HRP20220108T1 - Postupak za proizvodnju vortioksetina hbr alfa-oblika - Google Patents
Postupak za proizvodnju vortioksetina hbr alfa-oblika Download PDFInfo
- Publication number
- HRP20220108T1 HRP20220108T1 HRP20220108TT HRP20220108T HRP20220108T1 HR P20220108 T1 HRP20220108 T1 HR P20220108T1 HR P20220108T T HRP20220108T T HR P20220108TT HR P20220108 T HRP20220108 T HR P20220108T HR P20220108 T1 HRP20220108 T1 HR P20220108T1
- Authority
- HR
- Croatia
- Prior art keywords
- hbr
- toluene
- vortioxetine
- carboxylic acid
- solution obtained
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 17
- 238000004519 manufacturing process Methods 0.000 title claims 2
- VNGRUFUIHGGOOM-UHFFFAOYSA-N vortioxetine hydrobromide Chemical compound Br.CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 VNGRUFUIHGGOOM-UHFFFAOYSA-N 0.000 title claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 150000001735 carboxylic acids Chemical class 0.000 claims 6
- YQNWZWMKLDQSAC-UHFFFAOYSA-N vortioxetine Chemical compound CC1=CC(C)=CC=C1SC1=CC=CC=C1N1CCNCC1 YQNWZWMKLDQSAC-UHFFFAOYSA-N 0.000 claims 5
- 229960002263 vortioxetine Drugs 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
Classifications
-
- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
- C07D295/096—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 singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
-
- 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
- C07D295/08—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 singly bound oxygen or sulfur atoms
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (15)
1. Postupak za proizvodnju kristalnog vortioksetina HBr α-oblika naznačen XRPD refleksijama na 5.85, 9.30, 17.49 i 18.58 (°2θ) (±0.1°), proces koji se sastoji od koraka
a) dobivanje otopine vortioksetina u toluenu, pri čemu je toluen više od 90% čist;
b) miješanje navedene otopine dobivene u koraku a) s HBr i C1-C3 karboksilnom kiselinom da se dobije mješavina
b) na temperaturi iznad 10 °C; i
c) sakupljanje taloga dobivenog u koraku b).
2. Postupak prema zahtjevu 1 naznačen time što je koncentracija vortioksetina dobivena u koraku a) između 10 g/l toluena i 500 g/l toluena.
3. Postupak prema bilo kojem od zahtjeva 1-2, naznačen time što je koncentracija vortioksetina dobivena u koraku a) između 40 g/l toluena i 200 g/l toluena.
4. Postupak prema bilo kojem od zahtjeva 1-3, naznačen time što navedeni bitno čisti toluen sadrži više od 95 (w/w) % toluena.
5. Postupak prema bilo kojem od zahtjeva 1-4, naznačen time što je temperatura otopine dobivene u koraku a) između 0 °C i refluksa.
6. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time što je temperatura otopine dobivene u koraku a) između 25 °C i 40 °C.
7. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time što je temperatura otopine dobivene u koraku a) između 10 °C i 30 °C, kao što je oko 20 °C.
8. Postupak prema bilo kojem od zahtjeva 1-6, naznačen time što je količina HBr u koraku b) između 0.9 i 2 mola ekvivalenta u odnosu na količinu vortioksetina prisutnog u otopini dobivenoj u koraku a).
9. Postupak prema bilo kojem od zahtjeva 1-7, naznačen time što je količina HBr u koraku b) između 1 i 1.3 mola ekvivalenta u odnosu na količinu vortioksetina prisutnog u otopini dobivenoj u koraku a).
10. Postupak prema bilo kojem od zahtjeva 1-8, naznačen time što molarni omjer HBr:C1-C3 karboksilne kiseline u koraku b) iznosi 1:1 - do 1:10.
11. Postupak prema bilo kojem od zahtjeva 1-9, naznačen time što molarni omjer HBr: C1-C3 karboksilne kiseline u navedenoj mješavini od HBr u octenoj kiselini u koraku b) je 1:2 - do 1:4.
12. Postupak prema bilo kojem od zahtjeva 1-10, naznačen time što je temperatura mješavine b) iznad 10 °C i 40 °C ili niža.
13. Postupak prema bilo kojem od zahtjeva 1-11, naznačen time što navedena C1-C3 karboksilna kiselina je octena kiselina.
14. Postupak prema bilo kojem od zahtjeva 1-11, naznačen time što navedena C1-C3 karboksilna kiselina je propionska kiselina.
