Sulfur, Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/17)
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Patent number: 5770758Abstract: Compounds of the formula I ##STR1## and disulfides thereof and salts thereof are important intermediate products for the preparation of compounds having a microbicidal and plant-immunizing action, of the formula III ##STR2## In the compounds of the formulae I and III: X is halogen,n is 0,1,2 or 3;Z is CN, CO-A or CS-A,A is hydrogen, halogen, OR.sub.1, SR.sub.2 and N(R.sub.3)R.sub.4 ;R.sub.1 to R .sub.4 are hydrogen, a substituted or unsubstituted, open-chain, saturated or unsaturated hydrocarbon radical containing not more than 8 carbon atoms, a substituted or unsubstituted cyclic, saturated or unsaturated hydrocarbon radical containing not more than 10 carbon atoms, substituted or unsubstituted benzyl or phenethyl, a substituted or unsubstituted alkanoyl group containing not more than 8 carbon atoms, a substituted or unsubstituted benzoyl group or a substituted or unsubstituted heterocyclyl radical; or R.sub.3 and R.sub.Type: GrantFiled: December 20, 1996Date of Patent: June 23, 1998Assignee: Novartis CorporationInventors: Walter Kunz, Beat Jau
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Patent number: 5766610Abstract: Novel pharmaceutically/cosmetically-active polycyclic aromatic compounds have the structural formula (I): ##STR1## wherein Ar is a radical having one of the formulae (a)-(e): ##STR2## and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.Type: GrantFiled: April 26, 1995Date of Patent: June 16, 1998Assignee: Centre International De Recherches Dermatologiques GaldermaInventor: Jean-Michel Bernardon
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Patent number: 5756809Abstract: (2RS,3RS)-3-(2'-aminophenylthio)-2-hydroxy-3-(4"-methoxyphenyl)-propionic acid methyl ester, an important precursor for the preparation of the pharmaceutical active substance diltiazem, is obtained in a particularly high stereoselectivity and yield by addition of o-aminothiophenol onto 3-(4'-methoxyphenyl)-glycidic acid methyl ester if the reaction is carried out in the presence of alkali metal salts of weak acids in the presence of catalytic amounts of iron compounds.Type: GrantFiled: November 1, 1996Date of Patent: May 26, 1998Assignee: Bayer AktiengesellschaftInventors: Ferdinand Hagedorn, Helmut Fiege
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Patent number: 5750711Abstract: The dicarboxylic acid derivatives according to the invention have the following structure ##STR1## wherein X denotes O, S, (CF.sub.2).sub.m, C(CF.sub.3).sub.2 or CF.sub.2 --CF(CF.sub.3) (m=1 to 10), and R stems from the following compounds: fluoro- or trifluoromethyl- and nitro- or cyanophenols, thiophenols or -aminobenzenes, 4-hydroxy-, 4-mercapto- or 4-aminocoumarins, N-hydroxysuccinimides or N-hydroxymaleimides, 2-hydroxy- or 2-mercaptobenzoxazoles or -benzothiazoles and 1-hydroxy- or 1-mercaptobenzotriazoles.Type: GrantFiled: August 28, 1996Date of Patent: May 12, 1998Assignee: Siemens AktiengesellschaftInventors: Racai Sezi, Hellmut Ahne, Eberhard Kuehn
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Patent number: 5750763Abstract: The present invention provides:a process for producing an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR1## which process comprises reacting a disulfide compound represented by general formula: ##STR2## with a hydroxide of an alkali metal M.sup.1 in the presence of a sulfur compound represented by general formula (2):H.sub.(2-i) S(M.sup.1).sub.i (2)a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR3## which process comprises reacting the above-mentioned alkalimetal salt of an arylmercaptan compound with a halogenofattyacid ester compound represented by general formula (4):X.sup.1 R.sup.2 COOR.sup.3 (4)at pH 7-10; anda process for producing the above-mentioned alkoxycarbonylalkylthioaryl compound, which process comprises reacting the above-mentioned disulfide compound with the above-mentioned hydroxide of an alkali metal M.sup.Type: GrantFiled: November 8, 1995Date of Patent: May 12, 1998Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Tatsuo Sugiyama, Tadashi Nakayama
