Chalcogen Attached Indirectly To The Hetero Ring By Nonionic Bonding Patents (Class 549/427)
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Patent number: 5676884Abstract: Nonlinear optical (NLO) compositions are disclosed which contain polar disulfone-functionalized molecules (PDFMs) incorporated in a polymeric material. when aligned noncentrosymmetrically in the polymeric material, the PDFMs generate a second-order NLO response. There is also disclosed: a method of preparing a NLO composition; novel PDFMs and novel polymers; and a new process for preparing PDFMs.Type: GrantFiled: November 20, 1996Date of Patent: October 14, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: George V. Tiers, Robert J. Koshar, Louis M. Leichter
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Patent number: 5618959Abstract: A process for synthesizing prostaglandin E.sub.1, E.sub.2 and derivatives thereof is provided. The process is a "one-pot" method in which 2-furyllithium, copper cyanide, a lower alkyllithium reagent and either an (E)-alkenylstannane or a halogenide are combined with cyclopentenone (II) ##STR1## in which A, R.sup.6 and R.sup.7 are as defined herein. The reaction gives rise to the desired prostaglandin product in yields of 80% or higher.Type: GrantFiled: March 10, 1995Date of Patent: April 8, 1997Assignee: Vivus IncorporatedInventors: Miroslav Trampota, Bohumil Zak
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Patent number: 5543425Abstract: This invention relates to a method of inhibiting platelet aggregation comprising administering compounds having the following formula ##STR1##Type: GrantFiled: October 28, 1994Date of Patent: August 6, 1996Assignee: G. D. Searle & Co.Inventors: Steven P. Adams, Richard J. Lindmark, Masateru Miyano, Joseph G. Rico
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Patent number: 5536734Abstract: Crop protection agents contain dihydropyrans of the formula ##STR1## wherein the variable substituents are defined in the specification.Type: GrantFiled: June 21, 1994Date of Patent: July 16, 1996Assignee: BASF AktiengesellschaftInventors: Bernd Mueller, Siegbert Brand, Hubert Sauter, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5484949Abstract: The present invention relates to a method for the synthesis of .alpha., .beta.-unsaturated ketones which comprises, in the method for the synthesis of .alpha., .beta.-unsaturated ketones represented by general formula ##STR1## reacting aldehydes represented by general formulaR.sup.1 CHO(where R.sup.1 is as defined above) with alkali metal salt of acetoacetic acid represented by general formula ##STR2## (where M.sup..sym. is an alkali metal ion), in the presence as a catalyst of 3-azabicyclo[3,2,2]nonane, a cyclic secondary amine represented by general formula (1) ##STR3## a cyclic secondary amine represented by general formula (2) ##STR4## (where, l is 1 or more and up to 6, a ring with N is a 6-membered, 7-membered or 8-membered ring, the two neighbors of N are methylene, R.sup.3 is a lower alkyl group, its substitution position is at a carbon atom other than two those adjacent to N, and ##STR5## is an alicyclic group or a phenol group), or a secondary amine represented by general formula (3)CH.sub.3 NHCH.Type: GrantFiled: March 2, 1994Date of Patent: January 16, 1996Assignee: Nippon Soda Co., Ltd.Inventors: Keiichi Tsukashima, Masashi Nakajima, deceased, Masayoshi Fujimaru, Kenji Suzuki
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Process for producing (E)-alkoxyimino or hydroxyimino-acetamide compounds and intermediates therefor
Patent number: 5442063Abstract: The present invention relates to a process for producing (E)-alkoxyiminoacetamide compounds useful as agricultural fungicides and a process for producing (E)-hydroxyiminoacetamide compounds useful as intermediates for producing them. The present invention also relates to an industrial process for producing (E)-methoxyiminoacetamide compounds useful as agricultural fungicides. This process is advantageous in terms of the cost, safety and the like.Type: GrantFiled: November 2, 1993Date of Patent: August 15, 1995Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kuniyoshi Nishida -
