Ridazolol

Last updated
Ridazolol
Ridazolol.svg
Names
IUPAC name
5-Chloro-4-[2-[[3-(2-chlorophenoxy)-2-hydroxypropyl]amino]ethylamino]-1H-pyridazin-6-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H18Cl2N4O3/c16-11-3-1-2-4-13(11)24-9-10(22)7-18-5-6-19-12-8-20-21-15(23)14(12)17/h1-4,8,10,18,22H,5-7,9H2,(H2,19,21,23)
    Key: UUWABVCZFXKHSU-UHFFFAOYSA-N
  • InChI=1/C15H18Cl2N4O3/c16-11-3-1-2-4-13(11)24-9-10(22)7-18-5-6-19-12-8-20-21-15(23)14(12)17/h1-4,8,10,18,22H,5-7,9H2,(H2,19,21,23)
    Key: UUWABVCZFXKHSU-UHFFFAOYAL
  • C1=CC=C(C(=C1)OCC(CNCCNC2=C(C(=O)NN=C2)Cl)O)Cl
Properties
C15H18Cl2N4O3
Molar mass 373.23 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ridazolol is a pharmaceutical drug acting as a beta adrenergic receptor antagonist. It was investigated in the 1980 and 90s for its effects on coronary heart disease and essential hypertension (high blood pressure). [1] [2]

It is not known to be marketed anywhere in the world. [3]

Synthesis

Note that structural moiety #4 also appears in the synthesis of Darigabat & for GYKI-16306.

ChemDrug Synthesis: Patent: Ridazolol synthesis.svg
ChemDrug Synthesis: Patent:

The reaction between 2-(2-chlorophenoxymethyl)oxirane [2212-04-6] (1) and Ethylenediamine [107-15-3] (2) gives N-[3-(o-chlorophenoxy)-2-hydroxy-propyl]-ethylenediamine [66825-15-8] (3). Further reaction with 4,5-Dichloro-3(2H)-pyridazinone [932-22-9] (4) completed the synthesis of Ridazolol (5).

Related Research Articles

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References

  1. Fach, WA; Starke, E; Becker, HJ (1992). "Duration of the effect and dose-response relationship of ridazolol in patients with coronary heart disease". Zeitschrift für Kardiologie. 81 (6): 320–5. PMID   1353933.
  2. Rommel, Th.; Demisch, L. (1994). "Influence of chronic ?-adrenoreceptor blocker treatment on melatonin secretion and sleep quality in patients with essential hypertension". Journal of Neural Transmission. 95 (1): 39–48. doi:10.1007/BF01283029. PMID   7857585. S2CID   31936176.
  3. "Ridazolol search results". Drugs.com. Retrieved 2021-03-31.
  4. Castaer, J.; Prous, J.; Ridazolol. Drugs Fut 1986, 11, 12, 1044.
  5. Thomas Raabe, et al. U.S. Patent 4,532,239 (1985 to Sanofi Aventis Deutschland GmbH, Cassella Farbwerke Mainkur AG).