Oxy, Aldehyde Or Ketone Group In Acid Moiety Patents (Class 560/170)
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Patent number: 5134231Abstract: An amino acid compound of the formula: ##STR1## wherein R is a lower alkyl group, R.sub.1 is a hydrogen atom or a protecting group for carboxyl, R.sub.2 is a hydrogen atom, a protecting group for amino, an optionally substituted allyl group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group or an aryl group), a beta-hydroxyethyl group in which the hydroxyl group is optionally protected, a formylmethyl group in which the formyl group is optionally protected, a carboxymethyl group in which the carboxyl group is protected or a 2-furylmethyl group and X is an optionally protected carboxyl group, a hydroxymethyl group in which the hydroxyl group is optionally protected or a substituted mercaptomethyl group of the formula:--CH.sub.2 SR.sub.5(wherein R.sub.5 is an aryl group or an ar(lower)alkyl group), which is a useful intermediate in the synthesis of 1-alkylcarbapenem compounds.Type: GrantFiled: January 17, 1991Date of Patent: July 28, 1992Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Makoto Sunagawa, Yoshihito Nozaki, Akira Sasaki, Haruki Matsumura
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Patent number: 5118683Abstract: Compounds of the formula I ##STR1## wherein R.sup.5 represents C.sub.1 to C.sub.6 -alkyl or the group --(CH.sub.2).sub.n --Z--(CH.sub.2).sub.m --Ar;Z represents O, S or --CH.sub.2 --;n represents an integer of 1 to 8;m represents zero or an integer of 1 to 8;one of R.sup.1 and R.sup.2 represents the group ##STR2## and the other represents hydrogen or R.sup.7 CO--; R.sup.7 is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl, aryl, heteroaryl, --N(R.sup.9 R.sup.10), or R.sup.11 O--; R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are each independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl and Ar.sup.1 ; R.sup.6 and R.sup.11 are each independently C.sub.1 -C.sub.8 alkyl; Ar and Ar.sup.1 are each independently selected from the group consisting of phenyl or phenyl substituted by one or two substituents selected from the group consisting of R.sup.12, R.sup.13 O--; R.sup.14 S(O).sub.x --, R.sup.15 CO--, (R.sup.16 R.sup.17)NCO--, F, Cl, Br, I, NO.sub.2, CF.sub.3, CN, or phenyl; R.sup.12, R.sup.13, R.sup.Type: GrantFiled: June 13, 1990Date of Patent: June 2, 1992Assignee: Schering CorporationInventors: David J. Blythin, Ho-Jane Shue
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Patent number: 5113009Abstract: A cyclical process for producing and isolating a mineral acid salt of an amino acid methyl ester in high purity and yield from the reaction solution produced by esterifying an amino acid with methanol in methanol in the presence of a mineral acid, by cooling the resulting reaction solution to precipitate crystals of the mineral acid salt; filtering the crystals;drying the isolated wet crystals or washing with another organic solvent; and recycling the filtrate for reuse in the esterification reaction.Type: GrantFiled: December 26, 1989Date of Patent: May 12, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Masanobu Ajioka, Chojiro Higuchi, Takeshi Oura, Toshio Katoh, Akihiro Yamaguchi
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Patent number: 5105008Abstract: Betaines are produced in solid form by reacting a tert-amine with an alkyl haloalkanoate and hydrolyzing the resultant quaternary ammonium ester when the tert-amine/alkyl haloalkanoate reaction is conducted in a liquefied gas as the solvent and the hydrolysis is conducted in a liquefied gas solvent or a polar aprotic solvent in which the betaine is substantially insoluble. In a preferred embodiment, the tert-amine is an N-alkyldimethylamine, the haloalkanoate is ethyl chloroacetate, and the liquefied gas is carbon dioxide.Type: GrantFiled: July 1, 1991Date of Patent: April 14, 1992Assignee: Ethyl CorporationInventors: Joe D. Sauer, Kim R. Smith, James E. Borland, Jeffrey W. Perine
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Patent number: 5103048Abstract: The new compounds have the formula below ##STR1## in which R.sub.f is a perfluoroalkyl radical having 4 to 20 carbon atoms,x is 1 to 4,y is 1 to 10,X is Br, Cl or I, andR.sup.1 and R.sup.2 are hydrogen or a C.sub.1 to C.sub.4 -alkyl radical or a water-solubilizing aliphatic radical, with the proviso that at least one of the two substituents R.sup.1 and R.sup.2 is a water-solubilizing aliphatic radical.The surface-active compounds described are prepared by reacting a suitable epoxide with a suitable amine. They are used in particular for the preparation of foaming agents.Type: GrantFiled: December 26, 1990Date of Patent: April 7, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Knaup, Frank Wehowsky, Norbert Schmitt
