Rings Bonded Directly To Each Other Patents (Class 562/469)
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Patent number: 5631293Abstract: Amino acid-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic agent and a medicament containing themBenzoylguanidines of the formula I ##STR1## in which the radicals R(1) to R(5) have the meanings given in the description, are described. They are prepared by reacting a compound of the formula II ##STR2## in which R(1) to R(5) and L have the meanings given in the description, with guanidine. The compound I is suitable for the preparation of cardiovascular medicaments.Type: GrantFiled: September 8, 1995Date of Patent: May 20, 1997Assignee: Hoechst AktiengesellschaftInventors: Heinz-Werner Kleemann, Hans-Jochen Lang, Jan-Robert Schwark, Andreas Weichert, Wolfgang Scholz, Udo Albus
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Patent number: 5475132Abstract: R.sub.3, R.sub.4 and R.sub.5, each represents a hydrogen or halogen atom (at least one of R.sub.3, R.sub.4 and R.sub.5 being other than hydrogen or halogen); optionally substituted amino; optionally halogenated or hydroxylated alkyl, alkoxy, alkylalkoxy or alkylthio; or R.sub.3 and R.sub.4 (in the 3- and 4-positions) can together form a single divalent radical with 3 or 4 members containing 1 or 2 non-adjacent oxygen atoms; are useful as agricultural fungicides.Type: GrantFiled: May 27, 1994Date of Patent: December 12, 1995Assignee: Rhone-Poulenc AgrochimieInventors: Regis Pepin, Christian Schmitz, Guy-Bernard Lacroix, Philippe Dellis, Christine Veyrat
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Patent number: 5462954Abstract: Antagonists having a substituted phenyl phenol or a substituted phenolic biphenyl structure, and various derivatives thereof, are specific leukotriene antagonists. Their structures, use and synthesis are disclosed. Also, pharmaceutical formulations are disclosed for use in applications treating diseases or conditions characterized by excessive release of leukotriene B.sub.4, one of the metabolites of arachidonic acid.The primary LTB.sub.Type: GrantFiled: November 1, 1994Date of Patent: October 31, 1995Assignee: Eli Lilly and CompanyInventors: S. Richard Baker, Robert D. Dillard, Paul E. Floreancig, J. Scott Sawyer, Michael J. Sofia
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Patent number: 5393780Abstract: A 4-fluorobiphenyl derivative of formula (I): ##STR1## wherein A is a .omega.-oxycarbonyldihydroxybutyl group of formula (II): ##STR2## wherein R.sup.2 is a hydrogen atom, an alkyl group, an alkaline metal or an alkaline earth metal; a tetrahydropyranyl group of formula (III): ##STR3## or a .omega.-oxycarbonyl-3-oxobutyl group of formula (IV): ##STR4## wherein R.sup.3 is an alkyl group; R.sup.1 is an alkyl group. This 4-fluorobiphenyl derivative is useful as an effective component for a cholesterol or lipid lowering agent.Type: GrantFiled: March 25, 1994Date of Patent: February 28, 1995Assignee: Fujirebio Inc.Inventors: Masakatsu Matsumoto, Nobuko Watanabe, Eiko Mori, Miwa Ishihara, Tetsuaki Yamaura, Misao Aoyama, Hiroshi Ikawa, Hisako Kobayashi
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Patent number: 5391817Abstract: Certain novel biaryl compounds are effective phospholipase A.sub.2 (PLA.sub.2) inhibitors.Type: GrantFiled: December 21, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers SquibbInventors: Dane Springer, Bing-Yu Luh, Katharine M. Greene, Joanne J. Bronson, Muzammil M. Mansuri
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Patent number: 5371284Abstract: Phenyl acetylenic acetals and thioacetals and their use in the treatment of allergy, asthma, inflammation, arthritis, hyperproliferative skin disease, psoriasis or contact dermatitis are disclosed. Also disclosed are intermediates useful for producing said phenyl acetylenic acetals and thioacetals.Type: GrantFiled: July 23, 1993Date of Patent: December 6, 1994Assignee: Schering CorporationInventors: Richard J. Friary, Michael J. Green, Anil K. Saksena, Vera A. Seidl
