Oxy Patents (Class 562/444)
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Patent number: 4394305Abstract: Compounds which are carboxylic acids, or their salt, ester or amide derivatives, having an oxyalkylene amine oxide substituent at the alpha-carbon atom are disclosed. The compounds are useful as detergent surfactants which provide outstanding cleaning, particularly of oily soils, under cold water laundering conditions. Detergent compositions containing the compounds also preferably contain other surfactants, builders, and detergent adjunct materials.Type: GrantFiled: March 17, 1981Date of Patent: July 19, 1983Assignee: The Procter & Gamble CompanyInventor: Eugene P. Gosselink
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Patent number: 4391986Abstract: Threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its esters represented by the formula: ##STR1## wherein R.sub.1 represents naphthyl or a group of the formula ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino, an amino protected with acyl, lower alkyloxycarbonyl or carbamoyl, hydroxy or protected with acyl, lower alkyloxycarbonyl or carbamoyl, lower alkoxy, lower alkyl or phenyl group; R.sub.2 represents an amine protected with acyl, lower alkyloxycarbonyl or carbamoyl; and R.sub.3 represents hydrogen, lower alkyl having 1 to 6 carbon atoms or benzyl.Type: GrantFiled: November 28, 1980Date of Patent: July 5, 1983Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
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Patent number: 4386031Abstract: The present invention refers to N-Benzoyl-.omega.Type: GrantFiled: November 6, 1981Date of Patent: May 31, 1983Assignee: A. Nattermann & Cie GmbHInventors: Gerd Hilboll, Hans-Heiner Lautenschlager, Brigitte Stoll, Manfred Probst
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4384136Abstract: Amino acid fractions of different composition are obtained at different times by fractional filtration after neutralization of the hydrolysates. Tyrosine-rich and leucine-rich fractions are specifically treated and lead to the recovery of L-tyrosine, L-cystine, L-leucine and L-phenyl-alanine.Type: GrantFiled: December 4, 1981Date of Patent: May 17, 1983Assignee: Societe d'Assistance Technique pour Produits Nestle S.A.Inventor: Walter Steinmetzer
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Patent number: 4375555Abstract: A method for synthesizing alpha amino acids proceeding through novel intermediates of the formulas:R.sub.1 R.sub.2 C(OSOCl)CN, R.sub.1 R.sub.2 C(Cl)CN and [R.sub.1 R.sub.2 C(CN)O].sub.2 SOwherein R.sub.1 and R.sub.2 are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 12 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the synthesis methods of the prior art.Type: GrantFiled: June 29, 1981Date of Patent: March 1, 1983Assignee: The United States of America as represented by the United States Department of EnergyInventor: Jefferson W. Davis, Jr.
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Patent number: 4371705Abstract: A method for synthesizing alpha amino acids proceding through novel intermediates of the formulas: R.sub.1 R.sub.2 C(OSOCl)CN, R.sub.1 R.sub.2 C(Cl)CN and [R.sub.1 R.sub.2 C(CN)O].sub.2 SO wherein R.sub.1 and R.sub.2 are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 12 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the synthesis methods of the prior art.Type: GrantFiled: June 29, 1981Date of Patent: February 1, 1983Assignee: The United States of America as represented by the United States Department of EnergyInventor: Jefferson W. Davis, Jr.
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Patent number: 4370493Abstract: A method for synthesizing alpha amino acids proceding through novel intermediates of the formulas:R.sub.1 R.sub.2 C(OSOCl)CN, R.sub.1 R.sub.2 C(Cl)CN and [R.sub.1 R.sub.2 C(CN)O].sub.2 SOwherein R.sub.1 and R.sub.2 are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 10 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the snythesis methods of the prior art.Type: GrantFiled: June 29, 1981Date of Patent: January 25, 1983Assignee: The United States of America as represented by the Secretary of EnergyInventor: Jefferson W. Davis, Jr.
