N-protected/n-substituted-beta-amino hydroxy sulfonates

Details N-protected/n-substituted-beta-amino hydroxy sulfonates N-protected/n-substituted-beta-amino hydroxy sulfonates

C - Chemistry, Metallurgy

07

C

C07C 309/14 (2006.01) C07C 221/00 (2006.01) C07C 223/02 (2006.01) C07C 269/06 (2006.01) C07C 271/18 (2006.01) C07C 309/24 (2006.01) C07C 323/66 (2006.01) C07D 207/04 (2006.01) C07D 207/333 (2006.01) C07D 207/404 (2006.01) C07D 209/44 (2006.01) C07D 211/24 (2006.01) C07D 213/38 (2006.01) C07D 213/56 (2006.01) C07D 233/64 (2006.01) C07D 295/088 (2006.01) C07D 307/20 (2006.01) C07D 333/24 (2006.01) C07D 401/06 (2006.01) C07D 403/06 (2006.01)

Patent

CA 2237936

N-Protected/N-substituted alpha-amino aldehydes, which are useful as pharmaceuticals and pharmaceutical intermediates, can be stored and shipped in a more stable form as N-protected/N-substituted-beta-amino hydroxy sulfonates of formula (.alpha.), wherein W represents a cation which is capable of forming a sulfonate salt; R1 represents alkyl, alkenyl, alkyl substituted with one or more aryl radicals, cycloalkenylalkyl, alkanoyl, haloalkanoyl, aroyl, alkoxycarbonyl, aralokoxycarbonyl, heteroaralkoxy- carbonyl or 9-phenylfluoren-9-yl radicals; R2 represents hydrogen, alkyl, alkenyl, aralkyl, cycloalkyl, cycloalkenylalkyl or aryl radicals; or NR1R2 represents heterocyclo or heteroaryl radicals; and R3 represents alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, alkylthioalkyl, arylthioalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclo or cycloalkylalkyl radicals; or R2 and R3 together with the nitrogen and the carbon atom to which they are bonded form a heterocyclo radical; which can be readily converted back into the aldehyde under mild conditions. The present invention relates to N-protected/N-substituted-beta-amino hydroxy sulfonates and their use.

Des alpha-amino aldéhydes N protégés/substitués, qui sont utiles comme produits pharmaceutiques et comme intermédiaires pour des produits pharmaceutiques, peuvent être conservés et transportés sous une forme plus stable de bêta-amino hydroxysulfonates N protégés/substitués, ayant la formule ( alpha ). Dans cette formule, W représente un cation qui est capable de former un sel de sulfonate; R<1> représente des radicaux alkyle, alcényle, alkyle substitué avec un ou plusieurs radicaux aryle, cycloalcénylalkyle, alcanoyle, haloalcanoyle, aroyle, alcoxycarbonyle, aralcoxycarbonyle, hétéroaralcoxycarbonyle ou 9-phénylfluorèn-9-yle; R<2> représente des radicaux hydrogène, alkyle, alcényle, aralkyle, cycloalkyle, cycloalcénylalkyle ou aryle; ou NR<1>R<2> représente des radicaux hétérocyclo ou hétéroaryle; et R<3> représente des radicaux alkyle, haloalkyle, cyanoalkyle, hydroxyalkyle, alcoxyalkyle, aryloxyalkyle, alkylthioalkyle, arylthioalkyle, aryle, aralkyle, hétéroaryle, hétéroaralalkyle, cycloalkyle ou cycloalkylalkyle; ou R<2> et R<3> forment un radical hétérocyclo avec l'atome d'azote et l'atome de carbone auxquels ils sont fixés. Ces composés peuvent être facilement reconvertis en aldéhyde correspondant, dans des conditions douces. L'invention concerne également ces bêta-amino hydroxysulfonates N protégés/substitués et leur utilisation.

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