Of Benzene Ring Containing Compounds Patents (Class 564/304)
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Patent number: 5110987Abstract: A method of preparing a substituted derivative of sphingosine comprising the steps of reducing serine methyl ester by a hydride reagent to form an aldehyde or aldehyde derivative, adding acetylide anions to the aldehyde to form an erythro-isomer or propargyl alcohol and inverting the propargyl alcohol by S.sub.N 2 inversion to form a threo-isomer. Either isomer can then be deprotected to form an alkyne with a 2-aminopropane 1,3-diol head group; this alkyne can be reduced to form sphingosine or a sphingosine derivitive which can be functionalized at the 4 and 5 positions to form a substituted derivative of sphingosine.Type: GrantFiled: June 17, 1988Date of Patent: May 5, 1992Assignee: Emory UniversityInventors: Dennis Liotta, Alfred H. Merrill
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Patent number: 5039801Abstract: The invention provides an improved method for obtaining optically active amines, carbamates, and isocyanates by thermal fragmentation of optically active ureas through refluxing the ureas in C.sub.3 -C.sub.7 alcohol solution with or without catalytic amounts of alkali metal.Type: GrantFiled: August 28, 1987Date of Patent: August 13, 1991Assignee: The United States of America as represented by the Department of Health & Human ServicesInventors: Arnold Brossi, Bernhard Schonenberger
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Patent number: 5011995Abstract: Asymmetric hydrogenation of prochiral N-aliphatic ketimines to give optically active secondary amines at a temperature from -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 10.sup.7 Pa, with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY].sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or a diene ligand, Y is a chiral diphosphine the secondary phosphine group of which are attached through 2-4 C atoms and which, together with the Ir atom, forms a 5-membered, 6-membered or 7-membered ring, or Y is a chiral diphosphinite the phosphinite groups of which are attached via 2 C atoms and which, together with the Ir atom, forms a 7-membered ring, Z is Cl, Br or I and A.sup.- is the anion of an oxygen acid or complex acid, and, if appropriate, with the addition of an ammonium chloride, bromide or iodide or an alkali metal chloride, bromide or iodide.Type: GrantFiled: July 19, 1988Date of Patent: April 30, 1991Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Gerardo Ramos, Felix Spindler
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Patent number: 5011989Abstract: The optically active benzylamine derivatives of the present invention are very useful for use as the asymmetric ligand of an asymmetric reducing agent. By using the optically active amine-boron complex prepared from the compound of the present invention, optically active products can be obtained in a specifically high optical yield. Moreover, the separation and recovery of the reaction products and asymmetric ligand can be easily achieved.Type: GrantFiled: October 3, 1988Date of Patent: April 30, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Yoneyoshi, Gohfu Suzukamo, Yoji Sakito
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Patent number: 5002606Abstract: The optically active mixture of isomers of aRS,1'S(-)-N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylan iline has improved action against problem weeds over the racemic mixture of isomers known as "Metolachlor".Type: GrantFiled: December 7, 1984Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventors: Hans Moser, Christian Vogel
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Patent number: 5001251Abstract: An optically active amine compound and a method for preparing same are provided which compound has the structure ##STR1## in the form of its R-(+) enantiomer or S-(-) enantiomer, wherein R and R.sup.1 are independently H, lower alkyl or halogen, R.sup.2 is H or lower alkyl and R.sup.3 is lower alkyl, the optically active amine is useful in the optical resolution of DL-3-acylthio-2-methylpropanoic acid wherein acyl is acetyl or benzoyl. The optically active D-(+)-3-acylthio-2-methylpropanoic acids are used as intermediated for preparing antihypertensive agents, such as captopril.Type: GrantFiled: January 15, 1988Date of Patent: March 19, 1991Assignee: E. R. Squibb & Sons, Inc.Inventors: Patrick A. MacManus, Peter Walsh, Adrian J. Kilbane