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Patent number: 4352752Abstract: There is provided a novel process for the preparation of a dipeptide represented by the formula: ##STR1## wherein Ar represents an aromatic group; R.sup.1 represents a hydrogen atom, an alkyl group or an aryl group; R.sup.2 represents a hydrogen atom, an alkyl group or an aromatic group; Y represents a hydroxy group, an amino group or an acylamino group, which comprises subjecting a .beta.-lactam compound represented by the formula: ##STR2## wherein Ar, R.sup.1 and R.sup.2 have the same meanings as defined above, and X represents a hydroxy group, an amino group or an acylamino group, an azido group or a benzyloxy group, to hydrogenolysis in the presence of a catalyst. The process can be practiced without any complicated procedure as seen in the conventional processes for the preparation of peptides.Type: GrantFiled: March 5, 1981Date of Patent: October 5, 1982Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Shigemi Suga
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Patent number: 4350641Abstract: 4-Tert.-butoxyphenylglycinonitrile (I) ##STR1## and a process for the preparation of D-(-)-4-hydroxyphenylglycine (IIa) and L-(+)-4-hydroxyphenylglycine (IIb) ##STR2## wherein compound I is reacted in a conventional manner, in alcoholic solution and in the presence of a carbonyl compound, with about the equimolar amount of L-(+)-tartaric acid or D-(-)-tartaric acid and the D-(-)-I-L-(+)-tartrate or L-(+)-I-D-(-)-tartrate thereby obtained in crystalline form is converted to IIa or IIb respectively in aqueous acid solution at 20.degree.-110.degree. C. by splitting off the L-(+)-tartaric acid or D-(-)-tartaric acid, hydrolyzing the nitrile group and hydrolytically splitting off the tert.-butyl group.Type: GrantFiled: December 31, 1980Date of Patent: September 21, 1982Assignee: BASF AktiengesellschaftInventors: Dieter Degner, Hans J. Pander, Hardo Siegel
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Patent number: 4350826Abstract: The disclosure relates to a process for converting p-hydroxymandelic acid or a salt thereof to p-hydroxyphenylglycine. The product is a useful intermediate in the pharmaceutical industry.Type: GrantFiled: December 12, 1980Date of Patent: September 21, 1982Assignee: Imperial Chemical Industries LimitedInventors: Philip N. Edwards, Michael E. McMenim
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Patent number: 4349689Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4346105Abstract: Phenylacetic acid amide compounds of the formula ##STR1## in which R.sub.1 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.2 is hydrogen, lower alkyl, lower alkoxy, halogen having an atomic number of not more than 35 or trifluoromethyl, R.sub.3 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35 and R.sub.4 is hydrogen, lower alkyl, lower alkoxy or halogen having an atomic number of not more than 35, and in which R.sub.5 is a radical of aliphatic character containing the group R.sub.6, R.sub.6 and R.sub.7 are each hydrogen or together are a divalent aliphatic radical and the group of the formula --C(.dbd.O)--R.sub.8 (Ia) is a carboxyl group, which can be functionally modified, and their salts are useful as anti-inflammatory agents.Type: GrantFiled: December 17, 1980Date of Patent: August 24, 1982Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Gerhard Baschang
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Patent number: 4339589Abstract: Manufacture of 4-substituted oxazolinone-(5) compounds, which are intermediates for substituted aminoacids, by alkylation of 2-substituted or 3,4-disubstituted oxazolinone-(5) compounds in an aprotic solvent in the presence of a tertiary amine.Type: GrantFiled: August 5, 1980Date of Patent: July 13, 1982Assignee: BASF AktiengesellschaftInventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
