HRP20201198T1 - Kristalni 2-fluor-3-nitrotoluen i postupak njegove priprave - Google Patents
Kristalni 2-fluor-3-nitrotoluen i postupak njegove priprave Download PDFInfo
- Publication number
- HRP20201198T1 HRP20201198T1 HRP20201198TT HRP20201198T HRP20201198T1 HR P20201198 T1 HRP20201198 T1 HR P20201198T1 HR P20201198T T HRP20201198T T HR P20201198TT HR P20201198 T HRP20201198 T HR P20201198T HR P20201198 T1 HRP20201198 T1 HR P20201198T1
- Authority
- HR
- Croatia
- Prior art keywords
- fluoro
- nitrotoluene
- crystalline
- formula
- characteristic
- Prior art date
Links
- NBCNUIXYBLFJMI-UHFFFAOYSA-N 2-fluoro-1-methyl-3-nitrobenzene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1F NBCNUIXYBLFJMI-UHFFFAOYSA-N 0.000 title claims 14
- 238000000034 method Methods 0.000 title claims 13
- 238000002360 preparation method Methods 0.000 title claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000012296 anti-solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Claims (15)
1. Kristalni 2-fluor-3-nitrotoluen formule (I):
[image]
,
naznačen time što ima vrijednost početnog signala DSC između 25,0 i 26,0 °C, ili što ima vrijednost maksimalnog signala DSC između 26,0 i 27,5 °C, ili što ima karakteristični uzorak difrakcije rendgenskih zraka na prahu s karakterističnim signalom izraženim u vrijednostima 2-theta (2θ) na 14,3 ± 0,2.
2. Kristalni 2-fluor-3-nitrotoluen u skladu s patentnim zahtjevom 1, naznačen time što ima vrijednost početnog signala DSC između 25,0 i 26,0 °C i/ili vrijednost maksimalnog signala DSC između 26,0 i 27,5 °C i/ili što ima karakteristični uzorak difrakcije rendgenskih zraka na prahu s karakterističnim signalom izraženim u vrijednostima 2-theta (2θ) na 14,3 ± 0,2.
3. Kristalni 2-fluor-3-nitrotoluen u skladu s bilo kojim od patentnih zahtjeva od 1 do 2, naznačen time što ima vrijednost početnog signala DSC između 25,0 i 26,0 °C, te što ima karakteristični uzorak difrakcije rendgenskih zraka na prahu s karakterističnim signalom izraženim u vrijednostima 2-theta (2θ) na 14,3 ± 0,2.
4. Kristalni 2-fluor-3-nitrotoluen u skladu s bilo kojim od patentnih zahtjeva od 1 do 3, naznačen time što ima dodatni karakteristični uzorak difrakcije rendgenskih zraka na prahu s karakterističnim signalom izraženim u vrijednostima 2-theta (2θ) na 11,3 ± 0,2.
5. Kristalni 2-fluor-3-nitrotoluen u skladu s bilo kojim od patentnih zahtjeva od 1 do 4, naznačen time što ima vrijednost početnog signala DSC između 25,0 i 25,5 °C.
6. Kristalni 2-fluor-3-nitrotoluen u skladu s bilo kojim od patentnih zahtjeva od 1 do 2 i od 4 do 5, naznačen time što ima vrijednost maksimalnog signala DSC između 26,5 i 27,2 °C.
7. Postupak priprave kristalnog 2-fluor-3-nitrotoluena formule (I)
[image]
u skladu s bilo kojim od patentnih zahtjeva od 1 do 6, naznačen time što se navedeni postupak sastoji u kristaliziranju 2-fluor-3-nitrotoluena formule (I) iz smjese vode i otapala kojeg se bira između C1-C3 alkohola.
8. Postupak u skladu s patentnim zahtjevom 7, naznačen time što se postupak provodi otapanjem 2-fluor-3-nitrotoluena u otapalu kojeg se bira između C1-C3 alkohola, uz naknadno dodavanje vode kao protuotapala.
9. Postupak u skladu s bilo kojim od patentnih zahtjeva od 7 do 8, naznačen time što je C1-C3 alkohol metanol ili etanol.
10. Postupak u skladu s bilo kojim od patentnih zahtjeva od 7 do 9, naznačen time što je volumni omjer između otapala i vode 1:1.
11. Postupak u skladu s bilo kojim od patentnih zahtjeva od 7 do 10, naznačen time što je C1-C3 alkohol metanol ili etanol, a volumni omjer između otapala i vode je 1:1.
12. Postupak u skladu s bilo kojim od patentnih zahtjeva od 7 do 11, naznačen time što dodatno uključuje korak miješanja.
13. Postupak u skladu s patentnim zahtjevom 12, naznačen time što se korak miješanja provodi na temperaturi od 0 °C do 30 °C.
14. Postupak sinteze spoja formule (II):
[image]
,
ili njegovih soli,
naznačen time što se navedeni postupak sastoji u koracima:
– priprave kristalnog 2-fluor-3-nitrotoluena formule (I):
[image]
u skladu s bilo kojim od patentnih zahtjeva od 1 do 6 postupkom u skladu s bilo kojim od patentnih zahtjeva od 7 do 13;
– prevođenja navedenog kristalni 2-fluor-3-nitrotoluena u spoj formule (II).
