Piprozolin

Piprozolin (or piprozoline) is a medication for bile therapy.[1][2]

Piprozolin
Clinical data
ATC code
Identifiers
IUPAC name
  • Ethyl (2Z)-2-(3-ethyl-4-oxo-5-piperidin-1-yl-1,3-thiazolidin-2-ylidene)acetate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.037.512
Chemical and physical data
FormulaC14H22N2O3S
Molar mass298.40 g·mol−1
InChI
  • InChI=1S/C14H22N2O3S/c1-3-16-11(10-12(17)19-4-2)20-14(13(16)18)15-8-6-5-7-9-15/h10,14H,3-9H2,1-2H3/b11-10- Y
  • Key:UAXYBJSAPFTPNB-KHPPLWFESA-N Y
  (verify)

Synthesis

Compared to fenclozic acid, piprozolin shows choleretic rather than anti-inflammatory activity. That is, the compound is useful in those conditions where the flow of bile is to be increased.

Piprozolin synthesis:[3][4][5]

Condensation of ethyl mercaptoacetate with ethyl cyanoacetate leads to thiazolinone (4); an intermediate such as 3, involving addition of the mercaptide to the nitrile function can reasonably be invoked. M/ethylation with di(m)ethyl sulfate proceeds on nitrogen with the concomitant shift of the enamine to afford olefin (5). Bromination of the active methylene (6) followed by displacement of halogen by piperidine affords the choleretic piprozolin (7).

References
  1. Koss FW, Vollmer KO, Herrmann M (August 1972). "[Research with experimental animals on the mechanism of action of the new choleretic, 3-ethyl-4-oxo-5-piperidino-delta 2, alpha-thiazolidine-acetic acid ethyl ester (Piprozolin)]". Archives Internationales de Pharmacodynamie et de Therapie. 198 (2): 333–46. PMID 5074733.
  2. "Piprozolin". Drugs-about.com.
  3. Satzinger (1975). "Substituierte 2-Methylen-thiazolidone-(4)". Justus Liebigs Annalen der Chemie. 665: 150–165. doi:10.1002/jlac.19636650118.
  4. DE 2414345, Satzinger G, Herrmann M, Vollmer K, issued 1975, assigned to Goeecke
  5. US 3971794, Satzinger G, Herrmann M, Vollmer K, issued 1976, assigned to Warner-Lambert
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