Amide In Acid Moiety Patents (Class 560/41)
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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: 5131921Abstract: Motor fuel compositions comprising gasoline are improved to control octane requirement increase (ORI) by including an ester of an N-acyl sarcosinate acid or salt and a polyether polyol including oxyalkylene units selected from oxypropylene and/or oxybutylene.Type: GrantFiled: October 9, 1990Date of Patent: July 21, 1992Assignee: Texaco Inc.Inventors: Rodney L. Sung, Daniel T. Daly
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Patent number: 5118840Abstract: A method of crystallizing phenylalanine in the form of .alpha.-crystals at a temperature below .alpha..fwdarw..beta. transition temperature comprises:forming an aqueous solution of phenylalanine at a temperature above the .alpha..fwdarw..beta. transition temperature, the aqueous solution of phenylalanine including:(1) a specified amount of Nacl, or(2) NH.sub.4 Cl and a small amount of a surfactant; and cooling the solution below the .alpha..fwdarw..beta. transition temperature.Type: GrantFiled: July 12, 1991Date of Patent: June 2, 1992Assignee: Ajinomoto Co., Inc.Inventors: Mikiya Kano, Shinji Fujita, Tadashi Takemoto, Toshihisa Kato, Naoko Sugiyama
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Patent number: 5117031Abstract: This invention is characterized by synthesizing an active ester represented by the general formula ##STR1## using an active esterifying agent consisting of a sulfonium salt represented by the general formula ##STR2## and further reacting the above-said active ester with a nucleophilic agent represented by the general formula H-B-Y to produce an ester or amide represented by the general formula (W) d.A-B-Y.Type: GrantFiled: June 20, 1989Date of Patent: May 26, 1992Assignee: Sanshin Kagaku Kogyo Co. Ltd.Inventor: Katsushige Kouge
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Patent number: 5105007Abstract: The present invention is directed to a fluorescence polarization immunoassay for determining the phenylacetylglutamine (PAG) content in body fluids, to the various components needed for preparing and carrying out such an assay, and to the methods of making these components. Specifically, tracers, immunogens and antibodies are disclosed, as well as methods for preparing them. The assay is conducted by measuring the degree of polarization of plane polarized light that has been passed through a solution continuing sample, antiserum and tracer.Type: GrantFiled: June 26, 1991Date of Patent: April 14, 1992Assignee: Abbott LaboratoriesInventors: Maciej B. Adamczyk, Hossein A. Ghanbari, Donald D. Johnson
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Patent number: 5101066Abstract: There are provided novel compounds useful as selective extractants of metal values from aqueous systems comprising a plurality of such ionic species. There is further provided a process for the production of the novel compounds. The invention also relates to a process of selective metal extraction by means of the novel compounds of the invention.Type: GrantFiled: November 24, 1989Date of Patent: March 31, 1992Assignee: Yeda Research and Development Co. Ltd.Inventors: Abraham Shanzer, Jacqueline Libman, Shneior Lifson
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Patent number: 5098996Abstract: Radioactive fluorine can be easily introduced into biologically active molecules containing amino groups. A p-bromomethyl benzoyl group is coupled to the amino group of the biologically active molecule, and bromine is displaced by fluorine. Alternatively, the bromine on the bromomethylbenzoyl group is first displaced by fluorine, and the fluoromethyl benzoyl group is then coupled to the amino group of the biologically active molecule. The compounds so produced are useful in diagnostic nuclear medicine.Type: GrantFiled: March 15, 1988Date of Patent: March 24, 1992Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Kenneth A. Jacobson, Kenneth L. Kirk, David C. Furlano, Yechiel Shai