Patent number: 5428174Abstract: .alpha.,.beta.-Unsaturated ketones of the general formula I ##STR1## where R is an organic radical, are prepared by reacting a corresponding aldehyde R--CHO with acetoacetic acid or one of its salts in the presence of an amine in a two-phase reaction mixture by a process in which the reaction is carried out at a pH of from 6 to 8 in the presence of a catalytic amount of a primary amine.Type: GrantFiled: August 5, 1991Date of Patent: June 27, 1995Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5418232Abstract: A compound of formula (I) possesses excellent potassium channel opening activity and is effective on various diseases arising from contractions of blood vessels, bronchial smooth muscles, etc., for example, ischemic heart diseases exemplified by angina pectoris, asthma, pollakisuria, sequela of subarachnoid hemorrhage, peripheral arterioinfarct, and so on. The compound has potent and long-lasting antihypertensive activity, with the onset of the action being slow, excellent activity in increasing renal blood flow, and high safety, and is therefore particularly useful as an antihypertensive. ##STR1## The substituents are as defined in the specification.Type: GrantFiled: May 12, 1993Date of Patent: May 23, 1995Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Tetsuya Mimura, Hideo Kubo
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Patent number: 5412123Abstract: Derivatives of anthraquinone and anthracene are synthesized and formulated into pharmaceutical formulations. When the formulations are administered the derivatives act as ligands binding to an interrupting the biological chain of events associated with selectin receptors in the human body.Type: GrantFiled: February 8, 1993Date of Patent: May 2, 1995Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Peng C. Tang, John H. Musser
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Patent number: 5412120Abstract: A process for preparing monocarboxylic esters of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cyclo-alkyl acyl, aryl or C.sub.7 -C.sub.20 -aralkyl or together --(CH.sub.2).sub.n --X--(CH.sub.2).sub.m --,X is methylene, oxygen, sulfur, NH or NR.sup.3,R.sup.3 is C.sub.1 -C.sub.12 -alkyl, andn and m are each from 0 to 8, comprises reacting geminal dicarboxylic esters of the general formula II ##STR2## where R.sup.1 to R.sup.3 are each as defined above, at from 150.degree. to 400.degree. C. in the presence of catalysts.Type: GrantFiled: November 29, 1993Date of Patent: May 2, 1995Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Norbert Goetz, Thomas Kuekenhoehner, Werner Schnurr
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Patent number: 5391771Abstract: A process for the preparation of propane-1,2,3-tricarboxylic acid, tetrahydrofurfurylacetic acid and the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof, propane-1,2,3-trimethanol, 3-methyltetrahydrofuran, 3-(2'-hydroxyethyl)tetrahydrofuran, 4-hydroxymethyltetrahydropyran, 2-methyl-.gamma.-butyrolactone and/or 3-methyl-.gamma.-butyrolactone, comprises reacting citric acid or the C.sub.1 - to C.sub.20 -alkyl or C.sub.7 - to C.sub.12 -aralkyl esters thereof on hydrogenation catalysts in non-aqueous solvents at from 50.degree. to 400.degree. C. and at from 1 to 400 bar.Type: GrantFiled: September 30, 1993Date of Patent: February 21, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Juergen Weyer, Rolf Fischer, Christoph Sigwart
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Patent number: 5387700Abstract: A process for producing chlorosulfate and sulfamate esters of 2,3:4,5-bis-O-(1-methylethylidene)-.beta.-D-fructopyranose and (1-methylcyclohexyl)methanol is disclosed. The process involves a two step procedure involving in the first step reacting of an alcohol with sulfuryl chloride in the presence of a tertiary or heterocyclic amine base in a solvent selected from the group consisting of toluene, t-butyl methyl ether or tetrahydrofuran to produce a chlorosulfate intermediate, which is preferably stabilized by an aqueous wash and/or treatment with a base, and in the second step reacting of the resulting intermediate with an amine in a solvent selected from the group consisting of t-butyl methyl ether, tetrahydrofuran and lower alkanol.Type: GrantFiled: August 12, 1993Date of Patent: February 7, 1995Assignee: McNeilab, Inc.Inventors: Cynthia A. Maryanoff, Lorraine Scott, Kirk L. Sorgi
