Acotiamide hydrochloride

Base Information

• Chemical Name: Acotiamide hydrochloride
• CAS No.: 185104-11-4
• Molecular Formula: C21H30N4O5S.HCl
• Molecular Weight: 487.01
• UNII: 510791NN30
• DSSTox Substance ID: DTXSID30171717
• Wikidata: Q27260838
• NCI Thesaurus Code: C72222
• Mol file: 185104-11-4.mol

Synonyms:acotiamide;acotiamide hydrochloride;N-(2-(diisopropylamino)ethyl)-2-((2-hydroxy-4,5-dimethoxybenzoyl)amino)-1,3-thiazole-4-carboxamide;N-(N',N'-diisopropylaminoethyl)-(2-(2-hydroxy-4,5-dimethoxybenzoylamino)-1,3-thiazole-4-yl)carboxyamide;YM 443;YM-443;YM443 cpd;Z 338;Z-338

Chemical Property of Acotiamide hydrochloride

Chemical Property:

• PSA: 148.24000
• LogP: 4.72760
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 486.1703690
• Heavy Atom Count: 32
• Complexity: 586

Purity/Quality:

99.5% ^*data from raw suppliers

AcotiamideHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)N(CCNC(=O)C1=CSC(=N1)NC(=O)C2=CC(=C(C=C2O)OC)OC)C(C)C.Cl
• Recent NIPH Clinical Trials: A Double-blind Placebo Controlled Study of Acotiamide Hydrochloride for Efficacy on Gastrointestinal Motility of Patients with Functional Dyspepsia
• Description: Acotiamide Hydrochloride (YM-443, Z-338) is the hydrochloride salt form of acotiamide, a prokinetic agent with gastrointestinal (GI) motility-enhancing activity. It is a new orally active selective acetylcholinesterase inhibitor. Although the exact mechanism by which acotiamide exerts its effect has yet to be fully elucidated, this agent appears to inhibit acetylcholinesterase (AchE), an enzyme responsible for the breakdown of acetylcholine (Ach). Increased Ach concentrations lead to an improvement of gastric emptying and GI motility and eventually to a reduction of dyspepsia symptoms.
• Uses: Acotiamide Hydrochloride is an acetylcholinesterase inhibitor which has been shown to stimulate gastric motility and improve gastric motility dysfunction in rats (1,2). Acotiamide Hydrochloride has also been shown to improve meal-related symptoms of functional dyspepsia.

Technology Process of Acotiamide hydrochloride

There total 25 articles about Acotiamide hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester (877997-99-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-[(2-diisopropyl-aminoethyl)aminocarbonyl]-1,3-thiazole hydrochloride (185104-11-4)

Guidance literature:

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester; N',N'-diisopropyl-ethane-1,2-diamine; In toluene; at 100 ℃; for 5h;

With hydrogenchloride; In water; isopropyl alcohol;

Reference yield: 97.0%

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester (877997-99-4) + N',N'-diisopropyl-ethane-1,2-diamine (121-05-1) → N-[2-(diisopropylamino)ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxamide hydrochloride (185104-11-4)

Guidance literature:

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester; N',N'-diisopropyl-ethane-1,2-diamine; In toluene; at 70 - 100 ℃; for 5h; Inert atmosphere;

With hydrogenchloride; In water;

Reference yield: 89.7%

Acotiamide (185106-16-5) → 2-[N-(4,5-dimethoxy-2-hydroxybenzoyl)amino]-4-[(2-diisopropyl-aminoethyl)aminocarbonyl]-1,3-thiazole hydrochloride (185104-11-4)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; butan-1-ol; for 4h; pH=1 - 2; Cooling with ice;

upstream raw materials:

2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid methyl ester

N',N'-diisopropyl-ethane-1,2-diamine

isopropyl alcohol

butan-1-ol

Refernces

• 1、 -. "Industrial production method of acotiamide hydrochloride". Paragraph 0040-0043. . Retrieved 2019/06/07.
• 2、 -. "Acotiamide hydrochloride preparation method". . . Retrieved 2017/02/09.