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Patent number: 5096925Abstract: Disclosed are compounds of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, 2-imidazoly or 4,5-dihydro-2-imidazolyl or any said grouping substituted by lower alkyl; R and R.sub.o independently represent hydrogen, lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl in which aryl represents phenyl, pyridyl, thienyl, furyl, biphenyl or naphthyl, each unsubstituted or mono- or di-substituted by halogen, lower alkyl, hydroxy, acyloxy, lower alkoxy, trifluoromethyl or cyano; A represents straight chain (C.sub.2 -C.sub.5)-alkylene; or A represents straight chain (C.sub.2 -C.sub.Type: GrantFiled: April 11, 1990Date of Patent: March 17, 1992Assignee: Ciba-Geigy CorporationInventor: Gary M. Ksander
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Patent number: 5097060Abstract: A process for crystallizing L-alpha-aspartyl-L-phenylalanine methyl ester from its aqueous solution by cooling, which comprises adjusting the initial concentration of the ester so that the amount of a precipitated solid phase to be formed after cooling becomes about 10 grams or more per liter of the solvent, cooling the solution through conductive heat transfer through a cooled surface to form an apparently sherbet-like pseudosolid phase without causing forced flow by mechanical stirring or the like, and optionally further cooling the system after formation of the pseudosolid phase, is disclosed along with various apparatuses which may be used to carry out the invention.Type: GrantFiled: June 18, 1991Date of Patent: March 17, 1992Assignee: Ajinomoto Company IncorporatedInventors: Masayoshi Naruse, Haruo Kawasaki, Shinichi Kishimoto, Harutoshi Oura, Masao Nakamura, Hideo Takeda
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Patent number: 5096700Abstract: The subject invention involves halogenated amino acid derivatives useful as antimicrobial agents having the structure: ##STR1## wherein --R is hydrogen or 2-aminoethyl; --R' is hydroxy, alkoxy, aryloxy, or an amino acid residue bonded at the amino nitrogen; --R" is hydrogen or an amino acid residue bonded at the carbonyl carbon; --X is halogen; and --Y is hydrogen or halogen.Type: GrantFiled: September 28, 1990Date of Patent: March 17, 1992Assignee: The Procter & Gamble CompanyInventors: William L. Seibel, Joseph H. Gardner
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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: 5095137Abstract: The amides of cyclomethylen-1,2-bicarboxylic acids having the formula: ##STR1## wherein A represents ##STR2## R.sup.1 represents --H, --CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, ##STR3## R.sup.2 represents --H, CH.sub.3, --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2, --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --CH(CH.sub.3).sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.3, --CH.sub.2 --C.sub.6 H.sub.5, --C.sub.6 --H.sub.5 ;R.sup.3 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, ##STR4## R.sup.5 represents --H, --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 C.sub.6 H.sub.5, ##STR5## Y=--H, --CH.sub.3, --CH(CH.sub.3).sub.2 Z=--H,--CH.sub.3, --C(CH.sub.3).sub.3, --CH(C.sub.2 H.sub.5).sub.2, ##STR6## R.sup.4 =R.sup.5, ##STR7## m is 0 or 1 and n is an integer varying between 0 and 3, are endowed with ACE-inhibiting activity and are thus therapeutically useful as anti-hypertension agents.Type: GrantFiled: October 9, 1990Date of Patent: March 10, 1992Assignee: Laboratori Guidotti SpAInventors: Luigi Turbanti, Guido Cerbai, Marco Criscuoli
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Patent number: 5093478Abstract: In the esterification of glutathione with alcohol in the presence of acid catalyst, neutral glutathione monoester is isolated in high yields without the intermedite isolation of ester acid salt by treating the reaction mixture with base anion exchange resin (basic form) to neutralize the acid and bind the resulting acid anion and unesterified glutatione. Dehydrating agent is used to drive the reaction toward esterification. In the production of glutathione monester acid salts a soluble dehydrating agent is advantageously used.Type: GrantFiled: July 14, 1989Date of Patent: March 3, 1992Assignee: Cornell Research Foundation, Inc.Inventors: Owen W. Griffith, Ernest B. Campbell
