Phenylalanines Patents (Class 560/40)
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Patent number: 4426391Abstract: Novel prodrugs of methyldopa which are [(alkoxycarbonyl)oxy]alkyl esters of methyldopa are disclosed. Also, pharmaceutical compositions containing these compounds are disclosed. Upon administration to warm-blooded animals, these prodrugs liberate methyldopa along with innocuous side products.Type: GrantFiled: September 15, 1982Date of Patent: January 17, 1984Assignee: Merck & Co., Inc.Inventors: Jose Alexander, Chung Shih
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Patent number: 4421767Abstract: Compounds of the formula: ##STR1## wherein: X is fluorine, chlorine, or bromine;R is the group R.sub.2 as defined below;R.sub.1 is a group of the formula: ##STR2## or the group R.sub.2 as defined below; wherein R.sub.2 is: ##STR3## wherein R.sub.3 is hydrogen, (C.sub.1 -C.sub.4)alkyl, or (C.sub.1 -C.sub.4)alkoxy, andR.sub.4 is (C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxy;or a (C.sub.1 -C.sub.8)alkyl ester thereof; or a non-toxic pharmaceutically acceptable salt thereof, inhibit MAO in vivo and can be administered either alone or in combination with an aromatic L-amino acid decarboxylase inhibitor for the treatment of depression.Type: GrantFiled: September 13, 1982Date of Patent: December 20, 1983Assignee: Merrell Toraude et CompagnieInventors: Michael G. Palfreyman, Ian A. McDonald
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Patent number: 4418077Abstract: Fluorinated aminobutyric acid and diaminobutane compounds in vivo are inhibitors of gamma-aminobutyric acid transaminase and have the following formula: ##STR1## wherein: Y represents hydrogen or fluorine;Z represents --CH.sub.2 NR.sub.1 R.sub.2, where R.sub.1 and R.sub.2 are as defined below, or --COR.sub.3 where R.sub.3 is as defined below;R.sub.a represents hydrogen or R.sub.4, where R.sub.4 is as defined below;R.sub.1 represents hydrogen, C.sub.1 -C.sub.6 alkyl or phenyl-(C.sub.1 -C.sub.4 alkyl);R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.4 alkyl) or, when R.sub.a is hydrogen, R.sub.4, where R.sub.4 is as defined below;R.sub.3 represents hydroxy, or when R.sub.a is hydrogen, C.sub.1 -C.sub.8 alkoxy, --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are as defined below, or an aminocarboxylic acid residue derived by removal of an hydrogen atom from the amino moiety of an L-aminocarboxylic acid;each R.sub.4, independently, represents C.sub.2 -C.sub.Type: GrantFiled: August 21, 1981Date of Patent: November 29, 1983Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Fritz Gerhart, Michel Jung, Daniel Schirlin
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Patent number: 4404392Abstract: Resolution of the .alpha. and .beta. isomers of .alpha.-pivaloyloxyethyl-(S)-3-(3,6-dihydroxyphenyl)-2-methylalaninate is accomplished by; (a) forming the (+) hydrogen tartrate salt of the mixture; (b) fractionally crystallizing the .beta.-isomer salt; and (c) recovering the .alpha.-isomer from the mother liquor by treatment with first a base and second a mineral acid.Type: GrantFiled: November 16, 1981Date of Patent: September 13, 1983Assignee: Merck & Co., Inc.Inventors: Ramon J. Alabaster, Stanley H. B. Wright
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Patent number: 4401676Abstract: Novel .alpha.-ethynyl- and .alpha.-vinyl 3,4-disubstituted phenylalanines are disclosed. The compounds have pharmaceutical activity.Type: GrantFiled: June 1, 1977Date of Patent: August 30, 1983Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, David Taub
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Patent number: 4399121Abstract: Immunogen conjugates comprising N-aminoalkyl derivatives of iodothyronines, e.g., thyroxine and its lower alkyl esters, coupled to an immunogenic carrier material, and antibodies raised against such immunogen conjugates.Type: GrantFiled: March 29, 1982Date of Patent: August 16, 1983Assignee: Miles Laboratories, Inc.Inventors: James P. Albarella, Robert J. Carrico, Thomas M. Li
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Patent number: 4360533Abstract: Glyceryl esters of 1-methyl-2-(3,4-dihydroxyphenyl)alanine, pharmaceutical compositions and method of treatment are disclosed.Type: GrantFiled: December 14, 1981Date of Patent: November 23, 1982Assignee: Merck & Co., Inc.Inventor: Arthur A. Patchett
