds of formula (I) can be prepared, for example, by cyclizing a compound of the general formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, X represents a hydroxyl group or a halogen atom, one Y represents a group of the formula --CH.sub.2 COX and the other Y represents a hydrogen atom; optionally hydrolyzing the cyclized product; and optionally esterifying the product, and/or etherifying its enol group.Type: GrantFiled: September 24, 1980Date of Patent: October 18, 1983Assignee: Toa Eiyo Kagaku Kogyo Co. Ltd.Inventors: Tetsutaro Hayasaka, Kuniro Saito, Sen-ichi Narita, Takao Goto, Shin-ichi Yamada, Teruo Saito, Kazuyoshi Okutani
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Patent number: 4405642Abstract: A method for the treatment or prophylaxis of cardiac disorders in a mammal, comprising administering to such mammal a short-acting .beta.-blocking compound of the formula: ##STR1## wherein X is an ester-containing group; R may be lower alkyl, aralkyl or an ester-containing group; R.sub.1 may be lower alkyl; and Ar may be substituted or unsubstituted aromatic; or a pharmaceutically acceptable salt thereof. Novel compounds possessing short acting .beta.-adrenergic blocking activity are also disclosed.Type: GrantFiled: November 28, 1980Date of Patent: September 20, 1983Assignee: American Hospital Supply CorporationInventors: Sheung-tsam Kam, Paul W. Erhardt, Robert J. Borgman, John P. O'Donnell
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Patent number: 4401827Abstract: Novel acyl-derivatives of the .beta.-hydroxy-.gamma.-butyrobetaine are disclosed (typically pyruvyl carnitine hydrochloride) which are useful therapeutic agents in the treatment of cardiac disorders, hyperlipidoemias and hyperlipoproteinemias.Type: GrantFiled: December 28, 1981Date of Patent: August 30, 1983Assignee: Sigma-TauInventor: Paolo de Witt
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Patent number: 4400393Abstract: A novel bicyclooctane derivative represented by the formula: ##STR1## wherein R.sub.1 is hydrogen or C.sub.1-4 alkyl, X is ethylene or vinylene, and Y.sub.1 and Y.sub.2 are independently hydrogen or a hydroxyl-protecting group, or a pharmaceutically acceptable salt of said compound in which R.sub.1 is hydrogen. Said compound and pharmaceutically acceptable salt are chemically stable, have platelet anti-aggregation activity without undesirable pharmacological actions and exhibit the duration of high biological activity.Type: GrantFiled: March 24, 1981Date of Patent: August 23, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Shunsuke Sami, Akihiko Sugie, Keiichi Ono, Hajime Kawakami, Atsuyuki Kojima, Junki Katsube
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Patent number: 4391731Abstract: Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.Type: GrantFiled: August 3, 1981Date of Patent: July 5, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Arthur Boller, Martin Schadt, Alois Villiger
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Patent number: 4391982Abstract: The present invention provides compounds having the structure: ##STR1## wherein R.sup.1 represents alkoxy or aralkoxy, R.sup.2 represents hydrogen, alkoxy, aralkoxy, alkyl, aralkyl, or R.sup.1 and R.sup.2 taken together represent the group --O--CH.sub.2 --O--, R.sup.3 represents hydrogen, alkyl, aralkyl, acyl or a protecting group, Y represents Cl, Br, I or a leaving group; and X represents Cl, Br or I.The present invention also provides a process for preparation of compounds VI in a single step wherein X and Y are the same and represent Cl, Br, ,or I, and R.sup.3 is as previously defined except that in this instance, it does not represent a protecting group.According to another aspect of the present invention there are provided compounds VII-a and VII-b having the structure: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as previously defined, j is an integer having a value of 0 or 1, Z.sup.1 represents a non-reacting electron withdrawing group, and Z.sup.Type: GrantFiled: March 25, 1981Date of Patent: July 5, 1983Assignee: The University of RochesterInventors: Andrew S. Kende, Dennis P. Curran, Margaret L. King, Neil A. Feldstein