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Patent number: 5087728Abstract: A process for producing a carboxylic acid or an ester thereof represented by formula (I): ##STR1## wherein: R represents a hydrogen atom or a lower alkyl group; R.sup.1 represents a lower alkyl group; CH.sub.2 COOR.sup.3, wherein R.sup.3 represents a hydrogen atom or a lower alkyl group; or NHR.sup.4, wherein R.sup.4 represents a formyl group, an acetyl group, a benzoyl group, or a chloroacetyl group, andR.sup.2 represents a hydrogen atom, a lower alkyl group, or a phenyl group,which comprises hydrogenating an unsaturated compound represented by formula (II): ##STR2## wherein R, R.sup.1, and R.sup.2 are as defined above, in the presence of a rhodium or ruthenium complex catalyst having, as a ligand, BICHEP which means 2,2'-bis(dicyclohexylphoshino)-6,6'-dimethyl-1,1'-biphenyl represented by formula (III): ##STR3## is disclosed.Type: GrantFiled: July 11, 1990Date of Patent: February 11, 1992Assignee: Takasago International CorporationInventors: Hiroyuki Nohira, Hidemasa Takaya, Akira Miyashita
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Patent number: 5087729Abstract: Disclosed herein are benzylidene compounds represented by the formula (I): ##STR1## wherein A represents ##STR2## (wherein B represents hydrogen atom or an acetyl group, W represents hydrogen atom or --CH.sub.2 --CH.sub.2 --CO--O--R, X.sup.1, X.sup.2 and X.sup.3 represent independently hydrogen atom, a hydroxyl group or a methoxyl group (two or three of them may be the same or all of them may be different), Y represents oxygen atom or imino group (--NH--), Z represents a methyl group or a phenyl group, and R represents a straight chain alkyl group having 1 to 18 carbon atoms, or branched or cyclic alkyl group having 3 to 18 carbon atoms, provided that when A is ##STR3## R is not an alkyl group having 1 to 2 carbon atoms, and when A is ##STR4## and X.sup.1, X.sup.2 and X.sup.3 are hydrogen atom, R is not an alkyl group having 1 to 2 carbon atoms), a cosmetic composition containing the same and an ultraviolet absorber comprising the same.Type: GrantFiled: April 17, 1990Date of Patent: February 11, 1992Assignee: Ajinomoto Co., Inc.Inventors: Kazuhiro Matsuno, Toru Kobayashi, Takeshi Miyoshi, Hideaki Kawashima
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Patent number: 5075108Abstract: A compound of formula I ##STR1## wherein R.sub.1 is of formula II ##STR2## wherein R.sub.4 and R.sub.5, which may be the same or different, are bromo, chloro, iodo or alkylsulphonyl;R.sub.2 is of formula III ##STR3## wherein R.sub.6 and R.sub.7, which may be the same or different, are H, alkyl, aryl, carboxy, hydroxy or amino and n is 0-10; andR.sub.3 is hydroxy or a group capable of being cleared and replaced by a radical having an antigen binding site or R.sub.3 is a radical having an antigen binding site.Type: GrantFiled: December 21, 1987Date of Patent: December 24, 1991Assignee: Consolidated Pharmaceuticals, LimitedInventors: Ian F. C. McKenzie, Geoffrey A. Pietersz, Mark Smyth
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One-pot process for the preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride
Patent number: 5053532Abstract: A one-pot process for the preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride is disclosed (.alpha.-APM(HCl)). .alpha.-APM(HCl) is an intermediate in the preparation of aspartame.Type: GrantFiled: July 3, 1990Date of Patent: October 1, 1991Assignee: The Nutra Sweet CompanyInventors: John B. Hill, Yefim Gelman, Hugh L. Dryden, Jr., Robert Erickson, Kuang Hsu, Mark R. Johnson -
Patent number: 5047410Abstract: New pharmacologically active amidino and guanidino derivatives which are 5-HT.sub.3 receptor antagonists useful as antiemetic, gastric prokinetic and antimigrainic agents of the following general formula (I) ##STR1## , wherein the substituents are defined hereinbelow, which compounds are 5-HT.sub.3 receptor antagonists useful as antiemetic gastric prokinetic and antimigraine agents, inter alia.Type: GrantFiled: July 12, 1989Date of Patent: September 10, 1991Assignee: Istituto de Angeli S.p.A.Inventors: Arturo Donetti, Marco Turconi, Massimo Nicola, Rosamaria Micheletti