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Patent number: 5734077Abstract: New substituted 2,2-dimethyl-.omega.-phenoxyalkanoic acids and esters of formula: ##STR1## wherein: X, A, B, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and Z are as defined in the specification,The corresponding enantiomers and diastereoisomers, and the physiologically tolerable salts thereof with appropriate bases.The products of the invention may be used therapeutically.Type: GrantFiled: September 13, 1996Date of Patent: March 31, 1998Assignee: Adir ET CompagnieInventors: Gilbert Regnier, Claude Guillonneau, Jean-Paul Vilaine, Florence Mahlberg, Christine Breugnot
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Patent number: 5731452Abstract: 7-thiaprostaglandins having the formula (I) which inhibit cell migration induced by monocyte chemoattractant protein MCP-1/MCAF and other chemokines and can serve as drugs for the treatment of atherosclerosis, diabetic angiopathy, and other disorders, their enantiomers, mixtures of the same, and methods of production thereof.Type: GrantFiled: September 18, 1995Date of Patent: March 24, 1998Assignee: Teijin LimitedInventors: Toru Minoshima, Kenichiro Kataoka, Hiroko Tanaka, Koji Ishii, Noriaki Endo
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Patent number: 5728864Abstract: A liquid crystal compound of the formula (1) ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms,both X and Y are hydrogen atoms or one of X and Y is a fluorine atom and the other is a hydrogen atom,A is --CF.sub.3 or --C.sub.2 F.sub.5,m is an integer of 2 to 4,n is an integer of 2 to 4, andC* is an asymmetric carbon,having a ferrielectric phase in its phase sequence, or a ferrielectric liquid crystal composition containing the liquid crystal compound of the formula (1) having a ferrielectric phase, may be injected between substrates provided with nonlinear active elements, such as thin film transistors or diodes formed on each pixel, to form an active matrix liquid crystal display device.Type: GrantFiled: April 12, 1996Date of Patent: March 17, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yuki Motoyama, Tomoyuki Yui, Masahiro Johno, Maki Ito, Takahiro Matsumoto, Hiroshi Mineta
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Patent number: 5719292Abstract: The invention provides a process for preparing a coupler compound having a thioether group at the coupling site comprising reacting in the presence of a base (a) a coupler compound having at least one hydrogen at the coupling site with (b) a mixed disulfide comprising either a tetrazole group or an oxadiazole group linked to one sulfur atom and an alkyl or aryl group linked to the other sulfur atom.Type: GrantFiled: March 27, 1997Date of Patent: February 17, 1998Assignee: Eastman Kodak CompanyInventor: Joan C. Potenza
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Patent number: 5710296Abstract: A method for preparing phenyl esters in high yields under mild reaction conditions is provided. Particularly preferred phenyl esters prepared in accordance with the inventive method are alkanyloxy-benzene compounds having a C.sub.2-18 alkyl. The method is practiced by reacting a carboxylic acid with an acid halide either in the presence of or followed by the addition of a phenol.Type: GrantFiled: May 25, 1995Date of Patent: January 20, 1998Assignee: The Clorox CompanyInventors: LaFayette D. Foland, Thomas B. Ottoboni
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Patent number: 5654468Abstract: Disclosed are compounds of formula ##STR1## wherein R is hydroxy, esterified hydroxy or etherified hydroxy;R.sub.1 is halogen, trifluoromethyl or lower alkyl;R.sub.2 is halogen, trifluoromethyl or lower alkyl;R.sub.1 is halogen, trifluoromethyl, lower alkyl, aryl, aryl-lower alkyl, cycloalokyl or cycloalkyl-lower alkyl; orR.sub.3 is the radical ##STR2## wherein R.sub.8 is hydrogen, lower alkyl, aryl, cycloalkyl, aryl-lower alkyl or cycloalkil-lower alkyl; R.sub.9 is hydroxy or acyloxy; R.sub.10 represents hydrogen or lower alkyl; or R.sub.9 and R.sub.10 together represent oxo;R.sub.4 is hydrogen, halogen, trifluoromethyl or lower alkyl;X is --NR.sub.7, S or O;W is O or S;R.sub.5 represents hydrogen, lower alkyl or aryl-lower alkyl; andR.sub.6 represents hydrogen; orR.sub.5 and R.sub.6 together represent oxo provided that X represents --NR.sub.7 ;R.sub.Type: GrantFiled: July 15, 1996Date of Patent: August 5, 1997Assignee: Ciba-Geigy CorporationInventors: Naokata Yokoyama, deceased, Gordon Northrop Walker, Alan Joseph Main