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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: 4387241Abstract: This disclosure describes novel 16-aryloxy-17,18,19,20-tetranorprostanoic acids and derivatives thereof useful as bronchodilators and as hypotensive and contraceptive agents.Type: GrantFiled: November 1, 1974Date of Patent: June 7, 1983Assignee: American Cyanamid CompanyInventors: Charles V. Grudzinskas, Martin J. Weiss
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Patent number: 4379091Abstract: The present invention concerns tetraethylene glycol monoesters with 2-arylpropionic acids (known as anti-inflammatory agents). Said esters, while being endowed with the characteristics of low toxicity and gastric injuring effects shown by the related acids, differ advantageously from the latter because their anti-inflammatory activity is much more prolonged, and their bioavailability markedly better.Type: GrantFiled: February 11, 1981Date of Patent: April 5, 1983Assignee: Ausonia Farmaceutici s.r.l.Inventors: Paolo Ferruti, Ferdinando Danusso, Maria C. Tanzi, Giuseppe Quadro
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Patent number: 4374262Abstract: A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylating a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2-naphthol, which can be easily prepared from .beta.-naphthol, a readily available and inexpensive starting material.Type: GrantFiled: October 6, 1980Date of Patent: February 15, 1983Assignee: Celanese CorporationInventors: James L. McGinnis, Anthony B. Conciatori
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Patent number: 4367176Abstract: The present invention concerns diesters of polyethylene glycols (with n ranging between 4 approximately and 100 approximately) with 2-arylpropionic acids (known as anti-inflammatory agents). These esters, while possessing all the characteristics of low toxicity and gastric injuring effects shown by the related acids, differ advantageously from the latter because their anti-inflammatory activity is much more prolonged, and their bio-availability markedly better.Type: GrantFiled: February 11, 1981Date of Patent: January 4, 1983Assignee: Ausonia Farmaceutici s.r.l.Inventors: Paolo Ferruti, Ferdinando Danusso, Maria C. Tanzi, Giuseppe Quadro
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Patent number: 4365077Abstract: 11-Desoxy-16-aryloxy-.omega.-tetranorprostaglandins are disclosed. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins but they exhibit a greater tissue specificity of action.Type: GrantFiled: February 22, 1979Date of Patent: December 21, 1982Assignee: Pfizer Inc.Inventors: Jasjit S. Bindra, James F. Eggler, Michael R. Johnson, Thomas K. Schaaf
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Patent number: 4351950Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.Type: GrantFiled: January 2, 1980Date of Patent: September 28, 1982Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Patent number: 4349689Abstract: 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: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4349561Abstract: Novel 4-substituted-3-hydroxy-3-pyrroline-2,5-diones are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate kidney stone formation. A novel process for their preparation is also disclosed.Type: GrantFiled: November 5, 1979Date of Patent: September 14, 1982Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney, Haydn W. R. Williams
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Patent number: 4340498Abstract: New halogenated ester derivatives and liquid crystal compositions containing the same are provided. The derivatives are expressed by the general formula ##STR1## wherein X is ##STR2## R is 1-15C alkyl group or alkoxy group; and Y is carboxyl group. The derivatives are useful as component(s) of liquid crystal compositions which have higher mesomorphic temperature ranges, nevertheless have lower viscosities; and also have lower absolute values of dielectric anisotropy, nevertheless can be driven at lower voltages.Type: GrantFiled: January 23, 1981Date of Patent: July 20, 1982Assignee: Chisso CorporationInventor: Shigeru Sugimori
