Chemistry:Manidipine

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Manidipine is a calcium channel blocker (dihydropyridine type) that is used clinically as an antihypertensive.[1][2][3][4][5]

It was patented in 1982 and approved for medical use in 1990.[6]

Synthesis

Thieme Synthesis:[7] Patent:[8] Sino:[9][10][11][12][13][14][15]

The alkylation between N-(2-hydroxyethyl)piperazine [103-76-4] (1) and Benzhydryl Bromide [776-74-9] (2) gives 2-(4-benzhydrylpiperazin-1-yl)ethanol [10527-64-7] (3). The reaction with Diketene [674-82-8] (4) gives 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate [89226-49-3] (5). The reaction with 3-nitrobenzaldehyde [99-61-6] (6) and Methyl 3-aminocrotonate [14205-39-1] (7) completed the synthesis of Manidipine (8).

References

  1. ↑ "Manidipine: a review of its use in hypertension". Drugs 61 (12): 1777–1799. 2001. doi:10.2165/00003495-200161120-00010. PMID 11693466. http://drugs.adisonline.com/pt/re/drugs/abstract.00003495-200161120-00010.htm. Retrieved 2009-06-20. 
  2. ↑ "Manidipine: a review of its use in the management of hypertension". Drugs 64 (17): 1923–1940. 2004. doi:10.2165/00003495-200464170-00011. PMID 15329044. http://drugs.adisonline.com/pt/re/drugs/abstract.00003495-200464170-00011.htm. Retrieved 2009-06-20. 
  3. ↑ "Antihypertensive effect of manidipine". Drugs 65 (Suppl 2): 11–19. 2005. doi:10.2165/00003495-200565002-00003. PMID 16398058. http://drugs.adisonline.com/pt/re/drugs/abstract.00003495-200565002-00003.htm. Retrieved 2009-06-20. 
  4. ↑ "Manidipine-delapril combination in the management of hypertension". Vascular Health and Risk Management 3 (3): 255–263. 2007. PMID 17703633. 
  5. ↑ "Evaluation of manidipine hydrochloride, a new calcium antagonist, in the treatment of hypertensive patients with renal disorders". Current Therapeutic Research 52 (2): 248–253. August 1992. doi:10.1016/S0011-393X(05)80475-8. 
  6. ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 465. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA465. 
  7. ↑ Meguro, Kanji; Aizawa, Masahiro; Sohda, Takashi; Kawamatsu, Yutaka; Nagaoka, Akinobu (1985). "New 1,4-dihydropyridine derivatives with potent and long-lasting hypotensive effect.". CHEMICAL & PHARMACEUTICAL BULLETIN. 33 (9): 3787–3797. ISSN 0009-2363. doi:10.1248/cpb.33.3787.
  8. ↑ EP0094159 idem Kanji Meguro & Akinobu Nagaoka, US4892875 (1990 to Takeda Pharmaceutical Co Ltd).
  9. ↑ Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan, Maruti Ganpati Ghagare, WO20110203954 (2011 to Cipla Limited, Curtis, Philip Anthony).
  10. ↑ 刘玉海, et al. CN105924382 (2018).
  11. ↑ 金晓峰, et al. CN102875451 (2014 to CHANGZHOU PHARMACEUTICAL FACTORY CO LTD).
  12. ↑ 刘忠春, CN107337632 (2017).
  13. ↑ 谷志勇, et al. CN104292150 (2015).
  14. ↑ , CN103351362 (2013 to).
  15. ↑ http://en.cnki.com.cn/Article_en/CJFDTOTAL-ZHOU200402000.htm



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