Rings Bonded Directly To Each Other Patents (Class 562/469)
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Patent number: 4607116Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.Type: GrantFiled: March 8, 1984Date of Patent: August 19, 1986Assignee: Nippon Petrochemicals Company LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
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Patent number: 4601797Abstract: Hydroxyibuprofen is produced in good yield by reduction of p-isobutylacetophenone at the cathode in the presence of carbon dioxide. Hydroxyibuprofen is readily hydrogenolyzed to ibuprofen. Electrochemical carboxylation of other selected aryl methyl ketones is also effected.Type: GrantFiled: March 1, 1985Date of Patent: July 22, 1986Assignee: Monsanto CompanyInventor: John H. Wagenknecht
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Patent number: 4581463Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.Type: GrantFiled: August 10, 1984Date of Patent: April 8, 1986Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4578522Abstract: This invention relates to a method of synthesis of certain substituted carboxylic acids useful in lowering serum triglyceride and total cholesterol levels in mammals (including man) represented by the general formula I:Ar.sup.1 --Ar.sup.2 (I)whereinAr.sup.1 is selected from ##STR1## Ar.sup.2 is selected from ##STR2## and R is selected from C.sub.1-5 alkyl, halogen, perhalo-C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl, C.sub.1-4 acyl, C.sub.1-6 alkoxycarbonyl, amino or hydroxy.Type: GrantFiled: September 14, 1984Date of Patent: March 25, 1986Inventor: John F. Eaddy, III
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Patent number: 4567289Abstract: The methyl, ethyl, n-propy, 2-(acetylamino)ethyl, or 1-(2,3-dihydroxy)propyl ester of E-(3R,5S)-7-(4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl)-3,5-dihydroxy -6-heptenoic acid of structural formula: ##STR1## are HMG-CoA reductase inhibitors useful in the treatment of conditions associated with hypercholesterolemia.Type: GrantFiled: April 25, 1984Date of Patent: January 28, 1986Assignee: Merck & Co., Inc.Inventors: Alvin K. Willard, Frederick C. Novello, William F. Hoffman, Edward J. Cragoe, Jr.
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Patent number: 4542233Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.Type: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4523032Abstract: 3,5-Dialkyl-4-hydroxyphenyl-substituted acetic acids are prepared by reacting a 2,6-dialkylphenol with a haloform, a ketone and an alkali metal hydroxide. These 3,5-dialkyl-4-hydroxyphenyl-substituted acetic acids are also useful as stabilizers and in the preparation of derivatives thereof such as esters and the like.Type: GrantFiled: November 7, 1983Date of Patent: June 11, 1985Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4486599Abstract: Process for carboxylating 2',4'-difluoro-4-hydroxy-1,1'-diphenyl or a derivative thereof with an alkaline alkylcarbonate at atmospheric pressure to afford 2',4'-difluoro-4-hydroxy-(1,1'-diphenyl)-3-carboxylic acid.Type: GrantFiled: July 22, 1983Date of Patent: December 4, 1984Assignee: Zambon S.p.A.Inventors: Mariano Meneghin, Piero Piccinelli, Claudio Giordano
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Patent number: 4465855Abstract: Arylacetic acid derivatives of the formula ##STR1## with R.sup.1, R.sup.2 and R.sup.3 specifically defined and which are useful as antirheumatic and antiinflammatory pharmaceuticals are prepared by catalytic hydrogenation of new compounds of the formula ##STR2## in which R and R.sup.10 are also specifically defined. The method of making the latter compound is also set forth.Type: GrantFiled: April 15, 1982Date of Patent: August 14, 1984Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RtInventors: 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: 4459422Abstract: 6-Phenyl-, phenylalkyl- and phenylethenyl-4-hydroxytetrahydropyran-2-ones in the 4(R)-trans stereoisomeric forms are potent inhibitors of cholesterol synthesis by virtue of their ability to inhibit the enzyme, 3-hydroxy-3-methylglutaryl-coenzyme A reductase.Type: GrantFiled: June 10, 1982Date of Patent: July 10, 1984Assignee: Merck & Co., Inc.Inventors: Alvin K. Willard, Frederick C. Novello, William F. Hoffman, Edward J. Cragoe, Jr.
