Tiropramide

Tiropramide (INN) is an antispasmodic.[1]

Tiropramide
Clinical data
Other namesN-[3-[4-(2-Diethylaminoethoxy)phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • Nα-benzoyl-O-[2-(diethylamino)ethyl]-N,N-dipropyltyrosinamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H41N3O3
Molar mass467.654 g·mol−1
3D model (JSmol)
  • CCCN(CCC)C(=O)C(Cc1ccc(cc1)OCCN(CC)CC)NC(=O)c2ccccc2
  • InChI=1S/C28H41N3O3/c1-5-18-31(19-6-2)28(33)26(29-27(32)24-12-10-9-11-13-24)22-23-14-16-25(17-15-23)34-21-20-30(7-3)8-4/h9-17,26H,5-8,18-22H2,1-4H3,(H,29,32)
  • Key:FDBWMYOFXWMGEY-UHFFFAOYSA-N
  (verify)

Synthesis

The acylation of DL-Tyrosine [556-03-6] (1) with benzoyl chloride gives N,O-dibenzoyl-Tyrosine [14325-35-0] (2). Esterification with n-dipropylamine [142-84-7] (3) via the mixed anhydride method gave N,O-Dibenzoyl-DL-tyrosyl-N',N'-dipropylamide [57227-08-4] (4). Saponification of the ester in base gave N-Benzoyl-DL-tyrosyl-N',N'-dipropylamide [57227-09-5] (5). Ether formation with 2-Chlorotriethylamine [100-35-6] (6) completed the synthesis of Tiropramide (7).

References
  1. Vidal y Plana RR, Cifarelli A, Setnikar I (January 1981). "Mechanism of smooth muscle relaxation by tiropramide". The Journal of Pharmacy and Pharmacology. 33 (1): 19–24. doi:10.1111/j.2042-7158.1981.tb13694.x. PMID 6114146. S2CID 22487894.
  2. Serradell, MN; de Angelis, L.; Blancafort, P.; Castaer, J.; Tiropramide. Drugs Fut 1982, 7, 6, 413.
  3. DE2503992 idem Francesco Makovec, Luigi Rovati, Paolo Senin, U.S. patent 4,004,008 (1977 to Rotta Research Laboratorium S.P.A.).


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