HRP20211070T1 - 6-bromo-3-hidroksi-2-pirazinkarboksamid kristal i postupak za proizvodnju - Google Patents
6-bromo-3-hidroksi-2-pirazinkarboksamid kristal i postupak za proizvodnju Download PDFInfo
- Publication number
- HRP20211070T1 HRP20211070T1 HRP20211070TT HRP20211070T HRP20211070T1 HR P20211070 T1 HRP20211070 T1 HR P20211070T1 HR P20211070T T HRP20211070T T HR P20211070TT HR P20211070 T HRP20211070 T HR P20211070T HR P20211070 T1 HRP20211070 T1 HR P20211070T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrazinecarboxamide
- hydroxy
- bromo
- crystal
- acid
- Prior art date
Links
- KZBREXQQUFIWKD-UHFFFAOYSA-N 5-bromo-2-oxo-1h-pyrazine-3-carboxamide Chemical compound NC(=O)C1=NC(Br)=CN=C1O KZBREXQQUFIWKD-UHFFFAOYSA-N 0.000 title claims 14
- 239000013078 crystal Substances 0.000 title claims 9
- 238000004519 manufacturing process Methods 0.000 title claims 8
- SZPBAPFUXAADQV-UHFFFAOYSA-N 2-oxo-1h-pyrazine-3-carboxamide Chemical compound NC(=O)C1=NC=CN=C1O SZPBAPFUXAADQV-UHFFFAOYSA-N 0.000 claims 9
- 238000000634 powder X-ray diffraction Methods 0.000 claims 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (10)
1. Postupak za proizvodnju 6-bromo-3-hidroksi-2-pirazinkarboksamida, naznačen time, da obuhvaća:
(1) priprema suspenzije koja sadržava 3-hidroksi-2-pirazinkarboksamid i otapalo; i
(2) dodavanje broma suspenziji dobivenoj u koraku (1);
pri čemu
omjer sadržaja vode koja je sadržana u suspenziji dobivenoj u koraku (1) je manji od 5 % težinskog udjela u odnosu na 3-hidroksi-2-pirazinkarboksamid; a
omjer sadržaja 3-hidroksi-2-pirazinkarboksamida uključenog u 6-bromo-3-hidroksi-2- pirazinkarboksamid manji je od 300 ppm.
2. Postupak proizvodnje u skladu s patentnim zahtjevom 1, naznačen time, da nadalje obuhvaća:
(3) dobivanje kristala 6-bromo-3-hidroksi-2-pirazinkarboksamida koji ima kutove difrakcije od 5,5, 20,1, 23,7, 26,7, 27,5 i 28,1 ° u odnosu na 2θ u rendgenskoj difrakciji praha.
3. Postupak proizvodnje u skladu s patentnim zahtjevom 1, naznačen time, da nadalje obuhvaća:
(3) dobivanje kristala 6-bromo-3-hidroksi-2-pirazinkarboksamida koji ima kutove difrakcije od 5,5, 20,1, 23,7, 26,7, 27,5 i 28,1 ° u odnosu na 2θ u rendgenskoj difrakciji praha ;
(4) reakcija kristala dobivenog u koraku (3) s bazom, da se dobije sol 6-bromo-3- hidroksi-2-pirazinkarboksamida; i
(5) reakcija soli dobivene u koraku (4) s kiselinom, da se dobije kristal 6-bromo- 3-hidroksi-2-pirazinkarboksamida koji ima kutove difrakcije 7,1, 21,4, 25,2, 25,7, 27,1 i 28,8 ° u odnosu na 2θ u rendgenskoj difrakciji praha.
4. Postupak proizvodnje u skladu s patentnim zahtjevom 3, naznačen time, da:
baza za upotrebu u koraku (4) je jedna ili više baza odabranih između natrijevog hidroksida, natrijevog hidrogen karbonata i kalijevog hidroksida; a
kiselina za upotrebu u koraku (5) je jedna ili više kiselina odabranih između solne kiseline, dušične kiseline i sumporne kiseline.
5. Postupak proizvodnje u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time, da je 3-hidroksi-2-pirazinkarboksamid namijenjen za upotrebu u koraku (1) bezvodni oblik 3-hidroksi-2-pirazinkarboksamida.