15. Upotreba kristalnog 2-fluor-3-nitrotoluena formule (I) u skladu s patentnim zahtjevima od 1 do 6, naznačena time što je kristalni 2-fluor-3-nitrotoluen namijenjen sintezi spoja formule (II):
[image]
,
ili njegovih soli.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18182368.3A EP3594199B1 (en) | 2018-07-09 | 2018-07-09 | Crystalline 2-fluoro-3-nitrotoluene and process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201198T1 true HRP20201198T1 (hr) | 2020-11-13 |
Family
ID=62904314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201198TT HRP20201198T1 (hr) | 2018-07-09 | 2020-07-30 | Kristalni 2-fluor-3-nitrotoluen i postupak njegove priprave |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20210292271A1 (hr) |
| EP (1) | EP3594199B1 (hr) |
| JP (1) | JP7407166B2 (hr) |
| CN (1) | CN112654602A (hr) |
| AU (1) | AU2019303323A1 (hr) |
| CA (1) | CA3105559A1 (hr) |
| CY (1) | CY1123514T1 (hr) |
| DK (1) | DK3594199T3 (hr) |
| ES (1) | ES2815899T3 (hr) |
| HR (1) | HRP20201198T1 (hr) |
| HU (1) | HUE052049T2 (hr) |
| LT (1) | LT3594199T (hr) |
| MX (1) | MX2021000348A (hr) |
| PL (1) | PL3594199T3 (hr) |
| PT (1) | PT3594199T (hr) |
| SI (1) | SI3594199T1 (hr) |
| WO (1) | WO2020011626A1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ711225A (en) | 2013-03-14 | 2020-06-26 | Amgen Inc | A pharmaceutical formulation comprising omecamtiv mecarbil, processess and uses |
| IL270663B (en) | 2017-06-30 | 2022-08-01 | Amgen Inc | Synthesis of omecamtib from carbyl |
| WO2019006235A1 (en) | 2017-06-30 | 2019-01-03 | Amgen Inc. | METHODS OF TREATING CARDIAC INSUFFICIENCY WITH CARDIAC SARCOMER ACTIVATORS |
| IL272573B2 (en) | 2017-09-13 | 2023-10-01 | Amgen Inc | Sarcomere activating bisamide compounds and their uses |
| EP3837009A1 (en) | 2018-08-17 | 2021-06-23 | Amgen, Inc | Salts and crystal forms of omecamtiv mecarbil |
| JP2024509797A (ja) | 2021-03-10 | 2024-03-05 | アムジェン インコーポレイテッド | オメカムチブメカルビルの合成 |
| WO2024081611A1 (en) | 2022-10-11 | 2024-04-18 | Cytokinetics, Incorporated | Methods for treating heart failure by administering cardiac sarcomere activators |
| US11986474B1 (en) | 2023-06-27 | 2024-05-21 | Cytokinetics, Incorporated | Methods for treating heart failure by administering cardiac sarcomere activators |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR059339A1 (es) * | 2006-02-09 | 2008-03-26 | Chugai Pharmaceutical Co Ltd | Derivados de la cumarina para trastornos proliferativos de celulas, composicion farmaceutica y agente terapeutico que los contiene |
| CN101177400A (zh) | 2006-11-06 | 2008-05-14 | 吕铁环 | 一种生产2-氟-3-硝基甲苯的方法 |
| US8569378B2 (en) | 2007-07-20 | 2013-10-29 | Toshiyuki Sakai | p27 protein inducer |
| NZ711225A (en) | 2013-03-14 | 2020-06-26 | Amgen Inc | A pharmaceutical formulation comprising omecamtiv mecarbil, processess and uses |
-
2018
- 2018-07-09 DK DK18182368.3T patent/DK3594199T3/da active
- 2018-07-09 SI SI201830120T patent/SI3594199T1/sl unknown
- 2018-07-09 LT LTEP18182368.3T patent/LT3594199T/lt unknown
- 2018-07-09 PT PT181823683T patent/PT3594199T/pt unknown
- 2018-07-09 HU HUE18182368A patent/HUE052049T2/hu unknown
- 2018-07-09 PL PL18182368T patent/PL3594199T3/pl unknown
- 2018-07-09 ES ES18182368T patent/ES2815899T3/es active Active
- 2018-07-09 EP EP18182368.3A patent/EP3594199B1/en active Active
-
2019
- 2019-07-03 CA CA3105559A patent/CA3105559A1/en active Pending
- 2019-07-03 MX MX2021000348A patent/MX2021000348A/es unknown
- 2019-07-03 WO PCT/EP2019/067894 patent/WO2020011626A1/en active Application Filing
- 2019-07-03 CN CN201980058205.6A patent/CN112654602A/zh active Pending
- 2019-07-03 AU AU2019303323A patent/AU2019303323A1/en active Pending
- 2019-07-03 US US17/258,385 patent/US20210292271A1/en active Pending
- 2019-07-03 JP JP2021500471A patent/JP7407166B2/ja active Active
-
2020
- 2020-07-30 HR HRP20201198TT patent/HRP20201198T1/hr unknown
- 2020-09-15 CY CY20201100873T patent/CY1123514T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2021000348A (es) | 2021-06-08 |
| ES2815899T3 (es) | 2021-03-31 |
| CY1123514T1 (el) | 2022-03-24 |
| EP3594199A1 (en) | 2020-01-15 |
| EP3594199B1 (en) | 2020-07-01 |
| HUE052049T2 (hu) | 2021-04-28 |
| JP2021532076A (ja) | 2021-11-25 |
| PT3594199T (pt) | 2020-09-04 |
| AU2019303323A1 (en) | 2021-01-28 |
| CA3105559A1 (en) | 2020-01-16 |
| PL3594199T3 (pl) | 2020-11-16 |
| DK3594199T3 (da) | 2020-09-14 |
| JP7407166B2 (ja) | 2023-12-28 |
| WO2020011626A1 (en) | 2020-01-16 |
| LT3594199T (lt) | 2020-11-10 |
| SI3594199T1 (sl) | 2020-10-30 |
| US20210292271A1 (en) | 2021-09-23 |
| CN112654602A (zh) | 2021-04-13 |
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