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1. WO2017201241 - PREPARATION OF (S)-N-(5-((R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDIN-1-YL)PYRAZOLO[1,5-A]PYRIMIDIN-3-Y L)-3-HYDROXYPYRROLIDINE-1-CARBOXAMIDE

Publication Number WO/2017/201241
Publication Date 23.11.2017
International Application No. PCT/US2017/033257
International Filing Date 18.05.2017
IPC
C07D 487/04 2006.1
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
487Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
A61K 31/5025 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
495having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
50Pyridazines; Hydrogenated pyridazines
5025ortho- or peri-condensed with heterocyclic ring systems
A61P 35/00 2006.1
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
CPC
A61K 31/519
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31Medicinal preparations containing organic active ingredients
33Heterocyclic compounds
395having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
495having six-membered rings with two ; or more; nitrogen atoms as the only ring heteroatoms, e.g. piperazine ; or tetrazines
505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
519ortho- or peri-condensed with heterocyclic rings
A61P 35/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35Antineoplastic agents
A61P 43/00
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
43Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
C07D 487/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
487Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
Applicants
  • LOXO ONCOLOGY, INC. [US]/[US]
  • ARRAY BIOPHARMA INC. [US]/[US]
  • EARY, Charles Todd [US]/[US]
Inventors
  • EARY, Charles Todd
  • REYNOLDS, Mark
  • SPENCER, Stacey
  • JUENGST, Derrick
  • HACHE, Bruno
  • JIANG, Yutong
  • HAAS, Julia
  • ANDREWS, Steven W.
Agents
  • DORIGO, Andrea
  • LAVOIE, Teresa
Priority Data
62/338,35918.05.2016US
Publication Language English (en)
Filing Language English (EN)
Designated States
Title
(EN) PREPARATION OF (S)-N-(5-((R)-2-(2,5-DIFLUOROPHENYL)PYRROLIDIN-1-YL)PYRAZOLO[1,5-A]PYRIMIDIN-3-Y L)-3-HYDROXYPYRROLIDINE-1-CARBOXAMIDE
(FR) PRÉPARATION DE (S)-N-(5-((R)-2-(2,5-DIFLUOROPHÉNYL)PYRROLIDIN-1-YL)PYRAZOLO[1,5-A]PYRIMIDIN-3-YL)-3-HYDROXYPYRROLIDINE-1-CARBOXAMIDE
Abstract
(EN) Process for preparing (S)-N-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-l- yl)pyrazolo[l,5-a] pyrimidin-3-yl)-3-hydroxypyrrolidine-l-carboxamide (formula I) or a salt thereof by reacting phenyl(5-((R)-2-(2,5- difluorophenyl)pyrrolidin-l-yl)-3,3a-dihydropyrazolo[l,5-a]pyrimidin-3- yl)carbamate or a similar derivative (formula 13) with (S)-pyrrolidin-3- ol (formula 14). Process for preparing phenyl(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-l- yl)-3,3a-dihydropyrazolo[l,5-a]pyrimidin-3-yl)carbamate (formula 13) or a similar derivative by reduction of (R)-5-(2-(2,5-difluorophenyl) pyrrolidin-l-yl)-3-nitropyrazolo[l,5-a]pyrimidine (formula 11) to (R) -5-(2-(2,5-difluorophenyl)pyrrolidin-l-yl)pyrazolo[l,5-a]pyrimidin-3- amine (formula 12). Process for preparing (R)-2-(2,5-difluorophenyl)pyrrolidine(R) -2-hydroxysuccinate (formula 10) by treating (R)-N-((R)-l-(2,5- difluorophenyl)-3-(l,3-dioxan-2-yl)propyl)-2-methylpropane-2- sulfinamide (formula 19) with an acid and a reducing agent. (S)-N-(5-((R)-2-(2,5-difluorophenyl)-pyrrolidin-l-yl)-pyrazolo[l,5- a]pyrimidin-3-yl)-3-hydroxypyrrolidine-l-carboxamide, is a tyrosin kinase (TRK) inhibitor for trearing e.g. cancer.
(FR) L’invention concerne un procédé de préparation de (S)-N-(5-((R)-2-(2,5-difluorophényl)pyrrolidin-1-yl)pyrazolo[1,5-a] pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide (formule I) ou son sel par réaction de phényl(5-((R)-2-(2,5-difluorophényl) pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate ou d’un dérivé similaire (formule 13) avec du (S)-pyrrolidin-3-ol (formule 14). L’invention concerne un procédé de préparation de phényl(5-((R)-2-(2,5-difluorophényl) pyrrolidin-1-yl)-3,3a-dihydropyrazolo[1,5-a]pyrimidin-3-yl)carbamate (formule 13) ou d’un dérivé similaire par réduction de (R)-5-(2-(2,5-difluorophényl))pyrrolidin-1-yl)-3-nitropyrazolo[l,5-a] pyrimidine (formule 11) en (R)-5-(2-(2,5-difluorophényl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-amine (formule 12). L’invention concerne en outre un procédé de préparation de (R)-2-(2,5-difluorophényl)pyrrolidine(R)-2-hydroxysuccinate (formule 10) par traitement de (R)-N-((R)-1-(2,5-difluorophényl))-3-(1,3-dioxan-2-yl)propyl)-2-méthylpropane-2-sulfinamide (formule 19) au moyen d’un acide et d’un agent réducteur. (S)-N-(5-((R)-2-(2,5-difluorophényl)-pyrrolidin-1-yl)-pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-l-carboxamide, est un inhibiteur de la tyrosine kinase (TRK) destiné au traitement du cancer par exemple.
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