NZ764151B2 - Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof - Google Patents

Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof

Info

Publication number
NZ764151B2
NZ764151B2 NZ764151A NZ76415115A NZ764151B2 NZ 764151 B2 NZ764151 B2 NZ 764151B2 NZ 764151 A NZ764151 A NZ 764151A NZ 76415115 A NZ76415115 A NZ 76415115A NZ 764151 B2 NZ764151 B2 NZ 764151B2
Authority
NZ
New Zealand
Prior art keywords
fluoro
compound
preparation
solid forms
pyrazolo
Prior art date
Application number
NZ764151A
Other versions
NZ764151A (en
Inventor
Nadia Ahmad
Jean Damien Charrier
Chris Davis
I Jardi Gorka Etxebarria
Damien Fraysse
Ronald Knegtel
Maninder Panesar
Francoise Pierard
Joanne Pinder
Pierre Henri Storck
Original Assignee
Vertex Pharmaceuticals Incorporated
Filing date
Publication date
Application filed by Vertex Pharmaceuticals Incorporated filed Critical Vertex Pharmaceuticals Incorporated
Publication of NZ764151A publication Critical patent/NZ764151A/en
Publication of NZ764151B2 publication Critical patent/NZ764151B2/en

Links

Classifications

    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The present invention relates to radiolabelled compounds of formula I-A useful as inhibitors of ATR protein kinase. The invention relates to pharmaceutically acceptable compositions comprising the compounds of this invention; methods of treating of various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; intermediates for the preparation of the compounds of this invention; and solid forms of the compounds of this invention.

Claims (18)

1. A compound of Formula I-A: or a pharmaceutically able salt thereof, wherein: each Y1, Y2, Y3, Y4, Y5, Y6, and Y7 is independently en or deuterium; provided at least one of Y1, Y2, Y3, Y4, Y5, Y6, and Y7 is deuterium; each X1, X2, and X4 is independently selected from 12C or 13C; and X3 is independently selected from -12C(O)- or -13C(O)-.
2. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1, Y2, Y3, and Y4 are independently selected from ium or hydrogen; and Y5, Y6, and Y7 are deuterium.
3. The nd of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1 and Y2 are independently selected from deuterium or hydrogen; and Y3, Y4, Y5, Y6, and Y7 are deuterium.
4. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1, Y2, Y5, Y6, and Y7 are independently selected from ium or hydrogen; and Y3 and Y4 are deuterium.
5. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1, Y3, and Y4 are independently selected from deuterium or hydrogen; and Y2, Y5, Y6, and Y7 are deuterium.
6. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein X4 is 13C.
7. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein X1 and X4 are 13C.
8. The compound of claim 1 or the pharmaceutically acceptable salt f, wherein X3 is -13C(O)-.
9. The compound of claim 1 or the pharmaceutically able salt thereof, wherein Y1, Y3, Y4, Y5, Y6, and Y7 are hydrogen; Y2 is deuterium; and X4 is 13C.
10. The compound of claim 1 or the pharmaceutically able salt thereof, wherein Y1, Y2, Y3, and Y4 are hydrogen; Y5, Y6, and Y7 are deuterium; and X1 is 13C.
11. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1, Y3, Y4, Y5, Y6, and Y7 are en; Y2 is deuterium; and X1 is 13C.
12. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1, Y2, Y3, Y5, Y6, and Y7 are hydrogen; Y4 is deuterium; and X1 is 13C.
13. The compound of claim 1 or the pharmaceutically acceptable salt thereof, wherein Y1 is hydrogen; Y2, Y3, Y4, Y5, Y6, and Y7 are deuterium; X2 is 13C; and X3 is -13C(O)-.
14. A compound of Formula I-A: or a pharmaceutically acceptable salt thereof, wherein: each Y1, Y2, Y3, Y4, Y5, Y6, and Y7 is hydrogen; each X1, X2, and X4 is independently selected from 12C or 13C; and X3 is selected from -12C(O)- or -13C(O)-; wherein at least one of X1 and X4 is 13C or wherein X3 is )-.
15. The compound of claim 14 or the pharmaceutically acceptable salt thereof, wherein X4 is 13C.
16. The compound of claim 14 or the pharmaceutically acceptable salt thereof, wherein X1 and X4 are 13C.
17. The compound of claim 14 or the pharmaceutically acceptable salt thereof, wherein X3 is -13C(O)-.
18. The compound of claim 1, ntially herein bed with reference to any one of the Examples and/or
NZ764151A 2015-05-28 Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof NZ764151B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462008277P 2014-06-05 2014-06-05
NZ727649A NZ727649B2 (en) 2014-06-05 2015-05-28 Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof

Publications (2)

Publication Number Publication Date
NZ764151A NZ764151A (en) 2023-12-22
NZ764151B2 true NZ764151B2 (en) 2024-03-26

Family

ID=

Similar Documents

Publication Publication Date Title
MX2020003458A (en) Radiolabelled derivatives of a 2-amino-6-fluoro-n-[5-fluoro-pyrid in-3-yl]- pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, the preparation of said compound and different solid forms thereof.
SG10201804791UA (en) 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, its preparation, different solid forms and radiolabelled derivatives thereof
MX2009012168A (en) Pyrrolopyridine derivatives and their use as bace inhibitors.
WO2017205536A3 (en) Heterocyclic inhibitors of cbp/ep300 and their use in the treatment of cancer
PH12015501517A1 (en) Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease
WO2013049726A3 (en) Processes for making compounds useful as inhibitors of atr kinase
WO2015200481A8 (en) Mnk inhibitors and methods related thereto
WO2010108074A3 (en) Inhibitors of pi3 kinase
WO2009155527A3 (en) Phosphatidylinositol 3 kinase inhibitors
PH12020500201A1 (en) Pyrazolo and triazolo bicyclic compounds as jak kinase inhibitors
WO2013174930A3 (en) 7-oxo-thiazolopyridine carbonic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease
WO2008094992A3 (en) 2-aminopyridine derivatives useful as kinase inhibitors
TW200734311A (en) New compounds
WO2011138751A3 (en) Heterocyclic derivatives as alk inhibitors
WO2012048129A3 (en) Inhibitors of polo-like kinase
WO2012044727A3 (en) Manufacturing process for pyrimidine derivatives
PH12015500211A1 (en) 4-methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes
MX2014003801A (en) Pyrimidin-4-one derivatives and their use in the treatment, amelioration or prevention of a viral disease.
WO2013057251A3 (en) Heteroaryl hydroxamic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease
IN2014MN01756A (en)
WO2011079230A3 (en) Heterocyclic compounds as janus kinase inhibitors
WO2008128009A3 (en) Aminopyrimidines useful as kinase inhibitors
MX2015008288A (en) Pyridone derivatives and their use in the treatment, amelioration or prevention of a viral disease.
WO2014014794A3 (en) Mineralocorticoid receptor antagonists
WO2010140139A3 (en) Crystalline forms of 6-(1h- imadazol- 1-yl) -2-phenylquinazoline