Tripodal bisphosphonate derivatives

Abstract

The present invention describes tripodal bisphosphonate derivatives with a flexible basic framework for the functionalization of surfaces, and methods for their production and use. The central atom of the flexible framework is hereby a tertiary aliphatic carbon atom. A fourth remaining position of the flexible framework is suitable to be optionally functionalized by so-called click reactions, for example with biomolecules, polyethylene glycol or active agents. The compounds according to the present invention have the general formula X—C{(CH)—Y—C[PO(OH)]R}, wherein X stands for a group —(CH)—R, wherein p=0 to 10 and Ris selected from —H, —NH, —NO, —OH, —SH, —O—NH, —NH—NH, —N═C═S—, —N═C═O—, —CH═CH, —C≡CH, —COOH, —(C═O)H, —(C═O)RY stands for —CH—, —CH═CH—, —C≡C—, —O—, —S—, —S—S—, —NH—, —O—NH—, —NH—O—, —HC═N—O—, —O—N═CH—, —NR—, -aryl-, -heteroaryl-, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —NH—(C═O)—, —(C═O)—NH—, —NR—(C═O)—, —(C═O)—NR—, —NH—(C═O)—NH—, —NH—(C═S)—NH—, Rrepresents a hydrogen atom or a hydroxy group, Rstands for a linear or branched alkyl group and Rfor a linear or branched alkyl group or an aryl group. The production of the compounds occurs by reacting a compound X—C[(CH)—Y']with a reagent Y″C[PO(OH)]Rto the corresponding compound X—C{(CH)—Y—C[PO(OH)]R}and subsequent purification of the reaction product. Y′ and Y″ are hereby precursors of Y. The compounds according to formula (I) according to the present invention are suitable to be used in a method to functionalize surfaces. The X group of the compounds according to the present invention is suitable to be optionally coupled to an effector, for example, by means of click chemistry.