HRP20201984T1 - Priprema (s)-n-(5-((r)-2-(2,5-difluorofenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida - Google Patents
Priprema (s)-n-(5-((r)-2-(2,5-difluorofenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida Download PDFInfo
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- HRP20201984T1 HRP20201984T1 HRP20201984TT HRP20201984T HRP20201984T1 HR P20201984 T1 HRP20201984 T1 HR P20201984T1 HR P20201984T T HRP20201984T T HR P20201984TT HR P20201984 T HRP20201984 T HR P20201984T HR P20201984 T1 HRP20201984 T1 HR P20201984T1
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- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 32
- 150000003839 salts Chemical class 0.000 claims 17
- 238000000034 method Methods 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 239000003638 chemical reducing agent Substances 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
Classifications
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- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (11)
1. Postupak za pripremu spoja formule (I):
[image]
ili njegove soli,
koji obuhvaća:
(a) obradu izoliranog spoja formule 13:
[image]
ili njegove soli spojem formule 14:
[image]
ili njegovom solju da bi se oblikovao spoj formule (I);
i
(b) izborno formiranje soli spoja formule (I);
gdje je X halogen, C1-C6 alkoksi, C6-C10 ariloksi ili 5-člani heteroaril koji sadrži najmanje jedan dušik direktno vezan za C=O spoja formule 13, svaki izborno supstituiran jednim ili većim brojem supstituenata neovisno odabranih iz grupe koja se sastoji od C1-C6 alkila, C1-C6 haloalkila, halogena, CN, OH, C1-C6 alkoksi, i NR1R2, gdje je svaki od R1 i R2 neovisno odabran od vodika i C1-C6 alkila.
2. Postupak prema patentnom zahtjevu 1, koji dodatno obuhvaća korak pripreme spoja formule 13 obradom izoliranog spoja formule 12:
[image]
ili njegove soli, spojem koji ima formulu: XC(O)Z, kako bi se oblikovao spoj formule 13 ili njegova sol, pri čemu je Z odlazeća grupa odabrana od halogena, C1-C6 alkoksi, C6-C10 ariloksi i 5-članog heteroarila koji sadrži najmanje jedan dušik direktno vezan za C=O u XC(O)Z, svaki izborno supstituiran jednim ili većim brojem supstituenata neovisno odabranih iz grupe koja se sastoji od C1-C6 alkila, C1-C6 haloalkila, halogena, CN, OH, C1-C6 alkoksi, i NR5R6, gdje je svaki od R5 i R6 neovisno odabran od vodika i C1-C6 alkila;
pod uvjetom da ako je Z izborno supstituirani C1-C6 alkoksi, izborno supstituirani C6-C10 ariloksi, ili izborno supstituirani 5-člani heteroaril, tada su Z i X isti.
3. Postupak prema bilo kojem od patentnih zahtjeva 1 ili 2, koji dodatno obuhvaća korak pripreme spoja formule 12 obradom spoja formule 11:
[image]
ili njegove soli, sistemom za redukciju nitro grupe kako bi se oblikovao spoj formule 12 ili njegova sol;
i izoliranje spoja formule 12 ili njegove soli.
4. Postupak prema patentnom zahtjevu 3, gdje sistem za redukciju nitro grupe sadrži H2 i metal.
5. Postupak prema bilo kojem od patentnih zahtjeva 1-4, koji dodatno obuhvaća korak pripreme spoja formule 11 obradom spoja formule 5,
[image]
ili njegove soli, spojem formule 10:
[image]
ili njegovom solju, kako bi se oblikovao spoj formule 11, ili njegova sol.
6. Postupak prema bilo kojem od patentnih zahtjeva 1-5 koji dodatno obuhvaća korak pripreme spoja formule 10 obradom spoja formule 19:
[image]
ili njegove soli, kiselinom u prisustvu prvog reducirajućeg sredstva, da bi se oblikovao spoj formule 10 ili njegova sol,
pri čemu su R3 i R4 neovisno C1-4 alkil, ili mogu zajedno formirati petočlani, šestočlani ili sedmočlani prsten.