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Patent number: 5650533Abstract: The invention relates to 4-substituted isoxazole derivatives of formula I: ##STR1## wherein R, R.sup.1, R.sup.2, Q and n have the meaning defined in the description which possess valuable herbicidal properties.Type: GrantFiled: June 2, 1995Date of Patent: July 22, 1997Assignee: Rhone-Poulenc Agriculture Ltd.Inventors: David Alan Roberts, Susan Mary Cramp, Derek Ian Wallis, Jean-Paul Bulot
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Patent number: 5639903Abstract: The present invention is related to sulfonium salt compounds useful as an initiator of cationic polymerization and represented by a following general formula (I): ##STR1## wherein R.sub.1 is benzyl, phenyl, etc., R.sub.2, R.sub.3 and R.sub.4 are each independently hydrogen, alkyl, etc., R.sub.5 is hydrogen, alkyl, phenyl, etc., R.sub.6 is a group represented by a formula, --(CH.sub.2).sub.m --R.sub.11 wherein R.sub.11 is COR.sub.12, COOR.sub.13, OR,.sub.14, nitrile, OCOR.sub.15 or SOR.sub.16, wherein R.sub.12, R.sub.13, R.sub.14, R.sub.15 and R.sub.16 are each independently hydrogen, alkyl or phenyl, m is 0 or 1, and X represents SbF.sub.6, AsF.sub.6, PF.sub.6 or BF.sub.4.Type: GrantFiled: December 11, 1995Date of Patent: June 17, 1997Assignee: Nippon Soda Co., Ltd.Inventors: Eiji Takahashi, Hiroo Muramoto
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Patent number: 5633400Abstract: The invention relates to a process for the preparation of a compound of the formula (I) ##STR1## in which X is an optionally protected formyl group andR is a group which is itself inert to the reaction conditions of the synthesis,which comprises reacting a compound of the formula (II) ##STR2## where X is as defined above, with a substituted phenyl-halogen compound of the formula (III) ##STR3## where the substituent Hal is a halogen group and R is as defined above.Type: GrantFiled: May 24, 1995Date of Patent: May 27, 1997Assignee: Hoechst AktiengesellschaftInventors: Adalbert Wagner, Neerja Bhatnagar, Jean Buendia, Christine Griffoul
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Patent number: 5629436Abstract: N-arylmethylene ethylenediaminetriacetate, N-arylmethylene iminodiacetate or N,N'-diarylmethylene ethylenediaminediacetate type compounds and their use in combatting oxidative stress, and pharmaceutical and cosmetic compositions comprising said compounds. The invention also concerns a process for the preparation of said compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 13, 1997Assignee: L'OrealInventors: Jean-Baptiste Galey, Jacqueline Dumats
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Patent number: 5608101Abstract: Substituted aryl or heteroaryl in particular benzoyl bicycloalkane-diones and related compounds, intermediates therefor, synthesis thereof, and the use of said diones for the control of weeds.Type: GrantFiled: May 23, 1995Date of Patent: March 4, 1997Inventors: Shy-Fuh Lee, Takashi Nishizaka, Kenichi Komatsubara
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Patent number: 5599967Abstract: Compounds of the formula ##STR1## wherein the symbols have the meaning defined in the specification have retinoid-like biological activity.Type: GrantFiled: December 29, 1994Date of Patent: February 4, 1997Assignee: AllerganInventors: Vidyasagar Vuligonda, Richard L. Beard, Alan T. Johnson, Min Teng, Tae K. Song, Roshantha A. Chandraratna
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Patent number: 5578639Abstract: Certain compounds have been synthesized and found to be effective inhibitors of phospholipase A.sub.2 (PLA.sub.2), and thereby useful in the treatment of intestinal cholesterol absorption and the disease states arising therefrom, such as hypercholesterolemia and coronary artery disease.Type: GrantFiled: May 30, 1995Date of Patent: November 26, 1996Assignee: Warner-Lambert CompanyInventor: Reynold Homan
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Patent number: 5574064Abstract: The present invention provides an agricultural or horticultural fungicide including an effective amount of an amino-acid derivative represented by the formula: ##STR1## wherein R.sup.1 represents a lower alkyl group (optionally having at least one same or different substituent of a halogen atom, an alkoxy group, and a cyano group), R.sup.2 represents an ethyl group, or an n-propyl group, R.sup.3 represents a hydrogen atom or a lower alkyl group, R.sup.4 represents a hydrogen atom, R.sup.5, R.sup.6, and R.sup.7 independently represent a hydrogen atom or a lower alkyl group, R.sup.8 represents a hydrogen atom, or a lower alkyl group, Z.sup.1 and Z.sup.2 independently represent an oxygen atom or a sulfur atom, Z.sup.3 represents an oxygen atom, or a sulfur atom, Q represents a phenyl group, m represents an integer from 0 to 2, and n represents 0 or 1.Type: GrantFiled: December 28, 1994Date of Patent: November 12, 1996Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masaru Shibata, Kazuhiko Sugiyama, Norihisa Yonekura, Junetsu Sakai, Yoshiyuki Kojima, Shigeru Hayashi