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Patent number: 4996361Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature from -40.degree. to 80.degree. C., under a hydrogen pressure of 10.sup.6 to 10.sup.8 Pa and with the addition of catalytic amounts of a rhodium compound of the formula III or IIIa ##STR1## in which X is 2 olefin ligands or a diene ligand, Y is a chiral diphosphine in which the secondary phosphine groups are linked by 2-4 C atoms and which, together with the Rh atom, forms a 5-membered, 6-membered or 7-membered ring, or Y is a chiral disphosphinite in which the phosphinite groups are linked via 2 C atoms and which, together with the Rh atom, forms a 7-membered ring, Z is Cl, Br or I and A.sup.- is the anion of an oxygen acid or complex acid.Type: GrantFiled: July 30, 1987Date of Patent: February 26, 1991Assignee: The University of British ColumbiaInventors: William R. Cullen, Michael D. Fryzuk, Brian R. James, Guo-Jun Kang, James P. Kutney, Roberto Spogliarich, Ian S. Thorburn
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Patent number: 4994615Abstract: Asymmetric hydrogenation of prochiral N-arylketimines to give optically active secondary amines at a temperature of -20.degree. to 80.degree. C., a hydrogen pressure of 10.sup.5 to 6.10.sup.6 Pa with the addition of catalytic amounts of an iridium compound of the formula III or IIIa[XIrYZ] (III)or[XIrY.sup..sym. A.sup..crclbar. (IIIa)in which X is two olefin ligands or one diene ligand, Y is a chiral diphosphine, the secondary phosphine groups of which are linked by 2-4 C atoms and which, together with the Ir atom, forms a 5-, or 6- or 7-ring, or Y is a chiral diphosphinite, the phosphinite groups of which are linked via 2 C atoms and which together with the Ir atom forms a 7-ring, Z is Cl, Br or I and A.sup.63 is the anion of an oxygen acid or complex acid, and if appropriate with the addition of an ammonium or alkali metal chloride, bromide or iodide.Type: GrantFiled: July 29, 1987Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventors: Felix Spindler, Benoit Pugin
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Patent number: 4990666Abstract: A process for racemization of optically active amino alcohols by subjecting the amino alcohol to hydrogen under moderate temperature and pressure conditions while in contact with Raney cobalt.Type: GrantFiled: February 4, 1987Date of Patent: February 5, 1991Assignee: W. R. Grace & Co.-Conn.Inventor: Stephen G. Harsy
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Patent number: 4983771Abstract: A process for recovering optically pure D(+)alpha-phenethylamine which comprises addition of the racemic mixture to a water/acid solution, and as a resolving agent, optically active D(-)mandelic acid. An optically pure D(+)alpha-PEA mandelate salt is formed, crystallized out of solution and washed with water. The salt is broken with sodium hydroxide, or a similar base, and the D(+)PEA liberated is extracted with toluene. The D(+) PEA recovered by vacuum distillation is recovered in high yield, shows high enantiomeric purity.Type: GrantFiled: September 18, 1989Date of Patent: January 8, 1991Assignee: Hexcel CorporationInventors: William Bryker, Luis A. Avila
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Patent number: 4968837Abstract: Racemic 2-(N-propylamino)-5-methoxytetralin is resolved by treating it with a chiral diaroyltartaric acid in an organic solvent at an elevated temperature to form a salt of the amine and chiral diaroyltartaric acid which is soluble in the solvent at the elevated temperature, cooling to precipitate the salt, isolating it, and converting it to the free amine. The product is useful as an intermediate in the synthesis of optionally-active pharmaceutical, such as N-0437.Type: GrantFiled: July 28, 1989Date of Patent: November 6, 1990Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, Fred J. Impastato