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Patent number: 4433132Abstract: A class of polyesters comprising recurring units having certain bis(trifluoromethyl)biphenylene radicals is disclosed. The polyesters exhibit favorable solubility properties in certain organic solvents so as to facilitate the production of the polyesters via polycondensation methods to film- and fiber-forming molecular weights. Monomeric compounds comprising a bis(trifluoromethyl)biphenylene radical and useful for the production of the polyesters are also disclosed.Type: GrantFiled: September 2, 1982Date of Patent: February 21, 1984Assignee: Polaroid CorporationInventors: Howard G. Rogers, Russell A. Gaudiana, Richard A. Minns
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Patent number: 4432885Abstract: Decalins of the formula ##STR1## wherein ring A is aromatic or a trans-1,4-disubstituted cyclohexane ring; R.sup.2 is methyl, --CH.sub.2 R', --OR', --CO--R', --CN, --COOH, --CO--OR', --CO--SR' or --O--CO--R'; R.sup.1 is hydrogen, methyl, --CH.sub.2 R, --OR or --CH.sub.2 OR, or when R.sup.2 is methyl, --CH.sub.2 R', --OR' or --CO--R', R.sup.1 also can be --CN, --COOH, --CO--OR, --CO--SR or --O--CO--R; R and R' each are alkyl; and R.sup.1 and R.sup.2 each have up to 12 carbon atoms and together have at most 14 carbon atoms,their racemates and optically active antipodes, are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.Type: GrantFiled: December 9, 1981Date of Patent: February 21, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Kuno Schleich
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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: 4355174Abstract: 5(Halophenyl)Salicylic acids are prepared in the presence of a palladium catalyst system of high selectivity and turnover number.Type: GrantFiled: September 21, 1981Date of Patent: October 19, 1982Assignee: Merck & Co., Inc.Inventor: Ulf H. Dolling
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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: 4348322Abstract: The invention is concerned with novel dioxolane derivatives of the formula: ##STR1## in which R.sub.a is hydrogen or (1-4C)alkyl and R.sub.b is (1-4C)alkyl or phenyl optionally bearing a halogeno substituent; their production; and their use for the manufacture of certain known anti-arthritic acids of the formula: ##STR2## and, in particular, those acids in which R.sub.a =R.sub.b =methyl or R.sub.a =ethyl and R.sub.b =phenyl, by a novel reduction process. The preferred reduction procedures involve the use of an alkali metal borohydride or cyanoborohydride in the presence of a noble metal catalyst, or the use of an .alpha.-branched alkyl or cycloalkyl Grignard agent.The use of the derivatives of formula I avoids the need for potentially toxic reagents and reactive intermediates in the previously known processes for the production of the acids of formula V.Type: GrantFiled: March 11, 1981Date of Patent: September 7, 1982Assignee: Imperial Chemical Industries LimitedInventors: Philip N. Edwards, David M. G. Martin
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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: 4329496Abstract: A method is provided for converting aromatic bis(ether N-organo substituted phthalimides) to aromatic bis(ether anhydrides) by heating a bisphasic aqueous-organic mixture of aromatic bis(ether N-organo substituted phthalimide), phthalic anhydride and an exchange catalyst to effect an imide-anhydride exchange producing an aqueous phase containing aromatic bis 4ether phthalic acid) and an organic phase containing N-organo substituted phthalimide. The aromatic bis(ether phthalic acid) is then optionally dehydrated to the corresponding anhydride.Type: GrantFiled: April 3, 1981Date of Patent: May 11, 1982Assignee: General Electric CompanyInventor: Jimmy L. Webb
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Patent number: 4324904Abstract: The invention concerns the novel compounds dialkyl 2-(3-fluoro-4-nitrophenyl)-2-methylmalonate IIIa and dialkyl 2-(3-fluoro-4-aminophenyl)-2-methylmalonate IVa useful as intermediates in an improved process for making 2-(2-fluoro-4-biphenylyl)propionic acid, known as flurbiprofen, having the formula ##STR1## and ester thereof. It has anti-inflammatory activity which is about 240 times that of aspirin and analgesic activity which is about 180 times that of aspirin in standard laboratory tests. However, despite this high activity, the toxicity (LD.sub.50) is only 1.2 to 2.4 times greater than that of aspirin in standard laboratory tests.Also within the invention is a novel method of making the above intermediates and analogs thereof useful to prepare corresponding biaryl compounds which have pharmaceutical uses.Type: GrantFiled: December 19, 1979Date of Patent: April 13, 1982Assignee: The Upjohn CompanyInventors: Thomas A. Hylton, Jerry A. Walker
