HRP20211193T1 - Postupak za sintezu 2-hidroksi-6-((2-(1-izopropil-1h-pirazol-5-yl)-piridin-3-yl)metoksi)benzaldehida - Google Patents

Postupak za sintezu 2-hidroksi-6-((2-(1-izopropil-1h-pirazol-5-yl)-piridin-3-yl)metoksi)benzaldehida Download PDF

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HRP20211193T1
HRP20211193T1 HRP20211193TT HRP20211193T HRP20211193T1 HR P20211193 T1 HRP20211193 T1 HR P20211193T1 HR P20211193T T HRP20211193T T HR P20211193TT HR P20211193 T HRP20211193 T HR P20211193T HR P20211193 T1 HRP20211193 T1 HR P20211193T1
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compound
alkyl
image
process according
acid
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HRP20211193TT
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Zhe Li
Nathan GUZ
Yiyang SHAO
Julieana COCUZ
Markus Frieser
George Petros Yiannikouros
Liang LIAO
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Global Blood Therapeutics, Inc.
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Publication of HRP20211193T1 publication Critical patent/HRP20211193T1/hr

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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 two hetero rings
    • C07D401/04Heterocyclic 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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439Non 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/52Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (16)

1. Postupak za sintezu Spoja (I): [image] naznačen time, da postupak obuhvaća: Korak (i): obrađivanje spoja formule (2): [image] pri čemu svaki R je -CH(CH2R1)-OR2 ili tetrahidropiran-2-il opcionalno supstituiran s jednim, dva ili tri alkila; i pritom R1 je vodik ili alkil, i R2 je alkil; s kiselinom tako da se dobije spoj (1): [image] Korak (ii): reakcija spoja (1) sa spojem formule (3): [image] gdje LG je izlazna skupina pod alkilacijskim reakcijskim uvjetima tako da se dobije Spoj (I); i Korak (iii): opcionalno kristalizacija Spoja (I) iz Koraka (ii) od heptana i metil terc-butil etera na 45° +/-5 °C do 55° +/-5 °C.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da nadalje obuhvaća formilaciju spoja formule (4): [image] kako bi se dobio spoj formule (2): [image] pri čemu svaki R u spoju formule (2) i (4) je -CH(CH2R1)-OR2 ili tetrahidropiran-2-il opcionalno supstituiran s jednim, dva ili tri alkila; i R1 je vodik ili alkil, i R2 je alkil.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da nadalje obuhvaća reakciju spoja (5): [image] s vinil eterom formule CHR1=CHOR2 (gdje R1 je vodik ili alkil i R2 je alkil), ili 3,4-dihidro-2H-piranom opcionalno supstituiranim s jednim, dva ili tri alkila, u prisutnosti slabe kiseline kako bi se dobio spoj formule (4): [image] pri čemu svaki R je -CH(CH2R1)-OR2 (gdje R1 je vodik ili alkil i R2 je alkil) ili tetrahidropiran-2-il opcionalno supstituiran s jednim, dva ili tri alkila.
4. Postupak prema patentnom zahtjevu 3, naznačen time, da se spoj (4) obrađuje in situ s formilacijskim agensom tako da se dobije spoj (2).
5. Postupak prema patentnom zahtjevu 1 ili 2, naznačen time, da se spoj (2) obrađuje in situ s kiselinom tako da se dobije spoj (1).
6. Postupak prema bilo kojem od patentnih zahtjeva 1 do 5, u kojem se Spoj (I) kristalizira od heptana i metil terc-butil estera na 45° +/-5 °C do 55° +/-5 °C tako da daje Spoj (I) u bitno čistom Obliku II, naznačen time, da uzorak XRPD rendgenske difrakcije na prahu (Cu Kα radijacije) ima maksimum na jednom ili više od 13,37° 2θ, 14,37° 2θ, 19,95° 2θ ili 23,92° 2θ (od kojih je svaki ± 0,2° 2θ).
