Abstract: L-aspartyl-L-phenylglycine esters, e.g., L-aspartyl-L-phenylglycine methyl ester, are new compounds useful as sweeteners for various foods, beverages and compositions intended to be tasted, e.g., chewing gums, dentifrices, mouth washes. Such compounds can be made by reaction of a corresponding amide, such as asparagine, with an amino blocking agent, e.g., carbobenzoxy chloride, whereby a reaction with the amino group of the asparagine produces the corresponding carbobenzoxyamide, following which the amide is reacted with the methyl or other suitable lower alkyl ester of an amino acid, e.g., phenylglycine, to produce the corresponding peptide by reaction of the free carboxylic and amino groups, and subsequently, the carbobenzoxy group is removed by hydrogenolysis in the presence of a catalyst and the terminal amide of the peptide is converted to the corresponding acid by hydrolysis.
Abstract: Hexa- and heptapeptides of formula W-[X-Pro-Phe-Phe-Y-Z].sub.n H prepared by standard synthetic peptide techniques are anti-inflammatory, anti-rheumatoid arthritic and anti-ulcer agents.
Type:
Grant
Filed:
January 21, 1975
Date of Patent:
July 27, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Arthur F. Wagner, Frederick W. Holly, Tsau-Yen Lin, Tsung-Ying Shen, Ralph F. Hirschmann
Abstract: [2-Methyl-Ala.sup.6 ]LRH is described, as well as its preparation by solid phase methodology and intermediates in its production. The decapeptide is a luteinizing hormone releasing agent and is useful as an ovulation inducing agent and as a claudogenic/interceptive agent.
Abstract: An ester compound of the formula: ##EQU1## wherein R.sup.1 is hydrogen or hydroxy, R.sup.2 is alkyl of one to five carbon atoms, alkenyl of two to three carbon atoms, cycloalkyl of three to five carbon atoms or methylcycloalkyl of four to six carbon atoms and Y is alkylene of one to four carbon atoms, is disclosed. Several methods for preparing the compound[I] are also disclosed. The compound[I] is useful as a non-nutritive sweetening agent.
Abstract: Highly pure pyroglutamyl-histidyl-prolinamide is prepared by removing the protecting groups of the protected tripeptide by means of reductive deprotection with sodium in liquid ammonia followed by passing the crude deprotected tripeptide through a gel filtration means.
Abstract: Reduced bacitracin and pharmaceutically acceptable salts thereof obtained by treating bacitracin with a reducing agent. The resulting product has improved stability.
Abstract: Synthetic antigens related to luteinizing hormone-releasing hormone (hereinafter designated LH-RH) having the amino acid composition, pyroglutamyl-histidyl-tryptophanylseryl-tyrosyl-glycyl-leucyl-arginyl-prol yl-glycyl-poly-L-lysine (hereinafter designated pyroglu-his-trp-ser-tyr-glyleu-arg-pro-gly-poly-L-lys) and poly-L-lysyl-glutarylhistidyl-tryptophanyl-seryl-tyrosyl-glycyl-leucyl-arg inylprolyl-glycine amide (hereinafter designated poly-L-lysglutaryl-his-trp-ser-tyr-gly-leu-arg-pro-gly) are prepared by coupling the corresponding decapeptide with poly-L-lysine. The corresponding decapeptides are prepared by controlled stepwise procedures starting with individual amino acid components. These antigens have the property of inducing formation of antibodies to luteinizing hormone-releasing hormone (LH-RH) in animals.
Type:
Grant
Filed:
October 7, 1974
Date of Patent:
June 15, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Carl H. Hoffman, Harvey Schwam, Stephen F. Brady, Martin Hichens, Ruth F. Nutt
Abstract: When hydrogen halide salts of L-aspartic anhydride are reacted with lower alkyl esters of L-phenylalanine to produce the corresponding L-aspartyl-L-phenylalanine esters, a significant increase in yield and in the proportion of the .alpha.-isomer to the .beta.-isomer is achieved when the reaction is carried out in the presence of a lower alkanol and of a strong acid, such as sulfuric acid, hydrogen chloride, or mono-esters of sulfuric acid with a lower alkanol.
Abstract: Pyrimidine derivatives represented by the formula, ##SPC1##Wherein R.sub.1 and R.sub.2 are individually a hydrogen atom or a methyl group, and R.sub.3 is a group formed by removing the carboxyl group from a carboxylic acid, are quite useful in acylating compounds having amino and/or imino and/or hydroxyl groups. The pyrimidine derivatives can easily be prepared by reacting a 2-mercapto-4- and/or 6-methyl-substituted or unsubstituted pyrimidine with a carboxylic acid or a reactive derivative thereof in an inert solvent.
Abstract: The use of catalytic hydrogenolysis to selectively deblock protected moieties in sulfur containing compounds has not been a practical process due to poisoning of the catalyst by the sulfur compound. It has now been found that catalytic hydrogenolysis of sulfur compounds can be successfully carried out by conducting the reaction in liquid ammonia as solvent.
Type:
Grant
Filed:
March 20, 1974
Date of Patent:
June 1, 1976
Assignee:
The United States of America as represented by the Department of Health, Education and Welfare
Abstract: A process for the synthesis of peptides in a liquid phase wherein the peptide product, and intermediates in the peptide synthesis, are bound to a polyalkylene glycol polymer and wherein the polymer-bound peptide is separated from the liquid phase, e.g. for purposes of isolation or purification, by crystallizing the polymer-bound peptide.
Abstract: Crystalline thyrotropin releasing hormone (TRH) tartrate was obtained for the first time from a solution comprising TRH, tartaric acid and a certain solvent. The crystals are very pure and very stable against moisture for a long period of time.
Abstract: A novel dipeptide, L-aspartyl-aminomalonic acid methyl 2-methylcyclohexyl diester and its physiologically acceptable salts which are useful as a sweetener, and production thereof and sweetening compositions containing the dipeptide or its salt.
Abstract: Novel tripeptides are disclosed. These tripeptides have anti-depressant activity and thyrotropin releasing hormone activity. Processes for preparing these tripeptides are also disclosed.
Type:
Grant
Filed:
January 27, 1975
Date of Patent:
May 25, 1976
Assignee:
Merck & Co., Inc.
Inventors:
Daniel F. Veber, Frederick W. Holly, Ruth F. Nutt, Sandor L. Varga
Abstract: Synthetic hypocalcaemic dotriacontapeptide of the formulaH-Cys-Ser-Asn-Leu-Ser--Thr-Cys-Val-Leu-Ser-Ala-Tyr-Try-Arg-Asn-Leu-Asn-Asn- Phe-His-Arg-Phe-Ser-Gly-Met-Gly-Phe-Gly-Pro-Glu-Thr-Pro-OH Iand analogues and derivatives, salts and complexes thereof and process for their manufacture.
Type:
Grant
Filed:
December 10, 1971
Date of Patent:
May 11, 1976
Assignee:
Ciba-Geigy Corporation
Inventors:
Max Brugger, Friedrich Werner Kahnt, Bruno Kamber, Robert Neher, Bernhard Riniker, Werner Rittel, Peter Sieber, Herbert Zuber, Hendrik Marie Greven
Abstract: A synthetic decapeptide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L- arginyl-L-prolyl-glycinamide which has the hormonal activities of the luteinizing hormone releasing hormone (LRH) of the hypothalamus gland of mammals is produced by utilizing as the key starting materials, the amino acids, glutamic acid or pyroglutamic acid, histidine, tryptophan, serine, tyrosine, glycine, leucine, arginine, and proline. Synthesis of the decapeptide is accomplished by coupling, in appropriate combinations of appropriate protected forms of the amino acids, and finally deprotecting to yield the amide, L-pglutamyl-L-histidyl-L-tryptophanyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L- arginyl-L-prolyl-glycinamide.
Type:
Grant
Filed:
January 14, 1974
Date of Patent:
April 27, 1976
Inventors:
Karl Folkers, Bruce L. Currie, Jaw-Kang Chang, Hans Sievertsson, Conny Bogentoft