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Patent number: 4338457Abstract: The present invention relates to novel compositions of matter and novel processes for preparing these compositions of matter. Moreover, there are provided novel methods by which certain of these novel compositions of matter are employed for pharmacologically useful purposes.Type: GrantFiled: February 28, 1980Date of Patent: July 6, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4337207Abstract: Biologically active derivatives of norepinephrine are disclosed. Such derivatives are catecholamines wherein isoproterenol is modified by extending the isopropyl functional grouping to an alkyl, aryl, or alkyl-aryl chain of variable length where said chain terminates in a carboxylic acid functional group, or in a substituted amide functional group. Such derivatives are .beta.-adrenergic and a number of such derivatives e.g., 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid p-toluide, 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid para-n-butyl anilide; 6-(.beta.,3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid para-methoxy anilide; 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid paratrifluoromethyl anilide; and 6-(.beta.-3,4-dihydroxyphenyl-.beta.-hydroxy)-ethylamino heptanoic acid N-methyl para-toluide display a .beta.-adrenergic activity at least several orders of magnitude greater than isoproterenol itself.Type: GrantFiled: September 4, 1980Date of Patent: June 29, 1982Assignee: Regents of the University of CaliforniaInventors: Murray Goodman, Michael S. Verlander, Kenneth A. Jacobson, Kenneth L. Melmon, Neal Castagnoli
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Patent number: 4336405Abstract: There are described novel compounds which include a silver halide developing function, a colorless ligand which is a radical of an iminodiacetic acid and a radical containing an onium group. The compounds are useful in photography as silver halide developing agents and also may be complexed with metals to form dye developers.Type: GrantFiled: July 11, 1980Date of Patent: June 22, 1982Assignee: Polaroid CorporationInventor: Elbert M. Idelson
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Patent number: 4336267Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.Type: GrantFiled: May 19, 1980Date of Patent: June 22, 1982Assignee: Aktiebolaget HassleInventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
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Patent number: 4334069Abstract: Chemiluminescent-labeled conjugates of the formula: ##STR1## wherein one of R.sup.1 and R.sup.2 is hydrogen and the other is --NR.sup.3 R.sup.4 ; R.sup.3 is hydrogen or straight chain alkyl containing 1-4 carbon atoms and R.sup.4 isL(CO--HN--CH.sub.2).sub.nwherein n=2-8 and L(CO)-- is a hapten bound through an amide bond. The labeled conjugates are useful as reagents in specific binding assays for determining haptens or their specific binding partners in liquid media.Type: GrantFiled: July 24, 1978Date of Patent: June 8, 1982Assignee: Miles Laboratories, Inc.Inventors: Robert T. Buckler, Hartmut R. Schroeder
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Patent number: 4329502Abstract: Compounds are provided which can be used in the preparation of reagents useful for quantitatively determining the presence of b-adrenergic blocking agents. These compounds contain a derivative of the blocking agent which is linked to an antigen or enzyme, the antigen conjugates being useful for preparing antibodies, and the enzyme conjugates being useful as detectors in an immunoassay as well. Additionally carboxylic acids, esters and aldehydes which are derivatives of the blocking agents are provided which are useful in preparing the above conjugates.Type: GrantFiled: August 7, 1980Date of Patent: May 11, 1982Assignee: Syva CompanyInventors: Prithipal Singh, Marcel R. Pirio
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Patent number: 4326071Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.Type: GrantFiled: September 28, 1977Date of Patent: April 20, 1982Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4318898Abstract: What are disclosed are a diagnostic agent for visualizing the hepatobiliary system which agent contains Technetium-99m-labelled (2,4,5-trimethylacetanilido)-iminodiacetate in a suitable solvent, and a process for the preparation of this diagnostic agent; chloroacetic acid-(2,4,5-trimethylanilide) as an intermediate product and a process for the preparation thereof; and (2,4,5-trimethylacetanilido)-iminodiacetate and a process for the preparation thereof.Type: GrantFiled: December 19, 1979Date of Patent: March 9, 1982Assignee: Hoechst AktiengesellschaftInventors: Michael Molter, Gerhard Kloss, Eberhard Schickel