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Patent number: 5041607Abstract: A crystalline L-alpha-aspartyl-L-phenyl-alanine methyl ester product is disclosed. The product is obtained by crystallizing the ester from an aqueous solution, by cooling. The initial concentration of ester in the aqueous solution used provides at least 10 grams of precipitated solid phase per liter of solution. The solution is cooled through conductive heat transfer without effecting forced flow to form a sherbet-like pseudo solid phase.Type: GrantFiled: January 3, 1989Date of Patent: August 20, 1991Assignee: Ajinomoto Co., Inc.Inventors: Masayoshi Naruse, Haruo Kawasaki, Shinichi Kishimoto, Harutoshi Oura, Masao Nakamura, Hideo Takeda
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Patent number: 5039805Abstract: The compound of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 have the significance given in the description, can be used as medicaments for the therapy and prophylaxis of disorders such as thromboses, stroke, cardiac infarct, inflammations and arteriosclerosis as well as for the treatment of tumours.Type: GrantFiled: November 24, 1989Date of Patent: August 13, 1991Assignee: Hoffmann-La Roche Inc.Inventors: Leo Alig, Albrecht Edenhofer, Marcel Muller, Arnold Trzeciak, Thomas Weller
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Patent number: 5030732Abstract: Disclosed are some new aminoethylphosphinic acid derivatives useful as antibacterial agents.Type: GrantFiled: March 3, 1988Date of Patent: July 9, 1991Assignee: Merck & Co., Inc.Inventors: Yoshiharu Morita, Yasuo Hoshide, Ryoichi Ando, Masao Taniguchi
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Patent number: 5030654Abstract: A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.Type: GrantFiled: May 19, 1989Date of Patent: July 9, 1991Assignee: Pfizer Inc.Inventors: Ian T. Barnish, John C. Danilewicz, Keith James, Gillian M. R. Samuels, Nicholas K. Terrett, Michael T. Williams, Martin J. Wythes
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Patent number: 5021454Abstract: Benzoylaminoalkanoic acids and esters thereof are fungitoxic and useful for controlling fungi, particularly phytopathogenic fungi.Type: GrantFiled: October 6, 1989Date of Patent: June 4, 1991Assignee: Rohm and Haas CompanyInventor: Ashok K. Sharma
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Patent number: 5021430Abstract: Disclosed are compound of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, or each said grouping substituted by lower alkyl; R and R.sub.o independently represent lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl; A represents methylene; or A represents methylene substituted by lower alkyl, by lower alkylthio-lower alkyl, by aryl-lower alkylthio-lower alkyl, by arylthio-lower alkyl, by hydroxy-lower alkyl, by acyloxy-lower alkyl, by lower alkoxy-lower alkyl, by aryl-lower alkyloxy-lower alkyl, by aryloxy-lower alkyl, by amino-lower alkyl, by acylamino-lower alkyl, by guanidino-lower alkyl, by (C.sub.3 -C.sub.7)-cycloalkyl, by (C.sub.3 -C.sub.Type: GrantFiled: June 29, 1987Date of Patent: June 4, 1991Assignee: Ciba-Geigy CorporationInventor: Gary M. Ksander
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Patent number: 5017690Abstract: N-formyl amino acid or peptide is deformylated by reaction with aniline or methylene dianiline over noble metal catalyst, e.g., Pt-on-carbon. N-formanilide is formed as by-product. The process is particularly useful in deformylating N-formyl aspartame.Type: GrantFiled: August 11, 1989Date of Patent: May 21, 1991Assignee: W. R. Grace & Co.-Conn.Inventor: Jennifer M. Quirk
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Patent number: 5002692Abstract: Amides having the following structure: ##STR1## used in ferroelectric smectic liquid crystal mixtures, especially as pitch compensators and liquid crystal compositions containing them.Type: GrantFiled: December 1, 1988Date of Patent: March 26, 1991Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: George W. Gray, David Lacey, Kenneth J. Toyne, Richard M. Scrowston, Lawrence K. M. Chan, Madeline J. Bradshaw, Victoria Brimmell
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Patent number: 5001156Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 [OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.Type: GrantFiled: December 1, 1987Date of Patent: March 19, 1991Assignee: L'OrealInventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
