Plural Nitrogens Patents (Class 562/448)
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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: 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: 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: 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: 4238622Abstract: The amino acid 2-amino-4-(2-aminoethoxy)-trans-but-3-enoic acid can be conveniently prepared via novel intermediates from a 2,2'-disubstituted diethyl ether and a dialkyl N-protected amidomalonate starting material using a multi-step process. Preferred starting materials are bis-2-chloroethyl ether and diethyl acetamidomalonate. The process, in a preferred embodiment, proceeds through the key intermediate ethyl-2-acetamido-4-[2-(2-phthalimido)ethoxy]-but-2-enoate.Type: GrantFiled: August 15, 1977Date of Patent: December 9, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Dennis D. Keith, Manfred Weigele
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Patent number: 4235969Abstract: Compounds are provided for use in the preparation of reagents which can be used in immunoassays for the determination of benzamides of N,N-dialkylethyleneamines. A linking group is provided, at a particular site of the drug, which provides a link between the above compounds and an antigen, with the resulting conjugate being employed for the preparation of antibodies. The antibodies find particular use in competitive protein binding assays. Conjugates to enzymes are prepared which find particular use in homogeneous enzyme immunoassays.Type: GrantFiled: May 8, 1978Date of Patent: November 25, 1980Assignee: Syva CompanyInventors: Prithipal Singh, Marcel R. Pirio
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Patent number: 4225502Abstract: A novel chelating agent having the formula ##STR1## (a) each of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a member selected from the group consisting of (i) hydrogen; (ii) an alkyl group having 1-4 carbon atoms; (iii) --CN; (iv) --SO.sub.3 M.sub.1 ; (v) --COOM.sub.1 ; (vi) --OM.sub.3 ; (vii) --NO.sub.2 ; (viii) --OH; and ##STR2## in which each of R.sub.1 and R.sub.2 is an alkyl group having 1-4 carbon atoms;(b) each of M.sub.1, M.sub.2, M.sub.3, and M.sub.4 is a member selected from the group consisting of (i) a hydrogen ion; (ii) an alkali metal ion; (iii) 1/2 an alkaline earth metal ion; and (vi) an ammonium ion having the formula ##STR3## in which each of R.sub.3, R.sub.4, R.sub.5, and R.sub.6 is a member selected from the group consisting of (A) hydrogen; (B) an alkyl group having 1-4 carbon atoms; and (C) a hydroxyalkyl group having 1-4 carbon atoms; and(c) Z is a member selected from the group consisting of (i) hydrogen; and (ii) hydroxyl.Type: GrantFiled: February 7, 1977Date of Patent: September 30, 1980Assignee: W. R. Grace & Co.Inventors: Roger R. Gaudette, John L. Ohlson, Patricia M. Scanlon
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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: 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: 4175084Abstract: The invention relates to physiologically active compounds which are coupling products between an N-acyl aspartic acid and a biologically active amine such as dopamine or serotonin.Type: GrantFiled: June 27, 1977Date of Patent: November 20, 1979Assignee: Sentralinstitutt for Industriell ForskningInventors: Jan B. Boler, Karl-Ludvig Reichelt
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Patent number: 4147873Abstract: Novel vinyl 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## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; Z is R.sub.1 OCCH.dbd.CH-- or R.sub.1 OC(CH.sub.2).sub.n -- wherein n is an integer of from 1 to 3; 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 p-hydroxybenzyl; and the lactams thereof when Z is R.sub.1 OC(CH.sub.2).sub.Type: GrantFiled: July 1, 1977Date of Patent: April 3, 1979Assignee: Merrell Toraude et CompagnieInventors: Brian W. Metcalf, Michel Jung
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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: 4130582Abstract: A process for the preparation of phenolic ethylenediamine polycarboxylic acids in predominantly the ortho isomeric form which comprises reacting a phenol compound, ethylenediamine, glyoxylic acid and a base, said phenol compound functioning both as a reactant and as the sole solvent for the reaction system. The product can then be isolated or directly reacted with an iron salt to form the corresponding iron chelate.Type: GrantFiled: April 19, 1977Date of Patent: December 19, 1978Assignee: Ciba-Geigy CorporationInventors: Harris E. Petree, Hal L. Myatt, Alex M. Jelenevsky
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Patent number: 4116991Abstract: A chelating agent of the formula: ##STR1## wherein R.sub.1 through R.sub.5 are each selected from the group which consists of hydrogen, methyl, ethyl and propyl;S.sub.1 and S.sub.2 are each selected from the group which consists of hydrogen, --CH.sub.2 CH.sub.2 OH and alkyl having 1 to 12 carbon atoms;n is a whole number 1 through 4;Z.sub.1 through Z.sub.8 are substituents each selected from the group which consists of alkyl, alkoxyl, carboxy, formyl, acyl, carboxy substituted by alkyl, carboxamido, hydroxyl, amino, nitro, halo, and sulfo;Y.sub.1 is selected from the group which consists of --COOM.sub.2 and --CN;Y.sub.2 is selected from the group which consists of --COOM.sub.3 and --CN; andM.sub.1 through M.sub.4 are selected from the group which consists of hydrogen, ion, an alkali metal ion, ammonium and ammonium substituted by alkyl 1 to 4 times.Type: GrantFiled: April 14, 1975Date of Patent: September 26, 1978Assignee: Manufacture de Produits Chimiques ProtexInventor: Andre Leneuf
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Patent number: 4111981Abstract: Cephalosporin compounds having a substituted phenylglycyl substituent at the 7-position and any of a variety of groups at the 3-position are prepared by acylation of a 7-aminocephalosporanic acid. The compounds have antibacterial activity.Type: GrantFiled: April 28, 1977Date of Patent: September 5, 1978Assignee: SmithKline CorporationInventor: John Gerald Gleason