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ID-4708

Identifiers
IUPAC name 1-(2-amino-4-fluorophenyl)-4-piperidin-1-yl]butan-1-one
CAS Number	42048-72-6
PubChem CID	198237
ChemSpider	171579
CompTox Dashboard (EPA)	DTXSID70194864
Chemical and physical data
Formula	C22H24F4N2O2
Molar mass	424.440 g·mol
3D model (JSmol)	Interactive image
SMILES C1CN(CCC1(C2=CC(=CC=C2)C(F)(F)F)O)CCCC(=O)C3=C(C=C(C=C3)F)N
InChI 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.

Synthesis

The chemical synthesis of ID-4708 was reported:

• 2-Acetylbutyrolactone (1)
• 4-Fluoro-2-nitrobenzoic acid (2)
• 4-Fluoro-2-nitrobenzoyl chloride (3)
• 3-(4-Fluoro-2-nitrobenzoyl)oxolan-2-one (4)
• 4-Bromo-1-(4-fluoro-2-nitrophenyl)butan-1-one (5)
• 2-(3-Bromopropyl)-2-(4-fluoro-2-nitrophenyl)-1,3-dioxolane (6)
• 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine (7)
• PC86735492 (8)
• PC70620175 (9)

References

1. Honma T, Kitagawa S (April 1977). "". 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).

• 4-Phenylpiperidines
• Tertiary alcohols
• Aromatic ketones
• Butyrophenone antipsychotics
• Trifluoromethyl compounds
• Typical antipsychotics
• 4-Fluorophenyl compounds
• 2-Aminophenyl compounds