Cyclobutyl In Acid Moiety Patents (Class 560/123)
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Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
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Patent number: 4609673Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.Type: GrantFiled: December 18, 1984Date of Patent: September 2, 1986Assignee: Boehringer Mannheim GmbHInventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
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Patent number: 4600774Abstract: Cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides, amide derivatives thereof, a process for making the same, curable compositions containing cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof and cationically-sensitive monomers, and a process for using cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof as catalysts for the cure of cationically-sensitive monomers.Type: GrantFiled: June 13, 1985Date of Patent: July 15, 1986Assignee: Minnesota Mining and Manufacturing CompanyInventor: Robert J. Koshar
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Patent number: 4599419Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.Type: GrantFiled: July 9, 1984Date of Patent: July 8, 1986Assignee: Mitsubishi Chemical Industries, Inc.Inventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
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Patent number: 4594446Abstract: The invention relates to new antimicrobially active 3-cephem compounds, processes for preparing such compounds, new intermediate compounds comprising alkoxyimino dioxy butyric acid derivatives useful in said processes, and processes for preparation of said intermediates.Type: GrantFiled: January 14, 1985Date of Patent: June 10, 1986Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Ikuo Ueda, Takao Takaya, Masakazu Kobayashi, Takashi Masugi, Hisashi Takasugi, Hiromu Kochi, Tadashi Kitaguchi
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Patent number: 4593115Abstract: An 1-Iodoalkyl acylate, which is useful as the raw material for esterification of cephalosporins, penicillins, etc. is prepared in a high degree of purity and in high yield by (1) allowing a carboxylic acid iodide to react with an aldehyde, or (2) allowing a carboxylic acid chloride to react with a salt of hydriodic acid and then allowing the resulting product to react with an aldehyde, or (3) by simultaneously allowing a carboxylic acid chloride, a salt of hydriodic acid and an aldehyde to react with one another.Type: GrantFiled: November 21, 1984Date of Patent: June 3, 1986Assignee: Takeda Chemical Industries, Ltd.Inventors: Akio Miyake, Masayoshi Yamaoka
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Patent number: 4592870Abstract: This invention produces methyl esters and ethylene glycol esters by reacting carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and an acyl compound. Methyl ester and ethylene glycol ester are the predominant products. These esters are used as precursors in the formation of ethylene glycol, vinyl acylates such as vinyl acetate, ethylene oxide, ethylene carbonate and methanol.Type: GrantFiled: November 10, 1981Date of Patent: June 3, 1986Assignee: Union Carbide CorporationInventor: Bernard D. Dombek
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Patent number: 4570014Abstract: Novel plant growth regulant composition comprising as an active ingredient at least one cycloalkanecarboxylic acid compound of the formula ##STR1## in which R is hydroxyl, alkoxy, aralkoxy, amino, alkylamino, dialkylamino or the radicalO.sup..crclbar. M.sup..sym.whereinM.sup..sym. is one alkali metal ion equivalent or alkaline earth metal ion equivalent, or an ammonium, alkylammonium, dialkylammonium, trialkylammonium or tetraalkylammonium ion,R.sup.1 is amino or the radical ##STR2## wherein R.sup.2 is hydrogen, alkyl or aryl, orR.sup.1 is the radical --N.sup..sym. H.sub.3 X.sup..crclbar.,wherein X.sup.63 is chloride, bromide or iodide, and n is 1, 2, 3, 4 or 5,in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.Type: GrantFiled: December 15, 1981Date of Patent: February 11, 1986Assignee: Bayer AktiengesellschaftInventors: Rolf Schroder, Klaus Lurssen
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Patent number: 4570006Abstract: Amidino compounds represented by the formula ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful anti-trypsine, anti-plasmin, anti-kallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: October 24, 1984Date of Patent: February 11, 1986Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
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Patent number: 4544767Abstract: Hydrogenation of an acyloxyolefin is effected in the presence of at least one of an alkali and an alkaline earth metal salt of a carboxylic acid. In one embodiment, 1,4-diacetoxy-2-butene is converted to 1,4-diacetoxybutane employing potassium acetate.Type: GrantFiled: August 1, 1980Date of Patent: October 1, 1985Assignee: Phillips Petroleum CompanyInventor: Kiplin D. Cowan
