GB1019128A - Therapeutic compounds and preparation thereof - Google Patents

Therapeutic compounds and preparation thereof

Info

Publication number
GB1019128A
GB1019128A GB32345/64A GB3234564A GB1019128A GB 1019128 A GB1019128 A GB 1019128A GB 32345/64 A GB32345/64 A GB 32345/64A GB 3234564 A GB3234564 A GB 3234564A GB 1019128 A GB1019128 A GB 1019128A
Authority
GB
United Kingdom
Prior art keywords
compounds
reaction
compositions
diethylamino
effected
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
GB32345/64A
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.)
Richardson Vicks Inc
Original Assignee
Richardson Merrell 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
Application filed by Richardson Merrell Inc filed Critical Richardson Merrell Inc
Publication of GB1019128A publication Critical patent/GB1019128A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to compounds of the formula <FORM:1019128/C2/1> in which R and R1 are alkyl groups of 1-5 carbon atoms. The compounds may be prepared by (1) forming a trifluoromethylpropiophenone, (2) halogenating this to form an a -halotrifluoromethylpropiophenone and (3) aminating the latter with an appropriate dialkylamine. Reaction (1) may be effected by treating a trifluoromethylphenyl magnesium halide with propionic anhydride at below 0 DEG C. in an anhydrous solvent, or alternatively by treating a trifluoromethylbenzonitrile with ethyl magnesium halide to form an intermediate ketimine, which is then hydrolysed with aqueous mineral acid. Reaction (2) is preferably affected at a temperature up to 100 DEG C. with elemental bromine or chlorine, but other halogenating agents may also be used, e.g. N-bromosuccinimide, N - bromacetamide, sulphuryl chloride or N-chlorosuccinimide. Reaction (3) may be effected at 50-125 DEG C. in the presence of a solvent, which may be an excess of the dialkylamine. The products may be converted into salts, e.g. with hydrochloric, sulphuric, phosphoric, acetic, citric or benzoic acid. Examples are given of the manufacture of the hydrochlorides of a -diethylamino-o-, -m-, and -p-trifluoromethyl - propiophenones. The products are of therapeutic value (see Division A5).ALSO:As anorexigenic agents in pharmaceutical compositions, use is made of compounds of the formula <FORM:1019128/A5-A6/1> in which R and R1 are alkyl groups of 1-5 carbon atoms (see Division C2). The compounds may be used in the form of their salts. They may be mixed with solid or liquid pharmaceutical carriers suitable for oral or suppository administration, and examples are given of the preparation of tablets containing a -diethylamino-m-(or p-)-trifluoron methylpropiophenone hydrochloride. The compounds may also be included in food supplement compositions, e.g. in vitamin compositions, or used with other therapeutically active compounds, such as sedatives or laxatives.
GB32345/64A 1963-08-08 1964-08-07 Therapeutic compounds and preparation thereof Expired GB1019128A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30090963A 1963-08-08 1963-08-08

Publications (1)

Publication Number Publication Date
GB1019128A true GB1019128A (en) 1966-02-02

Family

ID=23161116

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32345/64A Expired GB1019128A (en) 1963-08-08 1964-08-07 Therapeutic compounds and preparation thereof

Country Status (3)

Country Link
ES (1) ES302968A1 (en)
FR (1) FR3590M (en)
GB (1) GB1019128A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2430933A1 (en) * 1978-07-13 1980-02-08 Synthelabo PROPIOPHENONE DERIVATIVES AND THEIR THERAPEUTIC APPLICATION

Also Published As

Publication number Publication date
ES302968A1 (en) 1965-01-16
FR3590M (en) 1965-10-04

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