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: 4411913
    Abstract: 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: Grant
    Filed: March 5, 1979
    Date of Patent: October 25, 1983
    Assignee: Sandoz Ltd.
    Inventors: Trevor G. Payne, Richard Berthold
  • Patent number: 4410548
    Abstract: Propanolamine derivatives of the formula: ##STR1## wherein R.sup.2 is CH.sub.3 SO or CH.sub.3 SO.sub.2 ;R.sup.3 is hydrogen, methyl or methoxy; orR.sup.2 and R.sup.3 are together --S(O).sub.m (CH.sub.2).sub.4 --when S is attached at R.sup.2 or --(CH.sub.2).sub.n S(O).sub.m -- when S is attached at R.sup.3 (where m=1 or 2 and n=3 or 4);R.sup.4 is hydrogen or alkyl C.sub.1-4 ;Z is --(CH.sub.2).sub.2 -- or ##STR2## and their non-toxic salts. Processes for the preparation and pharmaceutical compositions thereof. The compounds exhibit both .beta.-adrenoreceptor antagonist activity and vasodilator activity and are indicated for use in the treatment of hypertension.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: October 18, 1983
    Assignee: Reckitt & Colman Products Limited
    Inventors: Andrew J. G. Baxter, Malcolm Myers
  • Patent number: 4401832
    Abstract: Disclosed herein are .alpha.-[(alkylamino)methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: August 30, 1983
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4396629
    Abstract: Therapeutically useful 1-(substituted-amino)-3-[4-R.sub.1 O-3-(lower-alkylthio, lower-alkylsulfinyl or lower-alkylsulfonyl)phenoxy]-2-propanols are obtained by reacting a 4-R.sub.1 0-3-(lower-alkylthio, lower-alkylsulfinyl or lower-alkylsulfonyl)phenol with an epihalohydrin and reacting the resulting product with a primary amine. The compounds have both antihypertensive and .beta.-adrenergic blocking activity and are useful as antihypertensive agents.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: August 2, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Richard E. Philion
  • Patent number: 4387100
    Abstract: Phenoxy-aminopropanol derivatives of the formula ##STR1## wherein R is lower alkyl, X is oxygen or sulfur, n is the integer zero or 1, Y is methylene, ethylene or propylene or, when n is zero, Y can also be a group of the formula--CH.dbd.CH--C*H.sub.2 -- (a), wherein the double-bond is trans and the carbon atom marked with an asterisk is linked to Z, and Z is a 5-membered aromatic heterocyclic ring which contains one or more nitrogen atoms as the sole hetero atom (s), said heterocyclic ring is linked to Y via a nitrogen atom, and may be substituted by halogen, lower alkyl, lower alkoxy, aryl, cyano or carboxamido, or on adjacent carbon atoms by a group of the formula ##STR2## and pharmaceutically acceptable acid addition salts thereof are described. A process for the preparation of the compound of formula I and pharmaceutical preparations containing them are also described. The aforementioned compounds and salts possess .beta.-adrenergic blocking activity and antihypertensive activity.
    Type: Grant
    Filed: February 24, 1981
    Date of Patent: June 7, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter J. Machin
  • Patent number: 4379167
    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: July 5, 1977
    Date of Patent: April 5, 1983
    Assignee: A. H. Robins Company, Inc.
    Inventors: Carl D. Lunsford, Ying-Ho Chen
  • Patent number: 4376125
    Abstract: 1-(p-Amino-.alpha.,.alpha.-dimethylphenethylamino)-3-(1-naphthoxy)-2-propan ol, 1-(p-hydroxy-.alpha.,.alpha.-dimethylphenethylamino)-3-(1-naphthoxy)-2-pro panol, 1-(p-methyl-.alpha.,.alpha.-dimethylphenethylamino)-3-(1-naphthoxy)-2-prop anol, 1-(p-methoxy-.alpha.,.alpha.-dimethylphenethylamino)-3-(1-naphthoxy)-2-pro panol and the pharmaceutically acceptable acid addition salts thereof are effective, long lasting .beta.-adrenergic blocking agents and areas of indication are hypertension, angina pectoris, cardiac arrythmia, and the like.
    Type: Grant
    Filed: November 5, 1980
    Date of Patent: March 8, 1983
    Assignee: University of Virginia Alumni Patents Foundation
    Inventors: Gary Brooker, Wesley L. Terasaki, Joel M. Linden
  • Patent number: 4374840
    Abstract: A compound represented by the following formula ##STR1## wherein A represents a direct bond or the bond --0--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: February 11, 1981
    Date of Patent: February 22, 1983
    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: 4356322
    Abstract: A series of novel derivatives of phenoxyalkanolamine of the general formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen, alkyl of 1 to 2 carbon atoms, methoxy, halogen, nitro, amino or acylamino residues, and the salts thereof, are described, as are methods for their synthesis. The compounds are highly active .beta..sub.1 -specific sympathicomimetics with a partially antagonistic component.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: October 26, 1982
    Assignee: Veb Arzneimittelwerk Dresden
    Inventors: Dieter Lehmann, Klaus Femmer, Gottfried Faust
  • Patent number: 4351848
    Abstract: Alkylthiopropranolol, compositions, and methods of use in the treatment of cardio-vascular disorders in mammals.
    Type: Grant
    Filed: March 16, 1978
    Date of Patent: September 28, 1982
    Assignee: Drug Science Foundation
    Inventor: Thomas Walle
  • Patent number: 4341718
    Abstract: Disclosed herein are .alpha.-[(alkylamino)-methyl]-.beta.-aryloxy-benzeneethanols exhibiting antiarrhythmic activity and having the following formula: ##STR1## wherein R is hydrogen, halogen, lower alkyl, or lower alkoxy; X is phenyl, 1-naphthyl, or a phenyl group substituted by a halogen, a lower alkyl group, or a lower alkoxy group; R.sub.1 is lower alkyl; and pharmacologically acceptable acid addition salts thereof. Also disclosed is a process for the addition of an aryloxy group at the 3-position of a 3-phenyl-2-oxiranecarboxamide to produce an .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamide, said process comprising contacting an alkali metal aryloxide with said 3-phenyl-2-oxiranecarboxamide in the presence of a crown ether. Such .alpha.-hydroxy-.beta.-aryloxy-benzenepropanamides may then be reduced to produce the compounds of the invention.
    Type: Grant
    Filed: July 3, 1978
    Date of Patent: July 27, 1982
    Assignee: American Home Products Corporation
    Inventors: Dong H. Kim, Stanley C. Bell
  • Patent number: 4336267
    Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.
    Type: Grant
    Filed: May 19, 1980
    Date of Patent: June 22, 1982
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
  • Patent number: 4330677
    Abstract: The invention relates to polyethers having an an average molecule weight of 3000 to 5000 and having a propylene oxide proportion of 60 to 80% and an ethylene oxide proportion of 20 to 40%. Also included in the invention are compositions containing said polyethers and methods for the use of said polyethers and compositions, particularly for their anti-lipidaemic effect.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: May 18, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegfried Linke, Mithat Mardin, Hans P. Krause, Rudiger Sitt
  • Patent number: 4329502
    Abstract: 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: Grant
    Filed: August 7, 1980
    Date of Patent: May 11, 1982
    Assignee: Syva Company
    Inventors: Prithipal Singh, Marcel R. Pirio
  • Patent number: 4322220
    Abstract: Substituted phenol/epichlorohydrin/amine adducts as multipurpose, low concentration additives for hydrocarbon fuels, lubricating oils and mixtures thereof.
    Type: Grant
    Filed: July 5, 1977
    Date of Patent: March 30, 1982
    Assignee: Rohm and Haas Company
    Inventors: Warren H. Machleder, Joseph M. Bollinger
  • Patent number: 4322437
    Abstract: The present invention relates to a compound of formula I, ##STR1## wherein A is straight chain alkylene of 2 to 4 carbon atoms, or straight chain alkenylene of 2 to 4 carbon atoms,n is 1, 2 or 3,R is hydrogen or halogen of atomic number from 9 to 35, andeither (i) R.sub.1 is a group of formula II, ##STR2## wherein R.sub.2 and R.sub.3, independently, are hydrogen or alkyl of 1 to 4 carbon atoms, andR.sub.4 is alkyl of 1 to 4 carbon atoms, alkoxyalkyl of 2 to 5 carbon atoms, alkylthioalkyl of 2 to 5 carbon atoms, phenylalkyl or phenoxyalkyl or phenylthioalkyl, wherein the alkyl moiety has from 1 to 3 carbon atoms, or phenyl, the phenyl ring of each of the last four radicals being unsubstituted or mono-substituted by, or disubstituted independently by, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, hydroxy or halogen of atomic number from 9 to 35, andR.sub.5 is hydrogen,or (ii) R.sub.1 and R.sub.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 30, 1982
    Assignee: Sandoz Ltd.
