188973-81-1

Basic information

• Product Name: Carbamic acid, [[4-hydroxy-1-(6-oxo-6-phenylhexyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester
• CAS NO: 188973-81-1
• Molecular Formula: C23H36N2O4
• Molecular Weight: 404.55
• Mol File: 188973-81-1.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [[4-hydroxy-1-(6-oxo-6-phenylhexyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [[4-hydroxy-1-(6-oxo-6-phenylhexyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester(188973-81-1)
• EPA Substance Registry System: Carbamic acid, [[4-hydroxy-1-(6-oxo-6-phenylhexyl)-4-piperidinyl]methyl]-, 1,1-dimethylethyl ester(188973-81-1)

Safety Data

• Hazardous Substances Data: 188973-81-1(Hazardous Substances Data)

Upstream product

• 82777-11-5 6-bromo-1-phenyl-1-hexanone 
• 177948-02-6 4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine 
• 177948-01-5 [[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methyl]carbamic acid 1,1-dimethylethyl ester 
• 23804-68-4 4-(aminomethyl)-1-benzyl-4-hydroxypiperidine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19867-34-6 N-benzyl-1-oxa-6-azaspiro[2,5]-octane 

Relevant articles and documents

Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists

It is thought that selective 5-HT4 receptor agonists-such as 4-amino-5-chloro-2-methoxy-N-[1-(6-oxo-6-phenylhexyl)piperidin-4-ylmethyl] benzamide (2)-have the ability to enhance both upper and lower gastrointestinal motility without any significant adverse effects. Modification of 2 was performed. Variation of the piperidin-4-ylmethyl moiety of 2 led to a decrease in the binding affinity for the 5-HT4 receptor. Following conversion of the carbonyl group on the benzoyl part to a hydroxyl or sulfoxide group, the binding affinity for the 5-HT4 receptor was retained although the effect on defecation was reduced. Many of the 4-amino-5-chloro-2-methoxy-N- (piperidin-4-ylmethyl)benzamides that had a ether or sulfide moiety in the side-chain part at the 1-position of the piperidine exhibited high affinity for the 5-HT4 receptor. Among these, phenylthio 41c and benzylthio derivative 44 were selective 5-HT4 receptor agonists, and had a similar effect on defecation to compound 2.

BENZOIC ACID COMPOUNDS AND USE THEREOF AS MEDICAMENTS

Benzoic acid compounds of the formula STR1 wherein each symbol is as defined in the specification, optical isomers thereof and pharmaceutically acceptable salts thereof; pharmaceutical composition comprising this compound and pharmaceutically acceptable additive; and serotonin 4 receptor agonists, gastrointestinal prokinetic agents and therapeutic agents for various gastrointestinal diseases, which comprise this compound as active ingredient. The compounds of the present invention have high and selective affinity for serotonin 4 receptor, and show agonistic effects thereon. Accordingly, they are useful medications for the prophylaxis and treatment of various gastrointestinal diseases, central nervous disorders, cardiac function disorders, urinary diseases, and the like, as well as useful anti-nociceptors for analgesic use which increase threshold of pain.

BENZOIC ACID COMPOUNDS AND MEDICINAL USE THEREOF

A benzoic acid compound of the formula wherein each symbol is as defined in the specification, an optical isomer thereof and a pharmaceutically acceptable salt thereof. A pharmaceutical composition comprising this compound and a pharmaceutically acceptable additive, a serotonin 4 receptor agonist comprising this compound as an active ingredient, a gastrointestinal prokinetic agent and a therapeutic agent for gastrointestinal diseases. The compound of the present invention shows selective and high affinity for serotonin 4 receptors, activates same, is useful as a pharmaceutical agent for the prophylaxis and treatment of gastrointestinal diseases (e.g., reflux esophagitis; gastroesophageal reflux such as that accompanying cystic fibrosis; Barrett syndrome; intestinal pseudoileus; acute or chronic gastritis; gastric or duodenal ulcer; Crohn's disease; non-ulcer dyspepsia; ulcerative colitis; postgastrectomy syndrome; postoperative digestive function failure; delayed gastric emptying caused by gastric neurosis, gastroptosis, diabetes, and the like; gastrointestinal disorders such as indigestion, meteorism, abdominal indefinite complaint, and the like; constipation such as atonic constipation, chronic constipation, and that caused by spinal cord injury, pelvic diaphragm failure and the like; and irritable bowel syndrome), central nervous disorders (e.g., schizophrenia, depression, anxiety, disturbance of memory and dementia), cardiac function disorders (e.g., cardiac failure and myocardial ischemia), urinary diseases (e.g., dysuria caused by urinary obstruction, ureterolith, prostatomegaly, spinal cord injury, pelvic diaphragm failure, etc.), and shows superior absorption.