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Patent number: 5340931Abstract: Allene compounds have the formula:(CH.sub.2 .dbd.C.dbd.CH--O).sub.n --R--(A).sub.m (I)in which R is a substituted or unsubstituted mono- or polyvalent benzene, naphthalene, anthracene, azobenzene, bisphenol or polyphenyl (containing 2 to 10 benzene rings connected in line) nucleus, or a group--Ph--R.sup.1 --Ph-- (II)(in which each group Ph is a phenylene, halophenylene, alkylphenylene, cyanophenylene or alkoxyphenylene group, and the chain R.sup.1 linking the two group Ph is a C.sub.1 -C.sub.6 aliphatic hydrocarbon or an alicyclic hydrocarbon group, the chain optionally being interrupted by one or more oxygen atoms); A is a carboxyl or sulphonyl group or a group --CH.dbd.C.dbd.CH.sub.2 ; n is an integer of from 1 to 10; m is 0, 1, 2 or 3; and the sum of m and n is equal to the valence of the group R.They may be prepared by isomerization of corresponding propargyloxy compounds.Type: GrantFiled: March 15, 1989Date of Patent: August 23, 1994Assignee: Nippon Paint Co., Ltd.Inventors: Mitsuo Yamada, Hiromichi Kayano, Kei Aoki, Keizou Ishii
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Patent number: 5332857Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: July 6, 1992Date of Patent: July 26, 1994Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5312975Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.Type: GrantFiled: December 27, 1991Date of Patent: May 17, 1994Assignee: Zambon Group S.p.A.Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
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Patent number: 5296638Abstract: An improved process for preparing carboxylated 2-allyl-phenols of general formula (I): ##STR1## is disclosed, which consists of a first step of simultaneous esterification and etherification of a carboxylated phenol, subsequent rearrangement of the resulting product to yield allyl-carboxylated allyl-phenol and end saponification of the latter into carboxylated 2-allyl-phenol.Type: GrantFiled: August 20, 1992Date of Patent: March 22, 1994Assignee: Eniricerche S.p.A.Inventors: Alessandro Lezzi, Arnaldo Roggero, Ugo Pedretti, Cesarina Bonfanti
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Patent number: 5248815Abstract: The present invention relates to a stereospecific chemical synthesis of optically pure enantiomers of 2-aryl-alkanoic acids, especially those of the biologically active (S)-aryl-propionic acids, in good chemical yields, useful for preparing large quantities thereof, and having a high optical purity.Type: GrantFiled: December 27, 1991Date of Patent: September 28, 1993Inventor: Henrich H. Paradies
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Patent number: 5237092Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.Type: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
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Patent number: 5223640Abstract: This invention provides a process to prepare optically active .alpha.-aryl propionic acids without the need for resolving a racemic mixture. In one embodiment of the process, an acetophenone is sequentially converted to a 1-alkyne, then to an .alpha.-aryl .beta.-silylated acrolein, and then to an acrylic acid, which is then asymmetrically hydrogenated to an optically active .alpha.-aryl propionic acid.Type: GrantFiled: December 23, 1992Date of Patent: June 29, 1993Assignee: Hoechst Celanese CorporationInventors: Ahmed M. Tafesh, Sambasivarao Kotha, Kenneth G. Davenport
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Patent number: 5183935Abstract: A crystallization process of crude 5-(2',4'-difluorophenyl)-salicylic acid from a mixture of an aromatic hydrocarbon and an aliphatic ketone for preparing 5-(2',4'-difluorophenyl)-salicylic acid in form II substantially pure is described.Type: GrantFiled: July 29, 1992Date of Patent: February 2, 1993Assignee: Zambon Group S.p.A.Inventors: Claudio Giordano, Maurizio Paiocchi
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Patent number: 5177258Abstract: Biaryl derivatives are produced by coupling an aryl halide in an aqueous alkaline solution in the presence of a palladium catalyst, using formic hydrazide as the reducing agent.Type: GrantFiled: May 21, 1992Date of Patent: January 5, 1993Assignee: Bromine Compounds, Ltd.Inventors: Abram Becker, Ariel A. Ewenson, Bertha Croitoru
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Patent number: 5177245Abstract: Provided is a process for preparing optionally-substituted cyclohexenylhydroquinones starting from cyclohexanone.Type: GrantFiled: November 25, 1991Date of Patent: January 5, 1993Assignee: Eastman Kodak CompanyInventors: Dewey W. Fuller, Jr., Gether Irick, Jr.