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Patent number: 5385942Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where X and Y may be the same or different from each other and are each a hydroxyl group, a group represented by the formula --(--OCH.sub.2 --).sub.n --OR.sup.6, wherein n is 0 or 1 and R.sup.6 is a lower alkyl group, or an acyl group.Type: GrantFiled: March 1, 1993Date of Patent: January 31, 1995Assignee: Eisai Co., Ltd.Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
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Patent number: 5354874Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: November 30, 1993Date of Patent: October 11, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5349071Abstract: Processes for synthesizing tertiary alkynols by reacting carbonyl-group-containing compounds with alkynes in the presence of a basic catalyst are disclosed. Preferred products are 6,10,14-trimethyl-4-pentadecyn-6-ol compounds having the structure: ##STR1## A preferred, novel compound, 6,10,14-trimethyl-4-pentadecyne-2,6-diol, can be used in the synthesis of Vitamin E or Vitamin K.sub.1.Type: GrantFiled: November 25, 1992Date of Patent: September 20, 1994Assignee: Loyola University of ChicagoInventor: James H. Babler
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Patent number: 5319102Abstract: Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate compounds exhibit unexpectedly desirable selective herbicidal activity. Also disclosed are compositions comprising such compounds as well as a method of controlling the growth of undesirable plants employing such compounds.Type: GrantFiled: April 30, 1992Date of Patent: June 7, 1994Assignee: Uniroyal Chemical Company, Inc.Inventors: Robert G. Davis, Allyn R. Bell, John A. Minatelli
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Patent number: 5304661Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promotor activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##Type: GrantFiled: April 9, 1993Date of Patent: April 19, 1994Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5300654Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.Type: GrantFiled: July 15, 1991Date of Patent: April 5, 1994Assignee: Nippon Soda Co., Ltd.Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
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Patent number: 5292839Abstract: Novel unsaturated peroxyketals useful as molecular weight regulators in polymerization reactions are disclosed. Also disclosed are a polymerization process employing these novel unsaturated peroxyketals as molecular weight regulators, polymers and oligomers made by this process and articles of manufacture comprising one or more polymers or oligomers made by this process. These molecular weight regulating peroxyketals provide the ability to introduce an epoxy functionality to the oligomer or polymer as well as an additional functionality, in a manner which gives a higher monomer conversion and less by-products than with comparable chain transfer regulators.Type: GrantFiled: April 28, 1993Date of Patent: March 8, 1994Assignee: Akzo N.V.Inventors: Luc L. T. Vertommen, John Meijer, Bernard J. Maillard
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Patent number: 5286899Abstract: An efficient and commercially-viable method for the stereoselective transformation of a diol to an alcohol is disclosed. The present method is particularly well-suited for the preparation of the unnatural D-isomer of malic acid or its derivatives from the abundant naturally occurring L-tartaric acid or derivatives thereof.Type: GrantFiled: August 27, 1992Date of Patent: February 15, 1994Assignee: Sepracor, Inc.Inventor: Yun Gao
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Patent number: 5281720Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: October 26, 1992Date of Patent: January 25, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
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Process for preparing 4-hydroxypyrrolo(2,3-d)pyrimidine based antifolate compounds and intermediates