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Patent number: 4540810Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.Type: GrantFiled: September 20, 1979Date of Patent: September 10, 1985Assignee: Texaco Development CorporationInventor: John F. Knifton
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Patent number: 4539424Abstract: Linear esters, e.g., alkyl adipates, are facilely prepared by reacting an alcohol and carbon monoxide with a monoolefin, in the presence of cobalt, optionally hydrogen, and a tertiary nitrogen base, and in a reaction solvent which comprises a 5- or 6-membered monoheterocycle containing from 1 to 3 identical or different, non-adjacent oxygen and divalent sulfur heteroatoms, with the proviso that such heterocycle can also contain from one to two carbon-carbon double bonds, and, if a 5-membered heterocycle, can also contain a nitrogen heteroatom separated from an oxygen or sulfur heteroatom by at least one ring carbon atom and linked to one of the adjacent carbon atoms by a double bond.Type: GrantFiled: October 19, 1983Date of Patent: September 3, 1985Assignee: Rhone-Poulenc Chimie de BaseInventor: Jean Jenck
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Patent number: 4531010Abstract: A curing agent for fluorocarbon polymer coating compositions having the formula ##STR1## where R is R.sup.1 NH, R.sup.1 is an aliphatic or cycloaliphatic hydrocarbon radical, R.sup.2 is C or an aliphatic hydrocarbon group, R.sup.3 is H or CH.sub.3, where x is 3 when R.sup.2 is a hydrocarbon group and x is 4 when R.sup.2 is C; the curing agents form ambient curing fluorocarbon polymer coating compositions;These compositions are used to provide corrosion and abrasion resistant coatings for large structures in chemical plants, oil refineries, oil drilling platforms, and the interior of smoke stacks of large utility companies.Type: GrantFiled: December 30, 1983Date of Patent: July 23, 1985Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph A. Vasta
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Patent number: 4529813Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: March 14, 1980Date of Patent: July 16, 1985Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4526999Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit lipoxygenase, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 25, 1983Date of Patent: July 2, 1985Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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Patent number: 4514416Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with amidinophenol compound (III) and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: May 21, 1984Date of Patent: April 30, 1985Assignee: Torii & Co. Ltd.Inventors: Setsuro Fujii, Takashi Yaegashi, Toyoo Nakayama, Yojiro Sakurai, Shigeki Nunomura, Toshiyuki Okutome
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Patent number: 4506091Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an excess of alcohol and in the presence of an organotitanate catalyst, treating the crude mixture with a suitable chelate compound, removing the unreacted alcohol and hydrolyzing the treated titanium catalyst residues with steam, and recovering the purified ester by filtration.Type: GrantFiled: September 1, 1983Date of Patent: March 19, 1985Inventor: Donald L. Deardorff
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Patent number: 4496389Abstract: This disclosure relates to alkyl N-trifluoroacetyl-N-phosphonomethylglycine amide and hydrazide derivatives, to herbicidal compositions containing same and to the herbicidal use thereof. These amide and hydrazide derivatives are useful as pre-emergent and/or post-emergent herbicides.Type: GrantFiled: May 11, 1984Date of Patent: January 29, 1985Assignee: Monsanto CompanyInventors: John E. Franz, Robert J. Kaufman
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Patent number: 4490388Abstract: Amidino compounds represented by the formula (I) ##STR1## and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and anti-thrombin agents. Having strong anti-Cl (Clr, Cls) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula (II)R.sub.1 --COOH (II)with 4-(.beta.-amidinoethenyl)phenol represented by the formula (III) ##STR2## and, if necessary, can be transformed into pharmaceutically acceptable acid addition salts thereof.Type: GrantFiled: February 22, 1982Date of Patent: December 25, 1984Assignee: Torii & Co., Ltd.Inventors: Setsuro Fujii, Takuo Aoyama, Yojiro Sakurai, Toyoo Nakayama, Shigeki Nunomura, Takashi Yaegashi, Toshiyuki Okutome
