90182-92-6

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE is used as an anti-emetic agent for the treatment of nausea and vomiting. Its ability to block the 5-HT3 receptors helps in reducing the symptoms associated with motion sickness, chemotherapy, and postoperative recovery.
4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE is also used as a stimulant for promoting peristalsis, which aids in the movement of food through the digestive system, thus helping in the treatment of constipation and other gastrointestinal disorders.
Used in Research and Development:
4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE is used as a highly potent SR-3 antagonist and SR-4 agonist in the field of drug discovery and development. Its interaction with these receptors can provide valuable insights into the development of new therapeutic agents targeting various diseases and conditions.
Furthermore, 4-AMINO-N-1-AZABICYCLO[2.2.2]OCT-3-YL-5-CHLORO-2-METHOXYBENZAMIDE HYDROCHLORIDE activates the IK1 channel, which plays a crucial role in regulating the electrical activity of cardiac cells. This property makes it a potential candidate for the development of drugs targeting cardiac arrhythmias and other heart-related conditions.

Originator

Zacopride hydrochloride,ZYF Pharm Chemical

Manufacturing Process

4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide, fumarate [1:1]:In a closed system equipped with an oil bubbler, 30 ml of tetrahydrofuran were added to a mixture of 4-amino-5-chloro-2-methoxybenzoic acid, 2.02 g (0.010 mole) and 1,1'-carbonyldiimidazole, 1.62 g (0.010 mole) with stirring. When evolution of carbon dioxide ceased, nitrogen was bubbled through the reaction mixture for 1 hr. A solution of 3-aminoquinuclidine, 1.26 g (0.010 mole) in 10 ml tetrahydrofuran was added dropwise to the stirred reaction mixture and stirring at room temperature continued for 3 hrs. TLC analysis (3% conc. ammonium hydroxide solution in methanol) showed some product formation. The mixture was heated at reflux temperature for 18 hours and then concentraded to an oil. TLC analysis showed the presence of the product, imidazole and 3-aminoquinuclidine. The oil was dissolved in methylene chloride (75 ml) and washed twice with 50 ml portions of aqueous sodium bicarbonate solution. The methylene chloride layer was dried over anhydrous magnesium sulfate and concentrated to yield 2.0 g (67%) of a glassy amorphous solid, the free base of the title compound. In another reaction on a 0.020 mole scale, 5.18 g (83.8%) of the product as the free base was obtained.The products were combined, dissolved in methanol (20 ml) and the solution and treated with a solution of fumaric acid (2.73 g) in methanol (50 ml). Absolute ether was added to precipitate the salt which was collected by filtration and recrystallized from methanol-water (200:20) with isopropyl ether added to the point of incipient cloudiness. The recrystallized salt (5.38 g) melted at 223°-225°C. 4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide, hydrochloride, hydrate (1:1:1):To an isopropyl alcohol solution of the above free base of the title compound is added in equal molar amount of 37% (conc.) hydrochloric acid. A salt is separated by addition of acetone followed by filtration which is recrystallized from acetone-water to give the title compound, MP: 158°-160°C.

Therapeutic Function

Antiemetic, Peristaltic stimulant

Biological Activity

Highly potent 5-HT 3 receptor antagonist (K i = 0.38 nM) and 5-HT 4 receptor agonist (K i = 373 nM). Antiemetic and anxiolytic following systemic administration in vivo .

InChI:InChI=1/C15H20ClN3O2.ClH/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19;/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20);1H

Downstream Products

• 120713-29-3 4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-hydroxybenzamide, hydrochloride 
• 120713-17-9 4-Amino-N-(1-azabicyclo[2.2.2.]oct-3-yl)-5-chloro-2-hydroxybenzamide 

Relevant academic research and scientific papers

2-Alkoxy-n-(1-azabicyclo(2.2.2)-oct-3-yl) benzamides and thiobenzamides having an antischizophrenic activity

2-Alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamides and thiobenzamides having the formula wherein X is oxygen or sulphur; R1 is loweralkyl; and R2 is hydrogen, halo, 4,5-benzo, alkoxy or Am wherein Am is amino, methylamino or dimethylamino, and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof have antischizophrenic activity.

Anxiolytic-N-(1-Azabicyclo[2.2.2]Oct-3-yl) Benzamides and Thobenzamides

Compounds of general formula I: wherein:, , X represents oxygen or sulphur;, R1 represents loweralkyl;, R2 represents hydrogen, halo, 4,5-benzo, loweralkoxy, amino, methylamino or dimethylamino;, R3 represents hydrogen or loweralkyl;, and, n is 1 or 2, , and their pharmaceutically acceptable acid addition salts have anxiolytic activity. In particular, they have activity against anxiety induced by the withdrawal from ingested substances such as narcotics (eg cocaine), alcohol and nicotine.