168162-32-1

Basic information

• Product Name: Carbamic acid, (3-isocyanatophenyl)methyl-, 1,1-dimethylethyl ester
• CAS NO: 168162-32-1
• Molecular Formula: C13H16N2O3
• Molecular Weight: 248.282
• Mol File: 168162-32-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Carbamic acid, (3-isocyanatophenyl)methyl-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (3-isocyanatophenyl)methyl-, 1,1-dimethylethyl ester(168162-32-1)
• EPA Substance Registry System: Carbamic acid, (3-isocyanatophenyl)methyl-, 1,1-dimethylethyl ester(168162-32-1)

Safety Data

• Hazardous Substances Data: 168162-32-1(Hazardous Substances Data)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 121-44-8 triethylamine 
• 168162-30-9 3-(N-tert-butoxycarbonyl-N-methyl-amino)-benzoic acid 
• 168162-31-0 methyl 3-((tert-butoxycarbonyl)(methyl)amino)benzoate 
• 161111-23-5 tert-butyl 3-(methoxycarbonyl)phenylcarbamate 
• 4518-10-9 Methyl 3-aminobenzoate 
• 111331-82-9 3-[(tert-butoxycarbonyl)amino]benzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 99-05-8 meta-aminobenzoic acid 

Downstream Products

• 155488-25-8 N-((3R)-1-tert-Butylcarbonylmethyl-2,3-dihydro-2-oxo-5-(pyridin-2-yl)-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylaminophenyl)urea 

Relevant articles and documents

BENZODIAZEPINE DERIVATIVES AS CCK2/GASTRIN RECEPTOR ANTAGONISTS

The invention relates to benzodiazepine derivatives of formula (A) useful as CCK2/gastrin receptor antagonists, their preparation and their use in the treatment or prevention of disorders associated with CCK2/gastrin receptors, disorders caused by or associated with hypergastrinaemia, and gastric acid-related disorders.

(3R)-N-(1-(tert-butylcarbonylmethyl)-2,3-dihydro-2-oxo-5-(2-pyridyl)- 1H-1,4-benzodiazepin-3-yl)-N'-(3-(methylamino)phenyl)urea (YF476): A potent and orally active gastrin/CCK-B antagonist

A number of new 1,4-benzodiazepin-2-one-based gastrin/CCK-B receptor antagonists related to the archetypal analogue L-365,260, and more closely to the recently reported compound YM022, have been synthesized and evaluated for biological activity. The compounds were screened for their ability to inhibit the binding of [125I]CCK-8 to gastrin/CCK-B receptors prepared from rat brains and that of [3H]L-364,718 to CCK-A receptors from rat pancreas, and were shown to be potent and selective ligands for the gastrin/CCK-B receptor. Functional studies in vivo demonstrated the compounds to be antagonists of the receptor as evidenced by their ability to inhibit pentagastrin-induced gastric acid secretion in anesthetized rats. More extensive evaluation in viva included determination of ED50 values in the rat acid secretion model for selected compounds and an examination of the effect of these compounds on pentagastrin-induced gastric acid secretion in Heidenhain pouch dogs following oral and intravenous administration. Two compounds, i.e. (3R)-N- [1-[(tert-butylcarbonyl)methyl]-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4- benzodiazepin-3-yl]-N'-[3-(methylamino)phenyl]urea, 15c (YF476), and (3R)-N- [1-[(tert-Butylcarbonyl)methyl]-2,3-dihydro-2-oxo-5-(2-pyridyl)-1H-1,4- benzodiazepin-3-yl]-N'-[3-(dimethylamino)phenyl]urea hydrochloride, 15d, showed potent dose-dependent effects in both models with the former showing excellent oral bioavailability and an ED50 of 21 nmol/kg po in dogs. 15e is currently under clinical investigation for the treatment of gastro-oesophagal reflux disease (GORD).