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Patent number: 4358604Abstract: N-Aminoalkyl derivatives of iodothyronines, e.g., thyroxine and its lower alkyl esters, immunogen conjugates comprising the derivatives coupled to an immunogenic carrier material, and antibodies raised against such immunogen conjugates.Type: GrantFiled: November 4, 1981Date of Patent: November 9, 1982Assignee: Miles Laboratories, Inc.Inventors: James P. Albarella, Robert J. Carrico, Thomas M. Li
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Patent number: 4347375Abstract: A process for preparing .alpha.-amino acids or ester thereof having an .alpha.-vinyl substituent and certain intermediates are disclosed.Type: GrantFiled: December 3, 1980Date of Patent: August 31, 1982Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, William J. Greenlee
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Patent number: 4343947Abstract: Amides of carnitine or acyl-carnitines having general formula: ##STR1## wherein X.sup.- is a halogen anion, e.g. the chloride anionR is either hydrogen or an acyl radical, such as acetyl, propionyl or butyryl; andY is the residue of an optically active esterified amino-acid (e.g. the residue of L-phenylglycine methyl ester, ##STR2## are prepared by either (a) directly condensing D,L-carnitine (or acyl-D,L-carnitine) with an ester of an optically active aminoacid, or (b) preparing the acid halogenide of D,L-carnitine or acyl-D,L-carnitine and subsequently condensing it with an ester of an optically active aminoacid.The mixture of the diastereoisomer amides thus obtained is resolved by fractional crystallization from organic solvents into the respective separated diastereoisomers.Type: GrantFiled: December 29, 1980Date of Patent: August 10, 1982Assignee: Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.Inventors: Paolo De Witt, Maria O. Tinti
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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: 4325961Abstract: Novel substituted .alpha.-fluoromethyl-.alpha.-amino alkanoic acids and esters thereof are disclosed. The novel compounds have biological activity including decarboxylase inhibition.Type: GrantFiled: June 1, 1977Date of Patent: April 20, 1982Assignee: Merck & Co., Inc.Inventors: Janos Kollonitsch, Arthur A. Patchett
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Patent number: 4323704Abstract: Novel compounds of the formula ##STR1## wherein A is methylene, ethylene or ethylidene; R.sub.1 is --C.tbd.CH or --CH.dbd.CH.sub.2 ; R.sub.2 is hydrogen or COR wherein R 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 straight or branched lower alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.6 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.a is hydrogen, ##STR3## 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 ##STR4## wherein R.sub.7 is selected from hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl and p-hydroxybenzyl; and R.sub.b has the same meaning as defined for R.sub.a except R.sub.b is not ##STR5## and R.sub.a and R.sub.Type: GrantFiled: January 16, 1981Date of Patent: April 6, 1982Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung, Charles Danzin
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Patent number: 4311853Abstract: Novel Selenium derivatives of thyroxine and tri-iodothyronine have the formula: ##STR1## wherein M is I or H and either (a) R.sub.1 is OH or a carboxyl protecting group and R.sub.2 contains at least one Se, preferably .sup.75 Se, atom or (b) R.sub.2 is H or an amino protecting group and R.sub.1 contains at least one Se, preferably .sup.75 Se, atom.The compounds are useful in dual isotope assays of thyroid function.Type: GrantFiled: January 30, 1980Date of Patent: January 19, 1982Assignee: The Radiochemical Centre LimitedInventor: Gavin M. Cree
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Patent number: 4275220Abstract: A process for preparing .alpha.-amino acids or ester thereof having an .alpha.-vinyl substituent and certain intermediates are disclosed.Type: GrantFiled: August 6, 1979Date of Patent: June 23, 1981Assignee: Merck & Co., Inc.Inventors: Arthur A. Patchett, William J. Greenlee