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Patent number: 4490552Abstract: A novel process for the preparation of aryl esters of organic carboxylic acids in high isomer purity by decomposing a compound of the formula ##STR1## wherein Ar is an aryl radical, X is an acyloxy of an organic carboxylic acid and Y is selected from the group consisting of an acyloxy of an organic carboxylic acid and an anion of a strong organic and mineral acid in an aqueous media in the presence of a palladium salt or in the form of a two-phase reaction, wherein the aryl thallium salt is dissolved in water and the catalytic palladium salt is dissolved in a water-immiscible organic solvent and the reaction takes place with mixing.Type: GrantFiled: December 20, 1982Date of Patent: December 25, 1984Assignee: Rutgerswerke AGInventor: Ulrich Knips
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Patent number: 4485258Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.Type: GrantFiled: July 29, 1982Date of Patent: November 27, 1984Assignee: Mitsubishi Chemical Industries LimitedInventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
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Patent number: 4474977Abstract: The new amino-alcohol derivatives according to the invention have the formula: ##STR1## wherein: (a) R.sub.1 is hydrogen, an alkylthio C.sub.1 -C.sub.5 radical, a cycloalkylthio C.sub.5 -C.sub.6 radical, an alkoxy C.sub.1 -C.sub.5 radical, a cycloalkyloxy C.sub.5 -C.sub.6 radical, an alkyl C.sub.1 -C.sub.5 radical, a cycloalkyl C.sub.5 -C.sub.6 radical or a halogen atom;(b) R.sub.2 is a lower alkyl C.sub.1 -C.sub.3 radical;(c) R.sub.3 is an alkyl C.sub.1 -C.sub.18 radical, substituted or not, an alkenyl C.sub.6 -C.sub.18 radical substituted or not, a cycloalkyl C.sub.5 -C.sub.9 radical;(d) R.sub.4 is an acyl group having the formula: ##STR2## in which R.sub.5 represents an alkyl C.sub.1 -C.sub.10 substituted or not, an alkenyl C.sub.2 -C.sub.4, a cycloalkyl C.sub.3 -C.sub.8, a phenyl substituted or not or a cinnamyl radical, R.sub.4 being hydrogen if R.sub.1 is hydrogen, an alkyl, alkoxy, cycloalkoxy or cycloalkyl radical or a halogen atom.Type: GrantFiled: April 28, 1978Date of Patent: October 2, 1984Assignee: Continental Pharma S.A.Inventors: Georges Lambelin, Romeo Roncucci, Joseph Roba, Claude Gillet, Michel Snyers
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Patent number: 4431835Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430506Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4425360Abstract: The present invention provides pyruvic acid oximes of the general formula: ##STR1## wherein R is a hydrogen atom, a C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.6 alkoxy, cinnamyloxy, phenylamino, phenyl-N-alkylamino or phenylthio radical or an aryl or aryloxy radical, the aryl moiety of which can be substituted one or more times by C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halogen, hydroxyl, trifluoromethyl, amino, acetylamino, nitrile, nitro or methylenedioxy, A is a straight-chained or branched, saturated or unsaturated aliphatic hydrocarbon chain containing up to 10 carbon atoms, which can be substituted one or more times by halogen or hydroxyl, and R.sub.1 is a C.sub.1 -C.sub.8 alkyl radical, which can be substituted one or more times by halogen, hydroxyl, nitrile, phenyl or carboxyl, or is a nitrile or formyl group, with the proviso that when R--A-- is a methyl or ethyl radical, R.sub.1 is not a methyl radical or a nitrile group and when R--A-- is a benzyl radical, R.sub.Type: GrantFiled: September 8, 1981Date of Patent: January 10, 1984Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ruth Heerdt, Manfred Hubner, deceased, Hans Kuhnle, Felix H. Schmidt
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Patent number: 4423064Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.Type: GrantFiled: June 29, 1981Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4421693Abstract: An aminosulfenyl chloride derivative represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are defined in the specification, which is useful as an intermediate for the preparation of a carbamate derivative represented by the formula (III): ##STR2## wherein R.sup.1 and R.sup.2 are the same as defined above, the carbamate derivative having an insecticidal, miticidal or nematocidal activity, is disclosed. A process for preparing the aminosulfenyl chloride of the formula (I), and a process for preparing the carbamate derivative of the formula (III) using the aminosulfenyl chloride of the formula (I) are also disclosed.Type: GrantFiled: March 25, 1982Date of Patent: December 20, 1983Assignee: Otsuka Chemical Co., Ltd.Inventors: Takeshi Goto, Takashi Soeda, Nobuyoshi Asai, Akira Tanaka