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Patent number: 4319040Abstract: Improved process for the production of optical aCTIVE (D- or L-) threo-3-(3,4-dihydroxyphenyl)serine, which comprises subjecting racemic threo-3-(3,4-dibenzyloxyphenyl)-N-carbobenzyloxyserine to optical resolution by using as a resolving reagent an optical active amino alcohol derivative, and then subjecting the resulting optical active (D- or L-) threo-3-(3,4-dibenzyloxyphenyl)-N-carbobenzyloxyserine to hydrogenolysis.Type: GrantFiled: July 18, 1980Date of Patent: March 9, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Naohito Ohashi, Shoji Nagata, Kikuo Ioshizumi, Junki Katsube
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Patent number: 4317921Abstract: The chloramine T procedure is employed to provide radioiodinated T.sub.3 and radioiodinated T.sub.4 from T.sub.3 and T.sub.4, respectively, at specified pHs and mole ratios to provide for long shelf life. T.sub.3 is also radioiodinated to high specific activity radioiodinated T.sub.4, and purified after a specified waiting period to remove radioactive non-antigenic contaminants and thereby provide a long shelf life.Type: GrantFiled: April 25, 1979Date of Patent: March 2, 1982Assignee: Becton Dickinson & CompanyInventors: Max G. Reese, Richard H. Hales
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Patent number: 4297489Abstract: Certain 7-acylamido-3-(1-carboxy-loweralkyl-tetrazol-5-ylthiomethyl)-3-cephem-4-ca rboxylic acids and their salts and easily hydrolyzed esters of the 4-carboxyl group were synthesized and found to be potent antibacterial agents which exhibited good aqueous solubility. In a preferred embodiment the 7-substituent was 2'-aminomethylphenylacetamido.Type: GrantFiled: June 27, 1975Date of Patent: October 27, 1981Assignee: Bristol-Myers CompanyInventors: William J. Gottstein, Murray A. Kaplan, Alphonse P. Granatek
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Patent number: 4296125Abstract: Derivatives of benzoylphenoxyalkanoic acids corresponding to the formula: ##STR1## wherein: X represents for example a halogen, R.sup.1 and R.sup.2 represent for example alkyl groups, R represents for example an aminoacid; and the salts thereof are new products showing antilipaemic and anticholesterolemic pharmacological activity.Type: GrantFiled: February 21, 1980Date of Patent: October 20, 1981Assignee: Alpha Farmaceutici S.p.A.Inventors: Valerio Borzatta, Manlio Cristofori, Mauro Morotti, Giuseppe Mascellani
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Patent number: 4296127Abstract: Novel compounds are prepared by reacting essential or semi-essential amino acids with nitrogen-free analogues thereof, particularly alpha-keto and/or alpha-hydroxy analogues. The mixed salt reaction products are precursors of essential and semi-essential amino acids in the body, and mixtures of the salts are useful in the treatment of renal and hepatic disorders characterized by protein intolerance leading to deficiencies of various essential and semi-essential amino acids in the body. They may also be useful in the treatment of nitrogen wasting disorders and protein malnutrition. The novel compounds are generally far more palatable and soluble in aqueous solutions than the individual essential or semi-essential amino acids, nitrogen-free analogues thereof, or simple mixtures of these.Type: GrantFiled: April 18, 1979Date of Patent: October 20, 1981Assignee: The Johns Hopkins UniversityInventor: Mackenzie Walser
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Patent number: 4281180Abstract: A process for producing threo-3-amino-2-hydroxybutanoylaminoacetic acids comprises the steps of allowing to react a starting compound represented by the general formula: ##STR1## wherein R.sub.1 represents a naphthyl or a group of the formula: ##STR2## in which R.sub.6 and R.sub.7 represent individually hydrogen, halogen, amino or a protected amino, hydroxy or a protected hydroxy, a lower alkoxy or a lower alkyl and R.sub.2 represents a protected amino, with a starting compound represented by the general formula: ##STR3## wherein R.sub.3 represents hydrogen or an ester residue, to obtain threo-3-protected amino-2-hydroxy-4-oxobutanoic acid or its ester represented by the general formula: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 have the same meanings as above, and then reducing the same into threo-3-protected amino-2-hydroxybutanoic acid or its ester represented by the general formula: ##STR5## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: November 23, 1979Date of Patent: July 28, 1981Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hamao Umezawa, Takaaki Aoyagi, Tadashi Shirai, Rinzo Nishizawa, Masao Suzuki, Tetsushi Saino
