SYNTHESIS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETIL)AMINO]BUTANOIL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2-CARBOXAMIDE Russian patent published in 2023 - IPC C07D403/12 A61K31/403 

Abstract RU 2794748 C1

FIELD: medicine; pharmacology; pharmaceutical industry.

SUBSTANCE: group of inventions includes a method for producing (1R,2S,5S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-3-[(2S)-3,3-dimethyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide (compound of formula (I)) and its use for batch chemical industrial production, semi-continuous industrial production or continuous industrial production. The method for obtaining the compound of formula (I) consists in the dehydration of the compound of formula (II) using 2,4,6-trichloro-1,3,5-triazine in a solvent medium.

EFFECT: improved method of obtaining, leading to an increase in the yield and chemical purity of the compound of formula (I).

14 cl, 1 tbl, 2 ex

Similar patents RU2794748C1

Title Year Author Number
METHOD FOR PRODUCING (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3- DIMETHYL-2-[(2,2,2-TRIFLUORACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2-CARBOXAMIDE 2022
  • Belyj Petr Aleksandrovich
  • Lopatukhin Eduard Yurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaya Kira Yakovlevna
  • Belov Evgenij Yurevich
RU2794750C1
METHOD FOR PRODUCING (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3- DIMETHYL-2-[(2,2,2-TRIFLUORACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2-CARBOXAMIDE 2022
  • Belyj Petr Aleksandrovich
  • Lopatukhin Eduard Yurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaya Kira Yakovlevna
  • Belov Evgenij Yurevich
RU2794754C1
METHOD FOR PRODUCING (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3- DIMETHYL-2-[(2,2,2-TRIFLUORACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2-CARBOXAMIDE 2022
  • Belyj Petr Aleksandrovich
  • Lopatukhin Eduard Yurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaya Kira Yakovlevna
  • Belov Evgenij Yurevich
RU2794746C1
METHOD FOR PRODUCING (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3- DIMETHYL-2-[(2,2,2-TRIFLUORACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2-CARBOXAMIDE 2022
  • Belyj Petr Aleksandrovich
  • Lopatukhin Eduard Yurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaya Kira Yakovlevna
  • Belov Evgenij Yurevich
RU2794755C1
NOVEL FORMS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2827154C1
NOVEL FORMS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2827357C1
NOVEL FORMS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2827358C1
NOVEL FORMS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2827157C1
NOVEL FORMS OF (1R,2S,5S)-N-[(1S)-1-CYANO-2-[(3S)-2-OXOPYRROLIDIN-3-YL]ETHYL]-3-[(2S)-3,3-DIMETHYL-2-[(2,2,2-TRIFLUOROACETYL)AMINO]BUTANOYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXAMIDE 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2827158C1
NEW AZABICYCLOHEXANE DERIVATIVES 2023
  • Belyi Petr Aleksandrovich
  • Lopatukhin Eduard Iurevich
  • Korolev Vladimir Lvovich
  • Zaslavskaia Kira Iakovlevna
  • Korliukov Aleksandr Aleksandrovich
  • Buikin Petr Alekseevich
RU2811800C1

RU 2 794 748 C1

Authors

Belyj Petr Aleksandrovich

Lopatukhin Eduard Yurevich

Korolev Vladimir Lvovich

Zaslavskaya Kira Yakovlevna

Belov Evgenij Yurevich

Dates

2023-04-24Published

2022-04-15Filed