MX337683B - Proceso para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil -6-(2-piridinil) -4h-imidazo [1, 2-a] [1, 4] benzodiacepina-4-il] -propionico o la sal de sulfonato de benceno del mismo, y compuestos utiles en ese proceso. - Google Patents

Proceso para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil -6-(2-piridinil) -4h-imidazo [1, 2-a] [1, 4] benzodiacepina-4-il] -propionico o la sal de sulfonato de benceno del mismo, y compuestos utiles en ese proceso.

Info

Publication number
MX337683B
MX337683B MX2012003183A MX2012003183A MX337683B MX 337683 B MX337683 B MX 337683B MX 2012003183 A MX2012003183 A MX 2012003183A MX 2012003183 A MX2012003183 A MX 2012003183A MX 337683 B MX337683 B MX 337683B
Authority
MX
Mexico
Prior art keywords
bromo
propionic acid
benzodiazepine
pyridinyl
methyl ester
Prior art date
Application number
MX2012003183A
Other languages
English (en)
Other versions
MX2012003183A (es
Inventor
Stuart Gary Tilbrook
Andreas Schumacher
René Emmenegger
Original Assignee
Paion Uk Ltd
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 Paion Uk Ltd filed Critical Paion Uk Ltd
Publication of MX2012003183A publication Critical patent/MX2012003183A/es
Publication of MX337683B publication Critical patent/MX337683B/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La invención se refiere a un nuevo proceso para preparar metil éster de ácido 3-[(4S)-8-bromo-1-metil-6-(2-piridinil)-4H-imidazo[ 1,2-a] [1,4]benzodiacepina-4-il]-porpiónico o sulfonato de benceno de metil éster de ácido 3-[(4S)-8-bromo-1-metil-6-(2-pirid inil)-4H-imidazo [1,2-a] [1,4]benzodiacepina-4-il]-propiónico (P), que comprende hacer reaccionar metil éster de ácido 3-[(S)-7-bromo-2-((R y/o S)-2-hidroxi-propilamino)-5-piridin-2-il- 3H-benzo[e] [1,4]diacepin-3-il]-propiónico de la fórmula (EM) con un agente oxidante y opcionalmente tratar el producto de la reacción bajo condiciones ácidas, de manera que se produzca el compuesto de fórmula (F) o el compuesto (P), y nuevos compuestos útiles como materiales de inicio o como intermedios para realizar el proceso.
MX2012003183A 2009-09-18 2010-09-15 Proceso para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil -6-(2-piridinil) -4h-imidazo [1, 2-a] [1, 4] benzodiacepina-4-il] -propionico o la sal de sulfonato de benceno del mismo, y compuestos utiles en ese proceso. MX337683B (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09011914A EP2305647A1 (en) 2009-09-18 2009-09-18 Process for preparing 3-[(4S)-8-bromo-1-methyl-6-(2-pyridinyl)-4 H-imidazo[1,2-a][1,4]benzodiazepine-4-yl] propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process
PCT/EP2010/005668 WO2011032692A1 (en) 2009-09-18 2010-09-15 Process for preparing 3-[(4s)-8-bromo-1-methyl-6-(2-pyridinyl)-4h-imidazol[1,2-a][1,4]benzodiazepine-4-yl]propionic acid methyl ester or the benzene sulfonate salt thereof, and compounds useful in that process

Publications (2)

Publication Number Publication Date
MX2012003183A MX2012003183A (es) 2012-05-08
MX337683B true MX337683B (es) 2016-03-15

Family

ID=41467237

Family Applications (2)

Application Number Title Priority Date Filing Date
MX2012003183A MX337683B (es) 2009-09-18 2010-09-15 Proceso para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil -6-(2-piridinil) -4h-imidazo [1, 2-a] [1, 4] benzodiacepina-4-il] -propionico o la sal de sulfonato de benceno del mismo, y compuestos utiles en ese proceso.
MX2015018057A MX341093B (es) 2009-09-18 2010-09-15 Compuestos utiles para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(2-piridinil)-4h-imidazo[1, 2-a] [1, 4] benzodiacepina-4-il]-propionico o la sal de sulfonato de benceno del mismo.