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Patent number: 5525629Abstract: Hydroxamic acid derivatives of formula (I): ##STR1## wherein R.sup.1 represents hydrogen or an (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.6)alkyl, phenyl, substituted phenyl, phenyl(C.sub.1 -C.sub.6)alkyl, heterocyclyl, (C.sub.1 -C.sub.6)alkylcarbonyl, phenacyl or substituted phenacyl group;R.sup.2 represents hydrogen or a (C.sub.1 -C.sub.6)alkyl, (C.sub.2 -C.sub.6)alkenyl, phenyl(C.sub.1 -C.sub.6)alkyl, cycloalkyl(C.sub.1 -C.sub.6)alkyl or cycloalkenyl(C.sub.1 -C.sub.6)alkyl group,R.sup.3 represents a group --CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl or --CH.sub.2 CH.sub.2 CO.sub.2 (C.sub.1 -C.sub.4)alkyl;R.sup.4 represents hydrogen or a (C.sub.1 -C.sub.6)alkyl or phenyl(C.sub.1 -C.sub.6)alkyl group;R.sup.5 represents hydrogen or a methyl group;n is 0, 1 or 2;and A represents a (C.sub.1 -C.sub.6)hydrocarbon chain optionally substituted with one or more (C.sub.1 -C.sub.Type: GrantFiled: November 4, 1993Date of Patent: June 11, 1996Assignee: British Bio-Technology LimitedInventors: Michael J. Crimmin, William A. Galloway, Andrew J. Gearing
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Patent number: 5514794Abstract: Derivatized drugs are prepared with a linker consisting of a malonate, wherein the drug is linked through a methylene to the 2-position carbon of the malonate.Type: GrantFiled: January 22, 1991Date of Patent: May 7, 1996Assignee: Eli Lilly and CompanyInventor: Russell L. Barton
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Patent number: 5498798Abstract: Process for preparing 4-alkyl-3-chloroalkylsulfonylbenzenes of the formula (1) ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are each (C.sub.1 -C.sub.4)-alkyl.Type: GrantFiled: March 31, 1994Date of Patent: March 12, 1996Assignee: Hoechst AGInventors: Georg Folz, Theodor Papenfuhs
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Patent number: 5491170Abstract: .beta.-Carboxy sulfonyl compounds of the formula ##STR1## wherein R.sub.1 is aryl, R.sub.3 is hydrogen or alkyl, R.sub.3 and R.sub.4 are hydrogen or alkyl, Y is --O--, --S--, or --NR.sub.2 --, and R.sub.5 is alkyl or aryl are potent inhibitors of the enzyme acyl CoA:cholesterol acyltransferase (ACAT) and are thus useful for treating hypercholesterolemia and atherosclerosis.Type: GrantFiled: December 19, 1994Date of Patent: February 13, 1996Assignee: Warner-Lambert CompanyInventors: Helen T. Lee, Joseph A. Picard, Drago R. Sliskovic
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Patent number: 5481005Abstract: The invention relates to N-sulfonyl derivatives of formulae (I) and (I)' ##STR1## to their preparation, and to pharmaceutical compositions in which they are present. The compounds of formulae (I) and (I)' have an affinity for the vasopressin and ocytocin receptors.Type: GrantFiled: November 28, 1994Date of Patent: January 2, 1996Assignee: SanofiInventors: Jean Wagnon, Paul de Cointet, Dino Nisato, Claude Plouzane, Claudine Serradeil-Legal, Bernard Tonnerre
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Patent number: 5476944Abstract: The present invention relates to derivatives of cyclic phenolic thioethers of the formula: ##STR1## and the pharmaceutically acceptable salts thereof, which are inhibitors or stimulators of superoxide generation, and which may also inhibit cyclooxygenase and/or 5-lipoxygenase, to pharmaceutical compositions containing one or more of these compounds in combination with a pharmaceutically-acceptable carrier, and to medical methods of treatment employing these compounds.Type: GrantFiled: May 19, 1994Date of Patent: December 19, 1995Assignee: G. D. Searle & Co.Inventors: Richard A. Partis, Richard A. Mueller, Francis J. Koszyk, Richard M. Weier