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Patent number: 4414410Abstract: Alkyl esters, such as ethyl acetate, are prepared by contacting the corresponding next lower carbon number alkyl ester, such as methyl acetate, with carbon monoxide and hydrogen in the presence of an iodine or iodide-free catalyst composition comprising a ruthenium-containing compound, a cobalt containing compound and a quaternary phosphonium salt or base, and heating the mixture to an elevated temperature and pressure for sufficient time to produce the desired higher alkyl ester, and then recovering the same from the reaction mixture.Type: GrantFiled: January 13, 1982Date of Patent: November 8, 1983Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4388323Abstract: There are described hydroquinone-diethers endowed with a high acaricide activity, the processes for their preparation and their use as acaricides.Type: GrantFiled: March 17, 1981Date of Patent: June 14, 1983Assignee: Montedison S.p.A.Inventors: Pietro Massardo, Angelo Longoni, Paolo Piccardi
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4376789Abstract: Disclosed are novel polyhydric alcohol partial esters of polycarboxylic acids from Diels-Alder adducts of maleic anhydride and a straight chain unsaturated carboxylic acid having ten to twenty-five carbon atoms. The partial esters can be subsequently sulfated.The polyhydric alcohol can be a mono- or disaccharide such as sucrose or mannose.The partial esters are surfactants which are dermatologially acceptable and useful in personal products and skin-care products.Type: GrantFiled: March 4, 1981Date of Patent: March 15, 1983Assignee: Grillo-Werke AGInventors: Norbert Lowicki, Natvarlal B. Desai
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4365032Abstract: A monoester compound of a 2,2'-alkylidene bis(4,6-di-substituted phenol) useful as an antioxidant in synthetic polymers having good resistant to oxides of nitrogen fumes, represented by the formula (I), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a C.sub.1-4 alkyl group, a C.sub.5-6 cycloalkyl group or a methyl-substituted C.sub.5-6 cycloalkyl group; and one of R.sub.3 and R.sub.4 represents a hydrogen atom and the other represents a hydrogen atom or a C.sub.1-10 alkyl group or both of them represent a methyl group; R.sub.5 represents a C.sub.4-9 alkyl group, a C.sub.3-7 cycloalkyl group, a C.sub.2-4 alkenyl group, a phenyl group, a C.sub.1-4 alkyl-substituted phenyl group, a C.sub.1-4 alkoxy-substituted phenyl group, a mono- or di- C.sub.1-4 alkyl-substituted hydroxyphenyl group, a styryl group, a benzyl group or a pyridyl group, and a method of preparing such a monoester compound.Type: GrantFiled: November 4, 1981Date of Patent: December 21, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Akihiko Yosizato, Yoshinori Morifuji, Kunio Kondo, Masatsugu Yoshino
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Patent number: 4340603Abstract: Novel, transient inotropic prodrug forms of the N-(2-phenylethyl)-.omega.-phenylalkylamines, notably of dobutamine, have (i) the structural formula (I): ##STR1## with the proviso that at least one R.sup.1, R.sup.2 or OR.sup.1, when R.sup.7 and/or R.sup.10 is OR.sup.1, must be R.sup.3 COXCH(R.sup.4)-- or R.sup.3 COXCH(R.sup.4)O--, respectively.Type: GrantFiled: August 13, 1980Date of Patent: July 20, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4323513Abstract: This invention is concerned with improving ethylene glycol ester production from the reaction of carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and acyl compound by maintaining the combined concentration of methyl ester, ethylene glycol ester and water in the reaction medium at less than about 30 volume percent. In a preferred embodiment, a continuous process is operated in such a manner that the methyl ester, ethylene glycol ester and water products are removed from the reactor so as to maintain their total volume concentration in the reaction medium at less than about 30 percent.Type: GrantFiled: November 4, 1980Date of Patent: April 6, 1982Assignee: Union Carbide CorporationInventor: Bernard D. Dombek
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Patent number: 4313956Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.Type: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4309351Abstract: This invention relates to compounds of the formulae ##STR1## wherein n is an integer from 2 to 5; M is H, acyl, lower alkyl, or lower alkoxy alkyl; Q is H or lower alkyl; R is alkyl, alkenyl or analkyl; A is H; Y is OH, acyloxy or alkoxy, and when taken together, Y and A is oxo (O.dbd.), and to novel intermediates therefore.Type: GrantFiled: February 4, 1980Date of Patent: January 5, 1982Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4291061Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