    Inventors: Richard Berthold, Trevor G. Payne
  • Patent number: 4311708
    Abstract: The invention provides phenol ethers of the formula: ##STR1## whereinR is branched C.sub.3-4 alkyl, C.sub.3-4 cycloalkyl, branched cyano(C.sub.3-4 alkyl), phenyl(C.sub.2-3 alkyl), halophenyl(C.sub.2-3 alkyl), (C.sub.1-4 alkoxy)phenyl(C.sub.2-4 alkyl), or (C.sub.1-4 acyl)amino(C.sub.1-4 alkyl),alk is C.sub.1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is --O--, --S-- or --SO.sub.2 --; andR.sub.1 is --C.sub.1-4 alkyl- or --C.sub.1-4 alkoxy-,in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as .beta.-adrenergic blocking agents. Intermediates are also provided.
    Type: Grant
    Filed: March 14, 1979
    Date of Patent: January 19, 1982
    Assignee: Synthelabo
    Inventors: Philippe M. J. Manoury, Icilio A. G. Cavero, Henry Najer, Don P. R. L. Giudicelli
  • Patent number: 4296231
    Abstract: The use of compounds of the formula ##STR1## in which m is a number from 3 to 10, X is a grouping of the formula in which R is an alkyl having 4 to 10 C atoms or a phenyl which is unsubstituted or substituted by chlorine, bromine or alkyl or alkoxy each having 1 to 3 C atoms, and Y is a hydrogen atom or has the meaning defined for X, which are obtained by adding on 1 or 2 mols of an aliphatic or aromatic monoglycidyl ether to 1 mol of a dimethylaminoalkylamine, as a curing catalyst for epoxide resins or as a curing accelerator in curable mixtures consisting of epoxide resins and polycarboxylic anhydrides or polyhydric phenols.
    Type: Grant
    Filed: May 1, 1980
    Date of Patent: October 20, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Ferdinand Gutekunst, Rolf Schmid
  • Patent number: 4275058
    Abstract: 1-Indanyloxy- or tetrahydronaphthyloxy-3-amino-2-butanol derivatives, especially erythro-1-(7-methylindan-4-yloxy)-3-isopropylaminobutan-2-ol, processes for their manufacture and pharmaceutical compositions containing them. The compounds possess peripherally-selective .beta.-adrenergic blocking activity.
    Type: Grant
    Filed: February 5, 1979
    Date of Patent: June 23, 1981
    Assignee: Imperial Chemical Industries Limited
    Inventor: Howard Tucker
  • Patent number: 4263325
    Abstract: Amines of the formula I ##STR1## method of preparing the same and pharmaceutical compositions and method for treating cardiovascular disorders by blocking the .beta.-receptors of the heart in combination with a peripheral vasodilating activity.
    Type: Grant
    Filed: April 5, 1979
    Date of Patent: April 21, 1981
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Gustav B. R. Samuelsson, Bo T. Lundgren
  • Patent number: 4259086
    Abstract: Substituted phenol/epichlorohydrin/amine adducts as multipurpose, low concentration additives for hydrocarbon fuels, lubricating oils and mixtures thereof.
