Alkanol Group Only Between The Amino Nitrogen And The Ether Oxygen Which Is Bonded Directly To The Aryl Ring Or Ring System (i.e., Aryloxy Alkanol Amines) Patents (Class 564/349)
  • Patent number: 5426227
    Abstract: The invention relates to a new, industrially advantageous, process for the preparation of the known beta-adrenergic blocking agent, levobunolol, not requiring resolution of racemic bunolol, based on the enantioselective synthesis of an oxiranic intermediate which is then reacted with tert-butylamine. It consists of reacting 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone with (R)-(-)epichlorhydrine in an aprotic solvent, in the presence of a strong base at a temperature of over 90.degree. C., thus obtaining the intermediate chiral oxirane (S)-5-(2,3-epoxypropoxy)-3,4-dihydro-1-(2H)-naphthalenone with more than 95% optical purity, and then, the intermediate chiral oxirane is reacted with tert-butylamine.
    Type: Grant
    Filed: March 16, 1994
    Date of Patent: June 20, 1995
    Assignee: Medicham, S.A.
    Inventors: Alberto Stampa Diez Del Corral, Pelayo Camps Garcia, Maria del Carmen Onrubia Miguel, Carmen Arnalot Aguilar
  • Patent number: 5391735
    Abstract: The present invention relates to a new process for the preparation of 3-substituted derivatives of 1-amino-2-hydroxy-propane in the form of single diastereoisomers, to certain of these diastereoisomers, and to compounds which are intermediates in the new process of the invention.
    Type: Grant
    Filed: April 12, 1994
    Date of Patent: February 21, 1995
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Piero Melloni, Arturo D. Torre, Ettore Lazzari, Giuseppe Mazzini
  • Patent number: 5391476
    Abstract: Water-soluble, non-ionic surface active compounds are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently hydrogen or an alkyl group having from 1 to 4 carbon atoms;X is a hydrophobic substituted or unsubstituted arylene group or a hydrophobic substituted or unsubstituted alkylene group;Y.sup.1 and Y.sup.2 are each independently a chemical bond, --CO-- or --(CH.sub.2).sub.m NR.sup.3 CO--;m is an integer from 1 to 6;R.sup.3 is as defined for R.sup.1 and R.sup.2 ; and,Z.sup.1 and Z.sup.2 are each independently a hydrophilic polyhydroxyalkyl group. The compounds are particularly useful as coating aids for the coating of hydrophilic colloid layers in the preparation of photographic materials.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: February 21, 1995
    Assignee: Eastman Kodak Company
    Inventors: Alan R. Pitt, Ian M. Newington
  • Patent number: 5382689
    Abstract: Disclosed is a new process for preparing bevantolol hydrochloride suitable for industrial production in which bevantolol hydrochloride can be obtained in a high yield and HVA of an expensive material can be recovered. The process for the preparation of bevantolol hydrochloride comprises the steps of: causing 3-(m-tolyloxy)-1,2-epoxypropane (TOEP) to react with .beta.-(3,4-dimethoxyphenyl)ethylamine (HVA) of excess mole per mole of said TOEP; dissolving the reaction mixture in a halogenated hydrocarbon to give a solution; mixing the solution with hydrochloric acid; separating an organic layer from the resulting mixture; and obtaining 1-[(3,4-dimethoxyphenethyl)amino]-3-(m-tolyloxy)-2-propanol hydrochloride from the organic layer.
    Type: Grant
    Filed: October 1, 1992
    Date of Patent: January 17, 1995
    Assignee: Nippon Chemiphar Co., Ltd.
    Inventor: Yutaka Nomura
  • Patent number: 5347050
    Abstract: The compounds of formula I, ##STR1## wherein the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterified form, are useful as cardioselective .beta.-adrenoceptor blocking agents.
