A PROCESS FOR THE PREPARATION OF A COMPOUND

• Main Authors: KEITH JAMES CARL JR, LYTTLE CECIL RICHARD, MCDEVITT ROBERT EMMETT, GUNAWAN IWAN, MANAS ERIC STEVEN, HARRIS HEATHER ANNE, MALAMAS MICHAEL SOTIRIOS, COLLINI MICHAEL DAVID, ALBERT LEO MASSILLAMONEY
• Format: Patent
• Language: English
• Published: 07.08.2015
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HYGIENE; MEDICAL OR VETERINARY SCIENCE; METALLURGY; ORGANIC CHEMISTRY; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS

A process for the preparation of a compound of formula I, having the structure wherein R1 is alkenyl of 2-7 carbon atoms; wherein the alkenyl moiety is optionally substituted with hydroxyl, -CN, halogen, trifluoroalkyl of 1-6 carbon atoms, trifluoroalkoxy of 1-6 carbon atoms, -COR5, -CO2R5, -NO2, CONR5R6, NR5R6 or N(R5)COR6; R2 and R2a are each, independently, hydrogen, hydroxyl, halogen, alkyl of 1-6 carbon atoms, alkoxy of 1-4 carbon atoms, alkenyl of 2-7 carbon atoms, alkynyl of 2-7 carbon atoms, trifluoroalkyl of 1-6 carbon atoms, or trifluoroalkoxy of 1-6 carbon atoms; wherein the alkyl, alkenyl, or alkynyl moieties are optionally substituted with hydroxyl, -CN, halogen, trifluoroalkyl of 1-6 carbon atoms, trifluoroalkoxy of 1-6 carbon atoms, -COR5, -CO2R5, -NO2, CONR5R6, NR5R6 or N(R5)COR6; R3, and R3a are each, independently, hydrogen, alkyl of 1-6 carbon atoms, alkenyl of 2-7 carbon atoms, alkynyl of 2-7 carbon atoms, halogen, alkoxy of 1-4 carbon atoms, trifluoroalkyl of 1-6 carbon atoms, or trifluoroalkoxy of 1-6 carbon atoms; wherein the alkyl, alkenyl, or alkynyl moieties are optionally substituted with hydroxyl, -CN, halogen, trifluoroalkyl of 1-6 carbon atoms, trifluoroalkoxy of 1-6 carbon atoms, -COR5, -CO2R5, -NO2, CONRsRe, NR5R6 or N(R5)COR6; R5, R6 are each, independently hydrogen, alkyl of 1-6 carbon atoms or aryl of 6-10 carbon atoms; X is O, S, or NR7; R7 is hydrogen, alkyl of 1-6 carbon atoms, aryl of 6-10 carbon atoms, -COR5, -CO2R5 or -SO2R5; or a pharmaceutically acceptable salt thereof; comprising one of the following a) reacting a compound of formula wherein R1, R2, R2a. and X are as defined above with a compound of formula wherein R3 and R3a are as defined above and Y is halogen, -OH or hydroxyalkyl of 1 to 6 carbon atoms; or b) converting a compound of formula I as defined above to a pharmaceutically acceptable salt thereof; or c) resolving an Isomeric mixture of compounds of formula I as defined above to isolate an enantiomer of a compound of formula I or a pharmaceutically acceptable salt thereof,