Patent GB-916789-A (GB)
Title: Therapeutic resin complexes
IPC: A61K47/48
Filed: 1959-03-25
Abstract: The invention comprises a complex of phenyl-t-butylamine or cyclohexyl-t-butylamine with a cross-linked sulphonic acid cation exchange resin and a process for preparing a resin complex of the general formula: <FORM:0916789/IV(a)/1> in which R1 and R11 represent hydrogen, Y a benzene nucleus or a cyclopentyl or cyclohexyl ring, R represents hydrogen or halogen, a hydroxyl, C1-6 alkoxy, C1-6 alkyl, amino, or 3,4-methylenedioxy group, X and X1, which are the same or different, represent C1-6 alkyl, aryl, aralkyl or alkaryl groups, and A represents the anion of a sulphonic acid cation exchange resin, which comprises reducing the corresponding nitro compound to the amine in the presence of a sulphonic acid cation exchange resin or, when the amine is phenyl-t-butylamine, reacting 1-phenyl-1-hydroxy-2-methyl-2-nitropropane with thionyl chloride and catalytically reducing the 1-phenyl-1-chloro-2-methyl-2-nitropropane in the presence of a sulphonic acid cation exchange resin.  The complex may also be prepared by adsorbing the amine directly on the resin.  Suitable resins are Duolite C-20, IR-120, and XE-69. ("Duolite" is a Registered Trade Mark).  Specifications 577,707, 824,337 and U.S.A.  Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.ALSO:Phenyl-t-butylamine is prepared either by reducing 1 - phenyl - 1 - hydroxy - 2 - methyl-2-aminopropane with red phosphorus and hydriodic acid or by hydrogenating 2-phenyl2-chloro-1,1-dimethylethylamine in the presence of palladinized calcium carbonate.  Using Adams platinum oxide, alone, palladium on charcoal or Raney nickel as catalysts cyclohexyl-t-butylamine is prepared.  Cyclopentyl-t-butylamine is similarly prepared.  1 - Phenyl - 1 - hydroxy-2-methyl-2-aminopropane is prepared by condensing benzaldehyde with 2-nitropropane to give 1-phenyl-1-hydroxy-2-methyl-2-nitropropane which is reduced with zinc and acetic acid.  1 - Phenyl-1-chloro-2-methyl-2-nitropropane is prepared by reacting 1-phenyl-1-hydroxy-2-methyl-2-nitropropane with thionyl chloride.  Similarly are prepared from the appropriate benzaldehyde and nitropropane m-tolyl-, m-chlorophenyl- and m-aminophenyl-1-hydroxy2-methyl-2-nitropropanes which with thionyl chloride give the corresponding -1-chloro compounds. 2-Nitro-2,2-dimethyl-1-phenylethane is prepared either by reduction of 1-phenyl-1-hydroxy-2-methyl-2-nitropropane or by condensing benzyl chloride with 2-nitropropane.  Similarly are prepared 2-nitro-2,2-dimethyl-1-m-tolyl-, -m-chlorophenyl- and -m-aminophenylethanes.  1-Phenyl - 1 - chloro-2,2-dimethylaminoethane is prepared from 1-phenyl-1-hydroxy-2,2-dimethylaminoethane and thionyl chloride.  Specifications 577,707, 824,337 and U.S.A. Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.ALSO:Therapeutic compositions having appetite-suppressing properties comprise a pharmaceutical carrier and from 2 to 150 milligrams per dosage unit of an amine, present as a resin complex having the general formula <FORM:0916789/VI/1> in which Y represents a benzene nucleus or a saturated five-membered or six-membered carbon ring; R represents hydrogen, halogen, hydroxyl, amino, C1-6 alkoxyl, C1-6 alkyl or 3,4-methylene dioxy; X and X1 represent the same or different C1-6 alkyl, aralkyl, alkaryl or aryl groups; R1 and R11 are hydrogen atoms or C1-6 alkyl p  groups and A represents the anion of a sulphonic acid cation exchange resin.  Preferably the cross linkage and particle size of the resin are such that a dosage unit of the composition is therapeutically effective for a period of not less than 8 hrs. upon oral administration.  Suitable resins include Duolite C-20 ("Duolite" is a Registered Trade Mark), IR-120 and XE-69. Preferred compositions are tablets, capsules or pills which may contain a single daily dose unit, smaller units for multiple doses or larger units for division into single doses.  Specifications 577,707, 824,337 and U.S.A.  Specifications 2,204,539, 2,238,159 and 2,729,607 are referred to.