Clopimozide

Clopimozide (R-29,764) is a typical antipsychotic drug of the diphenylbutylpiperidine class.[1][2] It is very potent and has an extremely long duration of action, lasting at least one week with a single dose.[3][4][5] It was developed by Janssen Pharmaceutica but was never marketed.

Clopimozide
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 3-[1-[4,4-bis(4-fluorophenyl)butyl]-4-piperidyl]-6-chloro-1H-benzimidazol-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H28ClF2N3O
Molar mass496.00 g·mol−1
3D model (JSmol)
SMILES
  • Fc1ccc(cc1)C(c2ccc(F)cc2)CCCN5CCC(N4c3ccc(Cl)cc3NC4=O)CC5
InChI
  • InChI=1S/C28H28ClF2N3O/c29-21-7-12-27-26(18-21)32-28(35)34(27)24-13-16-33(17-14-24)15-1-2-25(19-3-8-22(30)9-4-19)20-5-10-23(31)11-6-20/h3-12,18,24-25H,1-2,13-17H2,(H,32,35)
  • Key:JCZYXTVBWHAWLL-UHFFFAOYSA-N

Synthesis
Patent (Ex VIII):[6]

The alkylation between 5-Chloro-1-(4-Piperidyl)-2-Benzimidazolinone [53786-28-0] (1) and 1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) [3312-04-7] (2) gives clopimozide (3).

See also

References
  1. De Cuyper HJ, Van Praag HM, Mulder WR (May 1979). "Therapeutical significance of clopimozide in the treatment of chronic psychotic patients". Acta Psychiatrica Scandinavica. 59 (5): 561–74. doi:10.1111/j.1600-0447.1979.tb00256.x. PMID 37697. S2CID 30954603.
  2. Knapen J, Bollen J, Brugmanns J, Rombaut N (1976). "[Treatment of chronic psychoses with oral clopimozide]". Acta Psychiatrica Belgica (in French). 76 (4): 644–57. PMID 798469.
  3. Janssen PA, Niemegeers CJ, Schellekens KH, Lenaerts FM, Wauquier A (August 1975). "Clopimozide (R 29 764), a new highly potent and orally long-acting neuroleptic of the diphenylbutylpiperidine series". Arzneimittel-Forschung. 25 (8): 1287–94. PMID 1242360.
  4. Floru L, Tegeler J (1978). "Clinical experiments with the new oral long-acting neuroleptic clopimozide (R 29 764)". Arzneimittel-Forschung. 28 (2): 341–4. PMID 25071.
  5. Bobon J, Parent M, Toussaint C, Pinchard A (1976). "[Long-acting neuroleptics. IV. Preliminary study of clopimozide (R 29764)]". Acta Psychiatrica Belgica (in French). 76 (1): 138–43. PMID 970182.
  6. Paul Adriaan Jan Janssen, 3 weitere », U.S. Patent 3,989,707 (1976 to Janssen Pharmaceutica N.V.).


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