| abstract |
1498377 Alkyne derivatives MERCK PATENT GmbH 18 June 1976 [19 June 1975] 25479/76 Heading C2C Novel compounds I in which R<SP>1</SP> is H, C 1-4 alkyl or phenyl, R<SP>2</SP> is H, C 1-6 aliphatic acyl or aroyl with up to 11 C atoms, each of R<SP>3</SP> and R<SP>4</SP> is H, F, Cl or Br and n is 0 or 1, provided that when R<SP>1</SP> is H or methyl, R<SP>2</SP> is H, R<SP>4</SP> is H and n is 0, R<SP>3</SP> is F, Cl or Br, and their physiologically acceptable metal salts, are prepared by solvolysing of compounds II in which Q is a functionally modified OH group, followed, if desired by acylating a resulting compound I in which R<SP>2</SP> is H, or converting a compound I to a salt thereof or liberating a compound I from a salt thereof. The radical Q in a compound II may be a group OM (where M is an equivalent of a metal or MgHal, CaHal, SrHal or BaHal), acyloxy, alkoxy or halogen. Compounds II in which Q is OM may be prepared by (a) reacting a ketone III with a metal acetylide or diamine complex thereof, or (b) reacting an enolate of the ketone III with acetylene, or (c) bu Grignard synthesis from a ketone of formula R<SP>1</SP>-CO-C#CH or R<SP>3</SP>, R<SP>4</SP>-C 6 H 3 -(O) n -(p)-C 6 H 4 -CO-C#CH or a lithium derivative thereof. Compounds II in which Q is acyloxy can be obtained by reacting a compound II in which Q is Cl or Br with an alkali metal salt of the appropriate acid. Pharmaceutical compositions having antiinflammatory, analgesic and anti - pyretic activity for enteral, parenteral or topical administration, comprise one of the above novel compounds together with a pharmaceutical carrier. |