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Patent number: 4277471Abstract: Biphenylylalkylamines which have anti-arrhythmic activity have been prepared. Pharmaceutical formulations containing such compounds and a method of treating cardiac arrhythmias are provided.Type: GrantFiled: February 22, 1980Date of Patent: July 7, 1981Assignee: Eli Lilly and CompanyInventors: William B. Lacefield, Richard L. Simon
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Patent number: 4269850Abstract: Complexes of enterochelin, and certain analogues thereof, with one of the metals indium and scandium are useful for the treatment of bacterial infections.Type: GrantFiled: May 2, 1979Date of Patent: May 26, 1981Assignee: National Research Development CorporationInventor: Henry J. Rogers
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Patent number: 4267193Abstract: N-substituted-4-(polyfluoro-2-hydroxy-2-propyl)anilines and compounds related thereto, useful as antihypertensive agents, are prepared by reaction of an N-substituted aniline with a polyfluoroacetone.Type: GrantFiled: May 4, 1979Date of Patent: May 12, 1981Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4264771Abstract: Manufacture of 4-substituted oxazolinone-(5) compounds, which are intermediates for .alpha.-substituted aminoacids, by alkylation of 2-substituted or 3,4-disubstituted oxozolinone-(5) compounds in an aprotic solvent in the presence of a tertiary amine.Type: GrantFiled: March 29, 1978Date of Patent: April 28, 1981Assignee: BASF AktiengesellschaftInventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
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Patent number: 4260823Abstract: Novel acetylenic derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein R is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR2## is hydrogen, a straight or branched lower alkyl group of 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; each R.sub.1 is the same and is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.3 R.sub.4 wherein each of R.sub.3 and R.sub.4 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms and can be the same or different, or ##STR3## wherein R.sub.5 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; and pharmaceutically acceptable salts and individual optical isomers thereof.Type: GrantFiled: July 2, 1979Date of Patent: April 7, 1981Assignee: Merrell Toruade et CompagnieInventors: Patrick J. Casara, Michel Jung, Brian W. Metcalf
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Patent number: 4243678Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.Type: GrantFiled: December 15, 1978Date of Patent: January 6, 1981Assignee: Byk Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4240975Abstract: Bestatin, which is [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, and related compounds which inhibit aminopeptidase B, leucino aminopeptidase and Bleomycin hydrolase, enhance the anti-tumor effect of Bleomycin and exhibit an antifertility effect were synthesized and tested.Type: GrantFiled: September 26, 1979Date of Patent: December 23, 1980Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Takaaki Aoyagi, Tomohisa Takita, Rinzo Nishizawa, Tetsushi Saino
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Patent number: 4238507Abstract: A new compound having the formula ##STR1## and now designated forphenicinol is produced, which exhibits an immunopotentiating activity. This new compound as well as its pharmaceutically acceptable salts and hydrates are useful for immunotherapy and treatment of immune diseases and disorders in living animals, including human beings. The new compound can be produced by hydrolysis of the corresponding aminonitrile compound of the formula ##STR2## or by reduction of forphenicine.Type: GrantFiled: March 16, 1979Date of Patent: December 9, 1980Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Tomio Takeuchi, Takaaki Aoyagi, Masaaki Ishizuka, Hajime Morishima, Ikuo Matsumoto, Takuzo Yamamoto
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Patent number: 4237305Abstract: Substituted phenylacetic acid compounds represented by the following general formula and preparation thereof: ##STR1## wherein R.sup.1 is hydrogen or protected carboxy,R.sup.2 is hydrogen, or protected amino, provided that when R.sup.1 is hydrogen, then R.sup.2 is protected amino, and when R.sup.2 is hydrogen, then R.sup.1 is protected carboxy,R.sup.3 is oxo, hydroxyimino or protected hydroxyimino,R.sup.4 is hydrogen or halogen, andm is an integer of 1 to 3.Type: GrantFiled: March 30, 1977Date of Patent: December 2, 1980Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Masashi Hashimoto, Osamu Nakaguti, Teruo Oku, Hidekazu Takeno