Patent number: 5278307Abstract: The present invention provides a process for preparing a 4-hydroxypyrrolo[2,3-d]pyrimidine derivative of the formula ##STR1## wherein R is NHC*H(COOR.sup.1)CH.sub.2 CH.sub.2 COOR.sup.1 or OR.sup.1 ;R.sup.1 is H or a carboxyl protecting group;the configuration about the carbon atom designated * is L;n is 0 or 1; andA is an aryl group optionally having, in addition to the COR substituent, one or two substituents selected from the group consisting of halo, hydroxy, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy; or a salt thereof, which comprises(a) halogenating a compound of the formula ##STR2## wherein R, R.sup.1, A and * are as defined above;j is 0 or 1; and(b) reacting 2,4-diamino-6-hydroxypyrimidine, or a salt thereof, with the reaction product from step (a), in the presence of a polar solvent.Type: GrantFiled: September 25, 1992Date of Patent: January 11, 1994Assignee: Eli Lilly and CompanyInventors: Charles J. Barnett, Thomas M. Wilson -
Patent number: 5260442Abstract: The invention concerns quinolinium salt intermediates of the formula I ##STR1## and processes for their manufacture; and their use in the manufacture of aryloxymethyl-substituted 1-alkyl-2-quinolone derivatives which are 5-lipoxygenase inhibitors.Type: GrantFiled: December 5, 1991Date of Patent: November 9, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Jonathan Hutton, David Waterson
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Patent number: 5254581Abstract: The invention concerns a cyclic ether derivative of the formula I ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a 9- or 10-membered bicyclic heterocyclic moiety;A.sup.1 is a direct link to X.sup.1 or (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar.sup.2 is optionally substituted phenylene or pyridylene;R.sup.1 includes hydrogen, (1-4C)alkyl, (1-4C)alkcxycarbonyl and (1-4C)alkylthio; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 5 to 7 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl or sulphonyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: February 2, 1993Date of Patent: October 19, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Pierre A. R. Bruneau, Robert I. Dowell, David Waterson
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Patent number: 5252755Abstract: A process for the preparation of 4-hydroxymethyltetrahydropyrans of the formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, aryl or C.sub.7 - to C.sub.20 -aralkyl, comprises reacting a tetrahydropyrancarboxylic ester of the formula II ##STR2## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, and R.sup.5 is hydrogen or C.sub.1 - to C.sub.12 -alkyl, at from 50.degree. to 400.degree. C. and at from 1 to 400 bar in the presence of hydrogen and a hydrogenation catalyst.Type: GrantFiled: December 14, 1992Date of Patent: October 12, 1993Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Thomas Ruehl, Horst Zimmermann, Norbert Goetz, Wolfgang Spiegler, Thomas Kuekenhoehner
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Patent number: 5246950Abstract: Thioformamide derivatives of the formula (I) ##STR1## wherein R represents an alkyl group; A represents either:(1) a phenyl group which is optionally substituted; or(2) heteroaromatic group (e.g. pyrid-3-yl, quinolin-3-yl);Y represents:an ethylene or methylene group or a direct bond; and B represents either:a) a phenyl, pyridyl, furyl or thienyl group, each of which may be optionally substituted, orb) a straight- or branched-chain alkyl, alkenyl, or cycloalkyl group, each of which may be optionally substituted.These compounds may be formulated into pharmaceutical preparations and have utility in the treatment of disorders associated with smooth muscle contraction.Type: GrantFiled: March 30, 1990Date of Patent: September 21, 1993Assignee: Rhone-Poulenc SanteInventors: Terance W. Hart, Bernard Y. J. Vacher, Brian W. Sharp
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Patent number: 5245041Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.Type: GrantFiled: December 18, 1991Date of Patent: September 14, 1993Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5231190Abstract: Squarylium compounds of the formula: ##STR1## wherein Q.sup.1 and Q.sup.2 are each independently a pyrylium, thiopyrylium, selenopyrylium, benzpyrylium, benzthiopyrylium or benzselenopyrylium nucleus, and R.sup.1 and R.sup.2 are each independently an aliphatic or cycloaliphatic group, can be prepared by reacting a squaric acid derivative of the formula: ##STR2## with a compound of the formula Q.sup.2 CH.sub.2 R.sup.2 in the presence of a base. The derivatives of Formula II may be prepared by condensing a 2,3,4,4-tetrahalocyclobut-2-en-1-one with a compound of the formula Q.sup.1 CH.sub.2 R.sup.1 in the presence of a base to produce a compound of the formula: ##STR3## wherein Q.sup.1 and R.sup.1 are as defined above, and X represents chlorine or bromine, and hydrolyzing the compound of Formula III. Alternatively, the derivatives of Formula II may be prepared by reacting a diester, monoacid chloride monoester or diacid chloride of squaric acid with a compound of the formula Q.sup.1 CH.sub.2 R.sup.Type: GrantFiled: May 6, 1991Date of Patent: July 27, 1993Assignee: Polaroid CorporationInventors: Donald A. McGowan, Paulina P. Garcia, John W. Lee, Thomas K. Spencer, Stephen J. Telfer, Michael J. Zuraw
