Suritozole

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Suritozole
Clinical data
ATC code
  • none
Identifiers
  • 5-(3-fluorophenyl)-2,4-dimethyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
JSmol)
  • Cn1c(=S)n(C)nc1-c2cccc(F)c2
  • InChI=1S/C10H10FN3S/c1-13-9(12-14(2)10(13)15)7-4-3-5-8(11)6-7/h3-6H,1-2H3 ☒N
  • Key:IWDUZEHNLHFBRZ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Suritozole (MDL 26,479) is an investigational

benzodiazepine receptor site on the GABAA ion channel complex, but does not have either anxiogenic or convulsant effects, unlike other BZD inverse agonists such as DMCM.[1] It was investigated for the treatment of depression and Alzheimer's disease,[2]
but clinical development seems to have been discontinued.

Synthesis

Synthesis:[3][4] ~85%:[5] Patents:[6][7] etc

The reaction between monomethylhydrazine [60-34-4] (1) and methyl isothiocyanate (Trapex) [556-61-6] (2) gave 2,4-dimethylthiosemicarbazide [6621-75-6] (3). Amide formation with 3-fluorobenzoyl chloride [1711-07-5] (4) yielded 1-(3-fluorobenzoyl)-2,4-dimethylthiosemicarbazide [110623-52-4] (5). Cyclization to Suritozole (6).

See also

References

  1. PMID 1330168
    .
  2. PMID 9158880
    .
  3. ^ Miller JA, Dudley MW, Kehne JH, Sorensen SM, Wenstrup DL, Kane JM (1992). "MDL 26,479". Drugs of the Future. 17 (1): 21–23.
  4. PMID 3373495
    .
  5. doi:10.1021/op700101g
    .
  6. ^ US5856350 idem Christopher Robin Dalton, John Michael Kane, John Herr Kehne, WO 1996033177  (1999 to Hoechst Marion Roussel, Inc.).
  7. ^ US5723624 idem Sandra K. Stolz-Dunn, David H. Louks, Yolanda M. Puga, Christian T. Goralski, WO 1996001812  (1998 to Merrell Pharmaceuticals Inc).
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