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Patent number: 4235896Abstract: Compounds of the formula ##STR1## in which A is lower alkyl, or a substituted or unsubstituted phenyl, thienyl, furyl, indolyl or thiaindolyl radical, R, X.sub.4 and X.sub.5 are hydrogen or lower alkyl, Y is hydrogen, hydroxy, etherified hydroxy, substituted amino, or N-attached heterocyclyl, X.sub.0 is O or OCH.sub.2 CH.sub.2 O, R' represents hydrogen, lower alkyl or acetyl; and acid-addition salts thereof, are novel and useful in pharmacy as hypolipaemiant, hypocholosterolaemiant and cholagogic agents or in the preparation of such agents.Type: GrantFiled: October 28, 1977Date of Patent: November 25, 1980Assignee: Orchimed S.A.Inventor: Andre Mieville
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Patent number: 4233456Abstract: Optically active 2-amino-2-phenylacetic acid of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, which are identical or different, denote hydrogen, halogen, hydroxy, alkyl, acyl, or alkoxy, is prepared by asymmetrical transformation of a corresponding DL-aminophenylacetonitrile with L(+)-tartaric acid. To this end the corresponding DL-2-amino-2-phenyl-acetonitrile is reacted with approximately equimolar amounts of L(+)-tartaric acid in the presence of at least one alkanol having from 1 to 5 carbon atoms and/or at least one carbonyl compound at a temperature of from 0.degree. to 50.degree. C. and the mixture is stirred for 2 to 120 hours at the indicated temperature. The crystallized transformation product is separated, hydrolyzed by treatment with an acid and the desired product is isolated.Type: GrantFiled: August 28, 1978Date of Patent: November 11, 1980Assignee: Riedel-de Haen AktiengesellschaftInventors: Horst Schmand, Wolfgang Dannenberg
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Patent number: 4230883Abstract: The invention relates to the hydrohalide salts of L-.alpha. -methyl-3,4-dihydroxyphenylalanine (methydopa). The method of preparing these and related compounds in the absence of water or other polar solvents is also shown.Type: GrantFiled: December 12, 1977Date of Patent: October 28, 1980Assignee: Merck & Co., Inc.Inventors: David D. Saperstein, Seemon H. Pines
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Patent number: 4228184Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: May 4, 1978Date of Patent: October 14, 1980Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, David W. Cushman
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Patent number: 4226804Abstract: Dihydrochalcones of the formula ##STR1## are disclosed wherein X is H or OH and R is lower alkyl. These materials are useful as sweeteners for edibles. A process for preparing these compounds using a novel intermediate is disclosed as are acid and base neutralization products of the subject dihydrochalcones.Type: GrantFiled: March 9, 1979Date of Patent: October 7, 1980Assignee: DynapolInventors: Grant E. DuBois, Rebecca A. G. Stephenson, Guy A. Crosby
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Patent number: 4220590Abstract: New optically active bis phosphine compounds which are usful in optically active catalysts. Such catalysts are particularly useful in catalytic asymmetric hydrogenation.Type: GrantFiled: July 31, 1978Date of Patent: September 2, 1980Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky, Billy D. Vineyard
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Patent number: 4218474Abstract: L- and DL-isomers of compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein R is hydrogen or methyl; R.sup.1 is alkynyl, alkenyl or cycloalkyl, each having from three to seven carbon atoms or alkyl having from one to six carbon atoms which may optionally be substituted by one or more groups selected from hydroxy, alkoxy, carboxy, amino, monoalkylamino, dialkylamino, phenyl and phenoxy, any such phenyl or phenoxy being optionally substituted with one or more hydroxy, alkyl or alkoxy groups, said alkyl and alkoxy optional substituents having from one to six carbon atoms; provided that R.sup.1 is other than 4-hydroxy-.alpha.-carboxybenzyl or 4-methoxy-.alpha.-carboxybenzyl. Said compounds are useful in treating diseases and conditions characterized by reduced blood flow, oxygen availability or carbohydrate metabolism in the cardiovascular system. The D-isomers of the compounds of formula (II) are substantially inactive in treating such diseases and conditions.Type: GrantFiled: October 30, 1978Date of Patent: August 19, 1980Assignee: Pfizer Inc.Inventors: Ian T. Barnish, Peter E. Cross, John C. Danilewicz