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Patent number: 5473066Abstract: Process for stereoselectivity preparing a cis-form of 5-(aminoalkylamino)-1,5-benzothiazepine derivative represented by formula (VI): ##STR1## is provided, said process comprising carrying out a stereoselective addition reaction of an o-(aminoalkylamino) thiophenyl derivative with a trans-substituted glycidic ester at an elevated temperature in a nonpolar solvent in the presence of a divalent or trivalent iron ion to prepare a threo-form intermediate, hydrolyzing the ester group of said intermediate, acetylating the hydroxyl group of said hydrolyzed compound, and subjecting said acetylated compound to a ring closure reaction to obtain the objective compound (VI).Type: GrantFiled: January 19, 1994Date of Patent: December 5, 1995Assignee: Shionogi & Co., Ltd.Inventors: Teruo Yamamori, Hiroshi Harada, Eiichi Oosugi, Katsunori Sakai
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Patent number: 5459134Abstract: A novel (fused) benz(thio)amide of the general formula: ##STR1## or a non-toxic salt thereof, wherein R.sup.4 represents:(i) when B represents a closed ring, a group of the general formula: ##STR2## wherein U represents an oxygen atom or a sulfur atom; or (ii) when B represents a divalent group, a group of the general formula: ##STR3## wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, n, m, p and q are as defined in the specification, and exclusing certain compounds as defined in the specification, depending on whether A represents a single bond or a group. The compounds are useful for the prevention and/or treatment of diseases induced by leukotrienes, 5.alpha.-reductase, phospholipase and aldose reductase in mammals, especially human beings.Type: GrantFiled: October 21, 1994Date of Patent: October 17, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Tsumoru Miyamoto, Yoshinobu Arai
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Patent number: 5446058Abstract: A novel (fused) benz(thio)amide of the general formula: ##STR1## or a non-toxic salt thereof, wherein A represents a single bond or a group as defined in the specification;B represents(i) a substituted or unsubstituted carbocyclic ring of 4 to 8 members being unreplaced or optionally having one, two or three carbon atom(s) replaced by oxygen, nitrogen and/or sulfur atom(s); or(ii) a divalent group of formula: ##STR2## T represents oxygen or sulfur; R.sup.1 represents a group of general formula: ##STR3## or (iv) a straight or branched alkyl, alkenyl or alkynyl group of from 1 to 20 carbon atom(s);R.sup.2 represents hydrogen or a straight or branched alkyl group of from 1 to 6 carbon atom(s);R.sup.' represents hydrogen, a halogen atom, a hydroxy group, a nitro group or a group --COOR.sup.7 ;R.sup.Type: GrantFiled: November 29, 1991Date of Patent: August 29, 1995Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masaaki Toda, Tumoru Miyamoto, Yoshinobu Arai
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Patent number: 5434265Abstract: The present invention provides novel HIV protease inhibitors, pharmaceutical formulations containing those compounds and methods of treating HIV infection.Type: GrantFiled: December 22, 1992Date of Patent: July 18, 1995Assignee: Eli Lilly and CompanyInventors: James E. Fritz, Marlys Hammond, Stephen W. Kaldor
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Patent number: 5416068Abstract: .alpha.-Phenylacrylic acid derivatives I ##STR1## n=1; y=1;R.sup.1 =methylR.sup.2 =methyl, ethyl or methoxymethylR.sup.3 =H;R.sup.4 is 2,5-dimethylphenyl, 2,5-dichloropehnyl, 2-methyl-5-chlorophenyl, 2,4-dimethylphenyl, 2-chloro-5-methylphenyl, 2,3,5-trimethylphenyl or 2-methyl-5-isopropylphenyl.W=oxygen;A is --O--, --S--, --OCH.sub.2 --, --SCH.sub.2 --, --CH.dbd.CH--, --CO--OCH.sub.2 -- or --N(CH.sub.3) --CH.sub.2 --; methods for their preparation, agents containing them for combating injurious fungi and pests, and their use.Type: GrantFiled: January 3, 1994Date of Patent: May 16, 1995Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Reinharad Kirstgen, Klaus Oberdorf, Hubert Sauter, Franz Roehl, Rainer Otter, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff, Christoph Kuenast
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Patent number: 5409939Abstract: This invention relates to compounds having the following formula ##STR1## which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine thio derivatives.Type: GrantFiled: February 12, 1993Date of Patent: April 25, 1995Assignee: G. D. Searle & Co.Inventors: Steven P. Adams, Richard J. Lindmark, Masateru Miyano, Joseph G. Rico