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Patent number: 5098999Abstract: 3,4-Dihydroxyphenylalanine wherein the amino group is protected with a 9-fluorenylmethyloxycarbonyl group, or a derivative thereof can be produced by reacting 3,4-dihydroxyphenylalanine with a boron compound or phosphorus compound to stabilize the hydroxyl groups, followed by introduction of a 9-fluorenylmethyloxycarbonyl group thereinto.Type: GrantFiled: August 17, 1990Date of Patent: March 24, 1992Assignee: Hitachi Chemical CompanyInventors: Yasuo Yamamoto, Yasuo Miyadera
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Patent number: 5095114Abstract: The invention relates to a process for the enantiomer-selective preparation of .gamma.-keto-.delta.-amino acid derivatives of the formula I ##STR1## characterized in that a compound of the formula II ##STR2## is converted, using a trialkylchlorosilane, into a compound of the formula III ##STR3## this compound is then reacted with a diazoacetate of the formula N.sub.2 CH.sub.2 COOR.sup.4 (R.sup.4 .noteq.H) to give a cyclopropane compound of the formula IV ##STR4## and then the compound IV is converted, by ring-opening and removal of the silyl groups, and where appropriate saponification, into the compound of the formula I, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 having the meanings indicated in claim 1.Type: GrantFiled: June 19, 1990Date of Patent: March 10, 1992Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Hans-Eckart Radunz, Hans U. Reissig
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Patent number: 5095133Abstract: Aminomethylene compounds of the formula ##STR1## can be prepared by reaction of C-H acid compounds of the formula ##STR2## with salts of the formula ##STR3## in the presence of alkoxides of the formulaM.sup.1 OR.sup.10 (IV)where the radicals R.sup.1 to R.sup.4, R.sup.7, R.sup.10, X.sup.- and M.sup.1 have the meaning mentioned in the description.Type: GrantFiled: July 16, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Helmut Kraus
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Patent number: 5089492Abstract: Acylamino carboxylic acid derivatives corresponding to the formula I ##STR1## in which the groups R.sup.1, R.sup.2, R.sup.3, Z.sup.1 and Z.sup.2 represent functional groups specified in the claims. The acylamino carboxylic acid derivatives have valuable pharmacological properties which, in particular, favorably influence nitrogen metabolism. The compounds are useful as active ingredients in pharmaceutical and/or dietetic compositions for treatment or prevention of nitrogen metabolism disturbances in large mammals caused, for example, by liver or kidney damage.Type: GrantFiled: May 24, 1990Date of Patent: February 18, 1992Assignees: Kali-Chemie AG, Pfrimmer Kabi GmbH & Co. KGInventors: Klaus Gerling, Henning Heinemanmn, Andreas Meier, Klaus Langer
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Patent number: 5089043Abstract: A heterocyclic oxy-phenoxyacetic acid derivative of the formula: ##STR1## , or its salt, which is useful as a herbicide.Type: GrantFiled: November 6, 1990Date of Patent: February 18, 1992Assignee: Shionogi & Co., Ltd.Inventors: Yoshio Hayase, Kohei Matsumoto, Kazuo Kamei, Kinya Ide, Toshio Takahashi
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Patent number: 5079260Abstract: The present invention relates to a method of treating an inflammatory condition, and to compounds and composition suitable for use in such a method, which compounds have the Formula: ##STR1## wherein: X is methylene, ethylene, ethyleneoxy, or oxygen;Q is ##STR2## where C' is a residue of a lipophilic amino acid, and Y is --CO.sub.2 H, --CH.sub.2 OH, --CONR.sub.1 R.sub.2, or --CO.sub.2 R.sub.1 where R.sub.1 and R.sub.2 hydrogen, alkyl, or aryl;R.sub.3 and R.sub.4 are, independently, hydrogen, alkyl or aryl; andA and B are, independently, hydrogen, fused phenyl, alkyl, aryl, alkaryl, aralkyl, alkoxy, alkoxyalkyl, halogen, or nitro;or pharmaceutically acceptable salts thereof.Type: GrantFiled: May 29, 1990Date of Patent: January 7, 1992Assignee: Nova Pharmaceutical CorporationInventors: Moshe Weitzberg, Ronald Burch, Barry Shearer