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Patent number: 4322563Abstract: Substituted biphenyl-2-carboxaldehydes are prepared in good yield by reacting palladium complexes of substituted benzaldehyde aniline Schiff bases with substituted phenylmagnesium bromides in the presence of at least six, preferably eight, molar equivalents of triphenylphosphine.Type: GrantFiled: February 11, 1981Date of Patent: March 30, 1982Assignee: Merck & Co., Inc.Inventor: William F. Hoffman
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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: 4304931Abstract: A process is disclosed for preparing arylpropionic acids of formula Ar--CH(CH.sub.3)--COOH, by reacting an aryl Grignard reagent with a metal pyruvate or with a pyruvamide, to form a hydroxy acid of formula Ar--C(OH)(CH.sub.3)--COOH or its amide, and converting the acid or amide to the product.Type: GrantFiled: August 2, 1979Date of Patent: December 8, 1981Assignee: The Boots Company LimitedInventors: John S. Nicholson, John L. Turner
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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: 4260802Abstract: A catalytic aromatic salicylate process comprising contacting a phenol, carbon monoxide, a base, and a Group VIIIB element selected from ruthenium, rhodium, palladium, osmium, iridium or platinum, an oxidant having an oxidation potential greater than that of said selected Group VIIIB element, and recovering at least a portion of the resulting salicylate.Type: GrantFiled: May 11, 1979Date of Patent: April 7, 1981Assignee: General Electric CompanyInventor: John E. Hallgren
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Patent number: 4252817Abstract: This invention provides new compounds of the formula, ##STR1## wherein R.sub.1 is alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 8 carbon atoms or phenyl,R.sub.2 is hydrogen or lower alkyl, andR.sub.3 is halogen, nitro, lower alkyl, methylthio, hydroxy, lower alkoxy, acyloxy or acylamino, with the proviso that when R.sub.3 is in the 5 position, and R.sub.1 and R.sub.3 are identical and signify a straight alkyl chain of 1 to 5 carbon atoms, R.sub.2 is lower alkyl,useful as anti-phlogistics.Type: GrantFiled: May 11, 1979Date of Patent: February 24, 1981Assignee: Sandoz Ltd.Inventors: Annemarie Closse, Walter Haefliger, Daniel Hauser
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Patent number: 4237315Abstract: A method of preparing compounds of the formula: ##STR1## wherein a novel palladium catalyst system is utilized comprising palladium together with C.sub.1-2 COO.sup.- ligands and halo ligands wherein the molar weight percent based on total ligand molar weight, of the C.sub.1-2 COO.sup.- ligand is from 30 to 60%; andwherein the ratio of the total molar weight of the ligands to the molar weight of palladium utilized is from 4:1 to 10:1; anda catalyst regeneration portion comprising from 0.1 to 8.0 parts of phosphomolybdenovanadic acid per part of palladium catalyst, and at least 20 parts of a solubilizing agent selected from ethylene carbonate, propylene carbonate, and sulfolane, per part of palladium catalyst.Type: GrantFiled: November 2, 1979Date of Patent: December 2, 1980Assignee: Merck & Co., Inc.Inventor: Ulf H. Dolling
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Patent number: 4225730Abstract: 5-(2,4-difluorophenyl)salicylic acid, an anti-inflammatory, anti-pyretic, analgesic agent is prepared by: (1) diazotizing 2,4-difluoroaniline in the presence of benzene to yield 2,4-difluorobiphenyl; (2) Friedel-Crafts acylation to produce 2',4'-difluoro-4-alkanoylbiphenyl; (3) oxidation of the alkanoyl group to produce 2',4'-difluoro-4-alkanoyloxybiphenyl; (4) hydrolysis of the alkanoyl group to produce 4-(2,4-difluorophenyl)phenol; and (5) Kolbe-Schmitt carboxylation to produce the final product.Type: GrantFiled: May 11, 1978Date of Patent: September 30, 1980Assignee: Merck & Co., Inc.Inventors: Howard Jones, Robert W. Houser
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Patent number: 4221920Abstract: An aromatic salicylate process comprising contacting a phenol, carbon monoxide, a base, a Group VIIIB element selected from ruthenium, rhodium, palladium, osmium, iridium or platinum and recovering at least a portion of an aromatic salicylate. The resulting aromatic salicylates are useful in plastics and lacquers as well as in pharmaceuticals.Type: GrantFiled: September 19, 1977Date of Patent: September 9, 1980Assignee: General Electric CompanyInventor: John E. Hallgren
