AR080332A1 - DERIVADOS DE CETOBENZOFURANO, PROCEDIMIENTO PARA SU SíNTESIS E INTERMEDIARIOS DE LA MISMA - Google Patents

DERIVADOS DE CETOBENZOFURANO, PROCEDIMIENTO PARA SU SíNTESIS E INTERMEDIARIOS DE LA MISMA

Info

Publication number
AR080332A1
AR080332A1 ARP110100607A ARP110100607A AR080332A1 AR 080332 A1 AR080332 A1 AR 080332A1 AR P110100607 A ARP110100607 A AR P110100607A AR P110100607 A ARP110100607 A AR P110100607A AR 080332 A1 AR080332 A1 AR 080332A1
Authority
AR
Argentina
Prior art keywords
benzoyl
benzofuran
group
butylamino
methylsulfonamido
Prior art date
Application number
ARP110100607A
Other languages
English (en)
Inventor
Bernard Grimaud
Philippe Vayron
Frederic Bailly
Irina Malejonock
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 AR080332A1 publication Critical patent/AR080332A1/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
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/83—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
    • 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
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

Landscapes

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

Abstract

Procedimiento de síntesis vía el acoplamiento entre una quinoneimina y una enaminona por una reaccion de Nenitzescu y a sus intermedios de síntesis. Reivindicacion 1: Derivado cetobenzofurano de formula (1) siguiente: en la que, ò G1 representa un grupo (i) alquilo, lineal o ramificado, (ii) halogenoalquilo, (iii) cicloalquilo, (iv) arilo, (v) alqueno o (vi) alquino; ò G3 representa (i) un grupo -NHSO2Rc o (ii) un grupo -NHRc, donde Rc representa (a) un grupo alquilo, lineal o ramificado, (b) un grupo cicloalquilo o (c) un grupo arilo; ò G5 representa un átomo de halogeno o un grupo -ORb donde Rb representa un átomo de hidrogeno, un grupo alquilo, halogenoalquilo, arilo, arilalquilo, heteroarilo, cicloalquilo, heterocicloalquilo o un grupo -alquilenoaminoalquilo, ò Ra representa un sustituyente elegido entre el átomo de hidrogeno, los átomos de halogeno, los grupos alquilo, halogenoalquilo, alcoxi y alcoxialquilo; ò na es un indice igual a 0, 1, 2, 3 o 4, estando dicho derivado cetobenzofurano en forma (i) de ácido, (ii) de base, (iii) de sal de adicion a un ácido o a una base, (iv) de hidrato o (v) de solvato, con excepcion del 2-n-butil-3-[4-(3-di-n-butilaminopropoxi)benzoílo]-5-metilsulfonamido-benzofurano, de sus sales, sus solvatos y sus hidratos y: - [(di-n-butilamino-2-etoxi)-4 benzoil]-3-n-butil-2-metulsulfonamido-5- benzofurano; - n-butilsulfonamido-5[(di-n-butilamino-3-propoxi)-4-benzoil]-3-n-butil-2-benzofurano; - fenil-2-[(di-n-butilamino-3-propoxi)-4 benzoil]-3-metilsulfonamido-5-benzofurano; - toluenosulfonato de [(di-n-butilamino-3-propoxi)-4 benzoil]-3-isopropil-2- metilsulfonamido-5-benzofurano; - hidrocloruro de [(di-n-butilamino-3-propoxi)-4 benzoil]-2-metil-3-metilsulfonamido-5-benzofurano; - [(di-n-butilamino-5-pentoxi)-4-benzoil]-3-n-butil-2-metilsulfonamido-5-benzofurano; - dioxalato de [(di-n-butilamino-3-propoxi)-4-benzoil]-3-etil-2-metilsulfonamido-5-benzofurano; - [(di-n-butilamino-3-propoxi)-4-benzoil]-3-n-propil-2-metilsulfonamido-5-benzofurano; - [(dietilamino-3-propoxi)-4-benzoil]-3-n-butil-2-metilsulfonamido-5-benzofurano; - oxalato de n-butil-2-(di-n-butilamino-3-propoxi)-4-ditercbutil-3,5-benzoil]-3-metilsulfonamido-5-benzofurano; - hemioxalato de n-butil-2[(di-n-butilamino-3-propoxi)-4-dimetil-3,5 benzoil]-3-metilsulfonamido-5-benzofurano; - fumarato ácido de [(di-n-butilamino-3-propoxi)-4-benzoil]-3-n-butil-2-tolilsulfonamido-5-benzofurano. Reivindicacion 15: Los intermedios de síntesis se eligen entre las enaminonas de formula 2 donde G1, G2, G5, Ra y na son tal como se definen en una cualquiera de las reivindicaciones 4 o 5, y G5 representa un átomo de halogeno o un grupo -ORb donde Rb representa un átomo de hidrogeno, un grupo halogenoalquilo, arilo, arilalquilo, heteroarilo, cicloalquilo, heterocicloalquilo o un grupo -alquilenoaniinoalquilo; y las dicetonas de formula 3 donde G1, G5, Ra y na son tal como se definen en una cualquiera de las reivindicaciones 4 o 5 y G5 representa un átomo de halogeno o un grupo -ORb donde Rb representa un grupo halogenoalquilo, arilo, arilalquilo, heteroarilo, cicloalquilo, heterocicloalquilo o un grupo -alquilenoaminoalquilo; (2) (3).
ARP110100607A 2010-03-02 2011-02-28 DERIVADOS DE CETOBENZOFURANO, PROCEDIMIENTO PARA SU SíNTESIS E INTERMEDIARIOS DE LA MISMA AR080332A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1051510A FR2957079B1 (fr) 2010-03-02 2010-03-02 Procede de synthese de derives de cetobenzofurane