6. Postupak za proizvodnju 6-bromo-3-hidroksi-2-pirazinkarboksamida, naznačen time, da obuhvaća:
(4) reakciju kristala 6-bromo-3-hidroksi-2-pirazinkarboksamida koji ima kutove difrakcije od 5,5, 20,1, 23,7, 26,7, 27,5 i 28,1 ° u odnosu na 2θ u rendgenskoj difrakciji praha s bazom da se dobije sol 6-bromo-3-hidroksi-2- pirazinkarboksamida; i
(5) reakcija soli dobivene u koraku (4) s kiselinom da se dobije kristal 6-bromo-3- hidroksi-2-pirazinkarboksamida koji ima kutove difrakcije od 7,1, 21,4, 25,2, 25,7, 27,1 i 28,8 ° u odnosu na 2θ u rendgenskoj difrakciji praha,
pri čemu je omjer sadržaja 3-hidroksi-2-pirazinkarboksamida uključenog u 6-bromo-3- hidroksi-2-pirazinkarboksamid manji od 300 ppm.
7. Postupak proizvodnje u skladu s patentnim zahtjevom 6, naznačen time, da:
baza za upotrebu u koraku (4) je barem jedna baza odabrana između natrijevog hidroksida, natrijevog hidrogen karbonata i kalijevog hidroksida; a
kiselina za upotrebu u koraku (5) je barem jedna kiselina odabrana između solne kiseline, dušične kiseline i sumporne kiseline.
8. Kristal 6-bromo-3-hidroksi-2-pirazinkarboksamida, naznačen time, da ima kutove difrakcije 7,1, 21,4, 25,2, 25,7, 27,1 i 28,8 ° u odnosu na 2θ u rendgenskoj difrakciji praha, pri čemu je omjer sadržaja 3-hidroksi-2-pirazinkarboksamida uključenog u 6- bromo-3-hidroksi-2-pirazinkarboksamid manji od 300 ppm.
9. Bezvodni oblik, naznačen time, da je bezvodni oblik 3-hidroksi-2- pirazinkarboksamida.
10. Bezvodni kristal 3-hidroksi-2-pirazinkarboksamida, naznačen time, da ima kutove difrakcije od 11,9, 13,2, 23,9 i 26,7 ° u odnosu na 2θ u rendgenskoj difrakciji praha.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562172958P | 2015-06-09 | 2015-06-09 | |
| PCT/JP2016/067114 WO2016199824A1 (ja) | 2015-06-09 | 2016-06-08 | ６－ブロモ－３－ヒドロキシ－２－ピラジンカルボキサミドの結晶およびその製造方法 |
| EP16807530.7A EP3309149B1 (en) | 2015-06-09 | 2016-06-08 | 6-bromo-3-hydroxy-2-pyrazinecarboxamide crystal and method for producing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211070T1 true HRP20211070T1 (hr) | 2021-10-01 |
Family
ID=57503297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211070TT HRP20211070T1 (hr) | 2015-06-09 | 2021-07-06 | 6-bromo-3-hidroksi-2-pirazinkarboksamid kristal i postupak za proizvodnju |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10266501B2 (hr) |
| EP (1) | EP3309149B1 (hr) |
| JP (1) | JP6705817B2 (hr) |
| CN (1) | CN107635976A (hr) |
| CY (1) | CY1124180T1 (hr) |
| DK (1) | DK3309149T3 (hr) |
| ES (1) | ES2865296T3 (hr) |
| HK (1) | HK1248236A1 (hr) |
| HR (1) | HRP20211070T1 (hr) |
| HU (1) | HUE054654T2 (hr) |
| LT (1) | LT3309149T (hr) |
| PL (1) | PL3309149T3 (hr) |
| PT (1) | PT3309149T (hr) |
| SI (1) | SI3309149T1 (hr) |
| WO (1) | WO2016199824A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111349049B (zh) * | 2020-02-28 | 2022-11-11 | 江苏阿尔法药业股份有限公司 | 一种法匹拉韦及其中间体的合成工艺 |