Family Applications After (1)

Application Number Title Priority Date Filing Date
MX2015018057A MX341093B (es) 2009-09-18 2010-09-15 Compuestos utiles para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(2-piridinil)-4h-imidazo[1, 2-a] [1, 4] benzodiacepina-4-il]-propionico o la sal de sulfonato de benceno del mismo.

Country Status (18)

Country Link
US (3) US9156842B2 (es)
EP (2) EP2305647A1 (es)
JP (1) JP5801309B2 (es)
KR (1) KR101801735B1 (es)
CN (1) CN102753525B (es)
AU (1) AU2010294873B2 (es)
BR (1) BR112012006053B1 (es)
CA (1) CA2774018C (es)
DK (1) DK2477967T3 (es)
ES (1) ES2555233T3 (es)
HK (1) HK1173437A1 (es)
HR (1) HRP20151316T1 (es)
HU (1) HUE028298T2 (es)
MX (2) MX337683B (es)
PL (1) PL2477967T3 (es)
PT (1) PT2477967E (es)
RU (1) RU2551848C2 (es)
WO (1) WO2011032692A1 (es)

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ES2709298B2 (es) 2017-10-13 2019-08-21 Moehs Iberica Sl Procedimiento para preparar metil ester de acido 3-[(4s)-8-bromo-1-metil-6-(piridin-2-il)-4h-imidazo[1,2-a][1,4]benzodiazepin-4-il]-propionico, y compuestos utiles en ese procedimiento
CN108033964B (zh) * 2017-12-28 2021-02-09 杭州奥默医药股份有限公司 一种吡啶基咪唑并苯并二氮杂卓丙酸酯化合物及其合成和应用
ES2827125A1 (es) * 2019-11-19 2021-05-19 Moehs Iberica Sl Intermedio util en la preparacion de remimazolam, su procedimiento de obtencion, y su uso en la obtencion de remimazolam
KR102526590B1 (ko) 2020-06-19 2023-04-28 하나제약 주식회사 3-[(4S)-8-브로모-1-메틸-6-(2-피리디닐)-4H-이미다조[1,2-a][1,4]벤조디아제핀-4-일]프로피온산 메틸 에스테르의 제조방법
CN112358483A (zh) * 2020-11-09 2021-02-12 中国药科大学 一类新型苯并二氮*类化合物、其制备方法及其用途
CN112321594B (zh) * 2020-12-07 2022-05-20 扬子江药业集团有限公司 一种苯并二氮杂䓬类药物的制备方法
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Also Published As

Publication number Publication date
HUE028298T2 (en) 2016-12-28
KR20120102603A (ko) 2012-09-18
CA2774018C (en) 2018-01-30
EP2477967A1 (en) 2012-07-25
US9512078B2 (en) 2016-12-06
CN102753525B (zh) 2015-09-02
US20120330007A1 (en) 2012-12-27
WO2011032692A1 (en) 2011-03-24
AU2010294873B2 (en) 2014-11-13
AU2010294873A1 (en) 2012-04-12
CN102753525A (zh) 2012-10-24
HRP20151316T1 (hr) 2016-01-15
BR112012006053B1 (pt) 2021-11-16
PT2477967E (pt) 2016-01-07
MX2012003183A (es) 2012-05-08
ES2555233T3 (es) 2015-12-29
US20170044135A1 (en) 2017-02-16
HK1173437A1 (zh) 2013-05-16
DK2477967T3 (en) 2015-12-21
RU2012115456A (ru) 2013-11-10
KR101801735B1 (ko) 2017-11-27
MX341093B (es) 2016-08-08
BR112012006053A2 (pt) 2020-11-03
US10000464B2 (en) 2018-06-19
CA2774018A1 (en) 2011-03-24
RU2551848C2 (ru) 2015-05-27
JP2013505207A (ja) 2013-02-14
US9156842B2 (en) 2015-10-13
US20150368199A1 (en) 2015-12-24
EP2305647A1 (en) 2011-04-06
JP5801309B2 (ja) 2015-10-28
EP2477967B1 (en) 2015-11-11
PL2477967T3 (pl) 2016-04-29

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