Benzomorphan derivatives

Abstract

Abstract BENZOMORPHANES OF THE FORULA: 3-R,6-R1,8-(X-CO-A-O-),11-R"-1,2,3,4,5,6-HEXAHYDRO-2,6- METHANO-3-BENZAZOCINE WHEREIN R IS METHYL, CYCLOPROPYLMETHYL OR CYCLOBUTYLMETHYL, R'' AND R" ARE THE SAME OR DIFFERENT, AND ARE STRAIGHT OR BRANCHED CHAIN HYDROCARBONS OF 1 TO 5 CARBON ATOMS, X IS OH, OR"" OR -N(-R4)-R5 WHEREIN R"'' IS ASTRAIGHT OR BRANCHED CHAIN, SATURATED OR UNSATURTED HYDROCARBON OF 11 TO 11 CARBON ATOMS, R4 AND R5 ARE THE SAME OR DIFFERENT, AND ARE HYDROGEN, A STRAIGHT OR BRANCHED CHAIN, SAURATED HYDROCARON OF 1 TO 4 CARBON ATOMS, OR R4 AND R5 TOGETHER WITH THE NITROGEN ATOM FORM A5- OR 6-MEMBERED HETEROCYCLIC RING WHICH MAY HAVE OXYGEN AS A SECOND HETEROATOM, AND A IS A BIVALENT, STRAIGHT OR BRACHED CHAIN, SATURATED OR UNSATURATED HYDROCARBON OF 1 TO 10 CARBON ATOMS, SAID HYDROCARBON SUBSTITUTED BY 1 OR MORE PHENYL MOIETIES, OR SAID HYDROCARBON SUBSTITUTED BY 1 OR MORE ALKYL, ALKOXY, HALOGEN, NITRO OR ACYLAMINO SUBSTITUTED PHENYL MOIETIES, AND PHARMACEUTICALLY ACCEPTABLE NON-TOXIC SALTS THEREOF ARE PRODUCED BY REACTING A BENZOMORPHAN OF THE FORMULA: 8-HO,6-R'',11-R",3-R-1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO- 3-BENZAZOCINE WHEREIN R'' AND R" ARE AS ABOVE DEFINED, AND Y IS HYDROGEN, METHYL, CYCLOPROPYLMETHYL, CYCLOBUTYLMETHYL, OR THE MOIETY -CO-R6, WHEREIN R6 IS CYCLOPROPYL OR CYCLOBUTYL, IN THE PRESENCE OF AN ACIDBINDING AGENT, OR BY REACTING SAID BENZOMORPHAN IN THE FORM O A METAL OR AMMONIUM SALT WITH A REACTIVE ESTER OF A HYDROXY COMPOUND OFTHE FORMULA: Z-A-OH WHEREIN A IS AS ABOVE DEFINED, AND Z IS CO-X OR CN TO GIVE A COMPOUND OF THE FORMULA 8-(Z-A-O-),6-R'',11-R",3-R-1,2,3,4,5,6-HEXAHYDRO-2,6- METHANO-3-BENZAZOCINE WHEREIN R,R'',R", A AND Z ARE AS ABOVE DEFINED, AND IN THE CASE WHERE Z IS CN, CONVERTING THIS GROUP INTO THE CORRESPONDING CO-H GROUP AND IF Y IS HYDROGEN OR -CO-R6, CONVERTING SAID HYDROGEN OR SAID MOIETY INTO A METHYL, CYCLOPROPYLMETHYL OR CYCLOBUTYLMETHYL MOIETY. THE BENZOMORPHANES ARE USEFUL AS ANALGESICS.

Inventors

• 👤 H Schubert
• 👤 F Hoffmeister

Bibliographic Details