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Patent number: 4960797Abstract: The invention relates to the new N-[2-/4-fluorophenyl/-1-methyl]-ethyl-N-methyl-N-propynyl amine of the Formula I ##STR1## and isomers and salts thereof. The compound of the formula I is useful as a selective MAO inhibitor.Type: GrantFiled: February 15, 1989Date of Patent: October 2, 1990Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Zoltan Ecsery, deceased, Jozsef Knoll, Eva Somfai, Zoltan Torok, Eva Szinnyei, Karoly Mozsolics
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Patent number: 4952730Abstract: The invention relates to a process for inverting the configuration at the optically active carbon atom (*) in compounds of the formula I ##STR1## in which A denotes a carbocyclic or heterocyclic aromatic radical and R denotes an aliphatic, cycloaliphatic or araliphatic hydrocarbon radical, by formylation, treating the resulting compounds with a strong acid or an acid halide and cleaving the oxazolinium derivatives thus obtained, by acid or alkaline hydrolysis, if appropriate via the stage of the N-formyl compound, and to oxazolinium derivatives of the formula III defined herein and formed as intermediate products.Type: GrantFiled: May 27, 1986Date of Patent: August 28, 1990Assignee: Hoechst AktiengesellschaftInventors: Hans-Jurgen Leuchs, Werner Mohler, Hanns-Eberhard Erle
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Patent number: 4950791Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.Type: GrantFiled: June 12, 1989Date of Patent: August 21, 1990Inventor: Herbert C. Brown
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Patent number: 4931525Abstract: In the chromatographic separation of a mixture of antipodes of optically active chemicals by passing a solution of such mixture over an optically active adsorbent to effect adsorption, and then eluting the adsorbed material, the improvement which comprises employing as the adsorbent particles of an optically active and cross-linked polymer containing the repeating structural unit ##STR1## in which R.sup.1 represents hydrogen or methyl, andR.sup.2 represents one of the stereoisomers of the eight possible stereoisomeric forms of each of the optically active radicals of the formulae ##STR2## Improved separation results. The pure monomers are also new.Type: GrantFiled: November 21, 1988Date of Patent: June 5, 1990Assignee: Bayer AktiengesellschaftInventors: Ulrich Schwartz, Rolf Grosser, Karl-Erwin Piejko, Bruno Bomer, Dieter Arlt
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Patent number: 4922021Abstract: The invention is directed to 1-(2,6-Dimethyl-Phenyl-amino)-2-Dimethyl-amino-Propane and the pharmaceutical composition thereof useful for the treatment of cardiac rhythm disorders.Type: GrantFiled: September 14, 1988Date of Patent: May 1, 1990Assignee: BASF AktiensellschaftInventors: Zoltan Zubovics, Lajos Toldy, Gyorgy Rabloczky, Andras Varro, Ferene Andrasi, Sandor Elek, Istvan Elekes
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Patent number: 4876282Abstract: The present invention provides 1-phenyl-(naphthalenyl)alkylamines which are selective inhibitors of serotonin uptake.Type: GrantFiled: November 25, 1987Date of Patent: October 24, 1989Assignee: Eli Lilly and CompanyInventors: David W. Robertson, David T. Wong
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Patent number: 4859771Abstract: An economical, one-pot process for resolution-racemization of primary amines with .alpha.-hydrogens via selective crystallization of diastereomeric chiral sulfonic acid salts and the subsequent in situ racemization of the other enantiomer by the catalytic addition of aromatic aldehydes, and a key process intermediate thereof.Type: GrantFiled: January 19, 1989Date of Patent: August 22, 1989Assignee: Merck & Co., Inc.Inventors: Paul J. Reider, Edward J. J. Grabowski