    Type: Grant
    Filed: April 13, 1993
    Date of Patent: September 13, 1994
    Inventors: Richard Berthold, William J. Louis
  • Patent number: 5334602
    Abstract: New aryloxy-alkylamine derivatives of the general formula I ##STR1## in which A signifies a benzene or thiophene ring, R and R.sub.1, independently of one another, each hydrogen, alkyl, halogen, CF.sub.3 or alkoxy, R.sub.2 alkyl, cycloalkyl, alkenyl, alkynyl, alkaryl or saturated or unsaturated aliphatic or aromatic acyl, R.sub.3 and R.sub.4 in each case hydrogen, alkyl, alkenyl, alkynyl or cycloalkyl with, in each case, up to 8 C-atoms, whereby R.sub.3 and R.sub.4 can be the same or different but are not simultaneously hydrogen or R.sub.3 and R.sub.4, together with the nitrogen atom connecting them, form a 5- to 7-membered saturated ring or a saturated heterocyclic ring which can possibly contain an oxygen or nitrogen atom as a further heteroatom in the ring, whereby an additional nitrogen atom can be substituted by an alkyl radical with up to 3 C-atoms, and their acid-addition salts possess interesting pharmaceutical properties and are especially suitable as anti-arrhythmics.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: August 2, 1994
    Assignee: Laevosan-Gesellschaft GmbH
    Inventors: Bernhard Lotz, Gerhard Greier
  • Patent number: 5319141
    Abstract: A process for making 5-(d-3-(tert-butylamino)-2-hydroxypropoxy)-1,2,3,4-tetrahydro-1-cis-2,3 naphthalenediol of the formula ##STR1## by reacting ##STR2## in an essentially water free environment with (a) M'IO.sub.3 wherein M' represents a suitable ion for forming the salt.(b) I.sub.2 (iodine)(c) CH.sub.3 COO.sup.- M".sup.+ wherein M" represents a suitable ion for forming the salt(d) glacial acetic acid and(e) ROH/M'"OH where R is alkyl and M'" is a suitable metal ion.
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: June 7, 1994
    Assignee: Acic (Canada) Inc.
    Inventor: Khashayar Karimian
  • Patent number: 5270161
    Abstract: Water-soluble, non-ionic surface active compounds are provided having the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently hydrogen or an alkyl group having from 1 to 4 carbon atoms;X is a hydrophobic substituted or unsubstituted arylene group or a hydrophobic substituted or unsubstituted alkylene group;Y.sup.1 and Y.sup.2 are each independently a chemical bond, --CO-- or --(CH.sub.2).sub.m NR.sup.3 CO--;m is an integer from 1 to 6;R.sup.3 is as defined for R.sup.1 and R.sup.2 ; and,Z.sup.1 and Z.sup.2 are each independently a hydrophilic polyhydroxyalkyl group. The compounds are particularly useful as coating aids for the coating of hydrophilic colloid layers in the preparation of photographic materials.
    Type: Grant
    Filed: July 29, 1991
    Date of Patent: December 14, 1993
    Assignee: Eastman Kodak Company
    Inventors: Alan R. Pitt, Ian M. Newington
  • Patent number: 5254595
    Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: October 19, 1993
    Assignee: Elf Sanofi
    Inventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
  • Patent number: 5187190
    Abstract: Compounds of the formula (I): ##STR1## wherein R.sup.1 is hydrogen or fluoro and R.sup.2 is hydrogen or C1-6 alkyl and salts thereof are described as agents for the treatment of obesity and related conditions. Processes for their preparation and intermediates are described.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventor: David J. Lecount
  • Patent number: 5166218
    Abstract: Tertiary and secondary amines of the formulas ##STR1## and ##STR2## wherein n is the integer 1 or 2,R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.
    Type: Grant
    Filed: August 12, 1991
    Date of Patent: November 24, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Leo Alig, Marcel Muller
  • Patent number: 5120874
    Abstract: A process for the preparation of 5-hydroxydiprafenone and its acid addition salts by catalytic removal of the benzyl group of the corresponding 5-benzyloxy compound is described.
    Type: Grant
    Filed: March 4, 1988
    Date of Patent: June 9, 1992
    Assignee: Helopharm W. Petrik GmbH & Co. KG
    Inventors: Gerd Petrik, Klemens Schubert
  • Patent number: 5118851
    Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: June 2, 1992
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5095151
    Abstract: There is described a process for the preparation of high yields of propranolol hydrochloride having a particle size within the range of 420 to 1200 microns wherein the propanolol hydrochloride is recrystallized from, as a solvent, a mixture of n-propanol and heptane.The propranolol hydrochloride macrocrystals are useful themselves in capsule pharmaceutical dosage forms and when coated with a sustained release coating composition, are useful in the manufacture of sustained action capsule and tablet pharmaceutical dosage.