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Patent number: 4220591Abstract: The (+), (-) and (.+-.) forms of the compounds of formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, andR.sup.2 is a hydrogen or methyl group or R.sup.1 and R.sup.2 together form a methylenedioxy group;R.sup.3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (d):(a) m-phenoxybenzyl(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-m-phenoxybenzyl(d) 3,4-methylenedioxy-benzyl, andR.sup.4 and R.sup.5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.The compounds of formula I in which R.sup.3 is one of group (a) to (d) are extremely active as insecticides (except when R.sup.1 is an amino group). The compounds also possess the property of contact repellency to insects.Type: GrantFiled: November 17, 1976Date of Patent: September 2, 1980Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, Reimund A. Walser
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Patent number: 4219668Abstract: Compounds of metabolites of 3-(4-biphenylylcarbonyl)propionic acid useful as anti-inflammatory and anti-platelet aggregation agents.Type: GrantFiled: July 5, 1979Date of Patent: August 26, 1980Assignee: American Cyanamid CompanyInventor: Fortunato S. Chiccarelli
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Patent number: 4216340Abstract: Improved method of preparing 5-(2,4-difluorophenyl)salicylic acid and derivatives which favors formation of the desired end product over other undesired isomers, comprising the steps of(a) diazotizing an aniline compound,(b) treating the diazonium salt with a salicylic acid ester compound blocked in the 3-position with an easily removed blocking group, preferably cloro,(c) removing the blocking group, and(d) hydrolyzing the ester to form the acid final product.Type: GrantFiled: May 2, 1979Date of Patent: August 5, 1980Assignee: Merck & Co., Inc.Inventors: Leonard M. Weinstock, Arthur S. Wildman, Carl Bagner
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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: 4188491Abstract: A process is disclosed for preparing arylpropionic acids of formula Ar--CH(CH.sub.3)--COOH, by reacting an aryl Grignard reagent with a metal pyruvate or with a pyruvamide, to form a hydroxy acid of formula Ar--C(OH)(CH.sub.3)--COOH or its amide, and converting the acid or amide to the product.Type: GrantFiled: March 24, 1978Date of Patent: February 12, 1980Assignee: The Boots Company LimitedInventors: John S. Nicholson, John L. Turner
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Patent number: 4179578Abstract: Stilbene derivatives having at least one further phenyl substituent in the para-position to a benzene ring in the stilbene are optical brighteners particularly suitable for incorporation on spinning masses.Type: GrantFiled: April 14, 1977Date of Patent: December 18, 1979Assignee: Sandoz Ltd.Inventors: Fritz Fleck, Hans Kittl, Salvatore Valenti
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Patent number: 4176196Abstract: Novel hypoglycemic agents comprising 3-hydroxy-3-arylcyclohexane-1-acetic acid, 3-arylcyclohexene-1-acetic acids and derivatives thereof are disclosed.Type: GrantFiled: November 4, 1977Date of Patent: November 27, 1979Assignee: Pfizer Inc.Inventor: Lawrence S. Melvin, Jr.
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Patent number: 4168385Abstract: This invention discloses .alpha.-aryloxy or .alpha.-arylthio para substituted phenyl acetic acid compounds that are useful in lowering sterol and triglyceride serum levels.Type: GrantFiled: February 17, 1977Date of Patent: September 18, 1979Assignee: American Cyanamid CompanyInventors: Ronald I. Trust, Francis J. McEvoy, Jay D. Albright
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Patent number: 4154697Abstract: Novel liquid crystals have the formula ##STR1## wherein two of the rings A, B and C are aromatic and the third is a trans-1,4-disubstituted cyclohexane ring and R is alkyl or alkoxy each of 1 - 12 C-atoms. These compounds are particularly useful as additional components in liquid crystal dielectrics whereby the clear point of the dielectric is raised and the viscosity thereof is not deleteriously affected.Type: GrantFiled: January 11, 1978Date of Patent: May 15, 1979Assignee: Merck Patent Gesellschaft mit beschraenkter HaftungInventors: Rudolf Eidenschink, Joachim Krause, Ludwig Pohl
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Patent number: 4153807Abstract: New compounds which are 2-(halogenated-hydroxy-substituted-4-biphenylyl)propionic acids, having, inter alia, anti-inflammatory activity.Type: GrantFiled: June 20, 1977Date of Patent: May 8, 1979Assignee: The Boots Company LimitedInventors: Stewart S. Adams, Bernard J. Armitage, John S. Nicholson
