PE20231553A1 - Proceso para preparar carbamato de metil {4,6-diamino-2-[5-fluoro-1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il} - Google Patents
Proceso para preparar carbamato de metil {4,6-diamino-2-[5-fluoro-1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}Info
- Publication number
- PE20231553A1 PE20231553A1 PE2022002944A PE2022002944A PE20231553A1 PE 20231553 A1 PE20231553 A1 PE 20231553A1 PE 2022002944 A PE2022002944 A PE 2022002944A PE 2022002944 A PE2022002944 A PE 2022002944A PE 20231553 A1 PE20231553 A1 PE 20231553A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- dmso
- formula
- fluorobenzyl
- pyrazolo
- Prior art date
Links
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
REFERIDO A UN PROCESO PARA PREPARAR CARBAMATO DE METIL {4,6-DIAMINO-2-[5-FLUORO-1-(2-FLUOROBENCIL)-1H-PIRAZOLO[3,4-B]PIRIDIN-3-IL]PIRIMIDIN-5-IL} DE FORMULA (I) EN FORMA CRISTALINA DE LA MODIFICACION I, DONDE EL DIFRACTOGRAMA DE RAYOS X DE DICHO COMPUESTO PRESENTA MAXIMOS PICO DE ANGULO 2 THETA EN 5.9, 6.9, 22.7; EN DONDE EL CLORHIDRATO DEL COMPUESTO (I) SE PREPARA CALENTANDO EL COMPUESTO DE FORMULA (IX) EN TETRAHIDROFURANO COMO SOLVENTE, AGREGANDO 1,0 EQ. A 1,2 EQ. CLOROFORMATO DE METILO, AGITANDO DENTRO DE UN TIEMPO DE REACCION DE 1H A 10H, Y AISLANDO EL CLORHIDRATO DEL COMPUESTO (I), LUEGO EL SOLVATO DE DI-DMSO DEL COMPUESTO DE FORMULA (I) SE PREPARA DISOLVIENDO EL CLORHIDRATO DEL COMPUESTO DE LA FORMULA (I) EN DMSO, ANADIENDO TRI-N-BUTILAMINA Y CARBONO ACTIVADO, RETIRANDO EL CARBONO ACTIVADO, CRISTALIZANDO EL SOLVATO DE DI-DMSO POR ENFRIAMIENTO Y ANADIENDO ACETATO DE ETILO, AISLANDO EL DI-DMSO EN FORMA CRISTALIZADA, Y LAVANDO CON UNA MEZCLA DE DMSO Y ACETATO DE ETILO; POSTERIORMENTE SE PREPARA LA FORMA CRISTALINA DE LA MODIFICACION I DEL COMPUESTO (I).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20180229.5A EP3925953A1 (en) | 2020-06-16 | 2020-06-16 | Process for preparing methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate |
| PCT/EP2021/066019 WO2021254981A1 (en) | 2020-06-16 | 2021-06-15 | Process for preparing methyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20231553A1 true PE20231553A1 (es) | 2023-10-03 |
Family
ID=71103286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2022002944A PE20231553A1 (es) | 2020-06-16 | 2021-06-15 | Proceso para preparar carbamato de metil {4,6-diamino-2-[5-fluoro-1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il} |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20230219952A1 (es) |
| EP (2) | EP3925953A1 (es) |
| JP (1) | JP7783201B2 (es) |
| KR (1) | KR20230025862A (es) |
| CN (3) | CN119954803A (es) |
| AR (1) | AR122635A1 (es) |
| AU (1) | AU2021294233A1 (es) |
| BR (1) | BR112022023035A2 (es) |
| CA (1) | CA3187147A1 (es) |
| CL (1) | CL2022003600A1 (es) |
| CO (1) | CO2022018232A2 (es) |
| CR (1) | CR20220647A (es) |
| IL (1) | IL298913A (es) |
| MX (1) | MX2022015952A (es) |
| PE (1) | PE20231553A1 (es) |
| TW (1) | TWI889841B (es) |
| WO (1) | WO2021254981A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI830835B (zh) * | 2018-12-17 | 2024-02-01 | 德商亞德維瑞醫藥有限公司 | 具改善性質之{4,6-二胺基-2-[5-氟-1-(2-氟芐基)-1H-吡唑並[3,4-b]吡啶-3-基]嘧啶-5-基}胺基甲酸甲酯活性化合物產物、其製造及調配物 |
| ES2956054B2 (es) * | 2022-05-03 | 2024-07-01 | Moehs Iberica Sl | 2-(5-FLUORO-1-(2-FLUOROBENCIL)-1H-PIRAZOLO[3,4-b]PIRIDIN-3-IL)-5-NITROSOPIRIMIDIN-4,6-DIAMINA O UNA SAL DE LA MISMA, PROCEDIMIENTO PARA SU PREPARACION Y SU USO EN LA SINTESIS DE VERICIGUAT |
| CN115043835B (zh) * | 2022-06-17 | 2023-05-09 | 常州制药厂有限公司 | 一种维立西呱的精制纯化方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19834044A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Neue substituierte Pyrazolderivate |