    Type: Grant
    Filed: May 21, 1985
    Date of Patent: March 10, 1992
    Assignee: American Home Products Corporation
    Inventors: Paul C. Guley, James S. Farina
  • Patent number: 5082969
    Abstract: Industrial process for obtaining an aryloxypropanolamine of chemical name 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol, characterized in that it comprises the following operating phases. By reacting 4-(2-methoxyethyl)phenol with epichlorohydrin in an alkaline aqueous medium at temperatures of between 0.degree. and 25.degree. C. a crude reaction product composed to the extent of 75-80% of 3-[4-(2-methoxyethyl)phenoxy]-1,2-epoxypropane and to the extent of 15-20% of 1-[4-(2-methoxyethyl)phenoxy]-3-chloro-2-propanol is obtained, after the appropriate extractions and washings, both compounds being suitable for reacting with isopropylamine in an aqueous medium and at temperatures ranging between 0.degree. and 30.degree. C. to obtain the desired aryloxypropanolamine of formula I.
    Type: Grant
    Filed: May 16, 1990
    Date of Patent: January 21, 1992
    Assignee: Esteve Quimica, S.A.
    Inventors: Josep M. Ribalta Baro, Gloria Oranias Olsina, Julio Campon Pardo
  • Patent number: 5068433
    Abstract: The present invention relates to a new process for the preparation of 3-substituted derivatives of 1-amino-2- hydroxy-propane in the form of single diastereoisomers, to certain of these diastereoisomers, and to compounds which are intermediates in the new process of the invention.
    Type: Grant
    Filed: June 11, 1990
    Date of Patent: November 26, 1991
    Assignee: Farmitalia Carlo Erba, S.r.l.
    Inventors: Piero Melloni, Arturo D. Torre, Ettore Lazzari, Giuseppe Mazzini
  • Patent number: 5064863
    Abstract: Tertiary and secondary amines of the formulas ##STR1## wherein n is the integer 1 or 2, p0 R is hydrogen, lower-alkanoyl or phenyl-lower-alkanoyl,X.sup.1 is phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position,X.sup.2 is lower-alkyl, phenoxymethyl optionally mono-fluorinated or mono-chlorinated in the ortho-position or phenyl optionally monosubstituted by fluorine, chlorine, trifluoromethyl or lower-alkoxy,Y is hydrogen or methyl, andZ is a phenyl or thienyl residue substituted as hereinafter described,and the physiologically and pharmaceutically compatible salts are described. The compounds of formulas I and V-1 have catabolic activity and can be used for the treatment of obesity and diabetes mellitus or for the treatment of conditions which are associated with an increased protein breakdown, or as feed additives for fattening animals. The compounds of formulas I and V-1 can be prepared starting from corresponding primary amines.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: November 12, 1991
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Leo Alig, Marcel Muller
  • Patent number: 5047425
    Abstract: Compounds of the formula ##STR1## wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the meanings mentioned in the description, processes and intermediates for their preparation, pharmaceutical compositions which contain them and their use in therapy in the treatment of cardiovascular diseases.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: September 10, 1991
    Assignee: Simes Societa Italiana Medicinali & Sintetici SpA
    Inventors: Cesare Casagrande, Francesco Santangelo, Luisa Calabi
  • Patent number: 4990668
    Abstract: Described is a process for preparing a racemic or chiral aryloxypropanolamine (1) or arylethanolamine (2) of the formula ##STR1## wherein Ar is aryl, substituted aryl, heteroaryl, or aralkyl and R is alkyl, substituted alkyl, aralkyl, or WB wherein W is a straight or branched chain alkylene of from 1 to about 6 carbon atoms and wherein B is --NR.sub.2 COR.sub.3, --NR.sub.2 CONR.sub.3 R.sub.4, --NR.sub.2 SO.sub.2 R.sub.3, --NR.sub.2 SO.sub.2 NR.sub.3 R.sub.4, or --NR.sub.2 COOR.sub.5, where R.sub.2, R.sub.3, R.sub.4, and R.sub.5 may be the same or different and may be hydrogen, alkyl, alkoxyalkyl, alkoxyaryl, cycloalkyl, alkenyl, alkynyl, aryl, heteroaryl, or aralkyl, except that R.sub.3 and R.sub.5 are not hydrogen when B is --NR.sub.2 SO.sub.2 R.sub.3 or --NR.sub.3 COOR.sub.5, or R.sub.3 and R.sub.4 may together with N form a 5- to 7-membered heterocyclic group.The process can be used to prepare beta-blocking agents, useful in the treatment of cardiac conditions.