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Patent number: 5409911Abstract: This invention relates to a prostaglandin-bisphosphonate compound of the formula: ##STR1## and its pharmaceutically acceptable salts. The claimed compounds are effective as delivery agents of prostaglandins to treat osteoporosis and related bone diseases. The claimed compounds also simultaneously deliver a bisphosphonate which inhibits bone resorption and delivers prostaglandins which increase bone formation in vivo.Type: GrantFiled: September 11, 1992Date of Patent: April 25, 1995Assignee: Merck & Co., Inc.Inventors: Peter C. Tyler, Robert N. Young, Gideon A. Rodan
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Patent number: 5387718Abstract: Alkylphenyl alkyl ethers or alkylphenyl alkyl thioethers, of the formula ##STR1## where U represents O or S; and R.sub.1 -R.sub.6 each independently represent an alkyl or aryl group with 1-6 C atoms, but R.sub.1 -R.sub.5 may each independently represent a functional group other than these, particularly --COOR (R=C.sub.1-4 alkyl), --NO.sub.2, --NH.sub.2, --O--CH.sub.2 --CH.sub.2 --OH, --OH, --CHO, --H, or -halogen;R.sub.1 -R.sub.5 may be bridged by suitable bifunctional substituents, such as, e.g., --(CH.sub.2).sub.x --, or --(CH.sub.2).sub.x --Z--(CH.sub.2).sub.y -- (where Z represents a hetero atom; x=0-7 and y=0-7), or by unsaturated substituents or anellated ring systems; may be produced in high space-time yield by reacting the corresponding phenol or thiophenol with a arylalkyl carbonate at a temperature of 70.degree.-300.degree. C. under elevated or normal pressure, in the presence of a monocyclic, bicyclic, polycyclic, or acyclic amidine as a catalyst.Type: GrantFiled: July 14, 1992Date of Patent: February 7, 1995Assignee: Huels AktiengesellschaftInventors: Gunther Kohler, Peter Bickert
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Patent number: 5387594Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical,and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: August 4, 1992Date of Patent: February 7, 1995Assignee: Centre International de Recherches Dermatologiques Galderma (Cird Galderma)Inventors: Jean-Michel Bernardon, William R. Pilgrim
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Patent number: 5362747Abstract: 2-Nitroaryl or 2-cyanoaryl compounds of the formula ##STR1## pharmaceutical compositions thereof, intermediates useful in the preparation of these compounds, and methods for treating disorders of vascular smooth muscles or diseases of the cartilage, macrophages, neurons, platelets, bronchial smooth muscles, optic muscles and gastrointestinal smooth muscles, in addition to sickle cell anemia, diabetes, synovitis, chondroarthritis and osteoarthritis by employing these compounds.Type: GrantFiled: November 3, 1993Date of Patent: November 8, 1994Assignee: Abbott LaboratoriesInventors: Marlon Cowart, James F. Kerwin
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Patent number: 5360909Abstract: Disclosed are phenoxyacetic acid compounds of formula (I): ##STR1## where X is a hydrogen atom, a lower alkyl group or a halogen atom;R1 is a carboxyl group or a lower alkoxycarbonyl group;Y is an oxygen atom, ##STR2## n is an integer of from 0 to 5; Z is ##STR3## R2 is a hydrogen atom or a lower alkyl group; and m is 0 or 1.The compounds and their physiologically acceptable salts are used as thromboxane A2 antagonistic agents, leukotriene antagonistic agents and/or anti-allergic agents.Type: GrantFiled: March 22, 1993Date of Patent: November 1, 1994Assignee: Terumo Kabushiki KaishaInventors: Azuma Igarashi, Sachiko Maeda, Katuyoshi Sugizaki, Takashi Shizawa, Atsumi Tajima, Kenichi Abe, Shinji Ozawa
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Patent number: 5359126Abstract: Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g.Type: GrantFiled: February 7, 1994Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventor: Charles A. McCombs
