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 PDFInfo
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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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- 238000000034 method Methods 0.000 title claims 18
- FWCVZAQENIZVMY-UHFFFAOYSA-N 2-hydroxy-6-[[2-(2-propan-2-ylpyrazol-3-yl)pyridin-3-yl]methoxy]benzaldehyde Chemical compound CC(C)N1N=CC=C1C1=NC=CC=C1COC1=CC=CC(O)=C1C=O FWCVZAQENIZVMY-UHFFFAOYSA-N 0.000 title 1
- 230000002194 synthesizing effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 238000005804 alkylation reaction Methods 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 230000003197 catalytic effect Effects 0.000 claims 3
- 230000022244 formylation Effects 0.000 claims 3
- 238000006170 formylation reaction Methods 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000011065 in-situ storage Methods 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical group C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 101150113676 chr1 gene Proteins 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical group [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims 1
- -1 methyl tert-butyl Chemical group 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
Classifications
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- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation 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
- C07C45/65—Preparation 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- 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
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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.
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 |
Publications (1)
Publication Number | Publication Date |
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HRP20211193T1 true HRP20211193T1 (hr) | 2021-10-29 |
Family
ID=60268009
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20211193TT HRP20211193T1 (hr) | 2016-05-12 | 2021-07-26 | Postupak za sintezu 2-hidroksi-6-((2-(1-izopropil-1h-pirazol-5-yl)-piridin-3-yl)metoksi)benzaldehida |
Country Status (20)
Country | Link |
---|---|
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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US9012450B2 (en) | 2011-12-28 | 2015-04-21 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
ES2864707T3 (es) | 2013-03-15 | 2021-10-14 | Global Blood Therapeutics Inc | Compuestos y usos de los mismos para la modulación de la hemoglobina |
US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
EA034922B1 (ru) | 2013-03-15 | 2020-04-07 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
KR101971385B1 (ko) | 2013-03-15 | 2019-04-22 | 글로벌 블러드 테라퓨틱스, 인크. | 헤모글로빈 조정을 위한 화합물 및 이의 용도 |
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EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
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NZ748072A (en) | 2017-03-20 | 2020-06-26 | Forma Therapeutics Inc | Pyrrolopyrrole compositions as pyruvate kinase (pkr) activators |
MA53668A (fr) | 2018-09-19 | 2021-09-15 | Forma Therapeutics Inc | Traitement de la drépanocytose avec un composé activant la pyruvate kinase r |
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US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
CA3120380A1 (en) | 2018-11-19 | 2020-05-28 | Global Blood Therapeutics, Inc. | 2-formyl-3-hydroxyphenyloxymethyl compounds capable of modulating hemoglobin |
BR112021012311A2 (pt) | 2018-12-21 | 2021-09-08 | Crystal Pharma, S.A.U. | Uso de um composto intermediário, processo para preparar voxelotor e composto intermediário |
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