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Patent number: 5166171Abstract: 6-Phenoxymethyl-4-hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, processes for the preparation of these compounds, their use as pharmaceuticals, pharmaceutical preparations and novel phenols and thiophenols Compounds of the general formula I ##STR1## and the corresponding open-chain dihydroxycarboxylic acids of the formula II ##STR2## in which X, Y and Z have the meanings given, and pharmacologically tolerated salts thereof with bases and pharmacologically tolerated esters thereof, processes for the preparation of these compounds, their use as pharmaceuticals and pharmaceutical preparations are described. Novel phenols and thiophenols of the formula III ##STR3## in which X, Y and Z have the meanings given, are also described.Type: GrantFiled: April 2, 1991Date of Patent: November 24, 1992Assignee: Hoechst AktiengesellschaftInventors: Heiner Jendralla, Gunther Wess, Wilhelm Bartmann, Gerhard Beck
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Patent number: 5155259Abstract: An aldose reductase inhibitor, comprising a compound of the formula (I) ##STR1## or a pharmaceutically acceptable salt thereof as the effective component, in which R is lower alkyl or cyclohexylmethyl and n is 2 or 3. The compounds of formula (I) and salts thereof according to the invention exhibit a superior aldose reductase inhibiting activity with simultaneous high stability, so that they are useful for the prevention and therapy of diabetic complications.Type: GrantFiled: August 8, 1991Date of Patent: October 13, 1992Assignee: Toyo Jozo Kabushiki KaishaInventors: Yukio Suzuki, Kouichi Kuno, Motoshi Shoda, Masao Yaso, Satoshi Yaginuma, Akira Asahi
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Patent number: 5151545Abstract: Variously substituted 3,5-dihydroxy-6,8-nonadienoic acids and esters, are blood cholesterol lowering agents and so are useful in the prevention and treatment of cardiovascular diseases such as atherosclerosis.Type: GrantFiled: March 27, 1990Date of Patent: September 29, 1992Assignee: Pfizer Inc.Inventors: Peter A. McCarthy, Frederick J. Walker
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Patent number: 5147892Abstract: Benzyl ketones of the formula ##STR1## where X is CH or N,Y is O or NR.sup.4,R.sup.1, R.sup.2 are H or alkyl,R.sup.3 is halogen, cyano, nitro, alkyl, cycloalkyl, alkoxy, haloalkyl, arylalkyl, arylalkoxy, aryloxy or aryl, and the aryl groups in turn may be substituted,R.sup.4 is OH, alkoxy or arylalkoxy andR.sup.5 is H, methyl, halogen or methoxy,and fungicides containing these compounds.Type: GrantFiled: June 27, 1991Date of Patent: September 15, 1992Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Hubert Sauter, Franz Roehl, Reinhard Doetzer, Gisela Lorenz, Eberhard Ammermann
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Patent number: 5145992Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 can be hydrogen, alkyl, alkoxy, halo, phenyl, substituted phenyl, or hydroxy; A can be S, O or --CH.sub.2 --; and Alk is straight or branched chain alkylene, with a base in an aprotic solvent, then reacting the resulting alkoxide with a monohaloacetic acid ester to give an alkoxyacetate followed by reaction of the alkoxyacetate with a hydrogen halide, organic acid or Lewis acid in nitromethane to give the corresponding .alpha.-alkoxyacetic acid which then may be recovered or may optionally be converted to the corresponding salt by contracting the .alpha.-alkoxyacetic acid with a base.Type: GrantFiled: May 6, 1991Date of Patent: September 8, 1992Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5138090Abstract: Substituted biphenyls can be prepared by reduction of appropriate ketones and, if appropriate, subsequent hydrolysis, cyclization, hydrogenation and separation of isomers. The substituted biphenyls can be used as active compounds in medicaments.Type: GrantFiled: February 27, 1990Date of Patent: August 11, 1992Assignee: Bayer AktiengesellschaftInventors: Peter Fey, Rolf Angerbauer, Walter Hubsch, Thomas Philipps, Hilmar Bischoff, Peter Petzinna, Delf Schmidt
