Imidafenacin (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

) is a

urinary The urinary system, also known as the urinary tract or renal system, consists of the kidneys, ureters, bladder, and the urethra. The purpose of the urinary system is to eliminate waste from the body, regulate blood volume and blood pressure, co ...

antispasmodic An antispasmodic (synonym: spasmolytic) is a pharmaceutical drug or other agent that suppresses muscle spasms. Smooth muscle spasm One type of antispasmodics is used for smooth muscle relaxation, especially in tubular organs of the gastrointest ...

of the

anticholinergic Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system. These agents inhibit the parasympathetic nervous sys ...

class. Pharmacol:

Synthesis

*The sidechain is a versatile precursor also used in the synthesis of:

Bezitramide Bezitramide is an opioid analgesic. Bezitramide itself is a prodrug which is readily hydrolyzed in the gastrointestinal tract to its active metabolite, despropionyl-bezitramide. Bezitramide was discovered at Janssen Pharmaceutica in 1961. It is m ...

, Piritramide,

Diphenoxylate Diphenoxylate is a centrally active opioid drug of the phenylpiperidine series that is used as a combination drug with atropine for the treatment of diarrhea. Diphenoxylate is an opioid and acts by slowing intestinal contractions; the atropine ...

, & others. Imidafenacin synthesis

The alkylation of Diphenylacetonitrile 6-29-3(1) with

1,2-dibromoethane 1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula . Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is ...

(2) gives 4-Bromo-2,2-Diphenylbutyronitrile 9186-58-8(3). Alkylation with 2-Methylimidazole (4) gives 4-(2-Methyl-1H-imidazol-1-yl)-2,2-diphenylbutanenitrile 14777-43-2(5). Partial hydrolysis of the nitrile to the amide completes the synthesis of ' (6).

References

Muscarinic antagonists Imidazoles Carboxamides {{genito-urinary-drug-stub