    Type: Grant
    Filed: December 4, 1985
    Date of Patent: February 5, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Khuong H. X. Mai, Ghanshyam Patil, William L. Matier
  • Patent number: 4952730
    Abstract: 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: Grant
    Filed: May 27, 1986
    Date of Patent: August 28, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Jurgen Leuchs, Werner Mohler, Hanns-Eberhard Erle
  • Patent number: 4945182
    Abstract: Hydroxyalkyl-phenoxy-propan-2-ol-3-amines are oculoselective .beta.-blockers useful in the treatment of elevated intraocular pressure with little or no effect on the pulmonary or cardiovascular system.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: July 31, 1990
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, David C. Remy, David A. Claremon
  • Patent number: 4902799
    Abstract: Novel bicyclic alkoxy- and alkylthio-substituted aminoalcohols of formula (I). The compounds show anti-hypertensive, platelet aggregation inhibiting, hypolipemic, antianoxic, spasmolytic, antithrombotic, calcium antagonizing and neuroleptic activity.
    Type: Grant
    Filed: June 4, 1987
    Date of Patent: February 20, 1990
    Assignee: Maggioni-Winthrop S.p.A.
    Inventors: Giampaolo Picciola, Mario Riva, Franco Ravenna, Piergiorgio Gentili
  • Patent number: 4897425
    Abstract: Cyclohexylamines of the formula ##STR1## where X is a single bond or an alkylene chain, Y is hydrogen or an aryl, cyclohexyl, 4-cyclohexylcyclohexyl, perhydro-1- or 2-naphthyl or piperidyl radical, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkenyl or arylalkyl, or R.sup.1 and R.sup.2 together form an alkylene group and, togehter with the N atom, form a ring, and acid addition salts thereof, with the exception of compounds in which X is a single bond, Y is cyclohexyl, R.sup.1 and R.sup.2 are hydrogen or methyl, and the compounds in which X is C.sub.6 -, C.sub.7 - and C.sub.8 -alkyl, Y is hydrogen and R.sup.1 and R.sup.2 together with the N atom whose substituents they are form a 2,6-dimethylmorpholine radical, and fungicides containing such cyclohexylamines.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: January 30, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Ernst Buschmann, Norbert Goetz, Ulrich Schirmer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4892671
    Abstract: New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) ##STR1## or a derivative thereof in which R.sup.1, R.sup.2 and R.sup.3 are, independently, hydrogen, a C.sub.1 -C.sub.15 straight or branched chain alkyl residue, a C.sub.5 -C.sub.12 cycloalkyl residue, a C.sub.6 -C.sub.15 aryl residue or C.sub.7 -C.sub.12 alkaryl residue, and R.sup.4 and R.sup.5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that(a) R.sup.4 and R.sup.5 are not simultaneously hydrogen,(b) when R.sup.4 and R.sup.5 are each --CH.sub.2 --CH.sub.2 --OH, R.sup.1 and R.sup.2 are not simultaneously hydrogen and R.sup.3 is not a pentyl residue and(c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent;as well as salts thereof.Some of the compounds of formula I are new.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: January 9, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert M. O'Neil, John D. Payne
  • Patent number: 4888447
    Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: December 19, 1989
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4864061
    Abstract: New substituted phenoxyalkanolamines and phenoxyalkanol-cycloalkylamines of the general formula I ##STR1## in which R.sup.1 and R.sup.2, which can be identical or different, denote alkyl groups with in each case 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together denote the group --(CH.sub.2).sub.n --, wherein n is the number 4 or 5, R.sup.3 denotes hydrogen, or an alkyl group or an acyl group with in each case 1 to 6 carbon atoms, R.sub.4 denotes an alkyl group with 1 to 4 carbon atoms or the cyclopropylmethyl group and R.sup.5 denotes hydrogen halogen or alkyl, and acid addition salts thereof, have a cardioselective .beta..sub.1 -adrenolytic and hypotensive action. They can be used as medicaments for the treatment of angina pectoris, hypertension and arrhythmias.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: September 5, 1989