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Patent number: 4845292Abstract: There are disclosed compounds of the formula ##STR1## R is --CH.sub.2 OH or --CO.sub.2 R.sup.3 ; R.sup.1 is hydrogen, lower alkyl, lower alkoxy or hydroxybenzyl;R.sup.2 is hydroxyloweralkyl or diloweralkoxyalkyl;R.sup.3 is hydrogen or lower alkyl;R.sup.4 is alkyl of 10-20 carbons atoms, phenylalkyl of 11-18 carbon atoms or phenoxyalkyl of 11-18 carbon atoms; orn is 1-3;or a pharmaceutically acceptable salt thereof, and their use in the prevention and/or treatment of conditions such as allergic rhinitis, allergic bronchial asthma and other naso-bronchial obstructive air-passageway conditions, other immediate hypersensitivity reactions such as allergic conjunctivitis and various inflammatory conditions.Type: GrantFiled: January 13, 1988Date of Patent: July 4, 1989Assignee: American Home Products CorporationInventors: William H. McGregor, Lisa A. Marshall, John H. Musser
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Patent number: 4845272Abstract: A method for optically resolving (.+-.)-cis or (.+-.)-trans-permethric acid which comprises reacting (.+-.)-cis-permethric acid and optically active 1-(p-tolyl)ethylamine or optically active cis-N-benzyl-2-(hydroxymethyl)cyclohexylamine, or reaction (.+-.)-trans-permethric acid and optically active 1-(p-isopropylphenyl)ethylamine, optically active 1-ethylbenzylamine or optically active cis-N-benzyl-2-(hydroxymethyl)cyclohexylamine.Type: GrantFiled: June 16, 1988Date of Patent: July 4, 1989Assignee: Kuraray Co., Ltd.Inventors: Hiroyuki Nohira, Shinichi Yoshida
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Patent number: 4833273Abstract: An improved process for the resolution of 1-aminoindanes into the R-isomer on a large scale is described. The resolving agent used in the process is R-N-acetyl-3,4-dimethoxyphenylalanine. The process is of intermediates in the production of certain adenosines and their pharmaceutically acceptable acid addition salts. The adenosines have desirable central nervous system and cardiovascular activities such as antipsychotic, sedative, antihypertensive, and antianginal.Type: GrantFiled: February 3, 1986Date of Patent: May 23, 1989Assignee: Warner-Lambert CompanyInventor: Om P. Goel
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Patent number: 4820734Abstract: The novel phenethylamine derivatives of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each signify hydrogen, halogen, trifluoromethyl, lower alkoxy, lower alkyl, hydroxy or nitro, with the proviso that at least one of R.sup.1 and R.sup.2 is different from hydrogen, R.sup.3 and R.sup.4 each signify lower alkyl, n signifies the number 1, 2, 3 or 4 and B signifies the group --CO-- or --CHOH--, and their pharmaceutically acceptable acid addition salts have interesting analgesic and antidepressant properties. These substances can be manufactured according to various methods which are known per se and can be used as medicaments in the form of pharmaceutical preparation.Type: GrantFiled: November 4, 1987Date of Patent: April 11, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Karl Bernauer, Hans Bruderer
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Patent number: 4814507Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylkene; Y is -(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.Type: GrantFiled: September 14, 1987Date of Patent: March 21, 1989Assignee: Mitsubishi Chemical Industries, LimitedInventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
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Patent number: 4814477Abstract: A new family of compounds known as dioxaphosphorinanes having the formula: ##STR1## wherein, M represents a hydrogen atom, a metal ion or an ammonium ion; R1 and R2, individually, represents a hydrogen atom, a halogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms or a nitro group or, together, represent a methylene dioxy group; and R3 and R4, individually, represents a halogen atom, an alkyl group having from 1 to 4 carbon atoms or a hydrogen atom so long as only one of the groups R3 and R4 represents a hydrogen atom or, together, represent a cyclohexyl group.A method for preparing these dioxaphosphorinanes by reacting phosphoryl chloride with a substituted 1-phenyl-1,3-dihydroxypropane is described. Also described is a method for resolving the new dioxaphosphorinanes into their optical isomers by reacting them with an optically active amino-compound.Type: GrantFiled: June 19, 1987Date of Patent: March 21, 1989Assignee: Oce-Nederland B.V.Inventors: Hans Wijnberg, Wolter T. Hoeve