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Patent number: 4994605Abstract: A method for crystallizing alpha-L-aspartyl-L-phenylalanine methyl ester (APM) is disclosed. The APM is crystallized from a C.sub.1 -C.sub.3 -alcohol/water solution (30-80:70-20 (v/v)). The ester crystallized by (i) concentrating the solution, (ii) cooling the solution, (iii) adjusting the water:alcohol ratio, or (iv) a combination thereof.Type: GrantFiled: April 25, 1989Date of Patent: February 19, 1991Assignee: Ajinomoto Co., Inc.Inventors: Shinichi Kishimoto, Katsumi Sugiyama
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Patent number: 4992558Abstract: Novel disperse dyes particularly suitable for dyeing textile material made of polyester fibers, said dyes being of the formula ##STR1## wherein X is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen,Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy-C.sub.1 -C.sub.4 alkoxy,R is hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.12 alkenyl or phenyl, or Y and R, when taken together with the nitrogen atom and the two carbon atoms linking them, form a 5- or 6-membered ring,B is straight-chain or branched C.sub.2 -C.sub.6 alkylene,A is a radical of formula ##STR2## in which W is C.sub.1 -C.sub.9 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl, halogen or C.sub.1 -C.sub.4 alkoxy,n is 0, 1, 2, or 3,Q is hydrogen or C.sub.1 -C.sub.4 alkyl,V is halogen, andm is 0, 1, 2, 3 or 4.Type: GrantFiled: July 7, 1989Date of Patent: February 12, 1991Assignee: Ciba-Geigy CorporationInventors: Peter Liechti, Antoine Clement
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Patent number: 4981865Abstract: The present invention includes N-hydroxyamide, N-hydroxyurea, N-hydroxythioamide, and N-hydroxythiourea derivatives of fenamates, indomethacin, cicloprofen, oxepinac, and indoprofen as dual inhibitors or selective inhibitors of cyclooxygenase and 5-lipoxygenase.Type: GrantFiled: May 26, 1989Date of Patent: January 1, 1991Assignee: Warner-Lambert Co.Inventors: Thomas R. Belliotti, Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, James B. Kramer, Jagadish C. Sircar
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Patent number: 4975444Abstract: Compounds of the formula ##STR1## wherein A is a carbocyclic, saturated or unsaturated ring; R.sup.1 is hydrogen or alkyl; R and R.sup.4 are each alkyl, cycloalkyl, benzyl or a readily hydrolyzable ester group; Y is a bond or a straight or branch alkylene; R.sup.2 is hydrogen, aryl, heterocyclic, R.sup.6 CONR.sup.5, R.sup.7 NR.sup.5 CO, R.sup.7 NR.sup.5 SO.sub.2 --or R.sup.8 SO.sub.2 NR.sup.5 --where R.sup.5 is hydrogen, alkyl or aralkyl; R.sup.6 is alkyl, aryl, aralkyl, heterocyclic, heterocyclyalkyl or a group of the formula ##STR2## where R.sup.9 is hydrogen, hydroxy, alkoxy, alkyl, hydroxyalkyl, aralkyl, alkylene, heterocyclic, heterocyclylalkyl, R.sup.12 CONH--, R.sup.12 SO.sub.2 NH-- or (R.sup.13).sub.2 N--; R.sup.10 and R.sup.11 are each hydrogen or alkyl; or R.sup.10 is hydrogen and R.sup.11 is aminoalkyl, imidazolylmethyl, aryl, aralkyl, aralkoxyalkoxy, hydroxyalkyl or methylthioalkyl; or R.sup.10 and R.sup.Type: GrantFiled: August 25, 1989Date of Patent: December 4, 1990Assignee: Pfizer Inc.Inventors: John C. Danilewicz, Keith James, Ryszard J. Kobylecki
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Patent number: 4962222Abstract: .alpha.-L-Aspartyl-L-phenylalanine methyl ester having low hygroscopicity is prepared by bringing a cake of .alpha.-L-aspartyl-L-phenylalanine methyl ester, which cake has been obtained by solid-liquid separation through a desired preparation process of .alpha.-L-aspartyl-L-phenylalanine methyl ester, into contact with an organic solvent of uniform phase so as to treat the cake with the organic solvent, subjecting the resulting mixture of the cake and organic solvent to solid-liquid separation to obtain a cake, and then drying the last-mentioned cake at a temperature not higher than 60.degree. C. The organic solvent is dry or contains water in an amount up to 30 wt.%.Type: GrantFiled: January 25, 1989Date of Patent: October 9, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4946987Abstract: Herein disclosed are N-naphthoylglycine derivatives having aldose reductase inhibiting activity. The derivatives are useful for treating, diabetic complications.Type: GrantFiled: June 20, 1988Date of Patent: August 7, 1990Assignee: Ayerst, McKenna & Harrison, Inc.Inventors: Kazimir Sestanj, Nedumparambil A. Abraham, Francesco Bellini, Adi Treasurywala