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Patent number: 4275217Abstract: A chiral .alpha.-amino acid having a hydrogen substituent in a position alpha to the carboxylic function thereof is prepared by subjecting a corresponding optical antipode with a chiral amino acid to a strong base whereby the proton in a position alpha to the carboxylic function is removed and thereafter reacting the resulting product with a chiral protonation agent.Type: GrantFiled: July 9, 1979Date of Patent: June 23, 1981Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Lucette Duhamel, Jean-Christophe Plaquevent
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Patent number: 4271187Abstract: A compound of the formula ##STR1## possesses antihypertensive activity. Also provided are methods for the preparation of the compounds as well as pharmaceutical formulations and methods for their use as antihypertensive agents.Type: GrantFiled: September 18, 1979Date of Patent: June 2, 1981Assignee: Merck & Co., Inc.Inventors: Joseph G. Atkinson, Clarence S. Rooney, Yves Girard, Edward L. Engelhardt
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Patent number: 4254273Abstract: Improved process for preparing esters of .alpha.-methyl-3,4-dihydroxyphenylalanine having pharmaceutical activity via novel N-(tert-butoxycarbonyl) intermediates.Type: GrantFiled: August 6, 1979Date of Patent: March 3, 1981Assignee: Merck & Co., Inc.Inventors: Burwell F. Powell, Ralph F. Hirschmann
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Patent number: 4250192Abstract: 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 alipahtic 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: April 25, 1979Date of Patent: February 10, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Gerhard Baschang
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Patent number: 4246424Abstract: A method for racemization of optically active amines which comprises contacting an optically active amine of the formula: ##STR1## wherein C* is an asymmetric carbon atom, R.sub.1 is alkyl, aralkyl or aryl and R.sub.2 is aryl or alkoxycarbonyl, the aryl or aralkyl moiety bearing optionally one or more alkyl or alkoxy groups on the aromatic ring, provided that R.sub.1 and R.sub.2 are always different from each other, with a catalyst comprising an alkali metal and a polycyclic aromatic hydrocarbon until a sufficient amount of the optically active amine is racemized.Type: GrantFiled: May 14, 1976Date of Patent: January 20, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Tsuneyuki Nagase, Gohu Suzukamo, Yoshio Suzuki
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Patent number: 4239902Abstract: The invention relates to N-carboxyacylaminoacid esters, a process for their production and their use as chromogenic substrates for the continuous and discontinuous determination of enzymes with a chymotrypsin-like specificity, in particular catheepsin G.Type: GrantFiled: March 8, 1979Date of Patent: December 16, 1980Assignee: Bayer AktiengesellschaftInventor: Eugen Schnabel
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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: 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: 4194052Abstract: A sulfonic acid salt of an acyloxyalkylamine is prepared by reaction of an organic acid or amino-acid with a sulfonic acid salt of an alkanolamine. Isocyanates are prepared therefrom by reaction with phosgene.Type: GrantFiled: May 1, 1969Date of Patent: March 18, 1980Assignee: Rohm and Haas CompanyInventors: Sheldon N. Lewis, Jerome F. Levy
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Patent number: 4158016Abstract: A method for racemization of optically active amines which comprises contacting an optically active amine of the formula: ##STR1## wherein C* is an asymmetric carbon atom, R.sub.1 is alkyl, aralkyl or aryl and R.sub.2 is aryl or alkoxycarbonyl, the aryl or aralkyl moiety bearing optionally one or more alkyl or alkoxy groups on the aromatic ring, provided that R.sub.1 and R.sub.2 are always different from each other, with a catalyst comprising an alkali metal and a polycyclic aromatic hydrocarbon until a sufficient amount of the optically active amine is racemized.Type: GrantFiled: December 16, 1977Date of Patent: June 12, 1979Assignee: Sumitomo Chemical Company, LimitedInventors: Tsuneyuki Nagase, Gohu Suzukamo, Yoshio Suzuki