    Assignee: Beiersdorf Aktiengesellschaft
    Inventor: Erich Cohnen
  • Patent number: 4816604
    Abstract: The compounds of formula I, ##STR1## where the substituents have various significances, and physiologically acceptable hydrolyzable derivatives thereof having the hydroxy group in the 2 position of the 3-aminopropoxy side chain in esterifield form, are useful as cardioselective .beta.-adrenoceptor blocking agents.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: March 28, 1989
    Assignee: William J. Louis
    Inventors: William J. Louis, Richard Berthold, Andre Stoll
  • Patent number: 4806555
    Abstract: Novel 1-aryloxy-4-amino-2-butanols of the formulaArO--CH.sub.2 --CHOH--CH.sub.2 --CH.sub.2 --NR.sup.1 R.sup.2wherein Ar is 1-naphthyl, 2-naphthyl, indene-4(or 5-)yl, 3-(or 5-)chloro-2-pyridyl, phenyl, monosubstituted phenyl or di-substituted phenyl, R.sup.1 is lower alkyl, phenyl, phenylalkyl, 2-hydroxymethyl-2-propyl, adamantyl or lower-cycloalkyl, R.sup.2 is hydrogen or lower alkyl, wherein R.sup.1 and R.sup.2 together with the adjacent nitrogen from a heterocyclic residue and the pharmaceutically acceptable acid addition salts thereof having local anesthetic, beta-adrenergic blocking, antihypertensive and antiarrhythmic properties are disclosed. The compounds are prepared by reacting novel 1-aryloxy-4-chloro-2-butanols with amines. Methods for the preparation of the novel 1-aryloxy-4-chloro-2-butanol intermediates are also disclosed.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: February 21, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Carl D. Lunsford, Ying-Ho Chen
  • Patent number: 4777293
    Abstract: A process for the preparation of an aryloxypropanolamine of the formulaAr--OCH.sub.2 CH(OH)CH.sub.2 NH--R Iwherein Ar is a carbocyclic or heterocyclic aromatic group and R is an alkyl or substituted alkyl group having 1 to 6 carbon atoms, characterized in subjecting a compound of the formula ##STR1## to oxidative cleavage to a dialdehyde of the formula ##STR2## which is then made subject to reduction, amination, acetal hydrolysis, and, where required, removal of a nitrogen protective group, to the formation of a compound of formula I, or an acid addition salt thereof, a compound of formula II and the preparation thereof from mannitol.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: October 11, 1988
    Assignee: Aktiebolaget Hassle
    Inventor: Bo R. Lamm
  • Patent number: 4772631
    Abstract: The invention concerns a series of novel phenoxyacetic acid ethers (and pharmaceutically acceptable salts thereof) of the formula I in which R.sup.1 is H or F, R.sup.2 and R.sup.3 are H or (1-3C)alkyl, Z is CH.sub.2 OH or a group --CO.R.sup.4 in which R.sup.4 is OH, NH.sub.2 or (1-6C)alkoxy. The invention also includes pharmaceutical compositions for use in treating obesity and related conditions and provides processes for the manufacture of the novel ethers.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: September 20, 1988
    Assignee: Imperial Chemical Industries PlC
    Inventors: Brian R. Holloway, Ralph Howe, Balbir S. Rao, Donald Stribling
  • Patent number: 4760182
    Abstract: Phenol ethers such as 1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-2-prop anol, otherwise known as betaxolol, of formula: ##STR1## are prepared from p-hydroxyphenethyl alcohol by first reacting at the phenolic group, with epichlorohydrin followed by isopropylamine, to prepare the required secondary amine-hydroxy side chain. Protection of the alcoholic group is not required during these steps. Then the secondary amine-alcohol group is protected by reaction with a suitable aldehyde such as benzaldehyde to form an oxazolidine ring protectant while the alcohol chain is elaborated. The oxazolidine ring protectant is removed by simple acid hydrolysis.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: July 26, 1988
    Assignee: Torcan Chemical Ltd.
    Inventors: Robert M. Ippolito, Stephen Vigmond
  • Patent number: 4751278
    Abstract: The adducts of monoepoxides with selected diamines, preferably m-xylylenediamine, are useful as curing agents for the curing of epoxy resin compositions at very low temperatures (25.degree.-50.degree. F., -4.degree. to 10.degree. C.).