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Patent number: 4801753Abstract: The present invention relates to novel biologically active tricyclic compounds, of the general formula I: ##STR1## and salts thereof, in which R.sub.1 represents hydrogen, alkyl of 1-6 carbon atoms, an optionally substituted aralkyl group or an acyl group,R.sub.2 represents hydrogen, alkyl (1-6 C), or an optionally substituted aralkyl group, orR.sub.1 +R.sub.2 together with the nitrogen atom represent a heterocyclic 5- or 6-membered ring, p1 X and Y each represent hydrogen, hydroxy, halogen, alkyl or alkoxy of 1-6 carbon atoms, nitro, CF.sub.3 or an acyloxy group, andthe dotted line signifies an optional extra bond.The compounds of the general formula I have valuable anti-depressant activity without a sustained influence on appetite.Type: GrantFiled: September 17, 1987Date of Patent: January 31, 1989Assignee: Akzona IncorporatedInventors: David S. Savage, Thomas Sleigh, John K. Clark
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Patent number: 4777291Abstract: The present invention provides a process for the epimerization of (+)-N-methyl-3-(2-methylphenoxy)- 3-phenylpropylamine to its racemic form with an anion forming compound in a suitable solvent.Type: GrantFiled: February 27, 1985Date of Patent: October 11, 1988Assignee: Eli Lilly and CompanyInventor: Jerry W. Misner
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Patent number: 4736060Abstract: Method for optical resolution of DL-cysteine by (1) reacting DL-cysteine with formaldehyde to prepare DL-thiazolidine-4-carboxylic acid (DL-TCA), (2) forming diastereomer salts of D-TCA and of L-TCA by reacting DL-TCA with an optically active 1-(1-naphthyl)ethylamine, (3) separating said diastereomer salts by difference of the solubilities thereof in a solvent, (4) recovering D-TCA from said diastereomer salt of D-TCA and finally obtain D-cysteine, and recovering L-TCA from said diastereomer salt of L-TCA and finally obtain L-cysteine.Type: GrantFiled: August 1, 1986Date of Patent: April 5, 1988Assignee: Nippon Rikagakuyakuhin Co., Ltd.Inventors: Keizo Tomuro, Yoshiharu Tamura, Yoko Morimoto, Shigeyoshi Katoh
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Patent number: 4658060Abstract: There is disclosed a multistep process for producing (-)-5-[(R)-1-hydroxy-2-((R)-1-methyl-3-phenyl-propyl)aminoethyl]salicylami de in high yields which does not require chromatography.The process is stereoselective for the desired products starting with the reaction of D-(+)-alpha-methylbenzylamine with benzylacetone followed by reduction of the resulting Schiff's base to form an amine as an R,R: R,S diastereomeric mixture, resolution of the mixture to obtain the R,R stereoisomer as a salt, conversion to a free base, reaction of the R,R free base with an O-protected alpha-bromo-3-carbamoyl-acetophenone to produce the corresponding R,R-ketobenzamide, reduction to produce a mixture of S,R,R;R,R,R hydroxybenzamide, removal of the protecting groups, resolution of the deprotected product and then conversion to the free R,R-amine.Type: GrantFiled: April 26, 1982Date of Patent: April 14, 1987Assignee: Schering CorporationInventors: Elijah J. Gold, Esther Babad, Lydia Peer, Wei K. Chang
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Patent number: 4602044Abstract: .beta.-Phenethanolamines are useful as antiobesity agents.Type: GrantFiled: December 19, 1983Date of Patent: July 22, 1986Assignee: Eli Lilly and CompanyInventors: Klaus K. Schmiegel, Walter N. Shaw
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Patent number: 4599444Abstract: The invention relates to a new process for separating the four stereoisomers of the cyclopropanecarboxylic acids of the formula ##STR1## wherein R stands for a methyl group or a halogen atom.Type: GrantFiled: February 17, 1984Date of Patent: July 8, 1986Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Elemer Foggassy, Ferenc Faigl, Rudolf Soos, Jozsef Rakoczi