Publications (1)

Publication Number Publication Date
AR080332A1 true AR080332A1 (es) 2012-03-28

Family

ID=42935523

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP110100607A AR080332A1 (es) 2010-03-02 2011-02-28 DERIVADOS DE CETOBENZOFURANO, PROCEDIMIENTO PARA SU SíNTESIS E INTERMEDIARIOS DE LA MISMA

Country Status (16)

Country Link
US (1) US8796489B2 (es)
EP (1) EP2542544A1 (es)
JP (1) JP2013521264A (es)
KR (1) KR20130045249A (es)
CN (1) CN102884056A (es)
AR (1) AR080332A1 (es)
AU (1) AU2011222828A1 (es)
BR (1) BR112012021865A2 (es)
CA (1) CA2791482A1 (es)
FR (1) FR2957079B1 (es)
MX (1) MX2012010121A (es)
RU (1) RU2012141889A (es)
SG (1) SG183516A1 (es)
TW (1) TW201139400A (es)
UY (1) UY33256A (es)
WO (1) WO2011107705A1 (es)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUP0900759A2 (en) 2009-12-08 2011-11-28 Sanofi Aventis Novel process for producing dronedarone
HUP1000010A2 (en) 2010-01-08 2011-11-28 Sanofi Sa Process for producing dronedarone
FR2958290B1 (fr) 2010-03-30 2012-10-19 Sanofi Aventis Procede de preparation de derives de sulfonamido-benzofurane
FR2958291B1 (fr) 2010-04-01 2013-07-05 Sanofi Aventis Procede de preparation de derives d'amino-benzofurane
HUP1000330A2 (en) 2010-06-18 2011-12-28 Sanofi Sa Process for the preparation of dronedarone and the novel intermediates
FR2962731B1 (fr) 2010-07-19 2012-08-17 Sanofi Aventis Procede de preparation de derives d'amino-benzoyl-benzofurane
FR2963006B1 (fr) * 2010-07-21 2013-03-15 Sanofi Aventis Procede de preparation de derives de nitro-benzofurane
HUP1000386A2 (en) 2010-07-22 2012-05-29 Sanofi Sa Novel process for producing dronedarone
EP2452938A1 (en) * 2010-11-12 2012-05-16 LEK Pharmaceuticals d.d. Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives
HUP1100167A2 (en) 2011-03-29 2012-11-28 Sanofi Sa Process for preparation of dronedarone by mesylation
HUP1100165A2 (en) 2011-03-29 2012-12-28 Sanofi Sa Process for preparation of dronedarone by n-butylation
FR2983198B1 (fr) 2011-11-29 2013-11-15 Sanofi Sa Procede de preparation de derives de 5-amino-benzoyl-benzofurane
EP2617718A1 (en) 2012-01-20 2013-07-24 Sanofi Process for preparation of dronedarone by the use of dibutylaminopropanol reagent
WO2013121235A2 (en) 2012-02-13 2013-08-22 Sanofi Process for preparation of dronedarone by removal of hydroxyl group
US9249119B2 (en) 2012-02-14 2016-02-02 Sanofi Process for the preparation of dronedarone by oxidation of a sulphenyl group
WO2013124745A1 (en) 2012-02-22 2013-08-29 Sanofi Process for preparation of dronedarone by oxidation of a hydroxyl group
US9238636B2 (en) 2012-05-31 2016-01-19 Sanofi Process for preparation of dronedarone by Grignard reaction
TW201536763A (zh) * 2013-08-27 2015-10-01 Gilead Sciences Inc 製備決奈達隆或其鹽類之製程
CN109384754B (zh) * 2017-08-14 2020-06-09 新发药业有限公司 一种盐酸决奈达隆的制备方法
CN107827764A (zh) * 2017-11-27 2018-03-23 上海应用技术大学 一种双β‑氨基酮或双β‑氨基酯类的制备方法
JP7686615B2 (ja) * 2019-07-08 2025-06-02 ナショナル ユニバーシティー オブ シンガポール 心臓治療薬