    Type: Grant
    Filed: October 31, 1979
    Date of Patent: March 31, 1981
    Assignee: Rohm and Haas Company
    Inventors: Warren H. Machleder, Joseph M. Bollinger
  • Patent number: 4258062
    Abstract: New phenoxy-amino-propanols of formula ##STR1## wherein R.sup.1 is alkenyl, alkynyl, alkoxyalkyl or alkenyloxyalkyl with 2-6 C atoms in each case or cycloalkyl with 3-8 C atoms; and R.sup.2 is alkyl or hydroxyalkyl with 1-6 C atoms in each case, cycloalkyl with 3-8 C atoms, aralkyl or aralkyl wherein the aryl radical is mono- to tri-substituted by alkyl, alkoxy, OH, F and/or Cl or mono-substituted by methylenedioxy, with a total of 7-15 C atoms in each case, and the physiologically acceptable acid addition salts thereof, exhibit various pharmacological properties including isoprenaline-antagonism on the heart rate and blood pressure.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: March 24, 1981
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rochus Jonas, Karl-Heinz Becker, Hans-Joachim Enenkel, Klaus Minck, Hans-Jochen Schliep
  • Patent number: 4252984
    Abstract: The invention provides phenol ethers of the formula: ##STR1## wherein R is branched C.sub.3-4 alkyl, C.sub.3-4 cycloalkyl, branched cyano(C.sub.3-4 alkyl), phenyl(C.sub.2-3 alkyl), halophenyl(C.sub.2-3 alkyl), (C.sub.1-4 alkoxy)phenyl(C.sub.2-4 alkyl), or (C.sub.1-4 acyl)amino(C.sub.1-4 alkyl),alk is C.sub.1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is --O--, --S-- or --SO.sub.2 --; andR.sub.1 is --C.sub.1-4 alkyl- or --C.sub.1-4 alkoxy-,in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as .beta.-adrenergic blocking agents. Intermediates are also provided.
    Type: Grant
    Filed: October 20, 1976
    Date of Patent: February 24, 1981
    Assignee: Synthelabo
    Inventors: Philippe M. J. Manoury, Icilio A. G. Cavero, Henry Najer, Don Pierre R. L. Giudicelli
  • Patent number: 4244969
    Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.
    Type: Grant
    Filed: February 13, 1975
    Date of Patent: January 13, 1981
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
  • Patent number: 4243681
    Abstract: A new class of alkylthiophenoxypropanolamine derivatives and methods for preparation are described. The compounds have vasodilating and antispasmodic activity, inhibit blood platelet aggregation and are substantially free of beta-adrenergic blocking effects. They are particularly valuable in the treatment of disease states responsive to vasodilation such as obstructive peripheral vascular diseases and cerebral vascular deficiencies. A representative and preferred embodiment of the invention consists of 1-[4-(1-methylethylthio)phenoxy]-3-(octylamino)-2-propanol.
    Type: Grant
    Filed: April 16, 1979
    Date of Patent: January 6, 1981
    Assignee: Mead Johnson & Company
    Inventors: Duane F. Morrow, William L. Matier
  • Patent number: 4241177
    Abstract: Compounds are provided which can be used in the preparation of reagents useful for quantitatively determining the presence of .beta.-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: Grant
    Filed: August 28, 1978
    Date of Patent: December 23, 1980
    Assignee: Syva Company
    Inventors: Prithipal Singh, Marcel R. Pirio
  • Patent number: T101305
    Abstract: This invention concerns novel 3-[(3-alkylamino-2-hydroxypropoxy)phenyl]-1,2-propanediols of the formula: ##STR1## wherein R is selected from the group consisting of straight or branched-chain lower alkyls (C.sub.1 -C.sub.6) and cycloalkyls (C.sub.1 -C.sub.6); R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and 2,3-dihydroxypropyl, with the proviso that R.sub.1 and R.sub.2 may not be the same; and R.sub.3 is selected from the group consisting of lower alkyls (C.sub.1 -C.sub.4) and lower alkoxys (C.sub.1 -C.sub.4); and the acid addition salts thereof. These novel compounds are useful as antiarrhythmic agents and .beta.-andrenergic blockers in mammals.This invention also concerns novel compounds of the formula ##STR2## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen and 2,3-dihydroxypropyl, with the proviso that R.sub.1 and R.sub.2 may not be the same; R.sub.3 is selected from the group consisting of lower alkyls (C.sub.1 -C.sub.4) and lower alkoxys (C.sub.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: December 1, 1981
    Inventors: Joseph W. Epstein, Leon Goldman, James D. Warren