Aldehyde Or Ketone Group In Acid Moiety Patents (Class 560/174)
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Patent number: 5646098Abstract: The invention relates to novel compositions comprising ene and free radical adducts of unsaturated and saturated hydrocarbons, and acyclic and cyclic vicinal polycarbonyl compounds such as diethyl ketomalonate and indantrione. The adducts are reacted with nucleophiles such as amines, electrophiles such as anhydrides and esters, and metal ions. Post-products are obtained via reaction of said products with capping reagents such as boric acid. Compositions containing said adducts, products and post-products include oleaginous substances such as fuels and lube oils.Type: GrantFiled: May 13, 1994Date of Patent: July 8, 1997Assignee: Exxon Chemical Patents IncInventor: Stanley J. Brois
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Patent number: 5627288Abstract: Disclosed are 3,7-dimethyl-4-oxo-7-octenoic acid and its alkyl esters which are intermediates for producing a fragrance, rosefuran and which are represented by: ##STR1## where R is H or a lower alkyl. The compounds [1] are obtained by reacting 2-methyl-3-alkoxycarbonylpropionic acid halide and 3-methyl-3-butenylmagnesium halide. The octenoic acid [1] is treated with acetic anhydride under heat in the presence of an acidic catalyst to give 3,7-dimethyl-2,6-octadien-4-olide. The olide is reduced in an ordinary manner to give rosefuran.Type: GrantFiled: March 11, 1996Date of Patent: May 6, 1997Assignee: Toyotama Perfumery Co., Ltd.Inventors: Hidemichi Fukawa, Masamichi Nishitani, Mitsuo Chiba, Ruriko Murakami
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Patent number: 5610314Abstract: A process is provided for preparing dioxolenone derivatives of the structure ##STR1## wherein R is alkyl or aryl and R.sub.3 is CO.sub.2 R.sub.2 (where R.sub.2 is alkyl or arylalkyl such as benzyl, diphenylmethyl or para-methoxybenzyl). Intermediates produced in the above process are also provided as well as a method for preparing squalene synthetase inhibitors employing such intermediates.Type: GrantFiled: April 3, 1995Date of Patent: March 11, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Peter T. W. Cheng, Chong-Oing Sun, Michael A. Poss
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Patent number: 5599813Abstract: Thiazolopyrimidine derivatives represented by the formula ##STR1## and salts thereof are provided, which are characterized by a carboxamide residue substituted with R.sup.4 and R.sup.5. The derivatives and salts thereof exhibit antiangiogenic activity and are useful for treatment and cure of diseases, the development of which may be related to angiogenesis, including diabetic retinopathy, various chronic inflammation conditions, growth or metastasis of malignant solid tumors, rheumatism and psoriasis.Type: GrantFiled: April 1, 1994Date of Patent: February 4, 1997Assignee: Daiichi Pharmaceutical Co., Ltd.Inventors: Hiroo Matsumoto, Noriko Tanaka, Kiyoshi Nakayama, Haruko Chatani, Michio Iwahana
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Patent number: 5569778Abstract: A process for preparing a fluorine-containing dicarbonyl compound of the formula: R.sup.1 COCFR.sup.2 COR.sup.3 in which R.sup.1 is a hydrogen atom, or a substituted or unsubstituted alkyl or aryl group; R.sup.2 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted alkyl or aryl group; and R.sup.3 is a hydrogen atom, or a substituted or unsubstituted alkyl, aryl, alkoxy or aryloxy group, provided that at least two of R.sup.1, R.sup.2 and R.sup.3 may together form a part of a cyclic structure with or without a hetero atom, by reacting a dicarbonyl compound of the formula: R.sup.1 COCHR.sup.2 COR.sup.3 in which R.sup.1, R.sup.2 and R.sup.3 are the same as defined above with fluorine (F.sub.2) in at least one solvent selected from the group consisting of halogenated hydrocarbons having 1 to 5 carbon atoms and nitrile compounds, or in a solvent in the presence of a salt, or an acid having pKa of 6 or less.Type: GrantFiled: April 28, 1995Date of Patent: October 29, 1996Assignee: Daikin Industries Ltd.Inventors: Teruo Umemoto, Ginjiro Tomizawa