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Patent number: 4946988Abstract: A process for the preparation of .alpha.-L-aspartyl-L-phenylalanine methyl ester hydrochloride (.alpha.-APM(HCl)) is disclosed. .alpha.-APM(HCl) is an intermediate in the preparation of aspartame.Type: GrantFiled: July 14, 1988Date of Patent: August 7, 1990Assignee: The NutraSweet CompanyInventors: John B. Hill, Yefim Gelman
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Patent number: 4944796Abstract: 2-(Disubstituted amino)acetamides of the formula ##STR1## wherein R is alkyl or phenyl; R.sup.1 is selected from the group consisting of amino, alkyl, allyl, substituted carbonyl wherein said substituent is haloalkyl, alkoxycarbonyl, alkylthio, carboxy, alkoxy, alkyl, vinyl, haloanilino, phenylthio, alkylamino, benzylamino, alkoxycarbonylalkyl or substituted carbamyl wherein the substituent is alkyl halocarbanilide; alkylthio thiocarbonyl; or mono-haloanilino carbonylmethylene, alkoxy carbonylmethylene, or carboxymethylene; R.sup.2 is hydrogen, alkyl or phenyl; X is halo or haloalkyl; and n is an integer selected from 1-3, inclusive; the compounds are useful as herbicidal agents.Type: GrantFiled: November 14, 1988Date of Patent: July 31, 1990Assignee: ICI Americas Inc.Inventor: Siok-Hui H. Wee
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Patent number: 4942255Abstract: A method for producing an .alpha.-aspartylphenylalanine derivative represented by formula (2), which comprises reacting a .beta.-aspartylphenylalanine derivative represented by formula (1): ##STR1## with a basic compound in an alcohol solvent in the presence of a hydroxide, sulfate, chloride, carbonate or acetate of an element selected from the group consisting of zinc, copper, nickel, magnesium, aluminum, iron, tin, silicon and titanium, wherein R.sub.1 and R.sub.2 represent hydrogen or an alkyl group having 1 to 4 carbon atoms.Type: GrantFiled: January 25, 1989Date of Patent: July 17, 1990Assignee: Ajinomoto Co., Inc.Inventors: Satoji Takahashi, Tadashi Takemoto
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Patent number: 4941992Abstract: Novel compounds suitable for use as chiral dopants in ferroelectric smectic liquid crystal materials comprising an optically active derivative of an .alpha.-amino acid of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of C.sub.1-20 alkyl or alkoxy, R is C.sub.1-20 n-alkyl and Y is C.sub.1-20 alkyl. A liquid crystal mixture and a device using these compounds are also described.Type: GrantFiled: July 17, 1987Date of Patent: July 17, 1990Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: Adam Jackson, Richard M. Scrowston, George W. Gray, David Lacey, Kenneth J. Toyne
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Patent number: 4939261Abstract: Disclosed are compounds of the formula ##STR1## wherein X and Y independently represent hydroxymethyl; cyano; carboxy; functionally modified carboxy selected from esterified carboxy, carbamoyl, and N-substituted carbamoyl; 5-tetrazolyl; 2-oxazolyl, 4,5-dihydro-2-oxazolyl, 2-imidazolyl or 4,5-dihydro-2-imidazolyl or any said grouping substituted by lower alkyl; R and R.sub.0 independently represent hydrogen, lower alkyl, (C.sub.3 -C.sub.7)-cycloalkyl-lower alkyl, or aryl-lower alkyl in which aryl represents phenyl, pyridyl, thienyl, furyl, biphenyl or naphthyl, each unsubstituted or mono- or di-substituted by halogen, lower alkyl, hydroxy, acyloxy, lower alkoxy, trifluoromethyl or cyano; A represents straight chain (C.sub.2 -C.sub.5)-alkylene; or A represents straight chain (C.sub.2 -C.sub.Type: GrantFiled: September 17, 1987Date of Patent: July 3, 1990Assignee: Ciba-Geigy CorporationInventor: Gary M. Ksander