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: June 14, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Vincent Brytus
  • Patent number: 4683245
    Abstract: This invention relates to a process for the separation of moprolol into its two optical antipodes, substantially characterized by the fact of salifying racemic moprolol with L(+)glutamic acid; treating the thus obtained mixture of diastereoisomeric salts with a water/alcohol mixture, in this way separating the L(+)glutamate insoluble salt of (+)moprolol; treating the resultant mother liquors which contain in solution the L(+)glutamate salt of (-)moprolol with a base so as to separate the laevorotatory isomer of crystalline moprolol, which finally undergoes a purification. The invention also relates to a pharmaceutical composition containing said laevorotatoryisomer of moprolol.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: July 28, 1987
    Assignee: SIMES S.p.A. Societa Italiana Medicinali e Sintetici
    Inventors: Giorgio Ferrari, Vittorio Vecchietti
  • Patent number: 4665094
    Abstract: Hydroxyalkyl-phenoxy-propan-2-olamines and novel esters thereof are oculoselective .beta.-blockers useful in the treatment of elevated intraocular pressure with little or no effect on the pulmonary or cardiovascular system.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: May 12, 1987
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Gerald S. Ponticello
  • Patent number: 4652681
    Abstract: Derivatives of propranolol which have the following structure: ##STR1## where R is X--(CH.sub.2).sub.n --O, X is NH.sub.2 or COOH, n is 1,2,3,4, or 5, provided that when n is 1, X must be COOH, and R is attached in the 4', 5', 6', 7' or 8' position. The compounds are useful in immunoassay applications to (1) conjugate to a protein carrier in order to prepare antibodies to propranolol and (2) to conjugate to a tracer moiety such as a radiolabeled ligand, an enzyme, an enzyme substrate or a fluorescent dye.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: March 24, 1987
    Assignee: Drug Science Foundation
    Inventors: Thomas D. Eller, Daniel R. Knapp
  • Patent number: 4652672
    Abstract: For the analytical and preparative separation of the optical isomers of optically active alkanolamines into their optically pure antipodes a new resolution method is presented which involves an ester formation of the alkanolamines with optically pure and symmetrically O,O disubstituted (R,R)- or (S,S)-tartaric acids. The derivitization reactions are carried out in aprotic solvents and the primary and secondary functions are blocked via ion-pair formations with strong acids, e.g. dichloroacetic acid. The tartaric acid anhydrides are predominantly used as reagents but other ester formation methods are also practicable. The mixture of the diastereomeric alkanolamine tartaric acid monoesters are separable into their optically active and pure isomers by various chromotographic separation techniques, e.g. straight or reverse phase LC, but also by extraction methods e.g. Soxhlet extraction.
    Type: Grant
    Filed: October 17, 1983
    Date of Patent: March 24, 1987
    Inventor: Wolfgang F. Lindner
  • Patent number: 4652584
    Abstract: Phenoxypropanol derivatives having a 2-acetylenic moiety on the phenyl group thereof of the following formula (I): ##STR1## and their use as anti-hypertensives, e.g. in man. Also part of the invention are pharmaceutical compositions and intermediates used in the synthesis.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: March 24, 1987
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Patent number: 4649160
    Abstract: Substituted phenoxy-aminopropanols of the formula ##STR1## wherein R is a branched-chain alkyl of 3 or 4 carbon atoms, R.sup.1 is hydrogen, halogen or lower alkyl and R.sup.2 and R.sup.3, independently, are hydrogen, halogen, lower alkyl, lower alkoxy or lower alkylthio, and pharmaceutically acceptable acid addition salts thereof, are described. A process for their preparation, as well as pharmaceutical preparations containing them are also described. The compounds of formula I and their salts possess cardioselective .beta.-adrenergic blocking activity and antihypertensive activity.
