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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
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/2017/201241 International Application No.: PCT/US2017/033257
Publication Date: 23.11.2017 International Filing Date: 18.05.2017
IPC:
C07D 487/04 (2006.01) ,A61K 31/5025 (2006.01) ,A61P 35/00 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
487
Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
02
in which the condensed system contains two hetero rings
04
Ortho-condensed systems
A HUMAN NECESSITIES
61
MEDICAL OR VETERINARY SCIENCE; HYGIENE
K
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
31
Medicinal preparations containing organic active ingredients
33
Heterocyclic compounds
395
having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
495
having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
50
Pyridazines; Hydrogenated pyridazines
5025
ortho- or peri-condensed with heterocyclic ring systems
A HUMAN NECESSITIES
61
MEDICAL OR VETERINARY SCIENCE; HYGIENE
P
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
35
Antineoplastic agents
Applicants:
LOXO ONCOLOGY, INC. [US/US]; 281 Tresser Blvd. 9th Floor Stamford, CT 06901, US
ARRAY BIOPHARMA INC. [US/US]; 3200 Walnut St. Boulder, CO 80301, US
EARY, Charles Todd [US/US]; US
Inventors:
EARY, Charles Todd; US
REYNOLDS, Mark; US
SPENCER, Stacey; US
JUENGST, Derrick; US
HACHE, Bruno; US
JIANG, Yutong; US
HAAS, Julia; US
ANDREWS, Steven W.; US
Agent:
DORIGO, Andrea; US
LAVOIE, Teresa; US
Priority Data:
62/338,35918.05.2016US
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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Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW
African Regional Intellectual Property Organization (ARIPO) (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: English (EN)
Also published as:
UAa201812601AU2017268371CA3024603IN201817047462MYPI 2018001918EP3458456
KR1020190039474BR112018073504ID2019/04669