7. Postupak prema patentnom zahtjevu 6, naznačen time, da se Spoj (I) kristalizira na 45° +/-5 °C do 55° +/-5 °C tako da daje Spoj (I) pri čemu je najmanje 95% po masi od Spoja (I) u Obliku II.
8. Postupak prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da LG jest klor.
9. Postupak prema bilo kojem od patentnih zahtjeva 1 do 8, naznačen time, da R jest -CH(CH3)-O-CH2CH3.
10. Postupak prema bilo kojem od patentnih zahtjeva 1 do 9, naznačen time, da kiselina za odstranjivanje R skupina je anorganska kiselina.
11. Postupak prema patentnom zahtjevu 10, naznačen time, da kiselina jest klorovodična kiselina.
12. Postupak prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da LG je klor i alkilacijska reakcija se izvodi u N-metil-2-pirolidinonu u prisutnosti natrijevog bikarbonata i katalitičke količine Nal.
13. Postupak prema bilo kojem od patentnih zahtjeva 1 do 11, u kojemu LG je klor i alkilacijska reakcija se izvodi u N-metil-2-pirolidinonu u prisutnosti natrijevog bikarbonata i katalitičke količine Nal i Spoj (I) se kristalizira od reakcijske smjese putem dodavanja vode na 40 °C do 50 °C tako da daje bitno čisti Oblik I, naznačen time, da uzorak XRPD rendgenske difrakcije na prahu (Cu Kα radijacije) ima maksimum na jednom ili više od 12,82° 2θ, 15,74° 2θ, 16,03° 2θ, 16,63° 2θ, 17,60° 2θ, 25,14° 2θ, 25,82° 2θ i 26,44° 2θ (od kojih je svaki ± 0,2° 2θ).
14. Postupak prema bilo kojem od patentnih zahtjeva 1 do 11, u kojemu LG je klor i alkilacijska reakcija se izvodi u N-metil-2-pirolidinonu u prisutnosti natrijevog bikarbonata i katalitičke količine Nal i Spoj (I) se kristalizira od reakcijske smjese putem dodavanja vode na 40 °C do 46 °C tako da daje Spoj (I) koji je najmanje 95% po masi Oblik I, naznačen time, da uzorak XRPD rendgenske difrakcije na prahu (Cu Kα radijacije) ima maksimum na jednom ili više od 12,82° 2θ, 15,74° 2θ, 16,03° 2θ, 16,63° 2θ, 17,60° 2θ, 25,14° 2θ, 25,82° 2θ i 26,44° 2θ (od kojih je svaki ± 0,2° 2θ).
15. Postupak prema bilo kojem od patentnih zahtjeva 3 do 14, naznačen time, da slaba kiselina jest piridinijev tosilat.
16. Postupak prema bilo kojem od patentnih zahtjeva 2 do 15, naznačen time, da formilacijski agens je n-BuLi i DMF.
HRP20211193TT 2016-05-12 2021-07-26 Postupak za sintezu 2-hidroksi-6-((2-(1-izopropil-1h-pirazol-5-yl)-piridin-3-yl)metoksi)benzaldehida HRP20211193T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662335583P 2016-05-12 2016-05-12
PCT/US2017/032104 WO2017197083A1 (en) 2016-05-12 2017-05-11 Process for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde
EP17796828.6A EP3454854B1 (en) 2016-05-12 2017-05-11 Process for synthesizing 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)-pyridin-3-yl)methoxy)benzaldehyde

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HRP20211193T1 true HRP20211193T1 (hr) 2021-10-29

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US (5) US10077249B2 (hr)
EP (2) EP3909941A1 (hr)
JP (2) JP7398193B2 (hr)
KR (3) KR20220139437A (hr)
CN (2) CN109152770A (hr)
AR (1) AR108435A1 (hr)
AU (2) AU2017261730B2 (hr)
CA (1) CA3023662A1 (hr)
DK (1) DK3454854T3 (hr)
EA (2) EA037014B1 (hr)
ES (1) ES2881426T3 (hr)
HR (1) HRP20211193T1 (hr)
HU (1) HUE055045T2 (hr)
IL (3) IL284406B2 (hr)
MX (3) MX2018013099A (hr)
PL (1) PL3454854T3 (hr)
PT (1) PT3454854T (hr)
SG (2) SG11201809344QA (hr)
TW (3) TWI663160B (hr)
WO (1) WO2017197083A1 (hr)

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