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Patent number: 5068397Abstract: Tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R.sub.f --E.sub.n --X--CH.sub.2).sub.3 CCH.sub.2 OH prepared from halogenated neopentyl alcohols and thiols of the formula R.sub.f --E.sub.n --SH, amines of the formula R.sub.f --E.sub.n --NH--R, alcohols of the formula R.sub.f --E.sub.n --OH, perfluoro-acids or amides, are described. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives, to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R.sub.f -neopentyl alcohol containing three perfluoroalkyl hetero groups.Type: GrantFiled: August 15, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
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Patent number: 5041651Abstract: The present invention relates to an asymmetrically modified borohydride type compound obtained by reacting an optically active amino alcohol represented by the formula, ##STR1## or its salt with an acid with a borohydride compound; its production method; and a method for producing an optically active alcohol derivative useful as fungicides, herbicides or plant growth regulators and represented by the formula, ##STR2## which comprises asymmetrically reducing a ketone compound represented by the formula, ##STR3## with the asymmetrically modified borohydride type compound.Type: GrantFiled: May 2, 1988Date of Patent: August 20, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Kazuhiko Hamada, Toshio Nishioka
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Patent number: 5036155Abstract: Process and intermediates for isopropyl 3S-amino-4-cyclohexyl-2R-hydroxybutyrate and 3S-amino-2R-hydroxy-5-methylhexanoate from R-malic acid. These products are of known utility in the synthesis of certain renin inhibitors.Type: GrantFiled: July 31, 1990Date of Patent: July 30, 1991Assignee: Pfizer Inc.Inventor: Robert W. Dugger
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Patent number: 5025103Abstract: Glycerol aminocarboxylates of the formula ##STR1## where n is from 0 to 10 andR is ##STR2## where L is iminodiacetate, aspartate, glutamate, sarcosinate, glycinate, serinate, hydroxyaspartate, ethanolaminoacetate, diethanolamino, alanate or taurinate andX is hydrogen, an alkali metal, ammonium or substituted ammonium,are prepared by esterifying glycerol or polyglycerols which contain up to 10 glycerol units with maleic anhydride or itaconic anhydride and addition of compound L-H where L is as defined above to the double bonds of the esters, and are used as complexing agents.Type: GrantFiled: January 19, 1990Date of Patent: June 18, 1991Assignee: BASF AktiengesellschaftInventors: Alfred Oftring, Stefan Birnbach, Rolf Fikentscher, Richard Baur, Alexander Kud, Ulrich Goeckel, Johannes Perner
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Patent number: 5023018Abstract: Use of polyhydroxyalkylamine-N,N-dialkylcarboxylic acids or their salts, as builders for detergents and cleaning agents. Compounds of formula ##STR1## where X represents a polyhydroxyalkyl group with 3 to 7 carbon atoms and which may be glycosidically linked to a mono-, di-, or oligosaccharide; and n is 1 to 3, are used as builders for detergents and cleaning agents.Type: GrantFiled: July 21, 1989Date of Patent: June 11, 1991Assignee: Huls AktiengesellschaftInventors: Heike Kelkenberg, Wulf Ruback
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Patent number: 5010105Abstract: Compounds of Formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.Type: GrantFiled: May 9, 1990Date of Patent: April 23, 1991Assignee: Merck & Co., Inc.Inventor: Ta J. Lee
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Patent number: 4990652Abstract: The reaction products of the alpha-halogenated half esters or amides of succinic acid and thiadiazole dimercaptides as new compositions of matter and their use as lubricant additives possessing multifunctional properties such as extreme pressure, antiwear, antioxidant and anticorrosion.Type: GrantFiled: November 21, 1989Date of Patent: February 5, 1991Assignee: Atochem North America, Inc.Inventors: James P. King, Sameeh S. Toukan