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Patent number: 4215223Abstract: The invention provides a process for the preparation of D(-).alpha.phenylglycine by resolution of DL.alpha.phenylglycine by means of D(+)camphorsulfonic acid. The present process enables the preparation of D(-).alpha.phenylglycine at a minimum loss of the very expensive starting materials, such as DL.alpha.phenylglycine and D(+)camphorsulfonic acid. The salts produced in this process are precipitated from the resolution filtrate and the filtrate may be discarded as effluent water without any danger to the environment.Type: GrantFiled: October 16, 1978Date of Patent: July 29, 1980Inventor: Gerard Kessels
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Patent number: 4208345Abstract: 2-Hydroxy-n-propylamines of formula, ##STR1## in which R is a mono- or dialkylphenolpoly-(C.sub.2-3)-alkyleneglycolether group bound through an oxygen atom and containing at least 8 (C.sub.2-3)alkyleneoxy units of which at least 50% are ethyleneoxy, R.sub.1 is hydrogen or alkyl, optionally substituted with hydroxyl or X, R.sub.2 is alkylene, optionally substituted with hydroxyl, and X is an acid group, the compounds being in free acid or salt form, are useful as surface active agents, especially for use as dispersing or emulsifying agents in textile lubricant and fat liquor emulsions, and as agents for the degreasing of pelts and leathers, as tanning auxiliary agents and for the desizing of textile materials.Type: GrantFiled: February 27, 1978Date of Patent: June 17, 1980Assignee: Sandoz Ltd.Inventor: Werner Amati
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Patent number: 4205185Abstract: A process for the preparation of racemic 4-hydroxyphenylglycine, in which phenol, glyoxylic acid (or a salt thereof) and ammonia are reacted together to produce the desired 4-hydroxyphenylglycine.Type: GrantFiled: August 31, 1978Date of Patent: May 27, 1980Assignee: Sterling Drug Inc.Inventors: Michael J. Elton, Arthur Jackson, John W. Harrison
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Patent number: 4201864Abstract: Compounds of formula (I): ##STR1## wherein: m is 1 or 2; n is 4 to 8; X is CO, protected CO, or CROH wherein R is hydrogen or C.sub.1-4 alkyl and wherein the OH moiety may be protected; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms; R.sub.3 is hydroxy, or protected hydroxy; R.sub.2 and R.sub.4 are separately hydrogen, C.sub.1-9 alkyl, C.sub.5-8 cycloalkyl, C.sub.5-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof; except that when one of R.sub.2 and R.sub.4 is hydrogen or C.sub.1-4 alkyl then the other of R.sub.2 and R.sub.4 cannot be hydrogen or C.sub.Type: GrantFiled: November 22, 1978Date of Patent: May 6, 1980Assignee: Beecham Group LimitedInventors: Frederick Cassidy, Gordon Wootton
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Patent number: 4191777Abstract: There are prepare half amides (semi-amides) of unsaturated aliphatic dicarboxylic acids of the formula: ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, a hydroxy group, a methyl group or a methoxy group or two of these together are a methylenedioxy group, R.sub.4 is hydrogen or a methyl group, R.sub.5, R.sub.6 and R.sub.7 independently are hydrogen or C.sub.1 -C.sub.4 alkyl groups and n is 0 or 1 and their salts with the proviso that in the case of the free acids N[2-(3-hydroxyphenyl)-2-hydroxyethyl]-maleic acid monoamide is excluded. The compounds have blood pressure raising activity and also have antidepressive activity.Type: GrantFiled: December 13, 1978Date of Patent: March 4, 1980Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals RoesslerInventors: Karl H. Kingler, Klause Thiemer, Fritz Stroman
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Patent number: 4189604Abstract: Bestatin, which is [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, and related compounds which inhibit aminopeptidase B, leucino aminopeptidase and Bleomycin hydrolase, enhance the anti-tumor effect of Bleomycin and exhibit an antifertility effect were synthesized and tested.Type: GrantFiled: June 24, 1977Date of Patent: February 19, 1980Assignee: Zaidan Hojin Biseibutsu Kagaku Kenkyu KaiInventors: Hamao Umezawa, Takaaki Aoyagi, Tomohisa Takita, Rinzo Nishizawa, Tetsushi Saino