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Patent number: 5136090Abstract: An aldose reductase inhibitor, comprising a compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof as the effective component, in which R denotes an alkyl of C.sub.1-12, ##STR2## wherein X.sub.1 and X.sub.2 are same or different and are hydrogen or halogen, cyclohexylmethyl, cyclohexyl, tetra-hydro-2H-pyran-1-yl-methyl, carboxy-lower alkyl or cyclo-lower alkyl and n is 2 or 3. These compounds exhibit a superior aldose reductase inhibiting activity with simultaneous high stability, and are for use in the prevention and therapy of diabetic complications.Type: GrantFiled: August 8, 1991Date of Patent: August 4, 1992Assignee: Toyo Jozo Kabushiki KaishaInventors: Yukio Suzuki, Kouichi Kuno, Motoshi Shoda, Masao Yaso, Satoshi Yaginuma, Akira Asahi
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Patent number: 5132312Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: November 27, 1990Date of Patent: July 21, 1992Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: John R. Regan, Kent E. Neuenschwander
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Patent number: 5087764Abstract: 1,4-disubstituted 2,3-difluorobenzenes according to formula I are suitable as intermediates for the synthesis of liquid crystalline compounds.Type: GrantFiled: May 12, 1989Date of Patent: February 11, 1992Assignee: Merck Patent Gesellschaft mit beschrankter HafungInventors: Volker Reiffenrath, Joachim Krause
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Patent number: 5041604Abstract: A process for producing a high quality di(aryloxy)alkane with a high yield by the use of readily commercially available materials, without using any particular solvent or agent and by means of a simple operation and a general apparatus is provided, which process comprises subjecting a halogenated alkane of the formula (II)X--A--Y (II)wherein X and Y each represent a halogen atom and A represents a lower alkylene group, and a phenol of the formula (III) ##STR1## wherein R.sub.1 to R.sub.5 each are same or different, represent hydrogen, halogen, lower alkyl, lower alkoxy, carboxylic acid salt, acyl or nitro group, and may form a ring in conjunction of two adjacent groups,to condensation reaction in the presence of an alkali in an aqueous medium to form a di(aryloxy)alkane of the formula (I) ##STR2## and is characterized (i) by carrying out the condensation reaction in a molar ratio of the compound of the formula (II): the phenol of the formula (III): the alkali in terms of monovalent base of 1:1.5 to 3.0:1.Type: GrantFiled: June 20, 1990Date of Patent: August 20, 1991Assignee: Sanko Kaihatsu Kagaku KenkyushoInventors: Toranosuke Saito, Masakatu Kitani, Takashi Ishibashi
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Patent number: 5019298Abstract: Disclosed are optically active aromatic carboxylic acid derivatives represented by the formula (I): ##STR1## (wherein R.sub.2 represents an alkoxyalkyl group having 1 to 20 carbon atoms or an alkyl group having 1 to 20 carbon atoms, which alkyl group may be substituted with a halogen atom; represents a number of 1 or 2; m represents a number of 0 or 1; and * indicates asymmetric carbon atom) and a process for producing such derivatives through the following reaction steps: ##STR2## The optically active aromatic carboxylic acid derivatives represented by the above-described formula (I) are useful as a liquid crystal material and can be also utilized as an intermeidate for the preparation of pharmaceuticals, agricultural chemicals and the like.Type: GrantFiled: April 25, 1988Date of Patent: May 28, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Masayoshi Minai, Takayuki Higashii
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Patent number: 5015764Abstract: A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises (i) forming a salt solution comprising said racemic mixture of a C.sub.1 to C.sub.6 linear or branched aliphatic carboxylic acid and an organic or inorganic base (ii) treating said salt solution with one-half molar equivalent of a chiral organic nitrogenous base having a base strength no stronger than said organic or inorganic base (iii) precipitating from the reaction solution formed in step (ii) the less soluble diastereomeric salt and (iv) separating said precipitated diastereomeric salt.Type: GrantFiled: June 18, 1990Date of Patent: May 14, 1991Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Fred J. Impastato