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Patent number: 4981992Abstract: A process for preparing an optically active 3-hydroxybutanoic acid represented by formula (I): ##STR1## wherein: R.sup.1 represents a protective group of carboxylic acid, andR.sup.2 represents a hydrogen atom; a lower alkyl group which may be substituted with a halogen atom; a lower alkoxy group; a phenyl group which may be substituted with a lower alkyl group or a lower alkoxy group; or a benzyloxy group which may be substituted with a lower alkyl group or a lower alkoxy group,is disclosed, comprising asymmetrically hydrogenating a 3-oxobutanoic acid ester represented by formula (II): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. The compound of formula (I) which is useful for synthesizing a 4-acetoxyazetidin-2-one derivative, a useful intermediate for obtaining penem antibiotics, can be prepared economically.Type: GrantFiled: November 14, 1989Date of Patent: January 1, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Yoshiki Okeda, Hiroyuki Nagashima, Hidonori Kumobayashi
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Patent number: 4978759Abstract: The process described makes it possible to obtain optically pure 4-amino-3-hydroxycarboxylic acids by means of a series of stereoselective steps. The starting material is an alpha-amino acid in the L or D configuration, with which Meldrum's acid is reacted. The resulting pyrrolone derivative is reduced prior to opening of the pyrrolidine ring. The invention also relates to the new products obtained by the said process and to the pyrrolone derivatives obtained as intermediates.Type: GrantFiled: July 2, 1986Date of Patent: December 18, 1990Assignee: Sanofi, S.A. and Institut National de la Sante et de la Recherche MedicaleInventors: Patrick Jouin, Dino Nisato, Bertrand Castro
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Patent number: 4960923Abstract: The process for preparing a novel product, pure crystalline methyl 2-acryloylamino-2-methoxyacetate, involves reacting pure crystalline, anhydrous acrylamido-glycolic acid in an anhydrous medium with methanol in the presence of hydrogen chloride. This is subsequently neutralized with an alkali metal bicarbonate, and then the mineral salts are filtered off. Finally, pure crystalline methyl 2-acryloylamino-2-methoxyacetate is obtained by taking up the concentrated reaction medium in 1,1,1-trichloroethane under vacuum.Type: GrantFiled: November 2, 1988Date of Patent: October 2, 1990Assignee: Societe Francaise HoechstInventors: Yani Christidis, Christian Sidot
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Patent number: 4959489Abstract: A process is provided for making an N-substituted acrylamide dialkyl acetal, such as acrylamidobutyraldehyde dimethylacetal (ABDA), by blocking the double bond in an acrylic acid ester with a nucleophile, such as methanol, removing excess nucleophile from the blocked ester, aminating the blocked ester with an amino dialkyl acetal in the presence of an aminolysis catalyst but in the absence of any protic solvent, and deblocking the double bond in the product by pyrolysis.Type: GrantFiled: October 2, 1989Date of Patent: September 25, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Andrew F. Nordquist, Robert K. Pinschmidt, Jr.
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Patent number: 4956495Abstract: A process for preparing unsaturated nitrogen containing acids such as acrylamidoglycolic acid utilizes a catalyst free route and low pH conditions. An unsaturated amide such as acrylamide is reacted with an aldehyde acid such as acid in an aqueous environment. The unsaturated nitrogen containing acids are typically produced in solution form and can be utilized as such.Type: GrantFiled: December 18, 1989Date of Patent: September 11, 1990Assignee: GenCorp. Inc.Inventor: Woodrow W. White
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Patent number: 4933475Abstract: Compounds having the formula ##STR1## R.sub.1 is hydrogen, benzyl or alkanoyl, X is C.sub.2-4 alkylene; andZ-W is alkyl, phenylalkyl or pyridylalkyl which can have an oxygen atom as part of the alkyl chain and their use as CNS agents, antidiarrheals and antiemetics. Processes for their preparation and intermediates therefor are described.Type: GrantFiled: February 28, 1989Date of Patent: June 12, 1990Assignee: Pfizer, Inc.Inventors: Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4929755Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and H.sub.2 O or an organic hydroxyl compound to produce an N-acyl-.alpha.-amino acid or ester, respectively, the improvement comprising using as the .alpha.-enamide reactant, an .alpha.