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ChemicalBook CAS DataBase List Deflazacort
14484-47-0

Deflazacort synthesis

9synthesis methods
Deflazacort is a glucocorticoid used as an anti-inflammatory and immunosuppressant. It is sold in the United Kingdom by Shire under the trade name Calcort. in Brazil as Cortax, Decortil, and Deflanil, and in Honduras as Flezacor. It is not available in the United States. Deflazacort is a prodrug. Its potency is around 70?–90% that of prednisone. Synthetic Description Reference: Nathansohn G, Winters G, Aresi V. Steroids possessing nitrogen atoms. IV. Further studies on the synthesis of [17alpha,16alpha-d]-oxazolino-corticoids. Steroids. 1969 Mar;13(3):383-97. PubMed PMID: 5789709. Synthetic Description Reference: Xu, Runxing. Process for preparing deflazacort. CN 108484714. (Assignee Yueyang Huanyu Pharmaceutical Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Liu, Xiang; He, Lian; Zhang, Jing. Method for synthesizing Deflazacort. CN 105777852. (Assignee Kamp Pharmaceuticals Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Forte, Luigi; Cancellieri, Calogero. Process for preparation of (11β,16β)-21-(acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (deflazacort). WO 9721722. (Assignee Gruppo Lepetit S.P.A., Italy) Synthetic Description Reference: Liu, Xirong; Xie, Laibin; Hu, Aiguo. Improved method for synthesis of Deflazacort from 11β-hydroxypregna-1,4-diene-3,20-dione[17α,16α-d]-2'-methyloxazoline. CN 101418032. (Assignee Hunan Steroid Chemicals Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Zhang, Shubing; Xie, Yanmin. Method for preparation of antiinflammatory and antiallergy agent Deflazacort. CN 102942613. (Assignee Tianjin Derchemist Science & Technology Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Li, Yaling; Wang, Shuli. Method for reducing 11-site ketone group of steroid. CN 105622713. (Assignee Tianjin Kingyork Group Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Hu, Aiguo; Xie, Laibin; Wu, Laixi. Preparation method of Deflazacort from 16(17)α-epoxyprednisolone by amination ring-opening, condensation ring-closing and ethyl esterification. CN 106008660. (Assignee Hunan Kerey Pharmaceutical Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Deng, Lianqiang; Li, Mingqing. Preparation method of Deflazacort from 11-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione as starting material. CN 106397532. (Assignee Jiangxi Yuneng Pharmaceutical Co., Ltd., Peop. Rep. China)
Synthetic Routes
  • ROUTE 1
  • 202112072125598676.jpg

    Reference: Nathansohn G, Winters G, Aresi V. Steroids possessing nitrogen atoms. IV. Further studies on the synthesis of [17alpha,16alpha-d]-oxazolino-corticoids. Steroids. 1969 Mar;13(3):383-97. PubMed PMID: 5789709.

  • ROUTE 2
  • 202112077157553022.jpg

    Reference: Xu, Runxing. Process for preparing deflazacort. CN 108484714. (Assignee Yueyang Huanyu Pharmaceutical Co., Ltd., Peop. Rep. China)

  • ROUTE 3
  • 202112074602440428.jpg

    Reference: Liu, Xiang; He, Lian; Zhang, Jing. Method for synthesizing Deflazacort. CN 105777852. (Assignee Kamp Pharmaceuticals Co., Ltd., Peop. Rep. China)

  • ROUTE 4
  • 202112079963296442.jpg

    Reference: Forte, Luigi; Cancellieri, Calogero. Process for preparation of (11β,16β)-21-(acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (deflazacort). WO 9721722. (Assignee Gruppo Lepetit S.P.A., Italy)

  • ROUTE 5
  • 202112073064783530.jpg

    Reference: Liu, Xirong; Xie, Laibin; Hu, Aiguo. Improved method for synthesis of Deflazacort from 11β-hydroxypregna-1,4-diene-3,20-dione[17α,16α-d]-2'-methyloxazoline. CN 101418032. (Assignee Hunan Steroid Chemicals Co., Ltd., Peop. Rep. China)

  • ROUTE 6
  • 202112073239578105.jpg

    Reference: Zhang, Shubing; Xie, Yanmin. Method for preparation of antiinflammatory and antiallergy agent Deflazacort. CN 102942613. (Assignee Tianjin Derchemist Science & Technology Co., Ltd., Peop. Rep. China)

  • ROUTE 7
  • 202112070717725771.jpg

    Reference: Li, Yaling; Wang, Shuli. Method for reducing 11-site ketone group of steroid. CN 105622713. (Assignee Tianjin Kingyork Group Co., Ltd., Peop. Rep. China)

  • ROUTE 8
  • 202112073459555693.jpg

    Reference: Hu, Aiguo; Xie, Laibin; Wu, Laixi. Preparation method of Deflazacort from 16(17)α-epoxyprednisolone by amination ring-opening, condensation ring-closing and ethyl esterification. CN 106008660. (Assignee Hunan Kerey Pharmaceutical Co., Ltd., Peop. Rep. China)

  • ROUTE 9
  • 202112076842060996.jpg

    Reference: Deng, Lianqiang; Li, Mingqing. Preparation method of Deflazacort from 11-hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione as starting material. CN 106397532. (Assignee Jiangxi Yuneng Pharmaceutical Co., Ltd., Peop. Rep. China)

202112072125598676.jpg

Reference: Nathansohn G, Winters G, Aresi V. Steroids possessing nitrogen atoms. IV. Further studies on the synthesis of [17alpha,16alpha-d]-oxazolino-corticoids. Steroids. 1969 Mar;13(3):383-97. PubMed PMID: 5789709.

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Yield:-

Steps:

Multi-step reaction with 6 steps
1: MeSO2Cl, SO2, collidine / dimethylformamide
2: aq. KOH / methanol / Heating
3: (i) I2, CaO, AIBN, THF, MeOH, (ii) /BRN= 506007/, Et3N, acetone
4: aq. CrO3 / acetone
5: (i) Br2, aq. HBr, AcOH, dioxane, (ii) LiBr, Li2CO3, DMF
6: (i) AcNHBr, HClO4, THF, (ii) Cr(OAc)2, nBuSH, DMSO

References:

Nathansohn,G. et al. [Steroids,1969,vol. 13,p. 383 - 397]

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