AR035663A1 - Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano - Google Patents

Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano

Info

Publication number
AR035663A1
AR035663A1 ARP010105714A ARP010105714A AR035663A1 AR 035663 A1 AR035663 A1 AR 035663A1 AR P010105714 A ARP010105714 A AR P010105714A AR P010105714 A ARP010105714 A AR P010105714A AR 035663 A1 AR035663 A1 AR 035663A1
Authority
AR
Argentina
Prior art keywords
dibutylamino
propoxy
nitro
benzoyl
hydrochloride
Prior art date
Application number
ARP010105714A
Other languages
English (en)
Inventor
Michel Biard
Original Assignee
Sanofi Aventis
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR035663A1 publication Critical patent/AR035663A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi)benzoil)-5-nitro-benzofurano de fórmula (1). Derivados benzoilos de fórmula general (2) así como su clorhidrato, en la cual R representa cloro o un grupo -OR1 en la cual R1 representa hidrógeno o un grupo alquilo C1-4 a excepción del clorhidrato de cloro-1 (di-n-butilamino-3 propoxi)-4 benzoilo. Procedimiento de preparación del compuesto de fórmula (1), en donde, en una fase orgánica constituida por uno o varios solventes elegidos entre hidrocarburos halogenados o no, se hace reaccionar 2-butil-5-nitro-benzofurano con clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo y estos, en presencia de un máximo de 3 equivalente molares de un ácido de Lewis como catalizador, luego se hidroliza para formar el compuesto deseado que se recupera en la fase orgánica. Procedimiento de preparación de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, en el cual se trata el clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano por medio de un agente básico, lo que da el compuesto deseado. Procedimiento de preparación de dronedarona y de sus sales farmacéuticamente aceptables, en la cual: a) en una fase orgánica, constituida por uno o varios solventes elegidos entre hidrocarburos halogenados o no, se hace reaccionar el 2-butil-5-nitro-benzofurano con el clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo y esto, en presencia de un máximo de 3 equivalente molares de un ácido de Lewis como catalizador, luego se hidroliza para obtener transitoriamente y sin aislamiento, el clorhidrato 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano que se recupera en la fase orgánica y que se trata por medio de un agente básico para formar el 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano; b) se hidrogena el compuesto así obtenido en presencia de un catalizador apropiado, lo que da 5-amino-2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil-benzofurano; c) se hace reaccionar el derivado de 5-aminobenzofurano así obtenido con cloruro de metanosulfonilo o con anhídrido metanosulfónico, la reacción tiene lugar en presencia de un aceptador de ácido, lo que da dronedarona que se puede hacer reaccionar, se se lo desea, con un ácido orgánico o inorgánico para formar una sal farmacéuticamente aceptable de ese compuesto. Procedimiento de preparación del clorhidrato del cloruro de 4-[3-(dibutilamino)propoxi]benzoilo, en el cual: a) se hace reaccionar el 1-dibutilamino-3-cloro-propano con un p-hidroxibenzoato de alquilo C1-4 y esto, en presencia de un agente básico para obtener un 4-[3-(dibutilamino)propoxi]benzoato de alquilo C1-4; b) se saponifica el éster así obtenido en presencia de un hidróxido de metal alcalino, luego se trata la sal así formada, por medio de ácido clorhídrico para formar el clorhidrato del ácido 4-[3-(dibutilamino)propoxi]benzoico; y c) se trata el clorhidrato así obtenido por medio de un agente de cloración, para obtener el compuesto deseado. El compuesto de fórmula (1) es particularmente útil como intermediario para preparar 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, a su vez, intermediario para la dronedarona. Los compuestos de fórmula (2) son particularmente útiles como intermediarios de síntesis, por ejemplo para la preparación del compuesto de fórmula (1). La dronedarona es particularmente útil en el campo cardiovascular, especialmente como agente antirrítmico.
ARP010105714A 2000-12-11 2001-12-10 Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano AR035663A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0016069A FR2817865B1 (fr) 2000-12-11 2000-12-11 Derive aminoalkoxybenzoyle sous forme de sel, son procede de preparation et son utilisation comme intermediaire de synthese

