Kenneth A James

US Patent:

6593492, Jul 15, 2003

Filed:

Oct 25, 2000

Appl. No.:

09/695884

Inventors:

Nnochiri Nkem Ekwuribe - Cary NC
Kenneth D. James - Mebane NC

Assignee:

Nobex Corporation - Durham NC

International Classification:

C07C 6702

US Classification:

560250

Abstract:

A methods of preparing a substantially pure enantiomer of an acylanilide such as Casodex (bicalutamide) and/or its derivatives includes resolving an intermediate compound having the structure of Formula I: wherein R is alkyl or haloalkyl having up to 4 carbons; R is alkyl having up to 6 carbon atoms; R is a direct link or alkyl having up to 6 carbon atoms; R is alkyl, alkenyl, hydroxyalkyl or cycloalkyl each of up to 6 carbons; or R is phenyl which bears one, two or three substituents independently selected from hydrogen, halogen, nitro, carboxy, carbamoyl and cyano, and alkyl, alkoxy, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, perfluoroalkyl, perfluoroalkylthio, perfluoroalkylsulphinyl, perfluoroalkylsulphonyl, alkoxycarbonyl and N-alkylcarbamoyl each of up to 4 carbon atoms, and phenyl, phenylthio, phenylsulphinyl and phenylsulphonyl; or R is naphthyl; or R is a 5- or 6-membered saturated or unsaturated heterocyclic which contains one, two or three heteroatoms selected from oxygen, nitrogen and sulfur, which heterocyclic may be a single ring or may be fused to a benzo-ring, and which heterocyclic is unsubstituted or bears one or two halogen, cyano or amino, or alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl each of up to 4 carbon atoms, or oxy or hydroxy substituents, or which if sufficiently saturated may bear one or two oxo substituents; and X is oxygen, sulfur, sulphinyl (âSOâ), sulphonyl (âSO â), imino (âNHâ) or alkylimino (âNR â) where R is alkyl having up to 6 carbon atoms. The resolved intermediate compound of Formula I is then treated under conditions sufficient to provide a substantially pure enantiomer of an acylanilide such as Casodex (bicalutamide) and/or its derivatives.

US Patent:

20020165406, Nov 7, 2002

Filed:

May 2, 2001

Appl. No.:

09/847229

Inventors:

Nnochiri Ekwuribe - Cary NC, US
Kenneth James - Mebane NC, US

International Classification:

C07C255/49
C07C235/32

US Classification:

558/418000, 564/199000

Abstract:

Methods of synthesizing an acylanilide include contacting a compound having the structure of Formula I: with a compound having the structure of Formula II: under conditions sufficient to provide a compound having the structure of Formula III: 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: under conditions sufficient to provide an acylanilide having the structure of Formula V:

US Patent:

20030045742, Mar 6, 2003

Filed:

Oct 10, 2002

Appl. No.:

10/268155

Inventors:

Nnochiri Ekwuribe - Cary NC, US
Kenneth James - Mebane NC, US

International Classification:

C07C317/32

US Classification:

558/413000

Abstract:

Methods of synthesizing an acylanilide include contacting a compound having the structure of Formula I: with a compound having the structure of Formula II: under conditions sufficient to provide a compound having the structure of Formula III: 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: under conditions sufficient to provide an acylanilide having the structure of Formula V: