Methods of synthesizing acylanilides including bicalutamide and derivatives thereof
AssigneeNobex Corporation
InventorsNnochiri N. Ekwuribe, Kenneth D. James JR.
Life of this patent
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Abstract
Methods of synthesizing an acylanilide include contacting a compound having the structure of Formula I: 1 with a compound having the structure of Formula II: 2 under conditions sufficient to provide a compound having the structure of Formula III: 3 and treating the compound of Formula III under conditions sufficient to provide an acylanilide. The compound of Formula III may be addition reacted with a compound having the structure of Formula IV: R5—X1—R6—R7 Formula IV under conditions sufficient to provide an acylanilide having the structure of Formula V: 4
Claims58
A method of synthesizing an acylanilide comprising:
- (a) contacting a compound having the structure of Formula I:
- 18
- wherein
- R1 is substituted or unsubstituted alkyl or haloalkyl;
- with a compound having the structure of Formula II:
- 19
- wherein
- R2 is cyano, carbamoyl, nitro, fluoro, chloro, bromo, iodo, or hydrogen;
- or alkyl, alkoxy, alkanoyl, alkylthio, alkylsulfinyl, or alkylsulfonyl each being substituted or unsubstituted and having up to 4 carbon atoms;
- or phenyl, phenylthio, phenylsulfinyl or phenylsulfonyl each being susbstituted or unsubstituted;
- R3 is cyano, carbamoyl, nitro, fluoro, chloro, bromo or iodo;
- or alkyl, alkoxy, alkanoyl, alkylthio, alkylsulfinyl, or alkylsulfonyl each being substituted or unsubstituted and having up to 4 carbon atoms;
- or phenyl, phenylthio, phenylsulfinyl or phenylsulfonyl each being substituted or unsubstituted;
- and
- R4 is hydrogen or halogen;
- under conditions sufficient to provide a compound having the structure of Formula III:
- 20
- and;
- (b) treating the compound of Formula III under conditions sufficient to provide an acylanilide.
A method of synthesizing bicalutamide comprising:
- (a) contacting a compound having the structure of Formula VI:
- 22
- with a compound having the structure of Formula VII:
- 23
- under conditions sufficient to provide a compound having the structure of Formula VIII:
- 24
- and;
- (b) treating the compound of Formula VIII under conditions sufficient to provide bicalutamide.
In a method for synthesizing an acylanilide, the improvement comprising:
- using a compound having the structure of Formula I:
- 26
- wherein
- R1 is substituted or unsubstituted alkyl or haloalkyl.
In a method for synthesizing bicalutamide and/or a functional derivative thereof, the improvement comprising:
- using a compound having the structure of Formula I:
- 27
- wherein
- R1 is substituted or unsubstituted alkyl or haloalkyl.
Dependencies are inferred from the claim text.