| DE10021069A1 (de) * | 2000-04-28 | 2001-10-31 | Bayer Ag | Substituiertes Pyrazolderivat |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| ES2553035T3 (es) * | 2009-11-27 | 2015-12-03 | Adverio Pharma Gmbh | Procedimiento para la preparación de {4,6-diamino-2-[1-(2-fluorobencil)-1H-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}-metilcarbamato de metilo y su purificación para el uso como principio activo farmacéutico |
| UY33041A (es) | 2009-11-27 | 2011-06-30 | Bayer Schering Pharma Aktienegesellschaft | Procedimiento para la preparaciòn de {4,6-diamino-2-[1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}carbamato de metilo y su purificaciòn para el uso como principio activo farmacèutico |
| DE102010021637A1 (de) * | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| NZ603799A (en) * | 2010-05-26 | 2014-10-31 | Bayer Ip Gmbh | The use of sgc stimulators, sgc activators, alone and combinations with pde5 inhibitors for the treatment of systemic sclerosis (ssc). |
| DE102010040233A1 (de) * | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| EP2751106B1 (de) * | 2011-09-02 | 2017-10-18 | Bayer Intellectual Property GmbH | Substituierte annellierte pyrimidine und ihre verwendung |
| EP2594197A1 (en) * | 2011-11-21 | 2013-05-22 | Technische Universität München | Tracking system and method |
| EA031602B1 (ru) * | 2011-11-25 | 2019-01-31 | Адверио Фарма Гмбх | Способы получения альдегидов |
| TWI830835B (zh) | 2018-12-17 | 2024-02-01 | 德商亞德維瑞醫藥有限公司 | 具改善性質之{4,6-二胺基-2-[5-氟-1-(2-氟芐基)-1H-吡唑並[3,4-b]吡啶-3-基]嘧啶-5-基}胺基甲酸甲酯活性化合物產物、其製造及調配物 |
| JP7471306B2 (ja) | 2019-01-22 | 2024-04-19 | アドヴェリオ・ファーマ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 4-(2,2,3,3-テトラフルオロプロピル)モルホリンを製造する方法 |
-
2020
- 2020-06-16 EP EP20180229.5A patent/EP3925953A1/en not_active Ceased
-
2021
- 2021-06-11 TW TW110121384A patent/TWI889841B/zh active
- 2021-06-15 CN CN202510143869.XA patent/CN119954803A/zh active Pending
- 2021-06-15 EP EP21732878.0A patent/EP4165028A1/en active Pending
- 2021-06-15 CR CR20220647A patent/CR20220647A/es unknown
- 2021-06-15 BR BR112022023035A patent/BR112022023035A2/pt unknown
- 2021-06-15 US US18/001,834 patent/US20230219952A1/en active Pending
- 2021-06-15 CA CA3187147A patent/CA3187147A1/en active Pending
- 2021-06-15 IL IL298913A patent/IL298913A/en unknown
- 2021-06-15 CN CN202510143868.5A patent/CN119954802A/zh active Pending
- 2021-06-15 JP JP2022577364A patent/JP7783201B2/ja active Active
- 2021-06-15 PE PE2022002944A patent/PE20231553A1/es unknown
- 2021-06-15 WO PCT/EP2021/066019 patent/WO2021254981A1/en not_active Ceased
- 2021-06-15 KR KR1020237001194A patent/KR20230025862A/ko active Pending
- 2021-06-15 CN CN202180043045.5A patent/CN115697978B/zh active Active
- 2021-06-15 MX MX2022015952A patent/MX2022015952A/es unknown
- 2021-06-15 AU AU2021294233A patent/AU2021294233A1/en active Pending
- 2021-06-16 AR ARP210101637A patent/AR122635A1/es unknown
-
2022
- 2022-12-15 CO CONC2022/0018232A patent/CO2022018232A2/es unknown
- 2022-12-15 CL CL2022003600A patent/CL2022003600A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL298913A (en) | 2023-02-01 |
| CN115697978A (zh) | 2023-02-03 |
| EP4165028A1 (en) | 2023-04-19 |
| TWI889841B (zh) | 2025-07-11 |
| EP3925953A1 (en) | 2021-12-22 |
| TW202214625A (zh) | 2022-04-16 |
| CL2022003600A1 (es) | 2023-04-28 |
| BR112022023035A2 (pt) | 2022-12-27 |
| CR20220647A (es) | 2023-03-03 |
| AR122635A1 (es) | 2022-09-28 |
| CN119954803A (zh) | 2025-05-09 |
| KR20230025862A (ko) | 2023-02-23 |
| AU2021294233A1 (en) | 2022-12-22 |
| MX2022015952A (es) | 2023-01-24 |
| US20230219952A1 (en) | 2023-07-13 |
| WO2021254981A1 (en) | 2021-12-23 |
| CA3187147A1 (en) | 2021-12-23 |
| CN119954802A (zh) | 2025-05-09 |
| CN115697978B (zh) | 2025-02-28 |
| CO2022018232A2 (es) | 2022-12-20 |
| JP7783201B2 (ja) | 2025-12-09 |
| JP2023530142A (ja) | 2023-07-13 |
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