Sulfur Or Selenium Patents (Class 562/556)
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Patent number: 4483869Abstract: A novel class of carnitine derivatives is disclosed which comprises thiocarnitine and the S-acyl thiocarnitines wherein the acyl radical is the radical of saturated organic acids having from 2 to 10 carbon atoms. The S-acyl thiocarnitines are prepared e.g. by reacting crotonoyl betaine halogenide with the corresponding thio-acid, while thiocarnitine is obtained by hydrolysis of an S-acyl thiocarnitine. These compounds are useful therapeutic agents, e.g. for the treatment of intoxications, liver malfunctions and burns.Type: GrantFiled: December 15, 1981Date of Patent: November 20, 1984Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Maria O. Tinti, Emma Quaresima, Paolo de Witt
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Patent number: 4461775Abstract: Hydroxythioether fatty acid derivatives of formula (I) ##STR1## wherein n is 2-5, m is 8-12, R.sup.1 is OH, O-loweralkyl, NH.sub.2, NH-loweralkyl or NH-carboxyalkyl, R.sup.2 is OH or O-lower-alkyl, X is H or NH.sub.2 or ##STR2## and salts thereof are useful in preventing or alleviating asthma or other allergic diseases.Type: GrantFiled: August 2, 1982Date of Patent: July 24, 1984Assignee: McNeilab, Inc.Inventors: Kerry G. Stanley, Winston Ho
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Patent number: 4460601Abstract: Dipeptides are claimed which consist of a mercaptoalkanoic acid and a derivative of said acid, namely an S-alkyl-, aralkyl-, aryl-, acyl- or aroyl derivative with methionine, a methionine ester or a methionine amide, as well as their salts with metallic cations and organic bases. These compounds have the property of protecting the liver against intoxications and have sedative and hypnotic properties.Type: GrantFiled: December 21, 1982Date of Patent: July 17, 1984Assignee: Maggioni Farmaceutici, S.p.A.Inventors: Giampaolo Picciola, Franco Ravenna, Mario Riva
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Patent number: 4459423Abstract: A process for producing efficiently and economically without using strong acids nor strong bases, .alpha.-amino acids from .alpha.-amino acid amides by hydrolyzing .alpha.-amino acid amides in an aqueous medium in the presence of ammonia. If necessary, the resultant hydrolyzate liquid from which .alpha.-amino acid has been removed may be reused.Type: GrantFiled: March 5, 1982Date of Patent: July 10, 1984Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masaharu Doya, Takako Uchiyama
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Patent number: 4448976Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R.sup.1 is lower alkyl or aralkyl, such as benzyl and the like; and R.sup.2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.Type: GrantFiled: February 7, 1983Date of Patent: May 15, 1984Assignee: Merck & Co., Inc.Inventor: Philippe L. Durette
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Patent number: 4444682Abstract: A method for sulfating a hydroxy amino acid or a residue of such an amino acid in a peptide by reaction with a reagent which is a tertiaryammonium salt of acetylsulfuric acid having the formula:[CH.sub.3 COOSO.sub.3 ].sup.- [R].sup.+wherein R is triethylamine, ethyldiisopropylamine, pyridine, 4-methylmorpholine or 4-N,N-dimethylaminopyridine. The .alpha.-amino group and any other labile side chains present may be protected or may be left unprotected at the time the sulfation takes place.Type: GrantFiled: November 4, 1982Date of Patent: April 24, 1984Assignee: The Salk Institute for Biological StudiesInventors: Jean E. F. Rivier, Botond Penke
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Patent number: 4443435Abstract: Novel, transient prodrug forms of biologically active agents containing mercapto groups have (i) the structural formula (I): ##STR1## wherein X is O, S, or NR.sup.5 ;R.sup.1 S is the residue of any biologically active agent R.sup.1 SH;R.sup.Type: GrantFiled: November 12, 1981Date of Patent: April 17, 1984Assignee: Merck & Co., Inc.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4438270Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: wherein Y is ClCH.sub.2, F.sub.2 CH--, F.sub.3 C--, ClCH.sub.2 --, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR1## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and 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## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.Type: GrantFiled: June 25, 1982Date of Patent: March 20, 1984Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4424354Abstract: Mammalian collagenase is inhibited by compounds of the formula ##STR1## or salts thereof, wherein R is hydrogen, alkanoyl of 2 to 10 carbon atoms or arylcarbonyl;R.sub.1 is of 3 to 8 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, aryl or arylalkyl;R.sub.2 is hydrogen, ##STR2## R.sub.3 is ##STR3## R.sub.4 is hydrogen, methyl, ethyl, or ##STR4## R.sub.5 and R.sub.6 are each independently selected as --OCH.sub.3 or --OCH.sub.2 CH.sub.3 or are combined as --OCH.sub.2 CH.sub.2 O-- or --O--(CH.sub.2).sub.3 --O--;R.sub.7 and R.sub.8 are each independently selected as hydrogen, methyl or ethyl or are combined as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 --O--CH.sub.2 CH.sub.2 --;R.sub.9 is hydrogen, methyl, ethyl ##STR5## m is an integer from 0 to 7; p is an integer from 1 to 3; AA.sub.n is an amino acid chain of from one to three amino acids; n is 1 or 1, 2 or 1, 2, 3;when p is 1, AA.sub.n is AA.sub.1 ;when p is 2, AA.sub.n is AA.sub.1 -AA.sub.2 ;when p is 3, AA.sub.n is AA.sub.1 -AA.sub.Type: GrantFiled: September 24, 1982Date of Patent: January 3, 1984Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, Tamara Dejneka