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Patent number: 5523459Abstract: A process for preparing an .alpha.-keto acid ester (oxo acid) of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, aliphatic alkyl group of 1-6 carbon atoms, phenyl group or benzyl group, and R.sup.2 is an aliphatic alkyl group of 1-6 carbon atoms, which comprises causing an .alpha.-hydroxycarboxylic acid ester of the formula: ##STR2## to react with molecular oxygen in a gaseous phase in the presence of copper phosphate, possibly, mounted on a solid carrier.Type: GrantFiled: March 27, 1995Date of Patent: June 4, 1996Assignee: Ube Industries, Ltd.Inventors: Koichi Hirai, Yasuo Nakamura, Kiyotaka Yoshii, Yasunori Fukuda
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Patent number: 5510510Abstract: Inhibition of farnesyl transferase, which is an enzyme involved in ras oncogene expression, and inhibition of cholesterol biosynthesis, are effected by compounds of the formula ##STR1## their enantiomers, diastereomers, and pharmaceutically acceptable salts, prodrugs, and solvates, wherein:x is --ONR.sup.1 C(O)--, --N(OR.sup.1)C(O)--, --NR.sup.1 C(O)--, --C(O)NR.sup.1 --, --NR.sup.1 S(O.sub.2)--, --C(O)O--, --OC(O)--, --C(O)--, --O--, --NR.sup.1 -- or --(S).sub.q --;Y is --CO.sub.2 R.sup.2, --SO.sub.3 R.sup.2 or --P(O) (OR.sup.2) (R.sup.3);R is alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkenylene or aryl;R.sup.3 is --(O).sub.t R.sup.4 ;R.sup.1, R.sup.2 and R.sup.4 are each independently hydrogen, alkyl, aryl or aralkyl;m and n are each independently 0 or an integer from 1 to 5;p and t are each independently 0 or 1; andq is an integer from 1 to 2.Type: GrantFiled: June 28, 1994Date of Patent: April 23, 1996Assignee: Bristol-Meyers Squibb CompanyInventors: Dinesh V. Patel, Scott A. Biller
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Patent number: 5493025Abstract: A polyfluoro beta-keto ester is prepared by reacting a polyfluoro acid anhydride or a polyfluorocarboxylic acid chloride with a carboxylic acid chloride in the presence of a tertiary amine.Type: GrantFiled: July 27, 1994Date of Patent: February 20, 1996Assignee: Rohm and Haas CompanyInventor: Lois M. Bryman
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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: 5457227Abstract: A novel, overall process for the preparation of a compound of the formula I: ##STR1## where R.sup.1 and R.sup.2 are each independently hydrogen, an alkyl group, a cycloalkyl group, an aryl group or, taken together with the carbon atom to which they are attached, form a cycloalkyl group; andR.sup.3 is hydrogen, an alkyl group, or an aryl group, or salts thereof, useful as intermediates in the preparation of HMG-CoA reductase inhibitors; novel methods within the overall process; and novel intermediates produced by those methods.Type: GrantFiled: October 8, 1993Date of Patent: October 10, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: John K. Thottathil, Yadagiri Pendri, Wen-Sen Li, David R. Kronenthal
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Patent number: 5457225Abstract: Disclosed is a process for the preparation of a 5-hydroxy-3-ketoester derivative of the formula: ##STR1## in which R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, and R.sup.2 represents an alkyl group or an aryl group, which comprises causing the reaction of an aldehyde compound of the formula R.sup.1 CHO in which R.sup.1 has the meanings as defined above and diketene in the presence of a metal compound selected from a titanium or aluminum compound having at least one group of --OR.sup.3 in which R.sup.3 represents an alkyl group or an aryl group. Further, a process for the preparation of an optically active substance of the 5-hydroxy-3-ketoester derivative causing the reaction of the above compounds in the presence of the metal compound and optically active Schiff base or a complex compound obtained by reacting the metal compound with the optically active Schiff base, also is disclosed.Type: GrantFiled: September 7, 1994Date of Patent: October 10, 1995Assignee: Ube Industries Ltd.Inventors: Nobuki Oguni, Masahiko Hayashi, Katsumasa Harada, Akio Matsushita