7. Postupak prema patentnom zahtjevu 6, gdje prvo reducirajuće sredstvo sadrži silan.
8. Postupak prema bilo kojem od patentnih zahtjeva 1-7, koji dodatno obuhvaća korak pripreme spoja formule 19 obradom spoja formule 17:
[image]
sistemom reagenasa koji sadrži:
(a)
(i) spoj koji ima formulu:
[image]
gdje je Y halogen, i
(ii) drugo reducirajuće sredstvo; ili
(b)
spoj koji ima formulu:
[image]
gdje M predstavlja M1 pri čemu je M1 monovalentni metal, ili M predstavlja M2Y, gdje je Y halogen, a M2 je divalentni metal.
9. Postupak koji obuhvaća korak obrade spoja formule 17:
[image]
sistemom reagenasa koji sadrži:
(a)
(i) spoj koji ima formulu:
[image]
gdje je Y halogen i
(ii) reducirajuće sredstvo; ili
(b)
spoj koji ima formulu:
[image]
gdje M predstavlja M1 pri čemu je M1 monovalentni metal, ili M predstavlja M2Y, gdje je Y halogen, a M2 je divalentni metal; kako bi se dobio spoj formule 19,
[image]
ili njegova sol, gdje su R3 i R4 neovisno C1-4 alkil, ili mogu zajedno formirati petočlani, šestočlani ili sedmočlani prsten.
10. Postupak prema patentnom zahtjevu 9, koji dalje obuhvaća korak obrade spoja formule 19 kiselinom u prisustvu reducirajućeg sredstva, kako bi se oblikovao spoj formule 10,
[image]
ili njegova sol.
11. Spoj koje ima strukturu formule 19:
[image]
ili njegova sol,
gdje su R3 i R4 neovisno C1-4 alkil, ili mogu zajedno formirati petočlani, šestočlani ili sedmočlani prsten.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662338359P | 2016-05-18 | 2016-05-18 | |
EP17726442.1A EP3458456B1 (en) | 2016-05-18 | 2017-05-18 | Preparation of (s)-n-(5-((r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide |
PCT/US2017/033257 WO2017201241A1 (en) | 2016-05-18 | 2017-05-18 | 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 |
Publications (1)
Publication Number | Publication Date |
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HRP20201984T1 true HRP20201984T1 (hr) | 2021-04-16 |
Family
ID=58794189
Family Applications (2)
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HRP20230704TT HRP20230704T1 (hr) | 2016-05-18 | 2017-05-18 | Priprava (s)-n-(5-((r)-2-(2,5-difluorfenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida |
HRP20201984TT HRP20201984T1 (hr) | 2016-05-18 | 2020-12-10 | Priprema (s)-n-(5-((r)-2-(2,5-difluorofenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida |
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HRP20230704TT HRP20230704T1 (hr) | 2016-05-18 | 2017-05-18 | Priprava (s)-n-(5-((r)-2-(2,5-difluorfenil)pirolidin-1-il)pirazolo[1,5-a]pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida |
Country Status (28)
Country | Link |
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US (1) | US11214571B2 (hr) |
EP (2) | EP3458456B1 (hr) |
JP (1) | JP7443057B2 (hr) |
KR (1) | KR102566858B1 (hr) |
CN (1) | CN110049987B (hr) |
AU (1) | AU2017268371B2 (hr) |
BR (1) | BR112018073504A2 (hr) |
CA (1) | CA3024603A1 (hr) |
CL (1) | CL2018003264A1 (hr) |
CO (1) | CO2018013015A2 (hr) |
DK (2) | DK3458456T3 (hr) |
ES (2) | ES2952056T3 (hr) |
FI (1) | FI3800189T3 (hr) |
HR (2) | HRP20230704T1 (hr) |
HU (2) | HUE053643T2 (hr) |
IL (1) | IL262964B (hr) |
LT (2) | LT3800189T (hr) |
MX (1) | MX2018014116A (hr) |
PE (1) | PE20190437A1 (hr) |
PL (2) | PL3800189T3 (hr) |
PT (2) | PT3800189T (hr) |
RS (2) | RS64698B1 (hr) |
RU (1) | RU2745953C2 (hr) |
SG (1) | SG11201810245WA (hr) |
SI (2) | SI3458456T1 (hr) |
UA (1) | UA127826C2 (hr) |
WO (1) | WO2017201241A1 (hr) |
ZA (1) | ZA201808534B (hr) |
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