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Patent number: 4151302Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are F, Cl or Br;Q is --CH(CH.sub.3)--CH.sub.2 --, --C(OH)(CH.sub.3)--CH.sub.2 -- or --C(CH.sub.3).dbd.CH--;Y is COOH, COOR.sup.3, CH.sub.2 OH or CH.sub.2 OAc;N is 0 or 1;R.sup.3 is alkyl or aryl of up to 8 carbon atoms or C.sub.6 H.sub.4 NHCOCH.sub.3 ; andAc is acyl of 1-8 carbon atoms;And physiologically acceptable salts thereof, are anti-inflammatory agents, which can be made from compounds of the formula Z--X, wherein Z is ##STR2## X can be converted to --Q--Y.Type: GrantFiled: August 19, 1977Date of Patent: April 24, 1979Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
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Patent number: 4131618Abstract: The invention relates to an improved method of preparing salicylic acid and derivatives from phenyl esters which comprises the step of fusing acetoxyphenyl, or derivative suitable for preparing the desired salicylic acid derivative, with M.sub.2 CO.sub.3 where M is potassium or sodium in the presence of carbon dioxide, at a temperature of from 150.degree. to 250.degree. C., and at a pressure of from atmospheric to 500 p.s.i.g.Type: GrantFiled: December 29, 1977Date of Patent: December 26, 1978Assignee: Merck & Co., Inc.Inventors: Leonard M. Weinstock, Arthur S. Wildman, Dennis M. Mulvey
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Patent number: 4131747Abstract: A process for preparing an .alpha.-substituted phenylalkanecarboxylic acid, having useful pharmaceutical properties such as analgesic, anti-inflammatory and anti-pyretic properties, from the corresponding ethylidenecyanoacetate by oxidation, hydrolysis, decarboxylation and oxidation.Type: GrantFiled: November 19, 1976Date of Patent: December 26, 1978Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masayasu Kurono, Masaaki Toda, Haruki Niwa, Syunji Kosuge, Takahumi Iida, Kenichi Narita
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Patent number: 4128574Abstract: A method is described for making organic polycarboxylic acids or anhydrides, such as aromatic ether bis(phthalic acid)s, based on a cyclic imide-cyclic anhydride exchange reaction at elevated temperatures in the presence of water. In addition to making organic polycarboxylic acid, organic imides are also generated.Type: GrantFiled: October 4, 1976Date of Patent: December 5, 1978Assignee: General Electric CompanyInventors: Ronald L. Markezich, Tohru Takekoshi
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Patent number: 4118420Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: March 25, 1976Date of Patent: October 3, 1978Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4117119Abstract: Prostaglandin analogues of the formula: ##STR1## wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents hydrogen or alkyl of 1 through 12 carbon atoms, R.sup.1, R.sup.2 and R.sup.3 represent hydrogen, or alkyl of 1 through 12 carbon atoms or an aryl group, with the proviso that at least one of the symbols R.sup.1, R.sup.2 and R.sup.3 represents an alkyl or aryl group, are new compounds possessing useful pharmacological properties; they are especially useful for the treatment of gastric ulceration.Type: GrantFiled: May 6, 1977Date of Patent: September 26, 1978Assignee: Ono Pharmaceutical CompanyInventors: Masayasu Kurono, Hisao Nakai, Takashi Muryobayashi
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Patent number: 4116980Abstract: A method is provided for converting aromatic bis(ether N-organo substituted phthalimide) to aromatic bis(ether anhydride) by heating an aqueous mixture under pressure, of aromatic bis (ether N-organo substituted phthalimide) and phthalic anhydride, or phthalic acid. An exchange is effected between phthalic anhydride or phthalic acid and the aromatic bis(ether N-organo substituted phthalimide) to produce a liquid phase mixture of aromatic bis(ether phthalic acid) and an aqueous vapor phase mixture of N-organo substituted phthalimide. The N-organo substituted phthalimide is selectively removed from the liquid phase mixture by venting the vapor phase therefrom.Type: GrantFiled: October 4, 1976Date of Patent: September 26, 1978Assignee: General Electric CompanyInventor: Jimmy L. Webb
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Patent number: 4115416Abstract: .alpha.-Phenoxyacetic acids, in which the .alpha.-position is substituted by an alkyl residue with 5 to 12 carbon atoms and the phenyl residue is substituted by a cycloaliphatic hydrocarbon residue which is unsaturated in the 1-position and is only singly unsaturated, and their esters and amides are useful as hypolipidaemic agents.Type: GrantFiled: September 9, 1976Date of Patent: September 19, 1978Assignee: Ciba-Geigy AGInventors: Alberto Rossi, Christian Egli