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Patent number: 4931582Abstract: Novel fluorinated, acrylamide monomers are prepared from 2-alkenyl azlactones reacted with fluorinated alcohols. The novel monomers have the formula ##STR1## wherein R.sup.1 and R.sup.6 are independently hydrogen or methyl;R.sup.2 and R.sup.3 independently can be an alkyl, cycloalkyl, or aryl group, or R.sup.2 and R.sup.3 taken together with the carbon to which they are joined can form a carbocyclic ring containing 4 to 12 ring atoms;R.sup.4 and R.sup.5 are independently hydrogen or lower alkyl;a is 0 or 1;b is 1 or 2;X is a single bond, CH.sub.2, CH.sub.2 OCH.sub.2, and CH.sub.2 CH.sub.2 OCH.sub.2 ; andR.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group when b is 1 and perfluorinated alkylene when b is 2.Novel polymers and copolymers can be prepared from the monomers of the invention.Type: GrantFiled: November 4, 1988Date of Patent: June 5, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen, Howell K. Smith, II
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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: 4925969Abstract: Ethyl-.beta.-benzoyacrylate is reacted with an alkali metal salt of (S)-alanine or an alkali metal salt of N.sup.6 -trifluoroacetyl-L-lysine to form the corresponding Michael addition product, and not less than an equivalent amount of acid is added after completion of the Michael addition to prevent conversion of the (S,S) form of the product to the (R,S) form.Type: GrantFiled: March 16, 1989Date of Patent: May 15, 1990Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Satomi Takahashi, Yasuyoshi Ueda, Kazuhiko Yamada, Yukio Yamada, Takehiko Yamane, Yoshifumi Yanagita, Yoshio Shimada, Kiyoshi Watanabe, Michio Nomura, Takehisa Ohashi, Kenji Inoue
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Patent number: 4923888Abstract: The present invention relates to novel compounds of the general formula (I), ##STR1## wherein R stands for hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or C.sub.1-4 acylamino group;R.sub.1 means hydrogen or a carboxyl-protective group; andR.sub.2 represents a --(CH.sub.2).sub.n --CO.sub.2 R.sub.5 group, whereinn is 1, 2, 3 or 4; andR.sub.5 stands for hydrogen or a carboxyl-protective group; orR.sub.2 means a --(CH.sub.2).sub.n --NH.sub.2 group, whereinn is 1, 2, 3 or 4of E and/or Z configurtion as well as their salts.The compounds according to the invention show a cytoprotective effect and promote the healing of the stomach ulcer. Their toxicity is low.Type: GrantFiled: September 26, 1988Date of Patent: May 8, 1990Assignee: Richter Gedeon Vegyeszeti Gyar RTInventors: Tamas Fodor, Laaszlo Dobay, Jaanos Fischer, Bela Stefkoo, Elemeer Ezer, Judit Matuz, Katalin Saghy, Laaszlo Szporny
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Patent number: 4918216Abstract: .alpha.-L-aspartyl-L-phenylalanine methyl ester or the hydrohalide thereof is prepared by esterifying .alpha.-L-aspartyl-L-phenylalanine or .alpha.-L-aspartyl-L-phenylalanine which has been formed in situ by treating an N-protected-.alpha.-L-aspartyl-L-phenylalanine in an aqueous solution of sulfuric acid or a methanol-containing aqueous solution of sulfuric acid in the presence of an alkali metal halide or alkaline earth metal halide in a medium composed of sulfuric acid, water and methanol, thereby to allow the resulting .alpha.-L-aspartyl-L-phenyl-alanine methyl ester to precipitate as its corresponding hydrohalide, and then isolating the hydrohalide; and when the preparation of the methyl ester is desired, neutralizing the hydrohalide.Type: GrantFiled: May 25, 1989Date of Patent: April 17, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Toshio Katoh, Chojiro Higuchi, Takeshi Oura, Akihiro Yamaguchi
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Patent number: 4914223Abstract: A composition of matter comprising an acrylamido-acyl or methacrylamido-acyl oligomer derived from at least one nucleophilic oligomer having at least one amino-, hydroxyl-, or thio-substituted polyoxyalkylene, polyalkyleneimine, polyester, polyolefin, polyacrylate, or polysiloxane oligomer, said nucleophilic oligomer having a molecular weight in the range of 200 to 20,000 is disclosed. Also disclosed are free radically polymerizable monomer-containing compositions containing said oligomers as well as acrylamido- and methacrylamido-acylated polymers which are the thermal or photocured products of said oligomers. In addition, a process is disclosed for providing said acrylamido- and methacrylamido-acylated oligomers which are useful, for example, in coatings, films, printing inks, adhesives, and saturants.Type: GrantFiled: August 17, 1988Date of Patent: April 3, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Jerald K. Rasmussen, Steven M. Heilmann, Frederick J. Palensky
