Sulpiride side-chain

FIGURE 16.11 The typical sulpiride side-chain results formally from a ring closure of the diethyl-aminoethyl side-chain of earlier prepared derivatives such as tiapride. Observe the intramolecular hydrogen bond that creates a pseudocycle and which can be mimicked by a covalent and constraint analog. ... 

Modification of the basic side-chain of metoclopramide has been the subject of numerous investigations. Earlier work led to the synthesis of YM 09151-2 (15a) [8], clebopride (15b) [9], dazopride (15c) [10] and cisapride (15d) [11]. Modification of the basic side-chain and aromatic ring substitution led to the synthesis of alizapride (4a) [5], sulpiride (16a) [ 12] and cinitapride (16b) [13]. Although a number of analogues have found clinical use for various indications,... 

Among the numerous benzamide drugs developed by the Delagrange scientists some have diethylaminoethyl side-chains (e.g. tiapride) whereas others, such as sulpiride, have A-ethyl-pyrrolidinyl-methyl side-chains that can... 

Usually chiral centers are eliminated in creating symmetry. Thus, in a series of muscarinic agonists derived from 3-aminopyridazines, one of the most favorable side-chains, was the racemic 2-Ai-ethylpyrroMmyl-methyl chain, that is, the side-chain of sulpiride (Figure 26.8). The 5-methyl-6-phenylpyridazine bearing this basic chain at its 3-amino function presented a 0.26 micromolar affinity for Ml muscarinic receptor preparations. ... 

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