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Patent number: 5221753Abstract: A process for the preparation of 1-(4-tetrahydropyranyl)- or 1-(4-tetrahydrothiopyranyl)prop-1-en-3-ones of the general formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1 - to C.sub.10 -alkyl, C.sub.1 - to C.sub.10 -alkoxy or aryloxy,R.sup.2 is hydrogen, C.sub.1 - to C.sub.4 -alkyl, or aryl which is unsubstituted or substituted by C.sub.1 - to C.sub.4 -alkyl and/or halogen, andX is oxygen or sulfur,by reacting 1-aminoprop-1-en-3-ones of the general formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, andR.sup.3 and R.sup.4, independently of one another, are hydrogen, C.sub.1 - to C.sub.4 -alkyl, aryl or together are a C.sub.2 - to C.sub.7 -alkylene chain,with a 4-tetrahydropyranyl- or 4-tetrahydrothiopyranylmagnesium halide of the general formula III ##STR3## where X is as defined above and Y is halogen, at from -20.degree. to 100.degree. C.,and novel 1-(4-tetrahydropyranyl)- or 1-(4-tetrahydrothiopyranyl)prop-1-en-3-ones are described.Type: GrantFiled: July 3, 1990Date of Patent: June 22, 1993Assignee: BASF AktiengesellschaftInventors: Shigeru Kozima, Masami Hatano
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Patent number: 5216167Abstract: Phenylacetic acid benzylamides having the following general structure ##STR1## wherein the substituents are defined herein, are disclosed, which compounds are hypoglcemic agents.Type: GrantFiled: June 21, 1990Date of Patent: June 1, 1993Assignee: Dr. Karl Thomae GmbHInventors: Wolfgang Grell, Rudolf Hurnaus, Gerhart Griss, deceased, Robert Sauter, Manfred Reiffen, Eckhard Rupprecht
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Patent number: 5210239Abstract: A quinone derivative useful in the treatment of hepatic diseases defined by the general formula: ##STR1## where R1 is selected from the group consisting of alkyl, alkenly, alkynyl or heterocycle, R2 is a substituted nitrogen containing radical wherein the substituents on said nitrogen are selected from the group consisting of hydrogen, substituted or unsubstituted lower alkyl or heterocycles, and where said nitrogen may be a ring heteroatom, and R3, R4 and R5, may be the same or different and each are hydrogen, lower alkyl or lower alkoxy groups.Type: GrantFiled: August 31, 1990Date of Patent: May 11, 1993Assignee: Eisai Co., Ltd.Inventors: Shinya Abe, Yasushi Okamoto, Katsuya Tagami, Shigeki Hibi, Junichi Nagakawa, Kazuo Hirota, Ieharu Hishinuma, Kaname Miyamoto, Takashi Yamanaka, Hiromitsu Yokohama, Tsutomu Yoshimura, Tohru Horie, Yasunori Akita, Koichi Katayama, Isao Yamatsu
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Method and apparatus for synthesis of highly isomerically pure stereoisomers of glycidol derivatives
Patent number: 5194637Abstract: Methods are provided for producing isomerically enriched camphorsulfonates, and in particular a diastereomerically enriched glycidyl camphorsulfonate by bromide-casylate exchange between an alkyl casylate and the bromide analog of the desired casylate, followed by separation of a higher melting diastereomer by selective recrystallization. There is also shown the production of a desired casylate by reacting a racemic or enantiomerically enriched arenesulfonate with a quaternary casylate. Randomization and recycling of an isomerically enriched casylate is provided by reaction with an achiral bromide analog in the presence of a quaternary salt. Specially adapted apparatus for conducting the randomization reaction is provided. There is also shown a process for producing an alkyl casylate by the reaction of a metal casylate and a quaternary casylate with a trialkyl phosphite in the presence of a slight molar excess of sulfuric acid.Type: GrantFiled: August 22, 1991Date of Patent: March 16, 1993Assignee: Syracuse UniversityInventor: Roger C. Hahn -