Publications (1)

Publication Number Publication Date
AR035663A1 true AR035663A1 (es) 2004-06-23

Family

ID=8857481

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP010105714A AR035663A1 (es) 2000-12-11 2001-12-10 Clorhidrato de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano, procedimiento para su preparacion, y procedimiento de preparacion de 2-butil-3-(4-[3-(dibutilamino)propoxi]benzoil)-5-nitro-benzofurano

Country Status (21)

Country Link
US (1) US6846936B2 (es)
EP (1) EP1351907B1 (es)
JP (2) JP4437004B2 (es)
CN (2) CN1295200C (es)
AR (1) AR035663A1 (es)
AT (1) ATE345319T1 (es)
AU (1) AU2002217227A1 (es)
BR (1) BR0116065B1 (es)
CA (1) CA2429268C (es)
CZ (1) CZ303489B6 (es)
DE (1) DE60124587T2 (es)
DK (1) DK1351907T3 (es)
ES (1) ES2276741T3 (es)
FR (1) FR2817865B1 (es)
HK (1) HK1055944A1 (es)
HR (1) HRP20030471B1 (es)
HU (1) HUP0500981A3 (es)
MX (1) MXPA03005223A (es)
PL (1) PL206029B1 (es)
SK (1) SK287770B6 (es)
WO (1) WO2002048078A1 (es)

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CN102070581B (zh) * 2011-01-19 2015-11-25 上海医药工业研究院 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-氨基苯并呋喃的制备
CN102070580B (zh) * 2011-01-19 2015-05-20 上海医药工业研究院 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-取代氨基苯并呋喃的制备
CN102070578B (zh) * 2011-01-19 2015-10-14 上海医药工业研究院 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-烷酰基氨基苯并呋喃的制备方法
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CN102690249B (zh) * 2011-03-22 2014-09-17 江苏康缘药业股份有限公司 一种决奈达隆的制备方法
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HUP1100167A2 (en) 2011-03-29 2012-11-28 Sanofi Sa Process for preparation of dronedarone by mesylation
WO2013014480A1 (en) 2011-07-26 2013-01-31 Sanofi Process for preparation of dronedarone using amide intermediary compound
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WO2013014479A1 (en) 2011-07-26 2013-01-31 Sanofi Reductive animation process for preparation of dronedarone using aldehyde intermediary compound
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Also Published As

Publication number Publication date
CN1295200C (zh) 2007-01-17
SK7272003A3 (en) 2003-11-04
FR2817865A1 (fr) 2002-06-14
SK287770B6 (sk) 2011-09-05
JP4437004B2 (ja) 2010-03-24
CN100371314C (zh) 2008-02-27
DE60124587T2 (de) 2007-09-20
CN1479706A (zh) 2004-03-03
CA2429268A1 (fr) 2002-06-20
JP2009024007A (ja) 2009-02-05
CZ20031611A3 (cs) 2003-08-13
AU2002217227A1 (en) 2002-06-24
DE60124587D1 (de) 2006-12-28
HK1055944A1 (en) 2004-01-30
US6846936B2 (en) 2005-01-25
HUP0500981A2 (en) 2006-03-28
ES2276741T3 (es) 2007-07-01
PL364774A1 (en) 2004-12-13
BR0116065A (pt) 2003-10-28
CA2429268C (fr) 2011-02-01
PL206029B1 (pl) 2010-06-30
ATE345319T1 (de) 2006-12-15
DK1351907T3 (da) 2007-03-26
EP1351907B1 (fr) 2006-11-15
HUP0500981A3 (en) 2012-09-28
BR0116065B1 (pt) 2014-03-25
MXPA03005223A (es) 2004-04-20
EP1351907A1 (fr) 2003-10-15
JP2004515536A (ja) 2004-05-27
US20040010032A1 (en) 2004-01-15
FR2817865B1 (fr) 2005-02-18
HRP20030471B1 (en) 2011-07-31
WO2002048078A1 (fr) 2002-06-20
HRP20030471A2 (en) 2004-08-31
CZ303489B6 (cs) 2012-10-17
CN1769262A (zh) 2006-05-10

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