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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: 4338457Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.Type: GrantFiled: February 28, 1980Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4336400Abstract: Mono-, di- and tri-esters of 3-(hydroxy or hydroxymethyl)-4-hydroxy-alpha-(aminomethyl)benzyl alcohols, obtained by methods involving reduction of the corresponding mono- and di-ester ketones, are useful for producing sympathomimetic effects, such as bronchodilation, of long duration with low cardiovascular stimulating effect, in warm-blooded mammals.Type: GrantFiled: August 30, 1978Date of Patent: June 22, 1982Assignee: Sterling Drug Inc.Inventors: Hiroaki Minatoya, Benjamin F. Tullar, Walter D. Conway
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Patent number: 4335055Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4335054Abstract: Compounds of the formula I ##STR1## in which p, m, Z, R, R' and Y are as defined in claim 1, can be obtained in a simple and economical manner by a novel process which comprises reacting a halide of the formula ##STR2## with the corresponding acrylic acid derivative, in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I), and functional derivatives prepared therefrom, are useful for the preparation of photocrosslinkable polymers, which can in particular be employed as (so-called) photoresists.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4329507Abstract: New substituted aryl ethylenes are disclosed which are produced by dehydration of the corresponding .alpha.- or .beta.-(substituted aryl)ethyl alcohols or by dehydrohalogenation of the corresponding .alpha.- or .beta.-(substituted aryl)ethyl halides.Type: GrantFiled: January 14, 1980Date of Patent: May 11, 1982Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Makoto Takeda, Masayuki Uchide, Hiroshi Iwane
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Patent number: 4328356Abstract: Esters of arylacetic acids, more particularly lower alcohol esters of arylacetic acids, including those substituted on the methylene group, are prepared by rearrangement of the corresponding alpha-halo-alkylarylketones with Ag compounds in lower alcohols and in an acid medium. From the alkyl esters so prepared, their respective free acids can be obtained, if desired, by various means such as hydrolysis or the shift with mineral acids of the alkaline salts prepared by reaction with alkali, etc.Type: GrantFiled: February 15, 1980Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Claudio Giordano, Francesco Casagrande
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Patent number: 4321275Abstract: The disclosure relates to novel 17,18,19,20-tetranor-prostanoic acid derivatives having prostaglandin-type properties, to a method for their manufacture, and also to pharmaceutical or veterinary compositions containing said novel derivatives and a method of inducing luteolysis in an animal host by use of said novel derivatives.Type: GrantFiled: May 30, 1974Date of Patent: March 23, 1982Assignee: Imperial Chemical Industries LimitedInventors: Jean Bowler, Neville S. Crossley
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Patent number: 4316985Abstract: There is presented a process for the manufacture of hexahydronaphthacene derivatives of the general formula ##STR1## wherein one of R.sup.1 and R.sup.2 represents a hydrogen atom and the other represents a hydrogen atom or a hydroxy group or R.sup.1 and R.sup.2 together represent a protected oxo group, R.sup.3 represents a hydrogen atom or a hydroxy or acyloxy group and R.sup.4 represents a lower alkyl or esterified carboxy group or a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 together form an oxo group or a protected oxo group and X represents a hydrogen atom or a hydroxy or acyloxy group or ##STR3## in which n stands for 1 or 2 and Y represents a hydrogen atom or an alkyl or acyl group.Also presented are certain of the novel derivatives per se and various novel intermediates in the process.Type: GrantFiled: January 11, 1980Date of Patent: February 23, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Cedric H. Hassall, Gareth J. Thomas