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Patent number: 5013864Abstract: A process for producing an .alpha.-alkoxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R--OH wherein R is alkyl, substituted alkyl, or cycloalkyl, or cycloalkyl alkyl with a base in an aprotic organic solvent to give an alkoxide followed by removal of the organic solvent and reaction of the alkoxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding alkoxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the alkoxy acetate salt with an acid.Type: GrantFiled: December 8, 1989Date of Patent: May 7, 1991Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A. Partis
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Patent number: 5011985Abstract: Levo-ciprofibrate or a pharmaceutically acceptable salt thereof is disclosed.Type: GrantFiled: May 11, 1990Date of Patent: April 30, 1991Assignee: Sterling Drug Inc.Inventors: Eugene H. Cordes, George J. Ellames, John M. Herbert, David I. Smith
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Patent number: 5011986Abstract: Dextro-ciprofibrate or a pharmaceutically acceptable salt thereof is disclosed.Type: GrantFiled: May 11, 1990Date of Patent: April 30, 1991Assignee: Sterling Drug Inc.Inventors: Eugene H. Cordes, George J. Ellames, John M. Herbert, David I. Smith
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Patent number: 5001128Abstract: Disclosed are novel 3-hydroxy-3-methylglutarylcoenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids and esters derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: December 15, 1989Date of Patent: March 19, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Kent W. Neuenschwander, Anthony C. Scotese
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Patent number: 4996234Abstract: Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: December 5, 1989Date of Patent: February 26, 1991Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: John R. Regan, Kent W. Neuenschwander
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Patent number: 4990660Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.Type: GrantFiled: December 21, 1988Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Ulrich Eichenauer
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Patent number: 4952724Abstract: A process for producing aryloxy acetic acids and salts thereof which comprises reacting an alcohol of the formula R-OH wherein R is aryl or substituted aryl with a base in an aprotic organic solvent to give an aryloxide followed by removal of the organic solvent and reaction of the aryloxide with a salt of a monohaloacetic acid in a polar aprotic solvent such as DMSO to give the corresponding aryloxyacetate salt which then may be recovered or may optionally be converted to the corresponding acid by contacting the aryloxyacetate salt with an acid.Type: GrantFiled: December 8, 1989Date of Patent: August 28, 1990Assignee: G. D. Searle & Co.Inventors: Arthur L. Campbell, Richard A. Mueller, John S. Ng, Richard A, Partis
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Patent number: 4950782Abstract: Polycarbonate resins are chain-terminated with a group selected from those of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each independently selected from the group consisting of hydrogen, halogen, hydrocarbyl of from 1 to 12 carbon atoms, inclusive; and halogen-substituted hydrocarbyl of 1 to 12 carbon atoms, inclusive; R.sub.1 is attached to a ring carbon atom at one of the 4, 5 or 6 positions; and R.sub.2 and R.sub.3 when taken together represent the divalent moiety of formula: --CH.dbd.CH.sub.2 --CH.sub.2 .dbd.CH--which effectively creates an additional fused aromatic ring structure. The resins exhibit a low plate-out when processed thermally.Type: GrantFiled: December 20, 1988Date of Patent: August 21, 1990Assignee: General Electric CompanyInventors: Daniel W. Fox, Edward N. Peters, Paul D. Sybert
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Patent number: 4917817Abstract: An optically active functional compound represented by the following formula (1) is disclosed: ##STR1## wherein R denotes an alkyl group having 1-14 carbon atoms; -X- denotes ##STR2## denotes a single bond, ##STR3## n=0, 1 or 2; and C* denotes an asymmetric carbon atom. The compound of the formula (1) may be produced through an optically active compound of the following formula (2) or (3): ##STR4## The compounds of the above formulas (1)-(3) are all characterized by a trifluoromethyl group providing a large spontaneous polarization attached to an asymmetric carbon atom.Type: GrantFiled: July 21, 1988Date of Patent: April 17, 1990Assignee: Canon Kabushiki KaishaInventors: Hiroyuki Nohira, Masanao Kamei, Hideki Kanazawa, Tetsuya Abe, Yoko Yamada, Yuko Etoh
