Suksdorfin analogs, compositions thereof, and methods for...

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C - Chemistry, Metallurgy

07

D

C07D 493/04 (2006.01) A61K 31/365 (2006.01) A61K 31/40 (2006.01) A61K 31/415 (2006.01) A61K 31/495 (2006.01) A61K 31/505 (2006.01) A61K 31/52 (2006.01) A61K 31/66 (2006.01) A61K 31/70 (2006.01) A61K 38/17 (2006.01) A61K 38/21 (2006.01) C07D 491/04 (2006.01) C07D 519/00 (2006.01)

Patent

CA 2213519

Compounds, including compositions and methods of making and using these compounds for treating retroviral infections, are provided according to formula (G-1), wherein M is O or NH; Z is O, NH or S; R240, and R250 are each H, C1-10 alkyl, C1-10 aryl, alkyl, amide, or CH2COOR260, where R260 is C1-10 alkyl or acyl; R200, R210, R220 and R230 are each H, halogen, hydroxyl, NH2, NH-alkyl, N-(alkyl)2, O-alkyl, O-acyl, COCF3, OCF3 or CH2COO NH-alkyl; or R200 and R210 form C5-C10 cyclo or heterocyclo optionally substituted with one or more of halogen, hydroxyl, NH2, NH-alkyl, N-(alkyl)2, O-acyl, O-alkyl, CO, CF3, OCF3 or CH2 COONH-alkyl; wherein C3 and C4 can be bound by a single or double bond; configurations at 3' or 4' can be (R) or (S); and R240 and R250 are either cis-.beta. or cis-.alpha., or trans-3'- $g(.alpha.) or trans-3'-$g(b) oriented. Stereoselectivity can be enhanced by preparing these compounds by catalytic asymmetric dihydroxylation.

L'invention concerne des composés ainsi que des compositons et des procédés de production et d'utilisation de ces composés dans le traitement d'infections rétrovirales, de la formule (G-1), formule dans laquelle M représente O ou NH; Z représente O, NH ou S; R<240> et R<250> représentent chacun H, alkyle C1-10, aryle C1-10, alkyle, amide ou CH2COOR<260>, où R<260> représente acyle ou alkyle C1-10; R<200>, R<210>, R<220> et R<230> représentent chacun H, halogène, hydroxyle, NH2, NH-alkyle, N-(alkyle)2, O-alkyle, O-acyle, COCF3, OCF3 ou CH2COO NH-alkyle; ou R<200> et R<210> forment cyclo ou hétérocyclo C5-C10 facultativement substitué par un ou plusieurs des éléments suivants: halogène, hydroxyle, NH2, NH-alkyle, N-(alkyle)<2>, O-acyle, O-alkyle, CO, CF3, OCF3 ou CH2 COONH-alkyle; C3 et C4 pouvant être liés par une liaison simple ou double; des configurations en 3' ou 4' peuvent représenter (R) ou (S); et R<240> ainsi que R<250> sont orientés soit cis- beta soit cis- alpha , soit trans-3'- DOLLAR g(a) soit trans-3'- DOLLAR g(b). On peut améliorer la stéréosélectivité par préparation de ces composés par dihydroxylation asymétrique catalytique.

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