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Patent number: 4388312Abstract: New quinone derivatives of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or two of R.sup.1 combine to represent --CH.dbd.CH--CH.dbd.CH--, R is amino which may be substituted or --OR.sup.4 wherein R.sup.4 is hydrogen, C.sub.1-4 alkyl or --CH.sub.2 --CH.dbd.C(CH.sub.3 --CH.sub.2 --.sub.m H (wherein m is an integer of 1 to 10), and n is an integer of 1 to 10 when R is amino which may be substituted, or n is an integer of 2 to 10 when R is --OR.sup.4, and their hydroquinone forms, have useful physiological activities such as blood-pressure decreasing and antiallergic activities.Type: GrantFiled: August 26, 1980Date of Patent: June 14, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Shinji Terao, Mitsuru Shiraishi, Kaneyoshi Kato
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Patent number: 4387104Abstract: A pyruvic acid hydrazone derivative of the formula: ##STR1## wherein R is an aryl radical optionally substituted by lower alkyl or is an aliphatic hydrocarbon radical which can be substituted by a lower alkoxy, a cycloalkyl or an optionally substituted aryl radical,A is an alkylene radical containing 2 to 8 carbon atoms, with at least 2 carbon atoms between B and the nitrogen atom, andB is an oxygen or sulphur atom;or a physiologically acceptable salt, ester or amide thereof which possesses hypoglycaemic activity.Type: GrantFiled: August 14, 1981Date of Patent: June 7, 1983Assignee: Boehringer Mannheim GmbHInventors: Ruth Heerdt, Hans P. Wolff, Fritz Kaiser, Wolfgang Schaumann, Hans Kuhnle
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Patent number: 4385183Abstract: This invention is directed to the telomerization of water-soluble monomers in an aqueous phase. More particularly, this invention is directed to a process for the telomerization of water-soluble monomers and water-insoluble telogens in aqueous phase, wherein the water-insoluble telogens are solubilized by the addition of an effectively solubilizing amount of surface-active compounds.Type: GrantFiled: June 4, 1981Date of Patent: May 24, 1983Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Rainer Hofer, Hans-Christoph Wilk, Bernd Wegemund
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Patent number: 4361703Abstract: N-acetyl-para-aminophenyl N'acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl-N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.Type: GrantFiled: March 23, 1981Date of Patent: November 30, 1982Assignee: Sterling Drug Inc.Inventors: George Margetts, Roderic S. Andrews, Jean Legros
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Patent number: 4346234Abstract: Sodium salt of mercaptopropionylglycine of formula: ##STR1## This salt is prepared by reacting 2-mercaptopropionylglycine with sodium-2-ethylhexanoate.It is a very active protector of the hepatic cell and it can be also efficaciously used as a mucolytic agent by inhalation or in the form of suppositories.Type: GrantFiled: April 29, 1980Date of Patent: August 24, 1982Inventor: Pietro Gargani
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Patent number: 4339600Abstract: Compounds for alleviating or reducing angiotensin related hypertension in hypertensive mammals comprising angiotensin converting enzyme inhibitors selected from a group of mercaptoacyl aminoacids.Type: GrantFiled: February 13, 1978Date of Patent: July 13, 1982Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, David W. Cushman
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Patent number: 4332813Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: May 7, 1980Date of Patent: June 1, 1982Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4330677Abstract: The invention relates to polyethers having an an average molecule weight of 3000 to 5000 and having a propylene oxide proportion of 60 to 80% and an ethylene oxide proportion of 20 to 40%. Also included in the invention are compositions containing said polyethers and methods for the use of said polyethers and compositions, particularly for their anti-lipidaemic effect.Type: GrantFiled: October 31, 1979Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventors: Siegfried Linke, Mithat Mardin, Hans P. Krause, Rudiger Sitt
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Patent number: 4324900Abstract: Disclosed is a chiral, total synthesis of thienamycin from D-glucose, which proceeds via intermediates I, II, and III and joins aldehyde IV or acid V, which are known to be useful in the total synthesis of thienamycin (VI): ##STR1## wherein R.sup.1 is hydrogen or a removable protecting group;R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms.Type: GrantFiled: March 30, 1981Date of Patent: April 13, 1982Assignee: Merck & Co., Inc.Inventor: Philippe L. Durette
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Patent number: 4297275Abstract: Mammalian collagenase is inhibited by compounds having the formula ##STR1## and salts thereof, wherein R.sub.1 is hydrogen or alkanoyl of 2 to 10 carbon atoms;R.sub.2 is hydroxy, amino, or ##STR2## R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms, ##STR3## R.sub.4 is hydroxy, amino, arginine, leucine, glutamine, alanine or glycine; andm is 0 or an integer of 1 to 9.Type: GrantFiled: February 14, 1980Date of Patent: October 27, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Joseph E. Sundeen, Tamara Dejneka
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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: 4288592Abstract: There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.Type: GrantFiled: April 30, 1979Date of Patent: September 8, 1981Assignee: American Cyanamid CompanyInventors: Michael M. Rauhut, Shin-Shyong Tseng
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Patent number: 4287362Abstract: A radioactive diagnostic agent which comprises a protein and a radioactive metallic element combined with intervention of a bifunctional chelating agent of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group and is characteristic in having high stability even after administered into a human body.Type: GrantFiled: January 18, 1980Date of Patent: September 1, 1981Assignee: Nihon Medi-Physics Co., Ltd.Inventors: Akira Yokoyama, Yasushi Arano
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Patent number: 4256761Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hyroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.Type: GrantFiled: July 13, 1979Date of Patent: March 17, 1981Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4250183Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.Type: GrantFiled: December 15, 1978Date of Patent: February 10, 1981Assignee: BYK Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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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: 4242256Abstract: Compounds being analogues of a dipeptide in which the nitrogen atom of the linking amide group of the dipeptide is replaced by trivalent group ##STR1## and in which, optionally, the carbonyl function of this linking group is replaced by the divalent group --CH.sub.2 -- are of value in the synthesis of isosterically modified peptides.Type: GrantFiled: June 29, 1979Date of Patent: December 30, 1980Inventors: Robert Sharpe, Michael Szelke
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Patent number: 4240823Abstract: Compounds of the formula: ##STR1## in which R.sub.1 is hydrogen, optionally halogenated alkyl, optionally halogenated cycloalkyl, optionally halogenated alkenyl, optionally halogenated aralkenyl or aryloxyalkenyl mono or bicyclic aryl (optionally substituted by halogen, alkyl, trifluoromethyl, nitro, cyano, amino, hydroxyl, alkoxy, aminosulphonyl or alkylcarbonyloxy), or monocyclic or bicyclic heterocyclic of 5-11 chain members and having one or two hetero-atoms (optionally substituted), and R.sub.2 is a carboxylic acid group or a salt or ester thereof, is found to have plant growth regulating activity.Type: GrantFiled: March 1, 1977Date of Patent: December 23, 1980Assignee: Philagro S.A.Inventors: Claude Clapot, Jean Vial, Jacqueline Mourier, Jean C. Boch
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Patent number: 4239915Abstract: Gem-perfluoroalkylthio group containing acids of the formula(R.sub.f --R.sub.1 --X--.sub.2 C(R.sub.2)--B--(COOH).sub.gand alkyl esters thereof, wherein R.sub.f is a perfluoroalkyl, R.sub.1 is alkylene or alkylenethio- or oxy- or imino- alkylene, R.sub.2 is hydrogen, alkyl or phenyl, B is a covalent bond, alkylene or alkanetriyl and g is 1 or 2, can be prepared by the addition of a perfluoroalkylthiol to aldehydo or keto acids or esters. The compounds are useful as surface active agents, as intermediates to fluorochemical chromium complexes with low surface energies, or as oil and water repellents for textiles.Type: GrantFiled: December 2, 1976Date of Patent: December 16, 1980Assignee: Ciba-Geigy CorporationInventor: Robert A. Falk
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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: 4204064Abstract: A method, composition and compounds useful in said compositions for treating the skin and scalp characterized by an excessive secretion of sebum to improve the condition thereof by reducing said excessive secretion of sebum includes topically applying to a human having skin and/or a scalp so characterized a cosmetic composition containing as an active ingredient a derivative of cysteine or cysteamine. The composition contains about 0.1-5 weight percent of said derivative and also contains as a carrier for the active ingredient, water, a mixture of water and a lower alkanol, a lower alkanol, a mixture of a lower alkanol and a cosmetic resin, a reducing agent, a neutralizing agent or a vegetable oil.Type: GrantFiled: January 24, 1978Date of Patent: May 20, 1980Assignee: L'OrealInventor: Gregoire Kalopissis
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Patent number: 4196300Abstract: Glycidates and thioglycidates substituted in the .alpha.-position with a long chain alkyl of from 11 to 16 carbons having hypoglycemic activity.Type: GrantFiled: August 18, 1978Date of Patent: April 1, 1980Assignee: McNeilabs, Inc.Inventors: Richard J. Mohrbacher, Winston Ho, Gene Tutwiler
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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