Patent number: 5189184Abstract: 2-(3'-butenyl)-3,4-dihydro-2H-pyrans of the general formula ##STR1## wherein R is a hydrogen group or an alkyl group with 1 to 6 carbon atoms. Methods for the synthesis of these compounds and their use as reactive modifiers or diluents for cationically curable monomers or polymers.Type: GrantFiled: July 29, 1991Date of Patent: February 23, 1993Assignee: Th. Goldschmidt AGInventors: Dietmar Schaefer, Andreas Weier, Christian Weitemeyer, Dietmar Wewers
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Patent number: 5141952Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein the dotted lines represent a possible endo or exo double bond, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 14 carbon atoms, aralkyl of 7 to 18 carbon atoms and ##STR2## R'.sub.2 is alkyl of 1 to 8 carbon atoms or aryl of 6 to 14 carbon atoms, X is --O-- or --NR--, R is selected from the group consisting of --OH, hydrogen, ##STR3## and --COOR', R' is hydrogen or alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms, all optionally substituted with at least one halogen or --OH, with the proviso that if Y is --OH, X is not --NH-- and their non-toxic, pharmaceutically acceptable addition salts of acids or bases having antibacterial and immunological properties.Type: GrantFiled: June 18, 1991Date of Patent: August 25, 1992Assignee: Roussel UclafInventors: Constantin Agouridas, Patrick Fauveau
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Patent number: 5136059Abstract: Propoxybenzene derivatives represented by the following formula ##STR1## wherein Ra represents a nitro group, an amino group which may have a protecting group or an --NHCH.dbd.C(COO--C.sub.1-6 -Alkyl).sub.2 group, Rb represents a hydrogen atom, a protecting group for the hydroxyl group or a substituted sulfonyl group and Xa and Xb, which may be the same or different, each represents a halogen atom, and processes for preparation thereof are disclosed. These derivatives are useful in preparing antibacterial agents.Type: GrantFiled: December 27, 1988Date of Patent: August 4, 1992Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Toshihiro Fujiwara, Tutomu Ebata
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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: 5120348Abstract: Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate compounds having the following formula: ##STR1## wherein n, R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification exhibit unexpectedly desirable selective herbicidal activity. Also disclosed are compositions comprising such compounds as well as a method of controlling the growth of undesirable plants employing such compounds.Type: GrantFiled: July 11, 1989Date of Patent: June 9, 1992Assignee: Uniroyal Chemical Company, Inc.Inventors: Robert G. Davis, Allyn R. Bell, John A. Minatelli
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Patent number: 5089509Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O, or NR' where R' is hydrogen or lower alkyl; R is hydrogen or lower alkyl; A is pyridyl, thienyl, furyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 0-2; and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.Type: GrantFiled: March 20, 1989Date of Patent: February 18, 1992Assignee: Allergan, Inc.Inventor: Roshantha A. S. Chandraratna
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Patent number: 5072029Abstract: The present invention relates to a process for the reaction of carboxylic acids with vinyl ethers using a non-polymeric pyridine hydrochloride and/or polymeric vinylpyridine hydrochloride as a catalyst.Type: GrantFiled: April 10, 1990Date of Patent: December 10, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Walter R. Hertler
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Patent number: 4973583Abstract: Pesticidal O-halogenocyclobutyl S-alkyl (di) thiophosph(on)ates of the formula ##STR1## in which x represents oxygen or sulphur,p represents zero, one or two,m represents zero, one or two,n represents 2, 3 or 4R.sup.1 represents alkyl, alkoxy which is optionally interrupted by oxygen or sulphur and can be substituted by halogen, or alkenyloxy, alkinyloxy, heterocyclyl-alkoxy or cycloalkoxy which is optionally substituted by alkyl and/or halogen,R.sup.2 represents alkyl which is optionally interrupted by oxygen or sulphur and can be substituted by halogen, or alkenyl, alkinyl or heterocyclyl-alkyl andR.sup.3 represents hydrogen or alkyl.Type: GrantFiled: June 1, 1989Date of Patent: November 27, 1990Assignee: Bayer AktiengesellschaftInventors: Bernd-Wieland Kruger, Dietmar Bielefeldt, Karl-Rudolf Gassen, Bernhard Homeyer, Benedikt Becker, Hans-Detlef Matthaei, Wilhelm Stendel
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Patent number: 4954524Abstract: Carbacyclin derivatives of Formula I ##STR1## wherein R.sub.1 is hydrogen or OR.sub.2, wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, ##STR2## or a heterocyclic residue; or R.sub.1 is NHR.sub.3 wherein R.sub.3 is an acid residue (acyl) or R.sub.2,n is 2, 3, 4, or 5,X is hydrogen or fluorine,A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--,W is a free or functionally modified hydroxymethylene group or a free or functionally modified ##STR3## wherein the OH-group can be in the .alpha.- or .beta.-position, D is ##STR4## a straight-chain, saturated aliphatic group of 1-10 carbon atoms, a branched, saturated or a straight-chain or branched, unsaturated aliphatic group of 2-10 carbon atoms, all of which can optionally be substituted by fluorine atoms,m is 1, 2, or 3,E is a direct bond, --C.tbd.C--, or --CR.sub.6 .dbd.CR.sub.7 -- wherein R.sub.6 and R.sub.7 are different from each other and are hydrogen or alkyl or 1-5 carbon atoms, or are hydrogen or halogen,R.sub.Type: GrantFiled: April 6, 1989Date of Patent: September 4, 1990Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Jorge Casals-Stenzel, Gerda Mannesmann, Ekkehard Schillinger, Michael H. Town
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Patent number: 4931581Abstract: A method and composition for the immunization of healthy useful plants against plant diseases containing as active ingredients compounds of formula ##STR1## in which: X is hydrogen, halogen, hydroxy, methyl, methoxy, HOOC or MOOC;Y is hydrogen, halogen, SO.sub.3 H, SO.sub.3 M, nitro, hydroxy or amino, M being the molar equivalent of an alkali metal or alkaline earth metal ion that is formed from a corresponding base or basic compound; andZ is cyano or --CO--A;A represents either --OH or --SH, the hydrogen atom of which may also be replaced by the molar equivalent of an inorganic or organic cationic residue,or wherein A represents any other organic residue which has a molecular weight of less than 900 and which may also contain one, or more than one, hetero atom, including the salts of the phytophysiologically tolerable 7-carboxylic acid or 7-thiocarboxylic acid with primary, secondary or tertiary amines or with inorganic bases.Type: GrantFiled: August 18, 1988Date of Patent: June 5, 1990Assignee: Ciba-Geigy CorporationInventors: Rolf Schurter, Walter Kunz, Robert Nyfeler
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Patent number: 4925590Abstract: Derivatives of 4-cyano-2,3-difluorophenol of the formula I ##STR1## wherein R.sup.1 is an alkyl group which has 1-12 C atoms and in which one or two CH.sub.2 groups can also be replaced by --O--, --CO--, --CO--O-- and/or --CH.dbd.CH--, no two 0 atoms being directly attached to one another,A.sup.1 and A.sup.2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, and in which one or two CH groups can also be replaced by N, or trans-1,4-cyclohexylene in which one or two non-adjacent CH.sub.2 groups can also be replaced by 0 atoms and/or S atoms,Z is --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, OCH.sub.2 --, --CH.sub.2 O, --C.tbd.C-- or a single bond,m is 0, 1 or 2 andQ is --CO-- or --CH.sub.2 --.Type: GrantFiled: March 9, 1989Date of Patent: May 15, 1990Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Georg Weber, Ulrich Finkenzeller
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Patent number: 4923882Abstract: This invention relates to amine derivatives and salts thereof. These compounds have an anti-ulcer activity which is effective to human beings and animals. This disclosure relates to such compound, a process for the preparation thereof and an anti-ulcer agent containing the same.Type: GrantFiled: October 16, 1986Date of Patent: May 8, 1990Assignee: Toyama Chemical Co., Ltd.Inventors: Shiro Hirai, Hiroshi Hirano, Hirotoshi Arai, Yasuo Kiba, Hisanari Shibata, Yoshikazu Kusayanag, Minako Yotsuji, Kazuhiko Hashiba, Kikuko Tanada