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Patent number: 5350872Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.Type: GrantFiled: October 29, 1993Date of Patent: September 27, 1994Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5344586Abstract: A novel antiferroelectric liquid crystal compound is disclosed which is represented by the following formula: ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from C.sub.3 -C.sub.18 alkyl groups, respectively, Rf is a lower fluoroalkyl group, X is a group selected from the group consisting of --O--, --COO--, --OCO--, and --CO--, or a single bond, (A) and (B) each is a group independently selected from the group consisting of phenyl, biphenyl, and naphthalene group which may be substituted with a halogen atom, and C having an asterisk indicates an asynunetric carbon atom. A process for producing the antiferroelectric liquid crystal compound is also disclosed.Type: GrantFiled: May 20, 1993Date of Patent: September 6, 1994Assignee: Showa Sheel Sekiyu Kabushiki KaishaInventors: Yoshiichi Suzuki, Hiroyuki Mogamiya, Koichi Tanaka, Yoshihiro Takagi, Katutoshi Hirose
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Patent number: 5326898Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen, lower alkyl of 1 to 6 carbons, halogen or lower alkoxy of 1 to 6 carbons; R.sub.5 and R.sub.5 ' independently are hydrogen or lower alkyl of 1 to 6 carbons; Y is oxygen or sulfur; Z is n-alkyl having 2 to 10 carbons, cyclo or branch-chained alkyl of 3 to 10 carbons, and straight chain alkenyl having 2 to 10 carbons, or cyclo or branched chained alkenyl of 3 to 10 carbons, and the Z-Y substituent is in a 1,2 (ortho) or 1,3 (meta) position on the phenyl ring relative to the ethene moiety; A is (CH.sub.2).sub.n where n is 0-5, lower branched chain alkyl having 3 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkenyl having 2 to 6 carbons and 1 or 2 double bonds, alkynyl having 2 to 6 carbons and 1 or 2 triple bonds; B is COOH or a pharmaceutically acceptable salt thereof, COOR.sub.8, CONR.sub.9 R.sub.10, --CH.sub.2 OH, CH.sub.2 OR.sub.11, CH.sub.2 OCOR.sub.11, CHO, CH(OR.sub.12).sub.2, CHOR.sub.Type: GrantFiled: February 11, 1992Date of Patent: July 5, 1994Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5321046Abstract: Disclosed herein are novel unsymmetrical dithiol ketals which are useful in the treatment or prevention of hypercholesterolemia, hyperlipoproteinemia, and atherosclerosis.Type: GrantFiled: October 27, 1992Date of Patent: June 14, 1994Assignee: Bristol-Myers Squibb CompanyInventors: Sing-Yuen Sit, John J. Wright, Jeff A. Field
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Patent number: 5314918Abstract: This invention relates to alkanoic acid compounds having phenyl and heteroarylthio substituents which are useful as leukotriene antagonists, processes for the preparation thereof, and pharmaceutical compositions containing such compounds.This invention also relates to methods of treating diseases in which leukotrienes are a factor by administration of an effective amount of the above compounds or compositions.Type: GrantFiled: April 2, 1992Date of Patent: May 24, 1994Assignee: SmithKline Beecham CorporationInventors: James S. Frazee, John G. Gleason, Ralph F. Hall
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Patent number: 5302741Abstract: D(+)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid, an important intermediate in the synthesis of diltiazem hydrochloride, is obtained in better yields and high optical purity by a novel resolution process comprising the reaction of 2 moles of the (.+-.) racemic acid with 1 mole of quinine and 1 mole of a base in a suitable polar solvent system to form a salt of the D(+) acid and quinine which precipitates; separating said salt and decomposing it with a strong base.Type: GrantFiled: July 12, 1993Date of Patent: April 12, 1994Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Ramy Lidor, Claude Singer
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Patent number: 5302751Abstract: A process is disclosed that is useful for separating the enantiomers of a racemic mixture of an aliphatic carboxylic acid having the formula ##STR1## where R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3 and R.sub.4 are independently different and are hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, substituted phenyl, naphthyl, substituted naphthyl, heteroaryl, substituted heteroaryl, haloalkyl, alkoxyalkyl, alkylthioalkyl, phenylalkyl, substituted phenylalkyl, heteroalkylalkyl, substituted heteroalkylalkyl or cycloalkylalkyl.Type: GrantFiled: January 21, 1992Date of Patent: April 12, 1994Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Alicia A. Potter