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Patent number: 4182891Abstract: Novel acetylenic derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Z is .beta.-methylthioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5' -yl)-S-methylthioethyl, .gamma.-guanidinopropyl, or RHN(CH.sub.2).sub.n --; n is the integer 3 or 4; each 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## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms, or ##STR3## wherein R.sub.3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and the lactams thereof when Z is RHN(CH.sub.Type: GrantFiled: July 1, 1977Date of Patent: January 8, 1980Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung
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Patent number: 4177277Abstract: A method for alleviating or reducing angiotensin related hypertension in hypertensive mammals comprises administering an effective amount of a compound having the general formula ##STR1## Intermediates for the preparation of such compounds are also included.Type: GrantFiled: September 15, 1978Date of Patent: December 4, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4176235Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: December 4, 1978Date of Patent: November 27, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Frank L. Weisenborn
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Patent number: 4160777Abstract: Textiles, particularly carpets, are endowed with oil and water repellency and soil resistance by treatment thereof with certain detergent-compatible fluorochemmical compounds which can also be used in conjunction with anionic or nonionic detergents to provide cleaning/treating compositions for cleaning such textiles simultaneously with the treatment. The textile treating compositions of the invention comprise certain detergent-compatible fluorochemical compounds which are dissolved and/or dispersed in a suitable liquid vehicle. The textile treating/cleaning compositions of the invention also contain an anionic and/or a nonionic detergent.Type: GrantFiled: January 14, 1977Date of Patent: July 10, 1979Assignee: Minnesota Mining and Manufacturing CompanyInventor: Basil L. Loudas
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Patent number: 4156786Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 26, 1978Date of Patent: May 29, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4154946Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 28, 1978Date of Patent: May 15, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4154960Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: June 29, 1978Date of Patent: May 15, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Michael E. Condon
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Patent number: 4146641Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: May 4, 1978Date of Patent: March 27, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, David W. Cushman
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Patent number: 4140864Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: March 24, 1978Date of Patent: February 20, 1979Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel A. Ondetti, Frank L. Weisenborn
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Patent number: 4127729Abstract: New derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: February 21, 1978Date of Patent: November 28, 1978Assignee: E. R. Squibb & Sons, Inc.Inventor: Miguel A. Ondetti
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Patent number: 4126634Abstract: Aminosulfonylcarboxylic acids and their manufacture from diamines and chlorosulfonylcarboxylic acids.Type: GrantFiled: August 1, 1977Date of Patent: November 21, 1978Assignee: BASF AktiengesellschaftInventors: Lucien Thil, Martin Fischer, Wolfgang Kindscher
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Patent number: 4123611Abstract: 6-Aminoacylamidopenicillanic acid or 7-amino-acylamidocephalosporanic acids are produced in high yields by acylating 6-aminopenicillanic acid or 7-aminocephalosporanic acid with an amino acid, or a functional equivalent thereof, having its amino group protected with N,N-disubstituted .beta.-keto acid amide, and then removing the protecting group from the resulting protected 6-aminoacylamidopenicillanic acid or protected 7-aminoacylamidocephalosporanic acid by hydrolysis.Type: GrantFiled: January 6, 1975Date of Patent: October 31, 1978Assignee: President of Osaka UniversityInventors: Toshiyasu Ishimaru, Yasutsugu Shimonishi, Hisayuki Sakurai, Minoru Hatanaka
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Patent number: 4116962Abstract: New substituted acyl derivatives of amino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: December 3, 1976Date of Patent: September 26, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel Angel Ondetti, Frank Lee Weisenborn
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Patent number: RE30337Abstract: Textiles, particularly carpets, are endowed with oil and water repellency and soil resistance by treatment thereof with certain detergent-compatible fluorochemical compounds which can also be used in conjunction with anionic or nonionic detergents to provide cleaning/treating compositions for cleaning such textiles simultaneously with the treatment. The textile treating compositions of the invention comprise certain detergent-compatible fluorochemical compounds which are dissolved and/or dispersed in a suitable liquid vehicle. The textile treating/cleaning compositions of the invention also contain an anionic and/or a nonionic detergent.Type: GrantFiled: November 27, 1978Date of Patent: July 15, 1980Assignee: Minnesota Mining and Manufacturing CompanyInventor: Basil L. Loudas