AR126268A1 - Síntesis de una sal de bis-mesilato de 4-amino-n-(1-((3-cloro-2-fluorfenil)amino)-6-metilisoquinolin-5-il)tieno[3,2-d]pirimidin-7-carboxamida y sus intermediarios - Google Patents
Síntesis de una sal de bis-mesilato de 4-amino-n-(1-((3-cloro-2-fluorfenil)amino)-6-metilisoquinolin-5-il)tieno[3,2-d]pirimidin-7-carboxamida y sus intermediariosInfo
- Publication number
- AR126268A1 AR126268A1 ARP220101697A ARP220101697A AR126268A1 AR 126268 A1 AR126268 A1 AR 126268A1 AR P220101697 A ARP220101697 A AR P220101697A AR P220101697 A ARP220101697 A AR P220101697A AR 126268 A1 AR126268 A1 AR 126268A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- amino
- methylisoquinolin
- thieno
- carboxamide
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 238000005810 carbonylation reaction Methods 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- -1 hexafluorophosphate Chemical compound 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
Abstract
Un proceso de elaboración de una sal de bis-mesilato de fórmula (1b) del inhibidor pan-RAF 4-amino-n-(1-((3-cloro-2-fluorofenil)amino)-6-metilisoquinolin-5-il)tieno[3,2-d]pirimidin-7-carboxamida. El proceso comprende numerosas reacciones eficaces clave, que incluyen una reacción de carbonilación catalizada por Pd robusta y ampliable para generar tienopirimidina de fórmula (2) y una reducción de grupo nitro catalizada por Pt/V/C altamente quimioselectiva para acceder al penúltimo intermediario de fórmula (7). El acoplamiento de amida final de fórmula (7) y de fórmula (2) se logró mediante un protocolo leve y seguro que usa N,N,N,N-tetrametilcloroformamidinio hexafluorofosfato (TCFH) como el agente de acoplamiento para producir un aducto 1:1 de la base libre y THF. El aducto proporcionó el compuesto de fórmula (1b) con excelente rendimiento, pureza y estabilidad de forma en una escala de producción de múltiples kilogramos después de reacción con MsOH y recristalización. Es posible producir un compuesto que tiene más de 95% de pureza mediante los métodos.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2021103873 | 2021-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR126268A1 true AR126268A1 (es) | 2023-10-04 |
Family
ID=82701899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP220101697A AR126268A1 (es) | 2021-06-30 | 2022-06-28 | Síntesis de una sal de bis-mesilato de 4-amino-n-(1-((3-cloro-2-fluorfenil)amino)-6-metilisoquinolin-5-il)tieno[3,2-d]pirimidin-7-carboxamida y sus intermediarios |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP4363424A1 (es) |
| KR (1) | KR20240027678A (es) |
| CN (1) | CN117580840A (es) |
| AR (1) | AR126268A1 (es) |
| AU (1) | AU2022303488A1 (es) |
| CA (1) | CA3225147A1 (es) |
| TW (1) | TW202311265A (es) |
| WO (1) | WO2023278981A1 (es) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2797927T (pt) | 2011-12-30 | 2019-10-30 | Hanmi Pharm Ind Co Ltd | Derivados de tieno[3,2-d]pirimidina com atividade inibidora de proteínas-cinases |
| EP3717489B1 (en) * | 2017-11-30 | 2023-12-27 | Hanmi Pharm. Co., Ltd. | Salts of 4-amino-n-(1-((3-chloro-2-fluorophenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide, and crystalline forms thereof |
-
2022
- 2022-06-28 KR KR1020247000357A patent/KR20240027678A/ko unknown
- 2022-06-28 CN CN202280046592.3A patent/CN117580840A/zh active Pending
- 2022-06-28 TW TW111124105A patent/TW202311265A/zh unknown
- 2022-06-28 WO PCT/US2022/073195 patent/WO2023278981A1/en active Application Filing
- 2022-06-28 AU AU2022303488A patent/AU2022303488A1/en active Pending
- 2022-06-28 CA CA3225147A patent/CA3225147A1/en active Pending
- 2022-06-28 AR ARP220101697A patent/AR126268A1/es unknown
- 2022-06-28 EP EP22747552.2A patent/EP4363424A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2022303488A1 (en) | 2024-01-04 |
| CA3225147A1 (en) | 2023-01-05 |
| WO2023278981A1 (en) | 2023-01-05 |
| EP4363424A1 (en) | 2024-05-08 |
| CN117580840A (zh) | 2024-02-20 |
| KR20240027678A (ko) | 2024-03-04 |
| US20230028651A1 (en) | 2023-01-26 |
| TW202311265A (zh) | 2023-03-16 |
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