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Patent number: 4894181Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.Type: GrantFiled: May 16, 1988Date of Patent: January 16, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
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Patent number: 4880560Abstract: An optically active lactic acid derivative represented by the following formula (Ia) or (Ib): ##STR1## wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1-16 carbon atoms,R.sup.1 is an alkyl group having 4-16 carbon atoms,m and n are respectively 1 or 2,k is 0 or 1, andC* is an asymmetric carbon atom.A liquid crystal composition containing the lactic acid derivative and a liquid crystal device using the liquid crystal composition are also disclosed.Type: GrantFiled: January 3, 1989Date of Patent: November 14, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Kenji Shinjo
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Patent number: 4876280Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1-3 alkyl, n-butyl, i-butyl or t-butyl, R.sub.2 is hydrogen or C.sub.1-3 alkyl,R.sub.3 is hydrogen or C.sub.1-3 alkyl,R.sub.4 is hydrogen, C.sub.1-3 alkyl, n-butyl, i-butyl or t-butyl,R.sub.5 is hydrogen, C.sub.1-3 alkyl, n-butyl, i-butyl, t-butyl, C.sub.1-3 alkoxy, n-butoxy, i-butoxy, fluoro, chloro, trifluoromethyl, phenoxy or benzyloxy,R.sub.6 is hydrogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, trifluoromethyl, phenoxy or benzyloxy, with the provisos that not more than one of R.sub.5 and R.sub.6 is trifluoromethyl, not more than one of R.sub.5 and R.sub.6 is phenoxy, and not more than one of R.sub.5 and R.sub.6 is benzyloxy, orR.sub.5 and R.sub.6 are attached to adjacent carbon atoms and taken together form a radical of the formula --CH.dbd.CH--CH.dbd.CH--,R.sub.6a is hydrogen, C.sub.1-2 alkyl, fluoro or chloro,X is --CH.sub.2 CH.sub.2 -- or ##STR2## wherein R.sub.7 is hydrogen or C.sub.1-3 alkyl, andR.sub.8 is hydrogen, R.Type: GrantFiled: March 10, 1988Date of Patent: October 24, 1989Assignee: Sandoz Pharm. Corp.Inventor: Robert E. Damon, II
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Patent number: 4863957Abstract: Disclosed are novel 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors useful as antihypercholesterolemic agents represented by the formula ##STR1## and the corresponding ring-opened hydroxy acids derived therefrom and pharmaceutically acceptable salts thereof.Pharmaceutical compositions containing said compounds and method of inhibiting the biosynthesis of cholesterol therewith are also disclosed.Type: GrantFiled: December 21, 1987Date of Patent: September 5, 1989Assignee: Rorer Pharmaceutical CorporationInventors: Kent W. Neuenschwander, John R. Regan, Benedict J. Kosmider
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Patent number: 4855321Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.Type: GrantFiled: July 18, 1988Date of Patent: August 8, 1989Assignee: Merck & Co., Inc.Inventors: Robert L. Smith, Gerald E. Stokker
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Patent number: 4812259Abstract: An optically active lactic acid derivative represented by the following formula (Ia) or (Ib): ##STR1## wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1-16 carbon atoms, R.sup.1 is an alkyl group having 4-16 carbon atoms, m and n are respectively 1 or 2, k is 0 or 1, and C* is an asymmetric carbon atom. A liquid crystal composition containing the lactic acid derivative and a liquid crystal device using the liquid crystal composition are also disclosed.Type: GrantFiled: October 23, 1986Date of Patent: March 14, 1989Assignee: Canon Kabushiki KaishaInventors: Kazuo Yoshinaga, Kazuharu Katagiri, Kenji Shinjo
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Patent number: 4786731Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.Type: GrantFiled: August 5, 1987Date of Patent: November 22, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell