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Patent number: 5453464Abstract: This invention provides the use and preparation of certain 2,2'-diacetyl-bisacetoacetates and bis(beta-ketoesters). These compounds are useful in coating formulations as crosslinkers in conjunction with polyester, acrylic and/or other hydroxylated resins to provide coatings that cure at about 100.degree. and 175.degree. C. Certain combinations of these crosslinkers and resins cure at unusually low temperatures and provide films with good combinations of flexibility, hardness and adhesion.Type: GrantFiled: April 28, 1994Date of Patent: September 26, 1995Assignee: Eastman Chemical CompanyInventors: J. Stewart Witzeman, Allen L. Crain
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Patent number: 5446158Abstract: A process is described for the total synthesis of the macrolide immunosuppressant, FK-506, and important tricarbonyl process intermediates thereof. The tricarbonyl intermediates can be produced by the mild oxidation of 2,3-dihydroxy carboxylate compounds containing olefin moieties.Type: GrantFiled: October 12, 1990Date of Patent: August 29, 1995Assignee: Merck & Co., Inc.Inventors: Todd K. Jones, Sander G. Mills, David Askin, Robert A. Reamer, Richard Desmond, David M. Tschaen, Ralph P. Volante, Ichiro Shinkai
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Patent number: 5434281Abstract: Process for the stereospecific synthesis of leukotriene B.sub.4 (LTB.sub.4) of 6Z, 8E, 10E configuration of formula ##STR1## in which a dibenzoate triether is prepared which is subjected to a reductive elimination according to the diagram ##STR2## so as to obtain a triether which is converted in order to obtain the leukotriene B.sub.4.Type: GrantFiled: May 31, 1994Date of Patent: July 18, 1995Assignee: L'OrealInventors: Guy Solladie, Guy Stone, Antonio Urbano-Pujol, Jean Maignan
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Patent number: 5420335Abstract: Novel parenteral nutrient compositions are disclosed. These compositions are sterile aqueous solutions containing an effective amount of at least one glycerol bisacetoacetate of the formula: ##STR1## wherein one R group is hydrogen, and two R groups are --COCH.sub.2 COCH.sub.3). These compositions are useful as a substitute for glucose in intravenous feeding.Type: GrantFiled: September 30, 1993Date of Patent: May 30, 1995Inventors: Ronald H. Birkhahn, Robert J. Clemens, John C. Hubbs
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Patent number: 5393764Abstract: The compounds of the present invention comprise substituted phenolic thioethers represented by the formula ##STR1## wherein: R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl or phenyl; R.sup.3 represents hydrogen or alkyl; X represents --(CH.sub.2).sub.w --B--(CH.sub.2).sub.y -- wherein B represents O, S, or CH.sub.2 and w and y can each independently be an integer from 0 to 3 with the proviso that the sum of w+y is equal to or less than 3; A represents O or S(O).sub.n wherein n is 0, 1 or 2; p is an integer from 1 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl of 1 to 4 carbon atoms; NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl and R.sup.6 is hydrogen, alkyl, heterocyclealkyl in which the hetercyclic ring may optionally be substituted; cycloalkyl; substituted cycloalkyl; phenyl; substituted phenyl; phenylalkyl; or substituted phenylalkyl; or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or R is (CH.Type: GrantFiled: August 25, 1993Date of Patent: February 28, 1995Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5391811Abstract: .alpha.-fluoro-.beta.-dicarbonyl compounds are prepared by reacting a halogenated dicarbonyl compound at temperatures of 20.degree. to 100.degree. C. with an addition product of hydrogen fluoride and a trialkylamine. This process is easy to carry out in technical terms and can also be carried out on a large scale.Type: GrantFiled: November 3, 1993Date of Patent: February 21, 1995Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5385913Abstract: Compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein Q, X and R are as defined below. The compounds of formula I are broad spectrum mammalian antibacterial agents and exhibit favorable selectivity against procaryotic cells.Type: GrantFiled: March 26, 1992Date of Patent: January 31, 1995Assignee: Pfizer Inc.Inventor: Paul R. McGuirk