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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: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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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: 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: 4298535Abstract: There is presented a synthetic process for the production of anthracyclinones, the aglycones of the anthracyclines. Also disclosed are novel intermediates in the above process. The end product aglycones may thereafter be utilized to produce biologically useful products such as carminomycin or adriamycin.Type: GrantFiled: October 20, 1980Date of Patent: November 3, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Pierre Vogel, Pierre-Alain Carrupt
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Patent number: 4294763Abstract: The present invention provides compounds having the structure: ##STR1## wherein R.sup.1 represents alkoxy or aralkoxy, R.sup.2 represents hydrogen, alkoxy, aralkoxy, alkyl, aralkyl, or R.sup.1 and R.sup.2 taken together represent the group --O--CH.sub.2 --O--, R.sup.3 represents hydrogen, alkyl, aralkyl, acyl or a protecting group, Y represents Cl, Br, I or a leaving group; and X represents Cl, Br or I.The present invention also provides a process for preparation of compounds VI in a single step wherein X and Y are the same and represent Cl, Br, or I, and R.sup.3 is as previously defined except that in this instance, it does not represent a protecting group.According to another aspect of the present invention there are provided compounds VII-a and VII-b having the structure: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as previously defined, j is an integer having a value of 0 or 1, Z.sup.1 represents a non-reacting electron withdrawing group, and Z.sup.Type: GrantFiled: March 5, 1980Date of Patent: October 13, 1981Assignee: University of RochesterInventors: Andrew S. Kende, Dennis P. Curran, Margaret L. King, Neil A. Feldstein
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Patent number: 4291168Abstract: Indanyloxy compounds having 2-alkynyl substituents which exhibit diuretic, saluretic, and uricosuric activity are described. The compounds are obtained according to a process involving selective etherification of a 5-hydroxyindanone followed by alkynylation with a silylated alkynyl bromide to provide novel silylated intermediates which are hydrolyzed to indanyloxy compounds such as (6,7-dichloro-1-oxo-2-phenyl-2-propargyl-5-indanyloxy)acetic acid.Type: GrantFiled: September 24, 1980Date of Patent: September 22, 1981Assignee: Mead Johnson & CompanyInventors: Porter C. Johnson, William L. Matier
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Patent number: 4288386Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: May 12, 1980Date of Patent: September 8, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld
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Patent number: 4284790Abstract: 3-Hydroxylbenzyl compounds of formula, ##STR1## in which each of R.sub.1, R.sub.2 and R.sub.3 is a hydrocarbon group, e.g. alkyl, R.sub.4 is hydrogen or alkyl, or forms with R.sub.1 --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, and Z is either an oxygen- or sulphur-containing group featuring at least one ester or amide moiety, or a disubstituted amino group, Z being bound to the rest of the molecule via the oxygen or sulphur atom, or nitrogen atom, respectively, are useful as antioxidants. Organic materials which are susceptible to the degradative effects of oxygen are treated with one or more of such compounds, e.g. by incorporation into the body of the organic material, in order to be stabilized against such effects.Type: GrantFiled: January 23, 1979Date of Patent: August 18, 1981Assignee: Sandoz Ltd.Inventors: Hans Hinsken, Horst Mayerhoefer, Wolfgang Mueller
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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: 4278678Abstract: Novel substituted oxy-cyclohexylacetic acid derivatives as antihyperlipidemic agents are given. The compounds have the formula ##STR1## wherein n is 1 or 2; m is 0, 1 or 2; R.sub.1 represents a halogen atom, trifluoromethyl, a lower alkyl, a lower alkoxy, a lower alkylcarbonyl, dimethylphenylmethyl, cyclohexyl, phenyl, halogenophenyl, phenoxy or halogenophenoxy group, and two of R.sub.1 groups can be bonded to form an orthocondensed saturated alkylene ring; Hal represents a halogen atom; and R.sub.2 represents a hydrogen atom or a lower alkyl group.Type: GrantFiled: November 16, 1979Date of Patent: July 14, 1981Assignee: Kaken Chemical Co., Ltd.Inventors: Yasuhiko Hamazaki, Kenji Seri, Nobuo Ishiyama, Toshiyuki Yamamoto, Masao Sakasai, Reiko Sato
