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ID-4708

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ID-4708
Identifiers
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H24F4N2O2
Molar mass424.440 g·mol−1
3D model (JSmol)
  • C1CN(CCC1(C2=CC(=CC=C2)C(F)(F)F)O)CCCC(=O)C3=C(C=C(C=C3)F)N

ID-4703 is a butyrophenone neuroleptic agent. It has the same structure as for trifluperidol but differs by the incorporation of an aniline amino group into the butyrophenone sidechain.

Whereas trifluperidol is a Belgian drug developed at Janssen Pharmaceuticals, ID-4708 was developed by a Japanese company called Sumitomo Chemical in the 1970’s.

ID-4708 when given at low doses reduced ambulation, while at higher doses defecation was inhibited.[1]

Synthesis

The chemical synthesis of ID-4708 was reported:[2][3]

ID-4708 synthesis
ID-4708 synthesis
  • 2-Acetylbutyrolactone [517-23-7] (1)
  • 4-Fluoro-2-nitrobenzoic acid [394-01-4] (2)
  • 4-Fluoro-2-nitrobenzoyl chloride [57750-82-0] (3)
  • 3-(4-Fluoro-2-nitrobenzoyl)oxolan-2-one [62513-47-7] (4)
  • 4-Bromo-1-(4-fluoro-2-nitrophenyl)butan-1-one [62513-48-8] (5)
  • 2-(3-Bromopropyl)-2-(4-fluoro-2-nitrophenyl)-1,3-dioxolane [62513-50-2] (6)
  • 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine [2249-28-7] (7)
  • PC86735492 (8)
  • PC70620175 (9)

References

  1. ^ Honma T, Kitagawa S. [Effects of minor tranquilizers and neuroleptics on open-field behavior in rats (author's transl)]. Nihon Yakurigaku Zasshi. 1977 Apr;73(3):337-45. Japanese. doi: 10.1254/fpj.73.337. PMID: 21127.
  2. ^ Honma T, Sasajima K, Ono K, Kitagawa S, Inaba S, Yamamoto H. Synthesis and preliminary pharmacology of a novel butyrophenone derivative, ID-4708. Arzneimittelforschung. 1974 Sep;24(9):1248-56. doi: 10.1002/chin.197451331. PMID: 4479786.
  3. ^ Kikuo Sasajima, et al. US4075346 (1978 to Sumitomo Chemical Co Ltd).