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Patent number: 4920232Abstract: Known and novel substituted acroleins of the general formula I ##STR1## where R.sup.1 is alkoxy, phenoxy, halogen, haloalkyl, haloalkoxy, haloalkylthiyl or nitro, n is an integer from 1 to 5, in the case of n being greater than 1 the R.sup.1 s being identical or different and in the event of nitro substitution the aromatic ring carrying not more than 3 nitro groups, and where R.sup.2 is alkyl, cycloalkyl, unsubstituted or substituted aryl or hetaryl or a nonaromatic heterocyclic radical, are prepared by reacting a phenylacetaldehyde of the general formula II ##STR2## with an aldehyde of the general formula III[R.sup.2 -CHO] IIIin the presence of a base and a solvent. These acroleins are useful to prepare hydroxymethyloxiranes which are intermediates in the synthesis of antimycotic and fungicidal azoylmethyloxiranes.Type: GrantFiled: June 27, 1988Date of Patent: April 24, 1990Assignee: BASF AktiengesellschaftInventors: Norbert Goetz, Stefan Karbach, Hans-Gert Recker
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Oxy-substituted-2-phenyl pyran derivatives and process for preparing same and perfumery uses thereof
Patent number: 4914083Abstract: Described are oxy-substituted-2-phenyl pyran derivatives defined according to the generic structure: ##STR1## wherein: (i) the dashed lines in the pyran ring each represents a carbon-carbon single bond; or one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines in the pyran ring is a carbon-carbon single bond;(ii) wherein R.sub.2 represents lower alkyl and R.sub.1 is hydrogen; or(iii) R.sub.1 and R.sub.2 represented by the moiety: ##STR2## taken together represents methylene and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations and cosmetic powders.Type: GrantFiled: July 14, 1989Date of Patent: April 3, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Wilhelmus J. Wiegers, Anton Van Ouwerkerk -
Patent number: 4912235Abstract: This invention relates to a process for making a compound of formula I ##STR1## in the form of a stereoisomer or mixture thereof, wherein R is hydrogen, lower alkyl; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta., or a pharmaceutically acceptable, non-toxic salt of the compound wherein R is hydrogen; novel intermediates useful for preparing these compounds; processes for making the intermediates; and a stereoisomer of the compound of formula I wherein R is methyl and X is hydrogen and a process for making same.Type: GrantFiled: June 7, 1988Date of Patent: March 27, 1990Assignee: Syntex (U.S.A.) Inc.Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
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Patent number: 4897397Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.Type: GrantFiled: December 16, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Neng Y. Shih, David J. Blythin
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Patent number: 4889939Abstract: Compounds suitable for being used as lubricants, having general formula:(I) RO--(C.sub.3 F.sub.6 O).sub.m --(CFXO).sub.n --CFX--L, or(II) R"CFXO--(C.sub.3 F.sub.6 O).sub.x (CFXO).sub.y --(C.sub.2 F.sub.4 O).sub.z --CFX--L, whereR=--CF.sub.3, --C.sub.2 F.sub.5, --C.sub.3 F.sub.7X=F, --CF.sub.3R"=F, --CF.sub.3, --C.sub.2 F.sub.5m=an integer from 3 to 100n=a finite integer, or =zero, wherefore m+n ranges from 3 to 100, provided that, if n is finite, m/n ranges from 5 to 20 and R is preferably =CF.sub.3, if n=zero, R is preferably --C.sub.2 F.sub.5 or --C.sub.3 F.sub.7x=a finite integer, or =zeroy, z=finite integers, such that x+y+z ranges from 5 to 200, while (x+z)/y ranges from 5 to 0.5, provided that when x=zero, z/y ranges from 1 to 0.5 and y+z ranges from 5 to 200 n while X is preferably F, and R"=LL=group Y-Z, where:Y=--CH.sub.2 O--, --CH.sub.2 --OCH.sub.2, --CF.sub.2, --CF.sub.Type: GrantFiled: April 11, 1988Date of Patent: December 26, 1989Assignee: Montedison S.p.A.Inventors: Gerardo Caporiccio, Ezio Strepparola, Mario A. Scarati
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Patent number: 4871756Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4, E.sub.4 and the slow reacting substance of anaphylaxis.As such, these compounds will be useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.Type: GrantFiled: February 17, 1987Date of Patent: October 3, 1989Assignee: Merck Frosst Canada, Inc.Inventors: John Gillard, Joshua Rokach, Patrice C. Belanger