Langbahn Team – Weltmeisterschaft

ID-4708

ID-4708
Identifiers
  • 1-(2-amino-4-fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidin-1-yl]butan-1-one
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
  • InChI=1S/C22H24F4N2O2/c23-17-6-7-18(19(27)14-17)20(29)5-2-10-28-11-8-21(30,9-12-28)15-3-1-4-16(13-15)22(24,25)26/h1,3-4,6-7,13-14,30H,2,5,8-12,27H2
  • Key:SBAFWLYMAPHVMW-UHFFFAOYSA-N

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