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Patent number: 5364970Abstract: A process for the hydroformylation of .alpha.-substituted, .alpha.-.beta.-unsaturated carbonyl compounds in the presence of a catalyst system based ona) a source of rhodium cations andb) a source of ligands of the formula MR.sub.1 R.sub.2 R.sub.3 wherein M represents a phosphorus, arsenic or antimony atom and R.sub.1, R.sub.2, and R.sub.3 independently represent substituted or non-substituted hydrocarbyl groups, together containing not more than 24 carbon atoms. At least one of R.sub.1, R.sub.2, and R.sub.3 is linked to M via an aliphatic carbon atom. The process is selective for the generation of alpha reaction products.Type: GrantFiled: January 25, 1994Date of Patent: November 15, 1994Assignee: Shell Oil CompanyInventors: Eit Drent, Eric Kragtwijk
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Patent number: 5344939Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.Type: GrantFiled: March 11, 1993Date of Patent: September 6, 1994Assignee: Prototek, Inc.Inventor: James T. Palmer
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Patent number: 5336484Abstract: Disclosed are x-ray contrast compositions for oral or retrograde examination of the gastrointestinal tract comprising a polymeric material capable of forming a coating on the gastrointestinal tract and an x-ray producing agent of the formula ##STR1## and methods for their use in diagnostic radiology of the gastrointestinal tract wherein ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene or lower-alkoxy-carbonyloxy,n is 1-5;y is 0-4; andw is 1-4.Type: GrantFiled: March 31, 1993Date of Patent: August 9, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5336800Abstract: Oxamides useful as dye intermediates have the formula ##STR1## where R.sup.1 and R.sup.2 are independently of each other hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,X is hydroxyl, nitro or a radical of the formula --NR.sup.3 R.sup.4, where R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkanoyl and R.sup.4 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,Z is C.sub.2 -C.sub.8 -alkylene, substituted or unsubstituted phenylene or substituted or unsubstituted naphthylene, or X--Z and R.sup.1 are, together with the nitrogen atom joining them together, the radical of the formula ##STR2## where R.sup.3 is as defined above,L is a bridge member andY is vinyl or a radical of the formula --C.sub.2 H.sub.4 --A, where A is hydroxyl or a group which is detachable under alkaline reaction conditions.Type: GrantFiled: January 4, 1993Date of Patent: August 9, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Siegel, Manfred Patsch, Knut Kessel
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Patent number: 5318769Abstract: Disclosed are contrast agents of the formula ##STR1## contained in aqueous compositions and methods for their use in diagnostic radiology of the gastrointestinal tract whereinX= ##STR2## Z=H, halo, C.sub.1 -C.sub.20 alkyl, cycloalkyl, lower alkoxy, cyano, where the alkyl and cycloalkyl groups can be substituted with halogen or halo-lower-alkyl groups;R=C.sub.1 -C.sub.25 alkyl, cycloalkyl, aryl, or halo-lower-alkyl, optionally substituted with halo, fluoro-lower-alkyl, lower-alkoxy, hydroxy, carboxy or lower-alkoxy carbonyl, lower-alkenyl, lower-alkynyl, lower-alkylene, lower-alkoxy-carbonyloxy;n=1-5;y=0-4; andw=1-4in an aqueous pharmaceutically acceptable carrier.Type: GrantFiled: March 31, 1993Date of Patent: June 7, 1994Assignee: Sterling Winthrop Inc.Inventors: Edward R. Bacon, Sol J. Daum, Kimberly G. Estep, Kurt A. Josef, Brent D. Douty, Carl R. Illig
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Patent number: 5274178Abstract: Terpene derivatives of formula I, their preparation and their use. In formula I, R represents a hydrogen atom or an alkanoyl radical and R' represents a hydrogen atom or an aliphatic hydrocarbon radical.Type: GrantFiled: December 22, 1992Date of Patent: December 28, 1993Assignee: Rhone-Poulenc SanteInventor: Claude Mercier