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Patent number: 5294724Abstract: 4-Hydroxytetrahydropyran-2-ones and the corresponding dihydroxycarboxylic acid derivatives, salts and esters, process for their preparation, their use as pharmaceuticals, and pharmaceutical preparations and precursors.Compounds of the formula I ##STR1## and the corresponding open-chain dihydroxycarboxylic acids of the formula II ##STR2## in which X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meanings indicated, and also their pharmacologically tolerable salts with bases and their pharmacologically tolerable esters, processes for the preparation of these compounds, their use as pharmaceuticals and pharmaceutical preparations are described. In addition, compounds of the formula III ##STR3## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X and Y have the meanings indicated are described.Type: GrantFiled: September 6, 1990Date of Patent: March 15, 1994Assignee: Hoechst AktiengesellschaftInventors: Heiner Jendralla, Gunther Wess, Kurt Kesseler, Gerhard Beck
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Patent number: 5290812Abstract: Phenoxyalkylcarboxylic acid derivatives represented by the following formula (I) ##STR1## having a strong and selective leukotriene antagonistic action and useful for prophylaxis and therapy of allergic diseases as asthma and processes of preparing the same.Type: GrantFiled: December 30, 1991Date of Patent: March 1, 1994Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Mitsuo Ohashi, Toshio Tanaka, Norihisa Ishikawa, Tetsuya Kishi
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Patent number: 5288742Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different, is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: March 18, 1992Date of Patent: February 22, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Philip N. Edwards, David Waterson
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Patent number: 5284971Abstract: Compounds of general formula (I) ##STR1## wherein R.sup.1 is (CH.sub.2).sub.n ((CHNR.sup.7 R.sup.8).sub.m C(O)R.sup.9 ; n=1-3; and m=0 or 1;R.sup.3 and R.sup.5 are independently Cl, Br, I, or CH.sub.3 ;R.sup.7 and R.sup.8 are independently H or (C.sub.1 -C.sub.4)alkyl;R.sup.9 is OH, (C.sub.1 -C.sub.4)alkoxy, or NR.sup.7 R.sup.8 ;R.sup.31 is H, Cl, Br, I, (C.sub.1 -C.sub.4)alkyl, (C.sub.4 -C.sub.6)cycloalkyl, (C.sub.1 -C.sub.4)haloalkyl, (C.sub.4 -C.sub.6)halocycloalkyl, or --CH(R.sup.10)Ar where Ar is selected from 5-hydroxypyrid-2-yl, 6-hydroxypyrid-3-yl, 6-hydroxypyridazin-3-yl, 6-methoxypyridazin-3-yl, 6-hydroxypyridazin-3-yl N-oxide, and 6-methoxypyridazin-3-yl N-oxide and R.sup.10 is H or (C.sub.1 -C.sub.4)alkyl;R.sup.41 is OH or a bioprecursor thereof; and the pharmaceutically acceptable salts thereof; are structural analogs of the thyroid hormones T.sub.3 and T.sub.4 and exhibit selective thyromimetic activity.Type: GrantFiled: July 16, 1992Date of Patent: February 8, 1994Assignee: Syntex (U.S.A.) Inc.Inventors: Keith A. Walker, Sharada S. Labadie, Denis J. Kertesz, Craig W. Laughton
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Patent number: 5284966Abstract: Intermediates for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers are described. The final compounds are useful intermediates for the synthesis of antibiotics like Chloramphenicol, Thiamphenicol and Florfenicol.Type: GrantFiled: December 18, 1992Date of Patent: February 8, 1994Assignee: Zambon Group S.p.A.Inventors: Marco Villa, Claudio Giordano, Silvia Cavicchioli, Silvio Levi
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Patent number: 5278338Abstract: A method for racemizing an optically active carboxylic acid, or ester thereof, of the formula: ##STR1## where R.sub.1 is hydrogen, hydroxy, halo, cyano, C.sub.1 to C.sub.6 linear or branched alkoxy, amino or substituted amino or the group ##STR2## is nitrile; R.sub.2, R.sub.3 and R.sub.4 are different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched haloalkyl, aralkyl, cycloalkyl, alkyl substituted cycloalkyl, C.sub.6 to C.sub.10 aryl, C.sub.1 to C.sub.6 linear or branched alkoxy, C.sub.6 to C.sub.10 aryloxy, C.sub.1 to C.sub.6 alkylthio, C.sub.3 to C.sub.8 cycloalkylthio, C.sub.6 to C.sub.10 arylthio, C.sub.6 to C.sub.10 arylcarbonyl, C.sub.4 to C.sub.8 cycloalkenyl, trifluoromethyl, halo, C.sub.4 to C.sub.5 heteroaryl, C.sub.10 to C.sub.14 aryl, or biphenyl unsubstituted or substituted with methyl or halo, comprising heating said optically active carboxylic acid or ester thereof in the presence of water at a temperature of from about 40.degree. C.Type: GrantFiled: November 4, 1992Date of Patent: January 11, 1994Assignee: Ethyl CorporationInventor: Rhonda L. Trace