| US11780817B2 (en) * | 2020-05-18 | 2023-10-10 | Weaver Labs, LLC | Methods for preparing Favipiravir |
| CN112851589B (zh) * | 2021-01-25 | 2022-10-11 | 山东邹平大展新材料有限公司 | 一种法匹拉韦中间体6-溴-3-羟基吡嗪-2-甲酰胺的制备方法 |
| CN113461622B (zh) * | 2021-08-11 | 2023-04-07 | 海正药业南通有限公司 | 一种法匹拉韦中间体6-溴-3-羟基吡嗪-2-甲酰胺的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4379767B2 (ja) | 2000-02-16 | 2009-12-09 | 富山化学工業株式会社 | 新規なピラジン誘導体またはその塩、それらを含有する医薬組成物並びにそれらの製造中間体 |
| KR101574567B1 (ko) * | 2007-09-27 | 2015-12-07 | 토야마 케미칼 컴퍼니 리미티드 | 6-플루오로-3-히드록시-2-피라진카보니트릴의 유기아민염 및 그 제조법 |
| JP5385309B2 (ja) * | 2009-01-28 | 2014-01-08 | 日本曹達株式会社 | ジクロロピラジン誘導体の製造方法 |
| JP5739618B2 (ja) | 2009-03-18 | 2015-06-24 | 富山化学工業株式会社 | ３−ヒドロキシ−２−ピラジンカルボキサミドの製造法 |
| JP5559604B2 (ja) | 2009-05-27 | 2014-07-23 | 富山化学工業株式会社 | ３，６−ジクロロ−２−ピラジンカルボニトリルの製造法 |
| CN102775358B (zh) * | 2012-08-22 | 2015-05-27 | 山东齐都药业有限公司 | 6-氟-3-羟基-2-吡嗪酰胺的制备方法 |
-
2016
- 2016-06-08 DK DK16807530.7T patent/DK3309149T3/da active
- 2016-06-08 EP EP16807530.7A patent/EP3309149B1/en active Active
- 2016-06-08 PT PT168075307T patent/PT3309149T/pt unknown
- 2016-06-08 HU HUE16807530A patent/HUE054654T2/hu unknown
- 2016-06-08 LT LTEP16807530.7T patent/LT3309149T/lt unknown
- 2016-06-08 WO PCT/JP2016/067114 patent/WO2016199824A1/ja active Application Filing
- 2016-06-08 US US15/580,731 patent/US10266501B2/en active Active
- 2016-06-08 SI SI201631237T patent/SI3309149T1/sl unknown
- 2016-06-08 PL PL16807530T patent/PL3309149T3/pl unknown
- 2016-06-08 CN CN201680033471.XA patent/CN107635976A/zh active Pending
- 2016-06-08 ES ES16807530T patent/ES2865296T3/es active Active
- 2016-06-08 JP JP2017523678A patent/JP6705817B2/ja active Active
-
2018
- 2018-06-15 HK HK18107817.6A patent/HK1248236A1/zh unknown
-
2019
- 2019-03-05 US US16/293,100 patent/US10519117B2/en active Active
-
2021
- 2021-05-26 CY CY20211100457T patent/CY1124180T1/el unknown
- 2021-07-06 HR HRP20211070TT patent/HRP20211070T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUE054654T2 (hu) | 2021-09-28 |
| US20190194146A1 (en) | 2019-06-27 |
| US20180141920A1 (en) | 2018-05-24 |
| ES2865296T3 (es) | 2021-10-15 |
| US10266501B2 (en) | 2019-04-23 |
| DK3309149T3 (da) | 2021-05-31 |
| PL3309149T3 (pl) | 2021-10-25 |
| US10519117B2 (en) | 2019-12-31 |
| EP3309149A1 (en) | 2018-04-18 |
| EP3309149B1 (en) | 2021-04-07 |
| CN107635976A (zh) | 2018-01-26 |
| JP6705817B2 (ja) | 2020-06-03 |
| JPWO2016199824A1 (ja) | 2018-03-29 |
| SI3309149T1 (sl) | 2021-09-30 |
| HK1248236A1 (zh) | 2018-10-12 |
| LT3309149T (lt) | 2021-06-25 |
| EP3309149A4 (en) | 2019-01-09 |
| CY1124180T1 (el) | 2022-05-27 |
| WO2016199824A1 (ja) | 2016-12-15 |
| PT3309149T (pt) | 2021-05-14 |
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