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US5066803A (en) * 1989-12-07 1991-11-19 Sterling Drug Inc. 2- and 3-aminomethyl-6-arylcarbonyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazines
FR2665444B1 (fr) * 1990-08-06 1992-11-27 Sanofi Sa Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant.
FR2817865B1 (fr) 2000-12-11 2005-02-18 Sanofi Synthelabo Derive aminoalkoxybenzoyle sous forme de sel, son procede de preparation et son utilisation comme intermediaire de synthese
FR2817864B1 (fr) 2000-12-11 2003-02-21 Sanofi Synthelabo Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese
IL146389A0 (en) * 2001-11-08 2002-07-25 Isp Finetech Ltd Process for the preparation of dronedarone
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EP1996588A4 (en) * 2006-03-03 2011-10-05 Torrent Pharmaceuticals Ltd NEW DUAL ACTION RECEPTOR (DARA) ANTAGONISTS OF ATI AND ETA RECEPTORS
GB0719180D0 (en) * 2007-10-02 2007-11-14 Cambrex Karlskoga Ab New process
UY32657A (es) 2009-05-27 2010-12-31 Sanofi Aventis Procedimiento para la fabricación de productos intermedios de dronedarona
TW201107303A (en) 2009-05-27 2011-03-01 Sanofi Aventis Process for the production of benzofurans
HUP0900759A2 (en) 2009-12-08 2011-11-28 Sanofi Aventis Novel process for producing dronedarone
HUP1000010A2 (en) 2010-01-08 2011-11-28 Sanofi Sa Process for producing dronedarone
FR2958290B1 (fr) 2010-03-30 2012-10-19 Sanofi Aventis Procede de preparation de derives de sulfonamido-benzofurane
FR2958291B1 (fr) 2010-04-01 2013-07-05 Sanofi Aventis Procede de preparation de derives d'amino-benzofurane
FR2973027A1 (fr) 2011-03-24 2012-09-28 Sanofi Aventis Procede de synthese de derives de cetobenzofurane
HUP1100166A2 (en) 2011-03-29 2012-12-28 Sanofi Sa Reductive amination process for preparation of dronedarone using amine intermediary compound
HUP1100167A2 (en) 2011-03-29 2012-11-28 Sanofi Sa Process for preparation of dronedarone by mesylation
HUP1100165A2 (en) 2011-03-29 2012-12-28 Sanofi Sa Process for preparation of dronedarone by n-butylation
WO2013014480A1 (en) 2011-07-26 2013-01-31 Sanofi Process for preparation of dronedarone using amide intermediary compound
WO2013014479A1 (en) 2011-07-26 2013-01-31 Sanofi Reductive animation process for preparation of dronedarone using aldehyde intermediary compound
WO2013014478A1 (en) 2011-07-26 2013-01-31 Sanofi Reductive amination process for preparation of dronedarone using carboxyl intermediary compound

Also Published As

Publication number Publication date
BR112012021865A2 (pt) 2016-05-17
EP2542544A1 (fr) 2013-01-09
JP2013521264A (ja) 2013-06-10
KR20130045249A (ko) 2013-05-03
CN102884056A (zh) 2013-01-16
US20130012729A1 (en) 2013-01-10
US8796489B2 (en) 2014-08-05
WO2011107705A1 (fr) 2011-09-09
TW201139400A (en) 2011-11-16
CA2791482A1 (fr) 2011-09-09
AU2011222828A1 (en) 2012-09-20
UY33256A (es) 2011-09-30
FR2957079A1 (fr) 2011-09-09
FR2957079B1 (fr) 2012-07-27
RU2012141889A (ru) 2014-04-10
MX2012010121A (es) 2012-09-12
SG183516A1 (en) 2012-10-30

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