    Type: Grant
    Filed: September 6, 1985
    Date of Patent: March 10, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter J. Machin
  • Patent number: 4612320
    Abstract: Compounds of the general formula ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n have the meanings given in the description, are useful for treating cardiac disorders.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: September 16, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Albrecht Franke, Josef Gries, Claus D. Mueller, Dieter Lenke
  • Patent number: 4582905
    Abstract: Convenient intermediates for preparing 3-substituted-2-hydroxypropyl aryl ether .beta.-blockers, a reaction to the intermediates of the following formula and a conversion to obtain the said .beta.-blockers are disclosed. ##STR1## (wherein X is hydrogen or halogen; Y is halogen, hydroxy, lower acyloxy, amino, lower alkylamino, lower aralkylamino, lower acylamino, di-lower alkylamino, lower alkyleneamino, N-lower alkyl-N-lower aralkylamino, di-lower acylamino, N-lower alkyl-N-lower acylamino or N-tri-lower alkylsilylamino;one of P and R combined together with Q represents lower alkylene or alkenylene optionally interrupted by O, N or S and optionally substituted by lower alkyl, lower aralkyl, lower carboxylic acyl, carboxy, protected carboxy; hydroxy, lower alkoxy, lower acyloxy, oxo; amino, lower alkylamino, lower acylamino, nitro, nitroso, lower alkylthio, lower sulfonic acyl or halogen;and the remaining R or P is hydrogen or halogen;and dotted line represents the presence of one or two double bonds).
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: April 15, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventor: Makiko Sakai
  • Patent number: 4571409
    Abstract: Novel aminopropanol derivatives of 2-hydroxy-.beta.-phenyl-propiophenones and their physiologically acceptable acid addition compounds, processes for their preparation and therapeutic agents which contain these derivatives and are useful as antiarrhythmic drugs.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: February 18, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Albrecht Franke, Josef Mueller, Helmut Lietz, Walter-Wielant Wiersdorff, Hans-Guenther Hege, Claus D. Mueller, Josef Gries, Dieter Lenke, Gerda von Philipsborn, Manfred Raschack
  • Patent number: 4540697
    Abstract: Novel aminopropanol derivatives of 2-hydroxy-.beta.-phenyl-propiophenones and their physiologically acceptable acid addition compounds, processes for their preparation and therapeutic agents which contain these derivatives and are useful as antiarrhythmic drugs.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: September 10, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Albrecht Franke, Josef Muller, Helmut Lietz, Walter-Wielant Wiersdorff, Hans-Gunther Hege, Claus D. Muller, Josef Gries, Dieter Lenke, Gerda von Philipsborn, Manfred Raschack
  • Patent number: 4535133
    Abstract: Polyether polyols modified with adducts of epoxy resins, such as the diglycidyl ether of Bisphenol A, and diamines, such as polyoxypropylenediamine, are described. The resulting modified polyether polyols have a molecular weight of from about 2,000 to 7,000 and are useful in the preparation of flexible polyurethane foams. The mole ratio of epoxy equivalents to amine equivalents in the adduct ranges from about 2/1 to 10/1.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: August 13, 1985
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Harold G. Waddill
  • Patent number: 4515814
    Abstract: New 3-phenoxypropan-2-ol derivatives of the formula: ##STR1## wherein R represents a cycloalkyl radical having 5 or 6 carbon atoms, X represents an oxygen atom or a bond, and R' represents the isopropyl or tert.-butyl radical, have been found to be useful in therapy, and more particularly in the treatment of cardiovascular diseases and glaucoma.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: May 7, 1985
    Assignee: Synthelabo
    Inventors: Alexander E. Wick, Jean Binet
  • Patent number: 4482562
    Abstract: A compound represented by the following formula ##STR1## wherein A represents a direct bond or the bond --O--CH.sub.2 --,B represents a C.sub.1 -C.sub.11 alkylene group bonded to a carbon atom of the aromatic ring D either directly or through --O--, --S--, --SO-- or --NH--,W represents a carbon or nitrogen atom,R.sub.1 represents a C.sub.3 -C.sub.7 alkyl group, a hydroxy-C.sub.1 -C.sub.6 alkyl group, or a phenyl- or diphenyl-alkyl group with the alkyl group having 1 to 4 carbon atoms,R.sub.2 represents a member selected from the group consisting of hydrogen, halogen, OH, C.sub.1 -C.sub.4 alkyl, NO.sub.2, C.sub.1 -C.sub.4 alkoxy, acetyl, allyloxy, carbamoyl and sulfamoyl, and when two or more R.sub.2 groups exist, they may be identical or different, andn represents 1, 2 or 3 and m represents 1 or 2, provided that n+m.gtoreq.4;and an acid addition salt thereof; a process for producing the same; and a pharmaceutical composition comprising aforesaid compound.
    Type: Grant
    Filed: September 3, 1982
    Date of Patent: November 13, 1984
    Assignee: Kowa Company, Ltd.
