Diphenylbutylpiperidine

Diphenylbutylpiperidines are a class of typical antipsychotic drugs which were all synthesized, developed, and marketed by Janssen Pharmaceutica.[1][2]

They include:

Additionally, Hoechst discovered R-56109 [84163-77-9] bearing the pendant ω-difluorophenylbutyl sidechain (PC13078368).[3] The piperidine portion of the molecule (R-56109) is of interest because it serves dual use in the synthesis of risperidone, paliperidone, ocaperidone, iloperidone, abaperidone and S18327. R-56109 was first invented by Hoechst (not Janssen) and appeared in a pair of patents on the butyrophenone design in 1982 (PC13078412).

Diphenylbutylpiperazines

Incorporating an additional nitrogen atom into the heterocyclic ring gives the closely related diphenylbutylpiperazines.

Examples of this include:

  1. Amperozide (antipsychotic).[4]
  2. Lidoflazine
  3. PR-000608
  4. FG5865 & FG-5893
  5. Mioflazine
  6. Difluanazine.[5][6]

References

  1. ^ Galizzi JP, Fosset M, Romey G, Laduron P, Lazdunski M (October 1986). "Neuroleptics of the diphenylbutylpiperidine series are potent calcium channel inhibitors". Proceedings of the National Academy of Sciences of the United States of America. 83 (19): 7513–7. Bibcode:1986PNAS...83.7513G. doi:10.1073/pnas.83.19.7513. PMC 386749. PMID 2429309.
  2. ^ Qar J, Galizzi JP, Fosset M, Lazdunski M (September 1987). "Receptors for diphenylbutylpiperidine neuroleptics in brain, cardiac, and smooth muscle membranes. Relationship with receptors for 1,4-dihydropyridines and phenylalkylamines and with Ca2+ channel blockade". European Journal of Pharmacology. 141 (2): 261–8. doi:10.1016/0014-2999(87)90271-8. PMID 2445589.
  3. ^ Strupczewski JT, Allen RC, Gardner BA, Schmid BL, Stache U, Glamkowski EJ, Jones MC, Ellis DB, Huger FP, Dunn RW (June 1985). "Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles". Journal of Medicinal Chemistry. 28 (6): 761–9. doi:10.1021/jm00383a012. PMID 2861286.
  4. ^ Figueras, Albert; Capellà, Dolors (1993). Antipsychotic drugs. Side Effects of Drugs Annual. Vol. 17. pp. 49–71. doi:10.1016/S0378-6080(05)80189-8. ISBN 978-0-444-82005-1.
  5. ^ "Difluanazine". PubChem. U.S. National Library of Medicine.
  6. ^ US 3267104, Hermans HK, Karl-Adolf SW, "1,4-Disubstituted piperazines and diazepines", issued 16 August 1966, assigned to Janssen Pharmaceutica NV 
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.