C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 491/04 (2006.01) C07D 243/04 (2006.01) C07D 317/14 (2006.01) C07D 317/28 (2006.01)
Patent
CA 2304513
The present invention concerns an improved process for the preparation of asymmetric cyclic ureas as well as intermediates in the preparation of asymmetric cyclic ureas of formula (VI): wherein: R7 is selected from the following: C1-C8 alkyl substituted with 0-3 R11; C2-C8 alkenyl substituted with 0-3 R11; C2-C8 alkynyl substituted with 0-3 R11; and a C3-C14 carbocyclic ring system substituted with 0-3 R11; R10 is C1-C10 alkyl, benzyl, naphthylmethyl, 3,4-methylenedioxybenzyl, or C1-C4 alkyl substituted with phenyl wherein said phenyl is substituted with 0-3 R10a; G taken together along with the oxygen atoms to which G is attached forms a group selected from: -O-C(-CH2CH2CH2CH2CH2-)-O-, -O-C(CH2CH3)2-O-, -O-C(CH3)(CH2CH3)-O-, -O- C(CH2CH2CH2CH3)2-O-, -O-C(CH3)(CH2CH(CH3)CH3)-O-, -O-CH(phenyl)-O-, OCH2O-, - OC(CH3)2O- and -OC(OCH3)(CH2CH2CH3)O-. In the process, a diamine of formula (I- a) is selectively monoacylated to give an asymmetric monoacylated diamine which can be converted into asymmetric intermediates. The asymmetric intermediates can be further alkylated, cyclized, and/or modified to give compounds which are useful as HIV protease inhibitors for the treatment of HIV infection. The invention allows for scalable preparation of a wide variety of asymmetrical cyclic ureas.
L'invention concerne un procédé amélioré pour la préparation d'urées cycliques asymétriques et l'élaboration d'intermédiaires intervenant dans ladite préparation. On procède à la monoacylation sélective d'une diamine de formule (I-a), afin d'obtenir une diamine monoacylée asymétrique susceptible d'être convertie en intermédiaires asymétriques, lesquels peuvent être ensuite alkylés, cyclisés, et/ou modifiés de manière à fournir des composés utiles comme inhibiteurs de protéase du VIH pour le traitement de l'infection par le VIH. L'invention donne la possibilité d'effectuer une préparation échelonnable d'une large gamme d'urées cycliques asymétriques.
Anzalone Luigi
Fortunak Joseph M.
Harris Gregory D.
Stone Benjamin R. P.
Valvis Ioannis I.
Dimock Stratton Llp
Dupont Pharmaceuticals Company
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