-enamide which has a chiral center that is essentially all L or D, thereby producing a reaction mixture containing diastereomeric N-acyl-.alpha.-amino acids or esters having two chiral centers, said mixture having essentially no enantiomeric pairs.Type: GrantFiled: December 19, 1986Date of Patent: May 29, 1990Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4929751Abstract: A vinyl tricarbonyl compound of the formula ##STR1## or its monohydrate of the formula ##STR2## wherein R.sub.1 is a hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, and cycloalkyl with 3 to 7 carbon atoms,R.sub.2 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic,R.sub.3 is hydrogen, halogen, unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl with 3 to 7 carbon atoms, cyano, nitro, or a heterocyclic, andR.sub.4 is unsubstituted or substituted C.sub.1 to C.sub.30 alkyl, unsubstituted or substituted aryl, arylalkyl, cycloalkyl are 3 to 7 carbon atoms. Such vinyl tricarbonyl compound is effective against tumor cells.Type: GrantFiled: October 19, 1987Date of Patent: May 29, 1990Assignee: Yale UniversityInventors: Harry H. Wasserman, Natesan Murugesan, John H. Van Duzer
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Patent number: 4916252Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a 1,3-diketone in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: June 16, 1988Date of Patent: April 10, 1990Assignee: Takasago International CorporationInventors: Noboru Sayo, Takao Saito, Hidenori Kumobayashi, Susumu Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 4898977Abstract: 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, halolactonisation 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: August 13, 1987Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Herold, Christof Angst
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Patent number: 4888440Abstract: A process is described for the preparation of aspartic acid 4-(phenylmethyl) ester from aspartic acid and benzyl alcohol, characterized by utilizing a reaction mixture which contains, per mole of aspartic acid, 10-40 moles of benzyl alcohol and 1-5 moles of acetyl chloride, by conducting the reaction at a temperature of -10.degree. C. to 50.degree. C., and by separating the product of the process, after reaction has taken place, by neutralization with organic bases.Type: GrantFiled: November 25, 1988Date of Patent: December 19, 1989Assignee: Diamalt AGInventor: Ludwig Wilschowitz
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Patent number: 4888439Abstract: A novel polyprenyl compound is identified with the formula and useful for a pharmaceutical drag. ##STR1## wherein X represents a group of the formula: ##STR2## (wherein R.sup.1 and R.sup.2, which may be the same or different, represent each a hydrogen atom, a lower alkyl group, a hydroxyalkyl group, or a lower alkenyl group); a group of the formula: ##STR3## (wherein A including the nitrogen atom shown represents a ring containing nitrogen and oxygen atoms); or a group of the formula: ##STR4## (wherein R.sup.3 represents a hydrogen atom or a lower alkyl group, and R.sup.4 represents a lower alkyl group); Y represents a group of the formula: ##STR5## or a group of the formula: ##STR6## (wherein R.sup.5 represents a hydrogen atom or a lower alkyl group), and n represents an integer of from 2 to 5.Type: GrantFiled: May 1, 1985Date of Patent: December 19, 1989Assignee: Eisai Co., Ltd.Inventors: Isao Yamatsu, Takeshi Suzuki, Shinya Abe, Kouji Nakamoto, Akiharu Kajiwara, Manabu Murakami, Kiyoshi Oketani, Hideaki Fujisaki
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Patent number: 4882341Abstract: The invention relates to amino substituted propenoates and their use against fungi.Type: GrantFiled: September 9, 1988Date of Patent: November 21, 1989Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Kay
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Patent number: 4879403Abstract: Compounds of the formula I ##STR1## in which the carboxyl group on carbon atom 3 is orientated in the endo-position relative to the bicyclic ring system of cis-configuration, and in which R.sup.1 denotes hydrogen, allyl, vinyl or a side-chain of a naturally occurring .alpha.-aminoacid, which may be protected, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl and Z denotes hydrogen, or Y and Z together denote oxygen, and X denotes alkyl, alkenyl or cycloalkyl, or aryl which is optionally mono-, di- or tri-substituted by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, a process for their preparation, agents containing these compounds and their use.Type: GrantFiled: November 2, 1988Date of Patent: November 7, 1989Assignee: Hoechst AktiengesellschaftInventors: Volker Teetz, Rolf Geiger, Hansjorg Urbach, Reinhard Becker, Bernward Scholkens
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Patent number: 4874395Abstract: A corrosion inhibitor composition for hydrocarbon fuels comprising a C.sub.10 -C.sub.24 alkenyl succinic anhydride esterified with between 0.5-1.5 moles of a water-soluble glycol and then neutralized with an amine.The invention also contemplates improved hydrocarbon fuels which comprise a major portion of such fuels which contain small quantities of the above described composition.Type: GrantFiled: September 2, 1988Date of Patent: October 17, 1989Assignee: Nalco Chemical CompanyInventor: George R. Meyer
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Patent number: 4868202Abstract: Novel 3-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sup.1 is cyano, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sup.2 is vinyl or a group --CH.sub.2 --CH.sub.2 --X, in which X is chlorine or bromine, or is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylsulfonyl, 4-bromophenylsulfonyl or 4-methylphenylsulfonyl, R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, and n is zero, one or two, have valuable microbicidal properties for controlling phytopathogenic plant pests, particularly phytopathogenic fungi.Type: GrantFiled: December 22, 1987Date of Patent: September 19, 1989Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4864055Abstract: A compound represented by the following formula: ##STR1## wherein R is a C.sub.3 -C.sub.24 olefinically unsaturated organic radical having functionality which renders the nitrogen atom electron deficient, the olefinic unsaturation functionality being polymerizable,R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl radical, orR and R.sup.1 together with the nitrogen atom can form an olefinically unsaturated 5 to 7-member ring which has functionality that renders the nitrogen atom electron deficient and the olefinic unsaturation functionality is polymerizable,R.sup.2 and R.sup.3 are hydrogen, a C.sub.1 -C.sub.4 alkyl or acyl radical, orR.sup.2 and R.sup.3 together are a C.sub.1 -C.sub.4 alkylene group,R.sup.4 is hydrogen or a C.sub.1 -C.sub.4 alkyl, acyl, ester, amide or acid group, andn is an integer from 1 to 10, provided n is not 1 when R is (meth)acryloyl, R.sup.2 and R.sup.3 are methyl and R.sup.1 and R.sup.4 are hydrogen.Type: GrantFiled: September 3, 1987Date of Patent: September 5, 1989Assignee: Air Products and Chemicals, Inc.Inventors: Robert K. Pinschmidt, Jr., Dale D. Dixon, William F. Burgoyne, Jr.
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Patent number: 4859788Abstract: Amino group containing curing component (A) for compounds (B) which contain epoxy or 1,3-dioxolan-2-one groups, comprising a reaction product of (a.sub.1) active CH alkyl esters of isocyanate adducts thereof with (a.sub.2) polyamines.Mixtures of (A) and (B) with or without diluents and additives give rapid curing even at low temperatures and high atmospheric humidity and are suitable in particular for paint formulations.Type: GrantFiled: April 7, 1988Date of Patent: August 22, 1989Assignee: Hoechst AGInventors: Gerhard Brindopke, Claus Godau, Walter Weber
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Patent number: 4845219Abstract: A compound of the general formula [I]: ##STR1## wherein R.sub.1 represents a higher alkyl group or an N-(higher alkyl)carbamoyl group, R.sub.2 represents a lower alkyl group, an acyl group having at least three carbon atoms, an N-(lower alkyl)carbamoyl group, an N-(lower alkyl)thiocarbamoyl group or a benzyl group, R represents a primary, secondary or tertiary amino group or a quaternary ammonium group, x is 1 or 2, y is a number of 0, 1 or 2, and z is an integer of 2-10, or a pharmaceutically acceptable salt thereof. The novel substances have both anti-tumor activity and platelet activating factor-inhibiting property, and they are effective as an anti-tumor agent without circulatory trouble.Type: GrantFiled: July 23, 1987Date of Patent: July 4, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Aono