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Patent number: 4276431Abstract: Alkali metal salts of hydroxybenzoates are claimed which are substantially anhydrous and free from hydrobenzoic acid and have the formula ##STR1## in which R.sup.1 denotes alkyl, alkenyl, cycloalkyl or aralkyl,R.sup.2 and R.sup.3 are identical or different and represent hydrogen, halogen, hydroxyl, amino, alkylamino, alkyl, alkoxy, aralkyl or aryl andMe denotes an alkali metal.Furthermore a process for the preparation of the said alkali metal salts of hydroxybenzoates, which are substantially anhydrous and free from hydrobenzoic acid, characterized in that a solution or suspension of a hydroxybenzoate of the formula ##STR2## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meaning, is neutralized with an alkali metal hydroxide at -10.degree. to +50.degree. C. until the degree of neutralization is 0.95 to 1.05, a degree of neutralization of 1.Type: GrantFiled: September 20, 1979Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Peter Schnegg, Walter Rapp, Bernhard Vosteen
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Patent number: 4268685Abstract: Esters of salicylamide with anti-inflammatory and analgesic action are disclosed.These esters have the following general formula: ##STR1## wherein R is a radical of an acid selected among d-2-(6'-methoxy-2'-naphtyl)-propionic acid, 2[[3-(trifluoromethyl)phenyl]-amino]-3-pyridine carboxylic acid, 2- {[3-(trifluoromethyl)-phenyl]-amino}-3-pyridincarboxylic acid, 2-(4-isobutyl-phenyl)-propionic acid, 4-allyloxy-3-chloro-phenylacetic acid, 2-(3-benzoylphenyl)-propionic acid, 2-[(2,3-dimethylphenyl)amino]-benzoic acid and 2[[3-trifluoromethyl)phenyl]-amino]benzoic acid.The process for preparing the subject esters comprises reacting a halide, preferably a chloride of the desired acid, with a solution of salicylamide.Type: GrantFiled: March 12, 1980Date of Patent: May 19, 1981Assignee: Neopharmed S.p.A.Inventor: Alberto Reiner
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Patent number: 4266074Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: July 16, 1975Date of Patent: May 5, 1981Assignee: Sumitomo Chemical Company LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4248889Abstract: 3,5-Dihydroxypentanoic ester derivatives of formula (I): ##STR1## wherein: A represents an alkylene group which is optionally substituted by one or more alkyl groups, or an alkenylene group;Z represents a substituted or unsubstituted aryl or aryloxy group; andR represents a C.sub.1 -C.sub.4 alkyl group) may be prepared by reacting a dianion of an acetoacetic ester with an aldehyde of formula Z-A-CHO (wherein A and Z are as defined above) and then reducing the resulting compound. These 3,5-dihydroxypentanoic ester derivatives have antihyperlipaemic activity and are thus valuable pharmaceuticals.Type: GrantFiled: October 26, 1979Date of Patent: February 3, 1981Assignee: Sankyo Company LimitedInventors: Hidehiko Oka, Akira Terahara, Akira Endo
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Patent number: 4240970Abstract: Novel products suitable for use as detergents in lubricant compositions are provided. Such products include the reaction products of (1) the product of reaction between an alkenylsuccinic acid, ester or anhydride and a hydroxyaromatic compound, (2) the product of reaction between (1) and an amine selected from the group consisting of an alkanepolyol such as an amino alkanediol and a polyalkylenepolyamine; (3) the reaction product of (2) and an aldehyde; (4) the reaction product of (3) with a metal salt capable of forming a stable complex with amines; (5) the reaction product of (2) with a metal salt; and (6) the product of reaction between an alkenylsuccinic acid or anhydride and an alkyl phenyl ether.Type: GrantFiled: December 18, 1979Date of Patent: December 23, 1980Assignee: Mobil Oil CorporationInventor: Sheldon Chibnik
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Patent number: 4238414Abstract: The present invention relates to novel 2-decarboxy-2-aminomethyl-6a-carba-PGI.sub.2 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.Type: GrantFiled: September 27, 1979Date of Patent: December 9, 1980Assignee: The Upjohn CompanyInventor: Douglas R. Morton, Jr.
