Imidafenacin

Imidafenacin (INN) is a urinary antispasmodic of the anticholinergic class. Pharmacol:[1]

Imidafenacin
Clinical data
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.216.585
Chemical and physical data
FormulaC20H21N3O
Molar mass319.40 g·mol−1
3D model (JSmol)
SMILES
  • CC1=NC=CN1CCC(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N
InChI
  • InChI=1S/C20H21N3O/c1-16-22-13-15-23(16)14-12-20(19(21)24,17-8-4-2-5-9-17)18-10-6-3-7-11-18/h2-11,13,15H,12,14H2,1H3,(H2,21,24) N
  • Key:SQKXYSGRELMAAU-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Synthesis
Synthesis:[2] Patent (~89%):[3] (~32%):[4] Sino:[5] Prec:[6]

The alkylation of Diphenylacetonitrile [86-29-3] (1)[7] with 1,2-dibromoethane (2) gives 4-Bromo-2,2-Diphenylbutyronitrile [39186-58-8] (3). Alkylation with 2-Methylimidazole (4) gives 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile [214777-43-2] (5). Partial hydrolysis of the nitrile to the amide completes the synthesis of Imidafenacin (6).

References
  1. Kobayashi F, Yageta Y, Segawa M, Matsuzawa S (2007). "Effects of imidafenacin (KRP-197/ONO-8025), a new anti-cholinergic agent, on muscarinic acetylcholine receptors. High affinities for M3 and M1 receptor subtypes and selectivity for urinary bladder over salivary gland". Arzneimittelforschung. 57 (2): 92–100. doi:10.1055/s-0031-1296589. PMID 17396619.
  2. Miyachi, Hiroyuki; Kiyota, Hiromi; Segawa, Mitsuru (1999). "Design, synthesis and antimuscarinic activity of some imidazolium derivatives". Bioorganic & Medicinal Chemistry Letters. 9 (20): 3003–3008. doi:10.1016/S0960-894X(99)00517-X.
  3. Yuuji Ishiguro, Yasuhiro Aizawa, Masahiro Aono, EP 1845091 (2007 to Kyorin Pharmaceutical Co., Ltd.).
  4. Hiroyuki Miyachi, Kei Okazaki, Hiromi Kiyota, Mitsuru Segawa, U.S. Patent 5,932,607 (1999 to Kyorin Pharmaceutical Co., Ltd.).
  5. Cai Hongfei, et al. CN 103772286 (2014 to Jiangxi Qingfeng Pharmaceutical Co Ltd).
  6. Jinchun Tang & Sunan Wang, CN1 02030682A (2010 to Changzhou Kangpu Pharmaceutical Co Ltd).
  7. Reid, Wm. B., Hunter, J. H. (October 1948). "Preparation of Diphenylacetonitrile". Journal of the American Chemical Society. 70 (10): 3515–3515. doi:10.1021/ja01190a509.


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