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Patent number: 4755617Abstract: A process for the preparation of 4'-hydroxybiphenyl-4-carboxylic acid by reacting a cyclohexanone-4-carboxylic acid compound with phenol in the presence of an acid catalyst, and then subjecting the resulting 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid compound to decomposition and dehydrogenation reactions in the presence of a base and a dehydrogenation catalyst. The aforesaid cyclohexanone-4-carboxylic acid compound is obtained by catalytically hydrogenating a 4-hydroxybenzoic acid compound in a secondary alcohol or tertiary alcohol solvent, and the reaction mixture thus obtained is directly used for the reaction with phenol.Type: GrantFiled: March 30, 1987Date of Patent: July 5, 1988Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tohru Miura, Teruyuki Nagata, Hideki Mizuta
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Patent number: 4736057Abstract: This invention concerns novel (4-substituted-2-phenylcyclohexyl)alkenoic and alkanoic acid derivatives of the formula I wherein one of Ra and Rb is hydrogen, hydroxy, (1-6C)alkyl, (1-6C)alkoxy, (3-6C)alkenyloxy or phenyl(1-4C)alkoxy and the other of Ra and Rb is hydrogen, (1-6C)alkyl, (1-6C)alkoxy or (3-6C)alkenyloxy; or Ra and Rb together form a (2-4C)alkylenedioxy or oxo group; benzene ring X optionally bears a substituent selected from halogeno, (1-6C)alkyl, (1-6C)alkoxy, hydroxy, (2-6C)alkanoyloxy, (1-6C)alkanoylamino, trifluoromethyl and nitro; n is 3-5; Y is ethylene or vinylene; and in the cyclohexane ring, the substituents at positions 1 and 2 have cis- or trans-relative stereochemistry; and the pharmaceutically acceptable salts, (1-6C)alkyl esters and (1-6C)alkanesulphonamides thereof. The compounds of formula I possess valuable pharmacological properties of use in medicines.Type: GrantFiled: November 9, 1984Date of Patent: April 5, 1988Assignee: Imperial Chemical Industries PLCInventors: Allen J. Guildford, Ralph W. Turner
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Patent number: 4686235Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: August 12, 1985Date of Patent: August 11, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Patent number: 4663465Abstract: 2,2-Dimethyl-3-arylcyclopropanecarboxylic acids and esters, suitable as insecticide intermediates, of the formula ##STR1## in which Ar is naphthyl or substituted furyl, thienyl or phenyl, andR.sup.1 is hydrogen or alkyl, are produced by subjecting ##STR2## to radical polymerization to produce ##STR3## reacting that with chlorine or bromine to produce ##STR4## and reacting that with an alkali metal or alkaline earth metal hydroxide or carbonate. Various intermediates II and III are new.Type: GrantFiled: December 4, 1985Date of Patent: May 5, 1987Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4661628Abstract: A new process for the optical resolution of racemic mixtures of .alpha.-naphthyl-propionic acids of formula ##STR1## This process comprises reacting a racemic mixture of a compound of formula ##STR2## with an optically active substance of formula R.sub.4 --NH.sub.2 (III), said substance being a .beta.-aminoalcohol, thus forming a pair of diastereoisomeric amides which are resolved into the single diastereoisomers by fractional crystallization. The obtained single diastereoisomeric amide is then hydrolyzed to give the desired optically active .alpha.-naphthyl-propionic acid of formula ##STR3## In the above compound I.fwdarw.III and VI, R.sub.1 is (C.sub.1-6)alkyl, R.sub.2 stands for hydrogen, halogen, mercapto, (C.sub.1-6)alkylthio, phenylthio, benzylthio, (C.sub.1-6)alkylsulfonyl, benzenesulfonyl, benzenesulfonyl substituted by halogen or (C.sub.1-4)alkyl, R.sub.3 is a reactive group and R.sub.4 is the residue of a primary or secondary alcohol.Type: GrantFiled: November 5, 1984Date of Patent: April 28, 1987Assignee: Alfa Chemicals Italiana S.p.A.Inventors: Vincenzo Cannata, Giancarlo Tamerlani
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Patent number: 4608441Abstract: Process for preparing an arylalkanoic acid by adding iodine to a mixture of an arylalkanone and an excess of an orthoester, heating of the mixture thus obtained, adding an inorganic base and finally an acid.Type: GrantFiled: July 12, 1985Date of Patent: August 26, 1986Assignee: BLASCHIM S.p.A.Inventors: Attilio Citterio, Laura Tinucci, Aldo Belli, Lucio Filippini