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Patent number: 4134991Abstract: A compound having the general formula ##STR1## in which R represents a hydrogen atom or a hydroxyl radical, R.sub.1 represents a hydrogen atom or a methyl radical, and R.sub.2 represents a phenylethyl radical, a C.sub.1 -C.sub.16 alkyl radical, or a C.sub.6 -C.sub.16 monocyclic, polycyclic or alicyclic radical optionally bonded through a methylene radical, and its pharmaceutically acceptable acid addition salts, the formula (I) having the L-configuration when R is OH and when R and R.sub.1 are both hydrogen, and having the DL-configuration when R is hydrogen and R.sub.1 is methyl.These compounds and salts are useful as medicaments in human and veterinary medicine for cardiovascular and/or neurological treatment.Type: GrantFiled: September 26, 1977Date of Patent: January 16, 1979Assignee: SynthelaboInventor: Camille G. Wermuth
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Patent number: 4123614Abstract: The present invention relates to novel assay reagents, their composition, methods of preparation, and use in the detection and measurement of various biological systems and/or components, e.g. enzymes, antibodies, antigens, and periodate concentration. This invention in its basic form utilizes a class of compounds having, inter alia., a backbone chain, an indicator group, and vicinal oxidizable groups.Type: GrantFiled: October 18, 1976Date of Patent: October 31, 1978Assignee: Syntex (U.S.A.) Inc.Inventor: David H. Rammler
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Patent number: 4105789Abstract: New carboxyalkylacylamino acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.Type: GrantFiled: May 10, 1976Date of Patent: August 8, 1978Assignee: E. R. Squibb & Sons, Inc.Inventors: Miguel Angel Ondetti, David W. Cushman
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Patent number: 4065566Abstract: There is provided, novel, transient pro-drug forms of L-DOPA (3,4-dihydroxy-L-phenylalanine), having the formula: ##STR1## wherein R represents a hydrogen atom, an acyl group, a ##STR2## group, a --CO-pyridyl group, and a --CO--R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-C.sub.1 -C.sub.2 dialkylamino acid or a C.sub.4 -C.sub.6 cycloalkylamino acid ##STR3## wherein R.sub.1 represents a member selected from the group consisting of a hydroxyl group and a --OM group, wherein M is an alkali metal (Na, K, etc.) or an ammonium ion; and wherein R.sub.2 represents a member selected from the group consisting of a ##STR4## group, a --CO-pyridyl group, and a --CO--R.sub.3 group, wherein R.sub.3 represents the residue of any N,N-(C.sub.1 -C.sub.2)-dialkylamino acid or a C.sub.4 -C.sub.6 -cycloalkylamino acid ##STR5## wherein R represents an acyl group; wherein R.sub.2 represents a hydrogen atom; and wherein R.sub.1 represents a --NHCH(R.sub.4)COOR.sub.5 group, wherein R.sub.Type: GrantFiled: September 7, 1976Date of Patent: December 27, 1977Assignee: INTERx Research CorporationInventors: Nicolae S. Bodor, Kenneth B. Sloan, Anwar A. Hussain
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Patent number: 4058530Abstract: Derivatives of .alpha.-methyl-3,4-dihydroxyphenylalanine which are useful in compositions as anti-hypertensive agents.Type: GrantFiled: March 18, 1976Date of Patent: November 15, 1977Assignee: Merck & Co., Inc.Inventor: Walfred S. Saari
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Patent number: 4058642Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, chlorine, hydroxyl, trifluoromethyl, methyl or methoxy, andR.sub.2 is hydrogen, alkyl of 1 to 2 carbon atoms or benzyl;And non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as the salts are useful as hypertensives.Type: GrantFiled: November 30, 1976Date of Patent: November 15, 1977Assignee: Boehringer Ingelheim GmbHInventors: Ernst-Otto Renth, Anton Mentrup, Kurt Schromm, Alexander Walland
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Patent number: 4051169Abstract: Derivatives of .alpha.-methyl-3,4-dihydroxyphenylalanine which are useful in compositions as anti-hypertensive agents.Type: GrantFiled: March 21, 1975Date of Patent: September 27, 1977Assignee: Merck & Co., Inc.Inventor: Walfred S. Saari