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Patent number: 4588746Abstract: Disclosed are e.g. certain novel 2-benzyl-3-(substituted)-phenoxypropylamines, their methods of synthesis and pharmaceutical compositions. Said compounds are useful as potent and centrally active serotonin uptake inhibitors for the treatment of psychotropic disorders, particularly depression.Type: GrantFiled: January 4, 1984Date of Patent: May 13, 1986Assignee: Ciba-Geigy CorporationInventor: Jeffrey W. H. Watthey
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Patent number: 4564641Abstract: 1-Oxo-2-phenyl-2-(2-alkylaminoethyl)-1,2,3,4-tetrahydronaphthalenes of the formula I ##STR1## where R.sup.1 and R.sup.2 are identical or different and are each hydrogen, halogen, trifluoromethyl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, R.sup.3 is C.sub.1 -C.sub.6 -alkyl and R.sup.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or benzyl, or R.sup.3 and R.sup.4 together may furthermore be a C.sub.2 -C.sub.5 -alkylene chain, and their salts with physiologically tolerated acids, and their preparation, are described.The novel compounds are useful active compounds for treating disorders.Type: GrantFiled: November 22, 1983Date of Patent: January 14, 1986Assignee: BASF AktiengesellschaftInventors: Werner Seitz, Hans-Jurgen Teschendorf, Alfred Michel, Martin Traut, Hans P. Hofmann, Horst Kreiskott
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Patent number: 4556676Abstract: Novel trans-isomeric derivatives of 4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine are useful as antidepressant agents. These novel compounds act to block the synaptosomal uptake of norepinephrine and serotonin (5-hydroxy-tryptamine), thereby alleviating abnormalities at central receptor sites. The preferred embodiment is the enantiomer trans-(1R)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalen amine and its pharmaceutically acceptable acid addition salts.Type: GrantFiled: September 5, 1980Date of Patent: December 3, 1985Assignee: Pfizer Inc.Inventors: Willard M. Welch, Jr., Charles A. Harbert, B. Kenneth Koe, Allen R. Kraska
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Patent number: 4542159Abstract: There are prepared compounds of the formula: ##STR1## wherein X is the group >C.dbd.O or >CH(OH), Y is the group ##STR2## R.sub.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, R.sub.3 is hydrogen or a hydroxy group and R.sub.1 is the adamantyl group or a saturated or single unsaturated C.sub.3 to C.sub.16 cycloalkyl group where the C.sub.3 to C.sub.16 cycloalkyl group can be substituted by a C.sub.1 -C.sub.4 alkyl group or a halogen atom and their salts. The compounds are useful in dilating the peripheral blood vessels and in lowering blood pressure.Type: GrantFiled: May 15, 1979Date of Patent: September 17, 1985Assignee: Degussa AkteinsellschaftInventors: Jurgen Engel, Axel Kleemann, Klaus Posselt, Fritz Stroman, Klaus Thiemer
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Patent number: 4497960Abstract: The invention declares new chiral, optically active compounds of the general formula ##STR1## wherein a 5 or 6 membered lactol ring (E), with X and Y meaning (CR.sup.1 R.sup.2).sub.n, with n=0 to 2 and R.sup.1, R.sup.2 =H, lower alkyl or aryl in any combination which does not impair the anomeric selectivity of I in forming acetals, is fused in a stereospecific manner to a bicyclo[2.2.Type: GrantFiled: December 6, 1982Date of Patent: February 5, 1985Inventor: Christian Noe
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Patent number: 4490392Abstract: A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.Type: GrantFiled: July 27, 1978Date of Patent: December 25, 1984Assignee: Tanabe Seiyaku Co., Ltd.Inventors: Muneyoshi Ikezaki, Takeshi Kanno, Hajime Iwai, Masanori Inamasu
