Ciclesonide, BTR-15, B-9207-015, BY-9010, Alvesco
环索奈德 环索奈德 Chemical Name: (R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate; 16alpha,17alpha-[(R)-Cyclohexylmethylenedioxy]-11beta-hydroxy-21-(isobutyryloxy)pregna-1,4-dien-3-one
CAS No. 126544-47-6, 141845-82-1 (deleted CAS)
项目整合开发状态: Registered-2004
项目研究机构: Altana (Originator), Teijin (Licensee), Aventis Pharma (Codevelopment)
合成路线:The acylation of 11beta,16alpha,17alpha,21-tetrahydroxypregna-1,4-diene-3,20-dione (I) with isobutyric anhydride in pyridine gives the 16,17,21-triester (III),which is condensed with cyclohexanecarbaldehyde (IV) by means of HCl and HClO4 in dioxane yielding the cyclic ketal (Va-b) as a diastereomeric mixture.Finally,this mixture is resolved by preparative HPLC over Lichrosorb RP-18 affording the desired (R)-isomer,the target compound.Alternatively,the monoacylation of the ketal 11beta,16alpha,17alpha,21-tetrahydroxypregan-1,4-diene-3,20-dione 16,17-O-cyclohexylmethylene ketal (VI) with isobutyric anhydride (II) by means of K2CO3 in acetone gives the previously described diastereomeric mixture (Va-b),which is resolved by crystallization in ethanol/water.
📌 参考资料/链接：
参考文献标题:Acetals and esters of 16alpha-hydroxyprednisolone and fluocinolone
文献作者:Calatayud,J.; Conde,J.R.; Luna,M.(Byk Elmu SA)
参考来源:BE 1005876; CH 683343; DE 4129535; ES 2034893; FR 2666585; GB 2247680; JP 1992257599; US 5482934
📄 详细内容
合成路线:The acylation of 11beta,16alpha,17alpha,21-tetrahydroxypregna-1,4-diene-3,20-dione (I) with isobutyric anhydride in pyridine gives the 16,17,21-triester (III),which is condensed with cyclohexanecarbaldehyde (IV) by means of HCl and HClO4 in dioxane yielding the cyclic ketal (Va-b) as a diastereomeric mixture.Finally,this mixture is resolved by preparative HPLC over Lichrosorb RP-18 affording the desired (R)-isomer,the target compound.Alternatively,the monoacylation of the ketal 11beta,16alpha,17alpha,21-tetrahydroxypregan-1,4-diene-3,20-dione 16,17-O-cyclohexylmethylene ketal (VI) with isobutyric anhydride (II) by means of K2CO3 in acetone gives the previously described diastereomeric mixture (Va-b),which is resolved by crystallization in ethanol/water.
参考文献标题:Process for R-epimer enrichment of 16,17-acetal derivs.of 21-acyloxy pregnan-1,4-dien-11beta,16alpha,17alpha-triol-3,20-dione derivs.
文献作者:Gutterer,B.; Amschler,H.; Flockerzi,D.(Byk Gulden Lomberg Chemische Fabrik GmbH)
参考来源:DE 19635498; WO 9809982
产品链接: CAS No. 126544-47-6›› 产品链接: CAS No.141845-82-1››