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Patent number: 4912221Abstract: The instant invention relates to optically pure, L-(S)forms of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid compounds and their method of preparation from optionally pure L-phenylalanine precursor compounds and their preparation utilizing novel in situ cationic catalyst systems.Type: GrantFiled: October 27, 1988Date of Patent: March 27, 1990Assignee: Occidental Chemical CorporationInventors: Neil J. O'Reilly, Henry C. Lin
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Patent number: 4900863Abstract: The .alpha.-linked dipeptide formed from aspartic acid and phenylalanine ester can be separated very well from the corresponding .beta.-linked component by recrystallizing the mixture from a buffered, aqueous solution.Type: GrantFiled: October 16, 1987Date of Patent: February 13, 1990Assignee: Hoechst AktiengesellschaftInventors: Erwin Schmidt, Reinhold Keller
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Patent number: 4897506Abstract: A method for preparing .alpha.-L-aspartyl-L-phenylalanine methyl ester having improved solubilization by the isolation thereof from an aqueous medium containing at least one additive selected from the group consisting of sodium alginate, sodium salt of carboxymethylcellulose, sodium starch glycolate and sodium polyacrylate.Type: GrantFiled: October 12, 1988Date of Patent: January 30, 1990Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuichi Mita, Takeshi Oura, Toshio Katoh, Chojiro Higuchi, Akihiro Yamaguchi, Masanobu Ajioka
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Patent number: 4897507Abstract: A method for producing .alpha.-L-aspartyl-L-phenylalanine dimethyl ester, which comprises reacting 3-benzyl-6-carboxymethyl-2,5-diketopiperazine or methyl ester thereof in a methanolic solvent substantially free from water in the presence of a strong acid.Type: GrantFiled: July 7, 1988Date of Patent: January 30, 1990Assignee: Ajinomoto Co., Inc.Inventors: Satoji Takahashi, Tadashi Takemoto
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Patent number: 4895842Abstract: A phenylalanine derivative having the formula (I): ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen provided that both R.sup.1 and R.sup.2 are not hydrogen at the same time;C.sub.1 -C.sub.8 alkyl which may be substituted with hydroxy, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkoxy, carbamoyl, sulfamoyl, pyridyl, or phenyl which may further be substituted with nitro, C.sub.1 -C.sub.4 alkoxy, or halogen;C.sub.6 -C.sub.8 cycloalkyl which may be substituted with hydroxy, C.sub.1 -C.sub.4 alkoxy, hydroxylcarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, or C.sub.1 -C.sub.4 alkyl;phenyl which may be substituted with halogen, nitro, trifluoromethyl, C.sub.1 -C.sub.4 alkoxy C.sub.1 C.sub.4 alkylmercapto, C.sub.1 -C.sub.4 alkylcarbonyl, phenylcarbonyl, hydroxycarbonyl, C.sub.1 -C.sub.4 alkoxycarbonyl, carbamoyl, sulfamoyl, amidino, pyridylcarbonyl, or C.sub.1 -C.sub.6 alkyl which may further be substituted with C.sub.1 -C.sub.Type: GrantFiled: September 29, 1986Date of Patent: January 23, 1990Assignees: Shosuke Okamoto, Showa Denko Kabushiki KaishaInventors: Shosuke Okamoto, Yoshio Okada, Akiko Okunomiya, Taketoshi Naito, Yoshio Kimura, Morihiko Yamada, Norio Ohno, Yasuhiro Katsuura, Yumi Seki
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Patent number: 4895834Abstract: The invention concerns novel renin-inhibitory peptides which are useful for treating renin associated hypertension, hyperaldosternoism, and congestive heart failure. Processes for preparing the peptides, compositions containing them and methods of using them are included. Also included is a diagnostic test using the compounds to determine the presence of renin-associated hypertension or hyperaldosteronism.Type: GrantFiled: November 2, 1987Date of Patent: January 23, 1990Assignee: Warner-Lambert CompanyInventors: James P. Hudspeth, James S. Kaltenbronn, Joseph T. Repine, William H. Roark, Michael A. Stier