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Patent number: 4411913Abstract: Compounds of formula I ##STR1## wherein (i) m is O, n is 2 and p is 1 or(ii) m is 0 or 1, n is 1, and p is 1 or(iii) m is 1, n is 1 or 2 and p is 0,R.sub.1 is (i) alkyl of 3 to 7 carbon atoms or (ii) phenylalkyl, phenoxyalkyl or phenylthioalkyl of 8 to 11 carbon atoms in the aggregate thereof and wherein the phenyl ring is separated by at least 2 carbon atoms from the nitrogen atom to which R.sub.1 is bound and wherein the phenyl ring is unsubstituted, or mono-substituted by, or independently disubstituted by, alkyl or alkoxy of 1 to 4 carbon atoms, halogen of atomic number from 9 to 35, trifluoromethyl or cyano,R.sub.2 and R.sub.3 are either together straight chain alkylene of 4 to 6 carbon atoms, or, independently, hydrogen or alkyl of 1 to 4 carbon atoms, with the proviso that when m is 1, n is 1 and p is 0 then at least one of R.sub.2 and R.sub.3 is other than hydrogen, andR.sub.4 and R.sub.5 are, independently, hydrogen or alkyl of 1 to 4 carbon atoms, are useful in the treatment of coronary disorders.Type: GrantFiled: March 5, 1979Date of Patent: October 25, 1983Assignee: Sandoz Ltd.Inventors: Trevor G. Payne, Richard Berthold
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Patent number: 4370500Abstract: There is provided a new compound: d-N-(2-amino-2-phenethyl-2-methoxyethylamine useful in the direct synthesis of levamisole. The compound is prepared by slurrying the racemic N-(2-amino-2-phenethyl)-2-methoxyethylamine with dibenzoyl-d-tartaric acid as the resolving agent in an aqueous acidic menstruum containing ammonium chloride, heating the resultant mixture, preferably under reflux, cooling and filtering the resultant mixture to recover crystals rich in the desired d-amine compound, hereinabove noted.Type: GrantFiled: November 6, 1978Date of Patent: January 25, 1983Assignee: American Cyanamid CompanyInventor: Nancy S. Kurose
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Patent number: 4302601Abstract: The present invention relates to phenoxypropane having the formula ##STR1## in which R.sup.1 and R.sup.2 are like or unlike and each is an alkyl group having 1-4 carbon atoms, R.sup.3 is hydrogen or an alkyl group having 1-4 carbon atoms, R.sup.4 is a halogen atom, preferably fluorine, chlorine or bromine, including their optical isomers and also their addition salts with acids.These compounds are of therapeutic value in the treatment of cardiovascular conditions.The invention also relates to methods of synthesis of these products including a synthesis which involves the production, as a intermediate of an 8-aza-4,9-dioxa-2,3-benzo-bicyclo-[4,2,1]-octane having the formula ##STR2## in which R.sup.1 and R.sup.4 are as above defined.Type: GrantFiled: March 12, 1980Date of Patent: November 24, 1981Assignee: C M IndustriesInventor: Henri Demarne
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Patent number: 4269788Abstract: Cyclohexadiene derivatives of the formula ##STR1## wherein R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are as hereinafter set forth, are described. The compounds of formula I are useful as analgesic agents.Type: GrantFiled: October 4, 1979Date of Patent: May 26, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Peter M. Muller, Rudolf Pfister, Rene Urban
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Patent number: 4259257Abstract: The invention relates to novel 1-phenyl-2-amino-1,3-propanediol-N-alkyl derivatives having the general formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl having from 1 to 8 carbon atoms or phenoxymethyl, andR.sub.2 is hydrogen, alkyl having from 1 to 8 carbon atoms or 2,2-diphenylethyl,with the proviso that if R.sub.1 is phenoxymethyl then R.sub.2 may stand only for methyl, and if R.sub.2 is 2,2-diphenylethyl then R.sub.1 may stand only for hydrogen, and its isomers and pharmaceutically acceptable salts. Furthermore, the invention relates to a process for preparing these compounds.The novel 1-phenyl-2-amino-1,3-propanediol-N-alkyl derivatives having the general formula I possess significant anti-anginose activity and show several other biological activities.Type: GrantFiled: September 7, 1979Date of Patent: March 31, 1981Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Laszlo Levai, Gabor Fazekas, Lujza Petocz, Katalin Grasser