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Patent number: 4221918Abstract: Carboxylic acid anhydrides are contacted with hydrogen in the presence of an insoluble metal hydrogenation catalyst and strong protonic acid to produce 1,1-diesters.Type: GrantFiled: October 30, 1978Date of Patent: September 9, 1980Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
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Patent number: 4217302Abstract: Esters of .alpha.-indenyl substituted aliphatic acids, intermediates therefor, synthesis thereof, and the use of said esters and compositions thereof for the control of pests.Type: GrantFiled: April 13, 1979Date of Patent: August 12, 1980Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4216172Abstract: A process for the preparation of a cyclobutanone of the formula ##STR1## in which R.sup.1 to R.sup.6 each independently is a hydrogen, halogen, cyano, alkoxy, alkoxycarbonyl, carboxamido, dialkylphosphono, alkyl, cycloalkyl, aryl, aralkyl or alkenyl radical, or two of them together with the carbon atom to which each is linked form a ring,comprising reacting an N,N-disubstituted carboxylic acid amide of the formula ##STR2## in which R.sup.7 and R.sup.8 each independently is an alkyl, cycloalkyl, alkenyl, aryl or aralkyl radical or together form a ring, with an inorganic acid halide, and then reacting the product with a tertiary amine, an olefin of the formula ##STR3## and a Lewis acid, and subsequently hydrolyzing the mass. Preferably isobutyric acid dimethylamide is employed as the carboxylic acid amide, phosgene is employed as the inorganic acid halide, triethylamine is employed as the tertiary amine and zinc chloride or titanium tetrachloride is employed as the Lewis acid.Type: GrantFiled: March 13, 1978Date of Patent: August 5, 1980Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4207241Abstract: 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the .alpha.-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, antipyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.Type: GrantFiled: March 27, 1978Date of Patent: June 10, 1980Assignee: Syntex CorporationInventors: John H. Fried, Ian T. Harrison
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Patent number: 4204071Abstract: Benzyl esters and thiolesters of 4-aryl-3-butenoic acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters for the control of pests.Type: GrantFiled: May 4, 1978Date of Patent: May 20, 1980Assignee: Zoecon CorporationInventors: Richard J. Anderson, Clive A. Henrick
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Patent number: 4204001Abstract: The disclosure relates to .omega.-aryl substituted .omega.-nor prostaglandin analogues bearing an oxygenated function at C-10, such as a hydroxy radical, or a 9,10- or 10,11-epoxide. A typical compound is 16-(3-chlorophenoxy)-9.alpha.,10.beta.,11.alpha.,15.alpha.-tetrahydroxy-17 ,18,19,20-tetranor-5-cis,13-trans-prostadienoic acid. Also disclosed are chemical processes for the manufacture of said compounds, pharmaceutical and veterinary compositions containing said compounds, and a method of achieving luteolysis in mammals by the use of such compounds.Type: GrantFiled: May 30, 1978Date of Patent: May 20, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jean Bowler, Graham E. Robinson
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Patent number: 4196127Abstract: There is provided a novel method of synthesizing certain heterocyclic quinones. In particular there is provided a novel and regiospecific synthesis of 9-acetyl-6,11-dihydroxy-4-methoxy-7,8,9,10-tetrahydronaphthacene-5,12-quin one (7,9-dideoxydaunomycinone) which is a known intermediate in the synthesis of daunomycinone. There is also provided a method of preparing analogs of 7,9-dideoxydaunomycinone which thus provide for the preparation of known and desired analogs of daunomycinone. Daunomycinone is a known compound which is an intermediate in the preparation of the clinically accepted naturally-occurring antitumor antibiotics daunomycin and its derivative adriamycin.Type: GrantFiled: June 1, 1978Date of Patent: April 1, 1980Assignee: Research CorporationInventors: Francis Johnson, Kyoung S. Kim