GB916789A - Therapeutic resin complexes - Google Patents

Therapeutic resin complexes

Info

Publication number
GB916789A
GB916789A GB10299/59A GB1029959A GB916789A GB 916789 A GB916789 A GB 916789A GB 10299/59 A GB10299/59 A GB 10299/59A GB 1029959 A GB1029959 A GB 1029959A GB 916789 A GB916789 A GB 916789A
Authority
GB
United Kingdom
Prior art keywords
phenyl
prepared
nitropropane
methyl
hydroxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB10299/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
US Filter Wallace and Tiernan Inc
Original Assignee
Wallace and Tiernan Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US726010A external-priority patent/US2990332A/en
Priority claimed from US753093A external-priority patent/US3084099A/en
Application filed by Wallace and Tiernan Inc filed Critical Wallace and Tiernan Inc
Publication of GB916789A publication Critical patent/GB916789A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
    • A61K47/585—Ion exchange resins, e.g. polystyrene sulfonic acid resin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
    • C07C205/03—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C205/04—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/08—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms
    • C07C205/09—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
    • C07C205/16—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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.
GB10299/59A 1958-04-02 1959-03-25 Therapeutic resin complexes Expired GB916789A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US726010A US2990332A (en) 1958-04-02 1958-04-02 Pharmaceutical preparations comprising cation exchange resin adsorption compounds and treatment therewith
US753093A US3084099A (en) 1958-08-04 1958-08-04 Therapeutic amine-resin complex composition and method of using same

Publications (1)

Publication Number Publication Date
GB916789A true GB916789A (en) 1963-01-30

Family

ID=27111252

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10299/59A Expired GB916789A (en) 1958-04-02 1959-03-25 Therapeutic resin complexes

Country Status (6)

Country Link
BE (1) BE577279A (en)
CH (1) CH391186A (en)
DK (1) DK104116C (en)
FR (1) FR465M (en)
GB (1) GB916789A (en)
NL (2) NL237722A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2332990A1 (en) * 1975-11-27 1977-06-24 Nicholas Ind Ltd PREPARATION OF ETHYLAMINE DERIVATIVES
EP0356035A2 (en) * 1988-08-12 1990-02-28 Astra Aktiebolag Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2332990A1 (en) * 1975-11-27 1977-06-24 Nicholas Ind Ltd PREPARATION OF ETHYLAMINE DERIVATIVES
EP0356035A2 (en) * 1988-08-12 1990-02-28 Astra Aktiebolag Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties
EP0356035A3 (en) * 1988-08-12 1991-04-03 Astra Aktiebolag Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties
WO1991011995A1 (en) * 1988-08-12 1991-08-22 Fisons Corporation Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties
AU654802B2 (en) * 1988-08-12 1994-11-24 Astra Aktiebolag Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties

Also Published As

Publication number Publication date
NL237722A (en)
FR465M (en) 1961-05-02
BE577279A (en) 1959-10-01
NL128079C (en)
CH391186A (en) 1965-04-30
DK104116C (en) 1966-04-04

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