    Inventors: Masami Shiratsuchi, Noboru Shimizu, Hiromichi Shigyo, Yoshinori Kyotani, Hisashi Kunieda, Kiyoshi Kawamura, Seiichi Sato, Toshihiro Akashi, Masahiko Nagakura, Naotoshi Sawada, Yasumi Uchida
  • Patent number: 4474986
    Abstract: A process for the preparation of propafenone wherein1. 2'-hydroxyacetophenone is reacted with epichlorohydrin,2. the resulting 2-(2',3'-epoxypropoxy)-acetophenone is reacted with propylamine,3. the resulting 2-(2'-hydroxy-3'-propylaminopropoxy)-acetophenone is reacted with benzaldehyde, accompanied by elimination of water, and4. the resulting 2-(2'-hydroxy-3'-propylaminopropoxy)-benzalacetophenone is hydrogenated.
    Type: Grant
    Filed: March 18, 1983
    Date of Patent: October 2, 1984
    Assignee: BASF Aktiengesellschaft
    Inventor: Helmut Lietz
  • Patent number: 4463190
    Abstract: Novel 1-aryloxy-4-amino-2-butanols of the formulaArO--CH.sub.2 --CHOH--CH.sub.2 --CH.sub.2 --NR.sup.1 R.sup.2wherein Ar is 1-naphthyl, 2-naphthyl, indene-4(or 5-)yl, 3-(or 5-)chloro-2-pyridyl, phenyl, monosubstituted phenyl or di-substituted phenyl, R.sup.1 is lower alkyl, phenyl, phenylalkyl, 2-hydroxymethyl-2-propyl, adamantyl or lower-cycloalkyl, R.sup.2 is hydrogen or lower alkyl, wherein R.sup.1 and R.sup.2 together with the adjacent nitrogen form a heterocyclic residue and the pharmaceutically acceptable acid addition salts thereof having local anesthetic, beta-adrenergic blocking, antihypertensive and antiarrhythmic properties are disclosed. The compounds are prepared by reacting novel 1-aryloxy-4-chloro-2-butanols with amines. Methods for the preparation of the novel 1-aryloxy-4-chloro-2-butanol intermediates are also disclosed.
    Type: Grant
    Filed: September 16, 1982
    Date of Patent: July 31, 1984
    Assignee: A. H. Robins Company, Inc.
    Inventors: Carl D. Lunsford, Ying-Ho Chen
  • Patent number: 4460605
    Abstract: The 2-[2'-hydroxy-3'-(1,1-dimethylpropylamino)-propoxy]-.beta.-phenylpropiophe none of formula I ##STR1## and its acid addition salts are described. Moreover, the preparation of this compound and of its acid addition salts is described. The compound and its acid addition salts have an antiarrhthymic effect. They can therefore be used for treating heart rhythm disorders.
    Type: Grant
    Filed: August 24, 1982
    Date of Patent: July 17, 1984
    Assignee: Helopharm W. Petrik & Co.
    Inventors: Gerd Petrik, Rolf Sachse
  • Patent number: 4450115
    Abstract: New amino-alcohol derivatives and processes for production thereof are disclosed. These compounds exhibit .alpha. and .beta.-adrenergic receptor blocking activity or they act to increase the flow of blood of certain organs.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: May 22, 1984
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiroshi Takizawa, Yoshimasa Oiji, Kazuhiro Kubo
  • Patent number: 4435426
    Abstract: The present invention relates to novel products, responding to general formula: ##STR1## in which R.sub.1 and R.sub.2 taken together represent an atom of oxygen .dbd.O or R.sub.1 represents hydrogen and R.sub.2 represents an OH radical, R.sub.3 designates an atom of hydrogen or a straight or branched alkyl radical, or an alkynyl group having from 1 to 6 atoms of carbon, R.sub.4 represents a straight or branched alkyl radical having from 1 to 6 atoms of carbon, R.sub.5 designates an atom of hydrogen, an alkyl group having from 1 to 4 atoms of carbon or an acylamine group and n=3 or 4; as well as to the acid addition salts of said products, to a process for preparing said products and to drugs, particularly active on the cardiovascular system, containing at least one of said products.
    Type: Grant
    Filed: May 25, 1982
    Date of Patent: March 6, 1984
    Assignee: Societe Anonyme dite: Sanofi
    Inventors: Henri Demarne, Jean Wagnon