http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-035663-A1
Outgoing Links
Predicate | Object |
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_0a9e6421e9257148abad101e1ce6c162 |
classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D307-80 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C217-22 |
classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C217-22 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D307-80 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07B61-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C65-21 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C69-92 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-60 |
filingDate | 2001-12-10-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0c67ac25cb75b12031fe47a18f102803 |
publicationDate | 2004-06-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | AR-035663-A1 |
titleOfInvention | 2-BUTIL-3- CHLORHYDRATE (4- [3- (DIBUTILAMINE) PROPOXI] BENZOIL) -5-NITRO-BENZOFURANE, PROCEDURE FOR PREPARATION, AND PREPARATION PROCEDURE FOR 2-BUTIL-3- (4- [3- (DIBUTILAMINE) PROPOXI] BENZOIL) -5-NITRO-BENZOFURANO |
abstract | 2-Butyl-3- (4- [3- (dibutylamino) propoxy) benzoyl) -5-nitro-benzofuran hydrochloride of formula (1). Benzoyl derivatives of the general formula (2) as well as its hydrochloride, in which R represents chlorine or a group -OR1 in which R1 represents hydrogen or a C1-4 alkyl group with the exception of chloro-1 hydrochloride (di-n- butylamino-3 propoxy) -4 benzoyl. Process for preparing the compound of formula (1), wherein, in an organic phase consisting of one or more solvents chosen from halogenated hydrocarbons or not, 2-butyl-5-nitro-benzofuran is reacted with 4- chloride chloride hydrochloride [3- (dibutylamino) propoxy] benzoyl and these, in the presence of a maximum of 3 molar equivalent of a Lewis acid as catalyst, are then hydrolyzed to form the desired compound that is recovered in the organic phase. Preparation process of 2-butyl-3- (4- [3- (dibutylamino) propoxy] benzoyl) -5-nitro-benzofuran, in which 2-butyl-3- hydrochloride is treated (4- [3- (dibutylamino) propoxy] benzoyl) -5-nitro-benzofuran by means of a basic agent, which gives the desired compound. Process for preparing dronedarone and its pharmaceutically acceptable salts, in which: a) in an organic phase, consisting of one or more solvents chosen from halogenated hydrocarbons or not, the 2-butyl-5-nitro-benzofuran is reacted with 4- [3- (dibutylamino) propoxy] benzoyl chloride hydrochloride and this, in the presence of a maximum of 3 molar equivalent of a Lewis acid as catalyst, is then hydrolyzed to obtain temporarily and without isolation, hydrochloride 2- butyl-3- (4- [3- (dibutylamino) propoxy] benzoyl) -5-nitro-benzofuran which is recovered in the organic phase and treated by means of a basic agent to form 2-butyl-3- ( 4- [3- (dibutylamino) propoxy] benzoyl) -5-nitro-benzofuran; b) the compound thus obtained is hydrogenated in the presence of an appropriate catalyst, which gives 5-amino-2-butyl-3- (4- [3- (dibutylamino) propoxy] benzoylbenzofuran; c) the derivative is reacted of 5-aminobenzofuran thus obtained with methanesulfonyl chloride or with methanesulfonic anhydride, the reaction takes place in the presence of an acid acceptor, which gives dronedarone that can be reacted, if desired, with an organic or inorganic acid to form a pharmaceutically acceptable salt of that compound. Preparation process of 4- [3- (dibutylamino) propoxy] benzoyl chloride hydrochloride, in which: a) the 1-dibutylamino-3-chloro propane is reacted with a C1-4 alkyl p-hydroxybenzoate and this, in the presence of a basic agent for obtaining a 4- [3- (dibutylamino) propoxy] C1-4 alkyl benzoate; b) the ester thus obtained is saponified in the presence of an alkali metal hydroxide, then the salt thus formed is treated, by means of hydrochloric acid to form 4- [3- (dibutylamino) propoxy] benzoic acid hydrochloride; and c) the hydrochloride thus obtained is treated by means of a chlorinating agent, to obtain the desired compound. The compound of formula (1) is particularly useful as an intermediate to prepare 2-butyl-3- (4- [3- (dibutylamino) propoxy] benzoyl) -5-nitro-benzofuran, in turn, intermediate for dronedarone. The compounds of formula (2) are particularly useful as synthesis intermediates, for example for the preparation of the compound of formula (1). Dronedarone is particularly useful in the cardiovascular field, especially as an antirhythmic agent. |
priorityDate | 2000-12-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 49.