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Patent number: 5274051Abstract: Novel carbonyl containing compositions are prepared by contacting, in the presence of a free radical initiator, a first compound selected from the group consisting of saturated hydrocarbons, substituted saturated hydrocarbons, polymers and mixtures thereof with a carbonyl containing compound or mixtures thereof having the structure: ##STR1## where X and Y are independently selected from OH, OR.sub.1, NR.sub.1 R.sub.2 and R.sub.1 wherein R.sub.1 and R.sub.2 are selected independently from the group consisting of aryl radicals or alkyl radicals of from 1 to 18 carbon atoms.Type: GrantFiled: November 5, 1992Date of Patent: December 28, 1993Assignee: Exxon Research & Engineering CompanyInventors: Stanley J. Brois, Jacqueline Ogletree
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Patent number: 5260424Abstract: Silylketene acetals, including "living" GTP polymers, are acylated or sulfonylated in the presence of GTP-effective catalysts with acyl or sulfonyl compounds to produce .beta.-ketoesters or .beta.-sulfonylesters; polymeric products, including capped, coupled and chain-extended polymers and block copolymers can be prepared.Type: GrantFiled: February 3, 1992Date of Patent: November 9, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Gordon M. Cohen, Hans J. Reich
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Patent number: 5245062Abstract: Ketone compounds are obtained by rearrangement of epoxides in the presence of iodide ions providing quaternary ammonium and phosphonium salts, optionally in admixture with alkali metal or alkaline earth metal iodides, are used as the rearrangement catalysts.Type: GrantFiled: July 20, 1992Date of Patent: September 14, 1993Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Gerhard Stoll, Elke Grundt
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Patent number: 5227515Abstract: There is disclosed a process for producing lower alkyl 2-keto-L-gulonate which comprises reacting 2-keto-L-gulonic acid with a lower alcohol in the presence of an acid, and simultaneously distilling off the resulting water together with the lower alcohol while continuously introducing a lower alcohol. By using the lower alkyl 2-keto-L-gulonate thus produced, L-ascorbate can be prepared in high purity and high yield.Type: GrantFiled: September 30, 1992Date of Patent: July 13, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Masaki Sokukawa, Yoshihiro Yasumura, Kaoru Makino
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Patent number: 5210272Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.Type: GrantFiled: August 14, 1991Date of Patent: May 11, 1993Assignee: Prototek, Inc.Inventor: James T. Palmer
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Patent number: 5210315Abstract: A process for producing an .alpha.-hydroxyketone represented by formula (I): ##STR1## wherein R.sup.1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or an alkoxycarbonyl group; and R.sup.2 and R.sup.3 each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group, provided that they do not simultaneously represent a hydrogen atom; or a pair of R.sup.1 and R.sup.2, a pair of R.sup.1 and R.sup.3, or a pair of R.sup.2 and R.sup.3 is taken together to form a ring; and the pair of R.sup.1 and R.sup.2 and the pair of R.sup.2 and R.sup.3 may form a ring simultaneously, is disclosed, comprising reacting a compound represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, with an oxidizing agent in the presence of a ruthenium compound and water. .alpha.-Hydroxyketones useful as physiologically active substances are produced with good selectivity and in high yield.Type: GrantFiled: October 18, 1991Date of Patent: May 11, 1993Assignee: Takasago International CorporationInventors: Takao Saito, Hidenori Kumobayashi, Shunichi Murahashi