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Patent number: 4841043Abstract: There is disclosed a process for producing carbapenam diazo intermediates of the formula ##STR1## wherein R.sup.1 is hydrogen or a hydroxy-protecting group,R.sup.2 is a lower alkyl having from 1-6 carbon atoms, andR.sup.3 represents a conventional carboxyl-protecting group.The processs comprises alkylating a 4-substituted azetidinone with the tin enolate of an .alpha.-bromoketone, in the presence of a silver salt, iodine, or iodine salt as a catalyst, and a strongly polar solvent. The .beta./.alpha. yield of the product diazo intermediate is approximately 3/1.Type: GrantFiled: August 3, 1987Date of Patent: June 20, 1989Assignee: Bristol-Myers CompanyInventors: Robert Deziel, Masaki Endo
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Patent number: 4827014Abstract: 2-Hydroxy-3-aminopropionic-N,N-diacetic acid and derivatives thereof are used in particular as complexing agents, bleaching agent stabilizers and builders in detergents.Type: GrantFiled: April 4, 1988Date of Patent: May 2, 1989Assignee: BASF AktiengesellschaftInventors: Richard Baur, Felix Richter, Stefan Birnbach, Rolf Fikentscher, Alfred Oftring, Ekhard Winkler, Werner Bochnitschek
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Patent number: 4820815Abstract: The invention provides azetidinones of the formula ##STR1## where R.sub.4 is hydrogen, amino or protected amino; R.sup.0 is H when R.sub.4 is amino or protected amino, or C.sub.1 -C.sub.4 alkyl when R.sub.4 is H; R.sub.1 is H, CH.sub.3, --CH.sub.2 --.sub.n Y where Y is OH, protected OH, --CH.sub.2 OH, protected --CH.sub.2 OH, halogen, COOH or protected COOH; n is 1 or 2; --CH.sub.2 --C(O)SR.sub.1 ' where R.sub.1 ' is e.g., C.sub.1 -C.sub.4 alkyl; R.sub.2 is H or protecting group and R.sub.3 is e.g., alkyl or phenyl. The azetidinones obtained are useful intermediates to carbapenems and carbacephems and monocyclic antibacterials, e.g., .alpha.-(dialkylphosphono)-[[3.beta.-[2-(2-aminothiazol-4-yl)-2-(syn)metho xyiminoacetylamino]azetidin-2-one-1-yl]]acetic acid and pharmaceutically acceptable salts thereof.Type: GrantFiled: September 1, 1987Date of Patent: April 11, 1989Assignee: University of Notre Dame du LacInventor: Marvin J. Miller
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Patent number: 4816598Abstract: The invention relates to 4-amino-butanoic acid derivatives of general formula: ##STR1## in which: M represents an alkali metal atom,R represents a protected amino group,R.sub.1 represents a labile group,R.sub.2 represents hydrogen, a branched- or straight-chain alkyl radical having from 1 to 6 carbon atoms, a lower methyloxyalkyl, a lower methylthioalkyl, a lower (lower alkyl)-aminoalkyl, a lower di-(lower alkyl)-aminoalkyl or a lower hydroxyalkyl radical or R.sub.2 represents one of the radicals of general formulae:Cy--A--, Cy--O--A'--, R--A'-- or R.sub.Type: GrantFiled: June 16, 1987Date of Patent: March 28, 1989Assignee: SanofiInventors: Marcel Descamps, Walter Verstraeten
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Patent number: 4788300Abstract: A process for preparing compounds (1) ##STR1## where Y is NR.sup.1 R.sup.2 or OR, R.sup.1 and R.sup.2 are hydrogen or C.sub.1-3 alkyl, and R is C.sub.1-3 alkyl, which comprises protecting the hydroxy group of a compound (2) ##STR2## cyclizing the product under basic conditions and removing the protecting group.Type: GrantFiled: August 29, 1986Date of Patent: November 29, 1988Assignee: I.S.F. Societa per AzioniInventors: Mario Pinza, Ugo C. Pfeiffer
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Patent number: 4767781Abstract: A compound of the formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl or acyl, R.sub.2 is hydroxy, alkoxy or amino, is useful as an antidiabetic agent.Type: GrantFiled: December 8, 1986Date of Patent: August 30, 1988Assignee: Takeda Chemical Industries, Ltd.Inventors: Susumu Shinagawa, Tsuneo Kanamaru, Setsuo Harada
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Patent number: 4760168Abstract: Reaction of an acrylamide with an alkyl glyoxylate or an alkyl glyoxylate hemiacetal provides an alkyl acrylamidoglycolate which can readily be alkylated to provide the alkyl ether thereof.Type: GrantFiled: February 20, 1987Date of Patent: July 26, 1988Assignee: American Cyanamid CompanyInventor: Peter J. Schirmann
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Patent number: 4743621Abstract: Carnitine acetyl carnitate dichloride, a precursor of carnitine and acetyl carnitine, is prepared by condensing noncarnitine tert-butyl ester with the acid chloride of acetyl carnitine chloride and methylating the product of the condensation with methyl iodide, thereby obtaining acetyl carnitate of carnitine chloride iodide. This product is hydrolized with trifluoroacetic acid, thereby eliminating the tert-butyl ester. The so-obtained acetyl carnitate of carnitine chloride iodide is converted into the desired compound by eluting a solution of the chloride iodide on a strongly basic ion-exchange resin activated in Cl.sup.- form.Type: GrantFiled: June 20, 1985Date of Patent: May 10, 1988Assignee: SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A.Inventor: Claudio Cavazza
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Patent number: 4721728Abstract: Compounds of the following general structure (I) ##STR1## where R.sub.1 stands for an acyl radical of the following structure (II) ##STR2## where p1 X.sup.- is a halogen atom and R.sub.4 is a C.sub.1 -C.sub.4 acyl radical or a hydrogen atomR.sub.2 stands for an R.sub.1 radical as defined above or for a hydrogen atomR.sub.3 stands for a substituted hydroxymethyl CH.sub.2 OR.sub.1 group, where R.sub.1 has the same value as defined above, or for a carboxyl group.Type: GrantFiled: October 7, 1986Date of Patent: January 26, 1988Assignee: SpA Societa' Prodotti Antibiotici S.p.A.Inventors: Tiberio Bruzzese, Franco Ottoni, Holger H. Van Den Heuvel
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Patent number: 4721803Abstract: In the process of hydrocarboxylating an .alpha.-enamide with CO and an organic hydroxyl compound to produce a N-acyl-.alpha.-amino acid ester, the improvement comprising using as the organic hydroxyl compound reactant, an organic hydroxyl compound which has a chiral center that is essentially all L or D, thereby producing a reaction mixture having essentially no enantiomeric pairs and containing diastereomeric N-acyl-.alpha.-amino acid esters having two chiral centers.Type: GrantFiled: October 29, 1985Date of Patent: January 26, 1988Assignee: The Standard Oil CompanyInventors: Mark C. Cesa, Robert A. Dubbert, James D. Burrington
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Patent number: 4719288Abstract: Compounds of the formula ##STR1## in which R.sub.1 represents hydrogen or acyl, X.sub.1 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to R.sub.1 and C-terminally to X.sub.2, X.sub.2 represents an optionally N-alkylated amino acid residue that is bonded N-terminally to X.sub.1 and C-terminally to the group --NR.sub.2 --, R.sub.2 represents hydrogen or lower alkyl, R.sub.3 represents hydrogen, alkyl, cycloalkyl, aryl-lower alkyl or aryl, R.sub.4 represents hydroxy or etherified or esterified hydroxy, R.sub.5 represents alkyl, cycloalkyl, aryl-lower alkyl or aryl, and R.sub.6 represents free or substituted amino or substituted hydroxy, and salts of such compounds having salt-forming groups inhibit the blood pressure-increasing action of the enzyme renin and can be used as anti-hypertensives.Type: GrantFiled: June 2, 1986Date of Patent: January 12, 1988Assignee: Ciba-Geigy CorporationInventors: Walter Fuhrer, Peter Buhlmayer, Vittorio Rasetti, Bernhard Riniker
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Patent number: 4716226Abstract: Novel 2-azetidinones of the formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, R.sub.1 is selected from the group consisting of hydrogen, --OH, protected hydroxy and --OCH.sub.2 --COOR', R' is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R.sub.2 is selected from the group consisting of alkyl of 1 to 4 carbon atoms and hydroxyl protective group and a novel process and novel intermediates for their preparation and a process for the preparation of compounds of the formula ##STR2## wherein R has the above definition, R'd is selected from the group consisting of hydrogen, --OH and protected hydroxyl and R.sub.3 is selected from the group consisting of hydrogen and R.sub.3 ', R.sub.3 ' is amino protective group which are useful intermediates.Type: GrantFiled: October 28, 1985Date of Patent: December 29, 1987Assignee: Roussel UclafInventors: Stephane Gero, Jeanine Cleophax, Alice Gateau-Olesker
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Patent number: 4713470Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxy-aromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.Type: GrantFiled: May 22, 1985Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Stanley B. Mirviss