Large-Scale Tandem Cyclization Applied to Potentially High-Volume SSTR4 Agonists,Organic Process Research & Development

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Large-Scale Tandem Cyclization Applied to Potentially High-Volume SSTR4 Agonists
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2024-05-29 , DOI: 10.1021/acs.oprd.4c00144
Louise M. Guard ₁ , John R. Rizzo ₁

Affiliation

Somatostatin receptor subtype 4 (SSTR4) antagonists are potential clinical targets for pain. We describe the efforts toward a robust large-scale synthesis of certain small-molecule SSTR4 agonist compounds. Previous routes used metal-mediated reactions and produced stereochemical mixtures. The molecule has a 3-azabicyclo[3.1.0]hexane ring system with cis-stereochemistry. A unique tandem cyclization at the multi-kilogram scale was employed to generate the fused ring system with exclusive cis-stereochemistry observed. The potential commercial synthesis is an efficient, economical process with good control points. This novel tandem cyclization was implemented to swiftly scale up a similar compound for early-phase studies.

中文翻译：

大规模串联环化应用于潜在高容量 SSTR4 激动剂

生长抑素受体亚型 4 (SSTR4) 拮抗剂是治疗疼痛的潜在临床靶标。我们描述了某些小分子 SSTR4 激动剂化合物的大规模合成的努力。以前的路线使用金属介导的反应并产生立体化学混合物。该分子具有顺式立体化学的3-氮杂双环[3.1.0]己烷环系统。采用公斤级的独特串联环化来生成稠合环系统，并观察到独特的顺式立体化学。潜在的商业合成是一种高效、经济的过程，具有良好的控制点。这种新颖的串联环化的实施是为了迅速扩大类似化合物的规模以进行早期研究。

更新日期：2024-05-29

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