Riodipine

Last updated
Riodipine
Ryodipine structure.svg
Names
Preferred IUPAC name
Dimethyl 4-[2-(difluoromethoxy)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Identifiers
3D model (JSmol)
ChemSpider
MeSH C045912
PubChem CID
UNII
  • InChI=1S/C18H19F2NO5/c1-9-13(16(22)24-3)15(14(10(2)21-9)17(23)25-4)11-7-5-6-8-12(11)26-18(19)20/h5-8,15,18,21H,1-4H3 X mark.svgN
    Key: AZVFIZVKGSPGPK-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C18H19F2NO5/c1-9-13(16(22)24-3)15(14(10(2)21-9)17(23)25-4)11-7-5-6-8-12(11)26-18(19)20/h5-8,15,18,21H,1-4H3
    Key: AZVFIZVKGSPGPK-UHFFFAOYAO
  • CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC=CC=C2OC(F)F)C(=O)OC
Properties
C18H19F2NO5
Molar mass 367.349 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Riodipine (INN; brand names Foridon and Ryosidine) is a calcium channel blocker. [1]

Synthesis

ChemDrug Synthesis: Patent: Riodipine synthesis.svg
ChemDrug Synthesis: Patent:

Hantzsch pyridine synthesis between 2-(Difluoromethoxy)benzaldehyde [71653-64-0] (1), Methyl acetoacetate [105-45-3] (2) and ammonia gave Riodipine (3).

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References

  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1076–. ISBN   978-1-4757-2085-3.
  2. Serradell, MN; Castaer, J.; Riodipine. Drugs Fut 1985, 10, 11, 922.
  3. Kastron VV, Dubur GJ, Shatz VD, Yagupolsky LM. Preparation and properties of ryodipine, an effective antihypertensive agent. Arzneimittelforschung. 1985;35(4):668-72. PMID: 4015732.
  4. Kastron, V. V., Dubur, G. Ya., Vitolin’, R. O., Kimenis, A. A., Selga, M. Ya., Kondratenko, N. V., Yagupol’skii, L. M., Tirzite, D. Ya., Fialkov, Yu. A., Shelezhenko, S. V. (November 1982). "Synthesis and pharmacological activity of 4-aryl-l,4-dihydropyridines". Pharmaceutical Chemistry Journal. 16 (11): 817–824. doi:10.1007/BF00770311.
  5. Valeria V. Kastron, et al. U.S. Patent 4,219,653 (1980 to INST ORGANIC KHIM AKAD UKRAIN, INST ORGANICHESKOGO SINTEZA AK).