15. Postupak prema bilo kojem od zahtjeva 1-12 naznačen time što navedeni HBr i navedena C1-C3 karboksilna kiselina zajedno predstavljaju 33 (w/w) % HBr otopljenog u octenoj kiselini.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201700264 | 2017-04-25 | ||
| PCT/EP2018/060192 WO2018197360A1 (en) | 2017-04-25 | 2018-04-20 | Process for the manufacture of vortioxetine hbr alpha-form |
| EP18721975.3A EP3615518B1 (en) | 2017-04-25 | 2018-04-20 | Process for the manufacture of vortioxetine hbr alpha-form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20220108T1 true HRP20220108T1 (hr) | 2022-04-15 |
Family
ID=62111030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220108TT HRP20220108T1 (hr) | 2017-04-25 | 2018-04-20 | Postupak za proizvodnju vortioksetina hbr alfa-oblika |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US11124491B2 (hr) |
| EP (1) | EP3615518B1 (hr) |
| JP (1) | JP7121751B2 (hr) |
| KR (1) | KR102551433B1 (hr) |
| CN (1) | CN110520415A (hr) |
| AU (1) | AU2018258947C1 (hr) |
| BR (1) | BR112018076411A2 (hr) |
| CA (1) | CA3059515A1 (hr) |
| CL (1) | CL2019003024A1 (hr) |
| CO (1) | CO2019011592A2 (hr) |
| CY (1) | CY1124974T1 (hr) |
| DK (1) | DK3615518T3 (hr) |
| ES (1) | ES2905962T3 (hr) |
| HR (1) | HRP20220108T1 (hr) |
| HU (1) | HUE057993T2 (hr) |
| IL (1) | IL270052B2 (hr) |
| LT (1) | LT3615518T (hr) |
| MA (1) | MA49056A (hr) |
| MX (1) | MX2019012765A (hr) |
| PL (1) | PL3615518T3 (hr) |
| PT (1) | PT3615518T (hr) |
| RS (1) | RS62823B1 (hr) |
| SG (1) | SG11201909678PA (hr) |
| SI (1) | SI3615518T1 (hr) |
| WO (1) | WO2018197360A1 (hr) |
| ZA (1) | ZA201906829B (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210087155A1 (en) * | 2018-02-06 | 2021-03-25 | Piramal Enterprises Limited | An improved process for the preparation of vortioxetine and salts thereof |
| CN112125868B (zh) * | 2020-09-25 | 2021-08-03 | 中山万远新药研发有限公司 | 一种氢溴酸伏硫西汀晶型及其制备方法、组合物与用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| KR101627901B1 (ko) * | 2006-06-16 | 2016-06-13 | 하. 룬트벡 아크티에 셀스카브 | 인지기능 장애의 치료를 위한, 세로토닌 재흡수, 5-ht3 및 5-ht1a 활성이 조합된 화합물로서의 1-[2-(2,4-디메틸페닐술파닐)-페닐]피페라진 |
| TW200848411A (en) * | 2007-03-20 | 2008-12-16 | Lundbeck & Co As H | Novel therapeutic uses of 1-[2-(2, 4-dimethylphenylsulfanyl)phenyl]-piperazine |
| TW201033181A (en) * | 2009-02-17 | 2010-09-16 | Lundbeck & Co As H | Purification of 1-[2-(2,4-dimethylphenylsulfanyl)phenyl]piperazine |
| BR112015006075B1 (pt) | 2012-09-19 | 2022-10-04 | Sandoz Ag | Composto cristalino, composição farmacêutica, uso do composto cristalino, hidrato cristalino do bromidrato de vortioxetina, método para a preparação do hidrato cristalino de bromidrato de vortioxetina, método para a preparação do composto cristalino e uso do hidrato cristalino de bromidrato de vortioxetina |
| EP3099669A1 (en) * | 2014-01-31 | 2016-12-07 | Egis Gyógyszergyár Zrt. | Process for the preparation of vortioxetine salts |
| US9687484B2 (en) | 2014-07-18 | 2017-06-27 | Dipharma Francis S.R.L. | Crystalline forms of an antidepressant compound |
| CN105367515B (zh) | 2015-05-08 | 2017-10-27 | 北京北陆药业股份有限公司 | 一种氢溴酸沃替西汀α晶型的制备方法 |
| CN104910099B (zh) | 2015-05-22 | 2017-03-08 | 扬子江药业集团有限公司 | 一种氢溴酸沃替西汀晶体的制备方法 |
| CN106316986B (zh) | 2015-07-03 | 2019-02-05 | 成都弘达药业有限公司 | 一种1-[2-(2,4-二甲基苯基硫烷基)苯基]哌嗪氢溴酸盐α型晶体的制备方法 |
-
2018
- 2018-04-20 PT PT187219753T patent/PT3615518T/pt unknown
- 2018-04-20 CA CA3059515A patent/CA3059515A1/en active Pending
- 2018-04-20 SG SG11201909678P patent/SG11201909678PA/en unknown
- 2018-04-20 US US16/604,313 patent/US11124491B2/en active Active
- 2018-04-20 HR HRP20220108TT patent/HRP20220108T1/hr unknown
- 2018-04-20 LT LTEPPCT/EP2018/060192T patent/LT3615518T/lt unknown
- 2018-04-20 MX MX2019012765A patent/MX2019012765A/es unknown
- 2018-04-20 AU AU2018258947A patent/AU2018258947C1/en active Active
- 2018-04-20 IL IL270052A patent/IL270052B2/en unknown
- 2018-04-20 RS RS20220047A patent/RS62823B1/sr unknown
- 2018-04-20 EP EP18721975.3A patent/EP3615518B1/en active Active
- 2018-04-20 WO PCT/EP2018/060192 patent/WO2018197360A1/en active Application Filing
- 2018-04-20 KR KR1020197031292A patent/KR102551433B1/ko active IP Right Grant
- 2018-04-20 SI SI201830537T patent/SI3615518T1/sl unknown
- 2018-04-20 ES ES18721975T patent/ES2905962T3/es active Active
- 2018-04-20 CN CN201880025179.2A patent/CN110520415A/zh active Pending
- 2018-04-20 PL PL18721975T patent/PL3615518T3/pl unknown
- 2018-04-20 JP JP2019557745A patent/JP7121751B2/ja active Active
- 2018-04-20 MA MA049056A patent/MA49056A/fr unknown
- 2018-04-20 HU HUE18721975A patent/HUE057993T2/hu unknown
- 2018-04-20 DK DK18721975.3T patent/DK3615518T3/da active
- 2018-04-20 BR BR112018076411-6A patent/BR112018076411A2/pt unknown
-
2019
- 2019-10-16 ZA ZA2019/06829A patent/ZA201906829B/en unknown
- 2019-10-18 CO CO2019011592A patent/CO2019011592A2/es unknown
- 2019-10-22 CL CL2019003024A patent/CL2019003024A1/es unknown
-
2022
- 2022-02-08 CY CY20221100108T patent/CY1124974T1/el unknown
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