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Patent number: 5202467Abstract: Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:ONOR.sup.4 [IV]wherein R.sup.4 is H, alkyl, halogen or SO.sub.3 H to give 7-halo-2-hydroxyiminoheptanoic acid ester [III]: ##STR3## wherein R.sup.1 and X are the same as above, followed by reacting the product with aldehyde or ketone; and intermediates therefor, and process for preparing said intermediates. Said haloketo acid derivatives are useful as intermediate for synthesis of cilastatin, which is useful as medicament, especially as dehydropeptidase inhibitor.Type: GrantFiled: February 7, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Takaharu Ikeda, Seiichi Kai, Masayoshi Minai
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Patent number: 5200553Abstract: Biologically active carboxylic acid esters which promote antitumor or immune response are selected from the group consisting of compounds having formulas (I), (II) and (III):XCH.sub.2 --CHX--CHX--C(.dbd.O)--O--Z (I)CH.sub.3 --CO--CH.sub.2 --C(.dbd.O)--O--Z (II)CH.sub.3 --CH.sub.2 --CO--C(.dbd.O)--O--Z (III)wherein X is H, or one X only may be OH; Z is --CHR--O--(O.dbd.Type: GrantFiled: July 25, 1988Date of Patent: April 6, 1993Assignee: Kupat Holim Health Insurance Institution of the General Federation of LaborInventors: Abraham Nudelman, Matitiahu Shaklai, Ada Rephaeli
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Patent number: 5194671Abstract: The invention relates to a process for the preparation of .beta.-ketocarboxylic acid esters of the general formula ##STR1## in which R.sup.1 is an alkyl radical having 1 to 4 C atoms, R.sup.2 is an alkyl radical or alkenyl radical having 2 to 15 C atoms or a phenyl radical and R.sup.3 is hydrogen or an alkyl or alkenyl radical having 1 to 6 C atoms, characterized in that acetocarboxylic acid esters of the general formula ##STR2## in which R.sup.1 and R.sup.3 are as defined, are reacted with calcium hydroxide or calcium oxide in the presence of an organic solvent and in the absence of water, the calcium chelate complexes formed are acylated with carboxylic acid chloride and the products are then cleaved with aqueous ammonium salt solution to form the .beta.-ketocarboxylic acid esters of formula (I).The .beta.Type: GrantFiled: March 11, 1992Date of Patent: March 16, 1993Assignee: Wacker-Chemie GmbHInventor: Josef Meier
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Patent number: 5166373Abstract: The present invention provides novel acyclic terpenes of the formula: ##STR1## which are useful as intermediates for the industrially advantageous production of sarcophytol A.Type: GrantFiled: December 30, 1991Date of Patent: November 24, 1992Assignee: Mitsubishi Kasei CorporationInventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
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Patent number: 5162552Abstract: A process for the preparation of 4-acetals of butene-1,4-dial of the formula ##STR1## where R is an alkyl, alkenyl, cycloalkyl or aralkyl radical of 1 to 12 carbon atoms which may contain alkoxy groups, or the two radicals R together form an alkylene or alkenylene radical of 2 to 10 carbon atoms which may contain alkoxy groups, and R.sup.1 is an alkyl, alkenyl or alkynyl radical of 1 to 12 carbon atoms which may be substituted by cycloaliphatic, aromatic or heterocyclic radicals or by hydroxyl, ether, thioether, acyl, alkylamino, carboxyl or carbalkoxy groups, or is an unsubstituted or substituted aryl radical or an alkoxy, alkylthio or acyloxy group, wherein a glyoxal monoacetal of the formula ##STR2## is reacted with an aldehyde of the formulaR.sup.1 --CH.sub.2 --CHO IIIat up to 150.degree. C., and novel acetals of butene-1,4-dial.Type: GrantFiled: April 30, 1987Date of Patent: November 10, 1992Assignee: BASF AktiengesellschaftInventors: Franz Merger, Rolf Fischer, Hans Horler, Juergen Frank
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Patent number: 5144057Abstract: 3-Oxocarboxylic acid esters are produced by acylation of the magnesium enolates of acetoacetic acid esters with carboxylic acid chlorides and cleavage of the acetyl group from the acylacetoacetic acid esters formed as the intermediate product. The yields and purity of the products are considerably improved by adding a tertiary amine during the acylation.Type: GrantFiled: October 11, 1991Date of Patent: September 1, 1992Assignee: Lonza Ltd.Inventor: Martin Eyer
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Patent number: 5142019Abstract: An oligomer of the structure: ##STR1## wherein R.sub.1 is hydrogen, lower alkyl having 1 to 5 carbon atoms or hydroxyalkyl having 1 to 5 carbon atoms; R.sub.2 and R.sub.3 are the same or different radicals selected from hydrogen, alkyl having 1 to 5 carbon atoms or one of R.sub.2 and one of R.sub.3 radicals joined together with the carbon atom to which they are attached to form cycloalkyl; R.sub.5 is hydrogen or methyl; R.sub.6 is alkyl having 1 to 6 carbon atoms, cycloalkyl of 5 to 6 carbon atoms and hydroxyalkyl of 2 to 6 carbon atoms. The oligomers can be used as reactive components with other materials containing co-reactive functional groups selected from hydroxyl, carboxylic acid, carboxylic acid anhydride and isocyanate. Reactive compositions can be formed which are useful as resinous film formers in coating applications which can be cured without the generation of formaldehyde.Type: GrantFiled: October 3, 1991Date of Patent: August 25, 1992Assignee: PPG Industries, Inc.Inventors: Padmanabhan Sundararaman, Rudolf Maska, Cynthia L. Verardi
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Patent number: 5138107Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.Type: GrantFiled: July 12, 1991Date of Patent: August 11, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5132475Abstract: A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of a quaternary ammonium fluoride catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 NF where R.sup.1, R.sup.2, and R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms.Type: GrantFiled: July 12, 1991Date of Patent: July 21, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Yoel Sasson
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Patent number: 5118833Abstract: The invention provides a novel process for produing .alpha. -keto-carboxylic acid esters that are useful as intermediates for the preparation of pharmaceutical drugs in high yield by oxidizing .alpha. -hydroxycarbocylic acid esters with hypochlorous acid in the presence of nitroxy radical.Type: GrantFiled: June 14, 1990Date of Patent: June 2, 1992Assignee: Kuraray Company, Ltd.Inventors: Toshiki Mori, Shigeaki Suzuki, Takashi Onishi, Kazuo Yamamoto
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Patent number: 5110869Abstract: Silylketene acetals, including "living" GTP polymers, are acylated or sulfonylated in the presence of GTP-effective catalysts with acyl or sulfonyl compounds to produce .beta.-ketoesters or .beta.-sulfonylesters; polymeric products, including capped, coupled and chain-extended polymers and block copolymers can be prepared.Type: GrantFiled: August 21, 1990Date of Patent: May 5, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventors: Gordon M. Cohen, Hans J. Reich
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Patent number: 5101070Abstract: A process for preparing valproic acid which comprises:(I) producing a 2,2-dipropyl acetoacetic acid ester from an acetoacetic acid ester,(II) deacetylating the 2,2-dipropyl acetoacetic acid ester with an alcohol to give a valproic acid ester, and(III) hydrolyzing the valproic acid ester. In the process of the present invention, valproic acid can be prepared in a high yield as not less than 85% by mole and by-products such as .alpha.-propyl-.beta.-ethyl acrylic acid and its esters which cannot be easily separated from valproic acid, are not entirely produced.Type: GrantFiled: July 5, 1988Date of Patent: March 31, 1992Assignee: Nippon Gohsei Kagaku Kogyo Kabushiki KaishaInventors: Toshio Yamamoto, Akira Yamashita, Noriyoshi Numoto
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Patent number: 5093532Abstract: Halogenomethylketones are prepared from nitro compounds by treating the latter in alcoholic solution with sodium alkoxide or potassium alkoxide, cooling to a temperature in the range -10.degree. to -100.degree. C. and then allowing the mixture to react with ozone at -10.degree. to -100.degree. C. The process is particularly suitable for the preparation of 1,1,1-trifluoroacetone from 1,1,1-trifluoro-2-nitropropane.Type: GrantFiled: July 31, 1991Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Jens Lorentzen
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Patent number: 5053527Abstract: The invention provides an improved process for the manufacture of alkyl pyruvates having general formula (I):CH.sub.3 --CO--COOR (I)where R represents a C.sub.1 to C.sub.8 alkyl radical, by controlled oxidation of the corresponding alkyl lactate.The process is characterized in that the controlled oxidation is carried out using an aqueous hydrogen peroxide solution in the presence of catalytic quantities of bromium.Type: GrantFiled: May 18, 1990Date of Patent: October 1, 1991Assignee: Societe Francaise HoechstInventors: Yani Christidis, Jean-Claude Vallejos
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Patent number: 5049698Abstract: A novel process for producing 2-chloro-1,3-diketo compounds of the formula ##STR1## wherein Q is an amino, substituted amino or hydrocarbyloxy group, e.g., --OCH.sub.3, wherein the 1,3-diketo precursor in solution in a low boiling alcohol is neulized in a special chlorinator with chlorine or a mixture of nitrogen and chlorine, and wherein the chlorination of the nebulized precursor solution takes place extremely rapidly at relatively high temperatures in a chlorination zone, the product being recovered by condensation on the cooled chlorinator walls and stripping of the alcohol solvent. A representative product is 2-chloro-N,N-dimethylacetoacetamide (2CDMAA), a useful intermediate for the production of insecticides, drugs, dyes and other complex compounds.Type: GrantFiled: April 24, 1986Date of Patent: September 17, 1991Assignee: Eastman Kodak CompanyInventor: Gordon C. Newland
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Patent number: 5032323Abstract: Epoxides are isomerized to ketones by contacting the epoxides with a catalyst effective amount of a substantially fully hydrogenated palladium catalyst at a temperature of from about 200.degree. C. to about 300.degree. C. while contacting the epoxides with hydrogen at a partial pressure of equal to or less than one atmosphere.Type: GrantFiled: March 28, 1990Date of Patent: July 16, 1991Assignee: Henkel Research CorporationInventor: Michael J. Virnig
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Patent number: 5026898Abstract: A process for regioselectively preparing phosphorylated cyclitols, in particular phosphorylated inositols such as myo-inositol 1,4,5-tris(phosphate) and muo-inositol 1,3,4,5-tetrakis(phosphate). Novel cyclitols produced by means of this process are also described.Type: GrantFiled: January 31, 1990Date of Patent: June 25, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Frank W. Hobbs, James L. Meek
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 5010189Abstract: The invention relates to novel processes and intermediates for the preparation of 5-amino-4-hydroxyvaleric acid derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl or the radical of a natural amino acid, R.sup.2 represents hydrogen, optionally substituted alkyl, cycloalkyl, cycloalkyl-lower alkyl, aryl, aryl-lower alkyl, amino, hydroxy, mercapto, sulphinyl, sulphonyl or the radical of a natural amino acid, and R.sup.3 represents optionally substituted hydroxy or amino, by sigmatropic rearrangement of a suitable allyl ester, halolactonization of the resulting .gamma.,.delta.-unsaturated acid or of a suitable derivative thereof, exchange of halogen for a nitrogen-containing nucleophile, opening of the lactone ring and freeing of the amino group. Compounds of the formula I are starting materials for the preparation of renin-inhibitors which have an anti-hypertensive action.Type: GrantFiled: October 24, 1989Date of Patent: April 23, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4997976Abstract: Compositions for parenteral nutrition comprising a nutritionally effective amount of a compound of the following formula: ##STR1## R.sup.2 is methyl or ethyl, and R.sup.3 and R.sup.4 are ##STR2## or H, and X is --C.dbd.O or --HC--OH,or a compound of the following formula: ##STR3## wherein R.sup.2 is methyl or ethyl, andX is --C.dbd.O or --C--OH,or mixtures thereof in association with a carrier.Type: GrantFiled: November 15, 1988Date of Patent: March 5, 1991Inventors: Henri Brunengraber, Sylvain Desrochers, Bernard R. Landau