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Patent number: 4289896Abstract: Phosphonic acids are suitable catalysts for the transesterification of alkyl esters of carboxylic acids with aliphatic or cycloaliphatic diols containing more than 3 carbon atoms.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventor: Lothar Buxbaum
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Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
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Patent number: 4275219Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: INTERx Research CorporationInventor: Jacob A. Zupan
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Patent number: 4265819Abstract: A process for the preparation of a dihalogenovinylcyclopropanecarboxylic acid or an ester thereof, of the formula ##STR1## in which Hal each independently is fluorine, chlorine or bromine,R.sup.1 and R.sup.2 each independently is hydrogen or C.sub.1-4 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a cycloaliphatic ring with up to 7 carbon atoms, andR.sup.3 is hydrogen, C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,which comprises reacting a 3-chloro-2-(2',2'-dihalovinyl)propanecarboxylic acid ester of the formula ##STR2## in which R.sup.4 is C.sub.1-4 -alkyl or optionally substituted arylmethyl or hetero-arylmethyl,with a base. The propane carboxylic acid esters are new and may be formed in situ by reacting a 3-(2',2'-dihalovinyl)-.gamma.-butyrolactone of the formula ##STR3## with a chlorinating agent and then with an alcohol of the formula R.sup.4 --OH.Type: GrantFiled: September 13, 1979Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventor: Reinhard Lantzsch
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Patent number: 4259350Abstract: Iodopropargyl derivatives of formula:IC.tbd.CCH.sub.2 OR[wherein R represents an alkanoyl group (which may be unsubstituted or have one or more halogen, cyano, substituted or unsubstituted .alpha.Type: GrantFiled: March 13, 1979Date of Patent: March 31, 1981Assignee: Sankyo Company LimitedInventors: Yasuhiro Morisawa, Kiyoshi Konishi, Mitsuru Kataoka
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Patent number: 4252738Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.Type: GrantFiled: March 17, 1978Date of Patent: February 24, 1981Assignee: Bayer AktiengesellschaftInventors: Willy Hartmann, Hans-Georg Heine
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Patent number: 4250183Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.Type: GrantFiled: December 15, 1978Date of Patent: February 10, 1981Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4231953Abstract: Fluoro substituted aryl esters and thiolesters of amino acids, intermediates therefor, synthesis thereof and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: June 4, 1979Date of Patent: November 4, 1980Assignee: Zoecon CorporationInventors: Clive A. Henrick, Barbara A. Garcia
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Patent number: 4232169Abstract: An operationally simple and economical process for preparing alpha-oxoesters is provided by reacting an acetylenic compound of formulaR--C.tbd.C--OR'with an oxidizing mixture composed of osmium tetroxide and an alkaline or alkaline earth chlorate and recovering the osmium tetroxide at the end of the reaction.Type: GrantFiled: April 24, 1979Date of Patent: November 4, 1980Assignee: Snamprogetti S.p.A.Inventors: Luciano Re, Alberto Brandt, Luciano Bassignani
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Patent number: 4224050Abstract: Chloroacetanilides are disclosed having the general formula: ##STR1## wherein R.sup.1 =H, or alkyl with 1-5 carbon atoms, or X;X=alkenyl, and preferably ##STR2## in which the various R.sup.2, which may be equal to or different from each other, are H or an alkyl with 1-3 carbon atoms;A=alkylene, optionally substituted, of the formula: ##STR3## in which the various R.sup.2, which may be equal to or different from each other, have the meanings specified above; andY=H; alkyl with 1-5 carbon atoms; alkenyl with 2-5 carbon atoms; alkinyl with 2-5 carbon atoms; phenyl; cycloalkyl with 3-8 carbon atoms; halogen; ##STR4## wherein R=H; alkyl with 1-5 carbon atoms; alkenyl or alkinyl with 2-5 carbon atoms; cycloalkyl with 3-8 carbon atoms; phenyl;The chloroacetanilide derivatives are useful in combatting infestations of infesting monocotyledons and dicotyledons during pre-emergence, by spreading the chloroacetanilide derivative on the soil adjacent thereto in quantities ranging from 0.25 kg/ha upwards.Type: GrantFiled: February 7, 1978Date of Patent: September 23, 1980Assignee: Montedison S.p.A.Inventors: Roberto Colle, Franco Gozzo, Giovanni Camaggi, Giorgio Siddi
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Patent number: 4220795Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.Type: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt