84386-11-8

Usage

Originator

Baxitozine,ZYF Pharm Chemical

Manufacturing Process

29.6 g of glyoxylic acid of 50% by weight are heated in water under reduced pressure until elimination of 80% of the water present, whereupon, after cooling, 84.1 g of 3,4,5-trimethoxy acetophenone are introduced into the reaction mixture. Heating is effected for 2 h at 95°-100°C under reduced pressure (about 50 mm/Hg), at the same time distilling off the residual water present. After cooling of the medium, 120 ml of water containing 11.6 g of sodium carbonate and ether are introduced, the aqueous phase is decanted and washed with : ether, whereupon the aqueous phase is acidified to a pH of 1 with 50% hydrochloric acid. The desired product is extracted with ethyl acetate. After elimination of the extraction solvent 31.5 g of the 4-(3,4,5- trimethoxyphenyl)-4-oxo-2-hydroxy butanoic acid, melting point 119°-120° are obtained (recrystallization from 1,2-dichloroethane). 15.8 g of 4-(3,4,5-trimethoxyphenyl)-4-oxo-2-hydroxy butanoic acid, 20 ml of acetic acid and 20 ml of concentrated hydrochloric acid (d-1.18) are heated for 2.5 h under reflux. The reaction medium is cooled and precipitated by water. The precipitate formed is filtered off. 10.5 g of the (E)-4-(3,4,5- trimethoxyphenyl)-4-oxo-2-butenoic acid, melting point 140°C are obtained (recrystallization from ethanol-water 1:1).

Therapeutic Function

Gastric cytoprotective; Antiulcer

InChI:InChI=1/C13H14O6/c1-17-10-6-8(9(14)4-5-12(15)16)7-11(18-2)13(10)19-3/h4-7H,1-3H3,(H,15,16)/b5-4+

Upstream product

• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 
• 298-12-4 Glyoxilic acid 
• 118779-14-9 N-methoxy-N-methyl-3,4,5-trimethoxybenzamide 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 118741-90-5 4,4-diethoxy-3',4',5'-trimethoxybut-2-ynophenone 
• 84386-09-4 4-(3,4,5-trimethoxyphenyl)-4-oxo-2-hydroxy butanoic acid 

Downstream Products

• 84386-15-2 (E)-methyl 4-oxo-4-(3,4,5-trimethoxyphenyl)but-2-enoate 
• 84386-13-0 Sodium salt of (E)-4-(3,4,5-trimethoxyphenyl)-4-oxo-2-butenoic acid 

Relevant academic research and scientific papers

Efficient synthesis of uracil-derived hexa- and tetrahydropyrido[2,3-d] pyrimidines

A reaction of 6-amino-1,3-dimethyluracil with 3-(hetero)aroylacrylic acids and their methyl esters leads to hexahydropyrido[2,3-d]pyrimidine-5-carboxylic acids or the corresponding methyl esters in high to excellent yields. One-pot oxidation of the acid d

Arylalkane, arylalkene and aryl azaalkane, medicaments containing said compounds and method for the production thereof

The present invention relates to compounds of general formula [in-line-formulae]R—Z1—Z2—Z3—R1, ??(I)[/in-line-formulae] wherein R, R1 and Z1 to Z3 are defined as in claim 1, the tautomers, the diastereomers, the enantiomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, particularly CGRP-antagonistic properties, pharmaceutical compositions containing these compounds, their use and processes for preparing them.

A New Method for the Preparation of (E)-3-Acylprop-2-enoic Acids

A new method for the preparation of (E)-3-acylprop-2-enoic acids ( = (E)-3-acylacrylic acids) of type II via acid catalyzed isomerization of the corresponding 3-acylprop-2-ynal acetals of type I (Scheme 1) has been found.The described reaction gives a rap

Gastric anti-secretory, anti-ulcer and cytoprotective properties of substituted (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids

A class of anti-secretory, anti-ulcer and cytoprotective agents, the substituted (E)-4-phenyl and heteroaryl-4-oxo-2-butenoic acids, is described.This chemical structure is not related to those of any known anti-cholinergic drugs, histamine H2-receptor antagonists or prostaglandins.Five compounds, 4-(2-methoxyphenyl)- 15, 4-(4-methoxyphenyl)- 22, 4-(3,4-dimethoxyphenyl)- 32, 4-(3,4,5-trimethoxyphenyl)- 40, and 4-(2-furanyl)-4-oxo-2-butenoic acid 44, have cytoprotective activity at a very low dose (0.6 mg/kg, p.o.) and anti-secretory and anti-ulcer activities at higher doses.One of these compounds, RU 38086 40, has been selected for clinical evaluation.Keywords - anti-ulcer agents / cytoprotective agents / (E)-4-phenyl- and heteroaryl-4-oxo-2-butenoic acids.

Derivatives of phenyl aliphatic carboxylic acids, and use thereof in treating gastric and gastro-duodenal ailments

A compound of the formula (I) STR1 in which the three methoxy radicals are in the 3,4,5, or 2,4,6 or 2,4,5 or 2,3,5 or 2,3,6 positions, in which either A and B together represent a double bond or else A represents a hydrogen atom and B represents a hydrox