182808-04-4

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate is used as an impurity in the production of Prucalopride (P838950) for the treatment of chronic constipation. Prucalopride, a selective 5-HT4 receptor agonist, is effective in managing this condition and is approved for use in Europe. The presence of methyl 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylate as an impurity is significant for the development and manufacturing process of Prucalopride.
Additionally, it serves as an intermediate in the preparation of the enterokinetic agent R108512, which is another application in the pharmaceutical industry. Its role as an intermediate highlights its importance in the synthesis of compounds with potential therapeutic uses.

Upstream product

• 123654-26-2 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid 
• 4093-31-6 methyl 2-methoxy 4-acetamido 5-chloro benzoate 
• 143878-29-9 4-acetamido-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid methyl ester 
• 202664-85-5 methyl 4-acetylamino-2-hydroxy-3-(2-hydroxyethyl)benzoate 
• 149466-67-1 methyl 4-acetylamino-2,3-dihydrobenzo[b]furan-7-carboxylate 
• 67-56-1 methanol 

Downstream Products

• 137211-64-4 4-amino-5-chloro-2,3-dihydro-N-(4-piperidinyl)benzofuran-7-carboxamide 
• 179474-81-8 prucalopride 
• 179474-85-2 prucalopride succinate 

Relevant academic research and scientific papers

Method for preparing prucalopride intermediate

The invention belongs to the field of medicine synthesis, and particularly relates to a method for preparing a prucalopride intermediate. The method comprises the following steps: performing acylation and demethylation reactions on 2-methoxy-4-acetylamino-5-chloro methyl benzoate (I) serving as an initial raw material at 0-20 DEG C under the action of a proper amount of an acylating agent and lewis acid to obtain an intermediate (II); adding an alkaline reagent into the intermediate (II), and performing cyclization reaction at 0-20 DEG C in a polar solvent to obtain an intermediate (III); adding hydrazine hydrate and absolute ethyl alcohol to the intermediate (III), and performing reduction reaction at 70-80 DEG C to obtain an intermediate (IV); performing hydrolysis reaction on the intermediate (IV) at 90-100 DEG C under the action of a sodium hydroxide solution to obtain sodium salt of an intermediate (V), and acidizing with hydrochloric acid to obtain the intermediate (IV). The synthesizing route has mild reaction condition, low production cost and high yield, and is suitable for industrial production.

PROCESSES FOR THE PREPARATION OF HIGHLY PURE PRUCALOPRIDE SUCCINATE AND ITS INTERMEDIATES

Provided herein are purification processes for the preparation of highly pure prucalopride succinate salt. Provided also herein are improved, commercially viable and industrially advantageous processes for the preparation of Prucalopride and its intermediate compounds, for example, methyl 4-acetylamino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylate and alkyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]-amino]-1-piperidinecarboxylate.

HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS

The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT4 receptors.

HETEROARYL COMPOUNDS AS 5-HT4 RECEPTOR LIGANDS

The present invention relates to novel compounds of formula (I), and their pharmaceutically acceptable salts and compositions containing them. The present invention also relates to a process for the preparation of above said novel compounds, and their pharmaceutically acceptable salts. The compounds of formula (I) are useful in the treatment of various disorders that are related to 5-HT4 receptors.

Prokinetic compounds

The present invention concerns novel oxadiazole derivatives of formula (I) STR1 the N-oxide forms, the pharmaceutically acceptable acid addition salts and the stereochemically isomeric forms thereof, wherein R1 is hydrogen or halo; R2 is C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; R3 is hydrogen; or R2 and R3 taken together may form a C2-3 alkanediyl radical wherein one or two hydrogen atoms may be replaced by C1-4 alkyl; R4 is hydrogen or C1-6 alkyloxy; X is a bivalent radical of the formula STR2 L is a radical of formula -Alk-R5 or -Alk--O--R6, Alk is C1-12 alkanediyl; R5 is hydrogen, cyano, C1-6 alkylcarbonyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, aryl, arylcarbonyl, tetrahydrofuran, dioxolane, dioxolane substituted with C1-6 alkyl, dioxane, dioxane substituted with C1-6 alkyl; R6 is hydrogen, aryl, C1-6 alkyl, hydroxyC1-6 alkyl, C1-6 alkylcarbonyl; aryl is defined as phenyl or phenyl substituted with up to three substituents selected from halo, C1-6 alkyl or C1-6 alkyloxy. It further relates to pharmaceutical compositions comprising them, processes for preparing said compounds and compositions, and the use thereof as a medicine, in particular in the conditions involving a decreased motility of the colon.