CA2549350A1 - Procede de cristallisation d'hydrochlorure de bupropion - Google Patents
Procede de cristallisation d'hydrochlorure de bupropion Download PDFInfo
- Publication number
- CA2549350A1 CA2549350A1 CA002549350A CA2549350A CA2549350A1 CA 2549350 A1 CA2549350 A1 CA 2549350A1 CA 002549350 A CA002549350 A CA 002549350A CA 2549350 A CA2549350 A CA 2549350A CA 2549350 A1 CA2549350 A1 CA 2549350A1
- Authority
- CA
- Canada
- Prior art keywords
- bupropion hydrochloride
- precipitating solvent
- product
- mixture
- bupropion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- IKBZAUYPBWFMDI-UHFFFAOYSA-N 5-bromo-4-methoxy-7-methyl-2,3-dihydro-1h-indene Chemical compound C1=C(Br)C(OC)=C2CCCC2=C1C IKBZAUYPBWFMDI-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 229960004367 bupropion hydrochloride Drugs 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 230000001376 precipitating effect Effects 0.000 claims abstract description 17
- 230000001960 triggered effect Effects 0.000 claims abstract description 10
- 238000001556 precipitation Methods 0.000 claims abstract description 8
- 239000002244 precipitate Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 238000004090 dissolution Methods 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 10
- 239000013078 crystal Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 4
- 229960001058 bupropion Drugs 0.000 description 3
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BTANRVKWQNVYAZ-BYPYZUCNSA-N (2S)-butan-2-ol Chemical compound CC[C@H](C)O BTANRVKWQNVYAZ-BYPYZUCNSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000000227 bioadhesive Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001493 electron microscopy Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne un procédé de cristallisation d'hydrochlorure de bupropion consistant (a) à dissoudre de l'hydrochlorure de bupropion dans un mélange comprenant du méthanol et un solvant de précipitation pour l'hydrochlorure de bupropion, (b) à enlever tout résidu insoluble, (c) à distiller la solution à une pression atmosphérique jusqu'au déclenchement de la réaction de précipitation, (d) à ajouter (I) un solvant de précipitation pour l'hydrochlorure de bupropion et (II) de l'acide chlorhydrique jusqu'à l'obtention d'un pH inférieur ou égal à 2, (e) à refroidir la masse à une température inférieure à 10 ·C, de préférence entre 0 et 3 ·C, et à séparer le précipité ainsi obtenu.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI20030762 ITMI20030762A1 (it) | 2003-04-11 | 2003-04-11 | Processo di cristallizzazione del bupropione cloridrato. |
| ITMI2003A000762 | 2003-04-11 | ||
| PCT/EP2004/050495 WO2004089873A1 (fr) | 2003-04-11 | 2004-04-09 | Procede de cristallisation d'hydrochlorure de bupropion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2549350A1 true CA2549350A1 (fr) | 2005-10-21 |
Family
ID=33156348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002549350A Abandoned CA2549350A1 (fr) | 2003-04-11 | 2004-04-09 | Procede de cristallisation d'hydrochlorure de bupropion |
Country Status (3)
| Country | Link |
|---|---|
| CA (1) | CA2549350A1 (fr) |
| IT (1) | ITMI20030762A1 (fr) |
| WO (1) | WO2004089873A1 (fr) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ561375A (en) | 2005-06-27 | 2011-06-30 | Biovail Lab Int Srl | Bupropion hydrobromide, and crystalline forms, compositions, and uses of this compound |
| WO2008099418A2 (fr) * | 2007-02-12 | 2008-08-21 | Alembic Limited | Procédé amélioré de préparation de chlohydrate de bupropion |
| US11969421B2 (en) | 2013-11-05 | 2024-04-30 | Antecip Bioventures Ii Llc | Bupropion as a modulator of drug activity |
| US12194006B2 (en) | 2013-11-05 | 2025-01-14 | Antecip Bioventures Ii Llc | Bupropion as a modulator of drug activity |
| US11534414B2 (en) | 2013-11-05 | 2022-12-27 | Antecip Bioventures Ii Llc | Bupropion as a modulator of drug activity |
| US11433067B2 (en) | 2013-11-05 | 2022-09-06 | Antecip Bioventures Ii Llc | Bupropion as a modulator of drug activity |
| US12109178B2 (en) | 2013-11-05 | 2024-10-08 | Antecip Bioventures Ii Llc | Bupropion as a modulator of drug activity |
| CN106431943B (zh) * | 2016-09-13 | 2021-03-26 | 迪嘉药业集团有限公司 | 一种盐酸安非他酮结晶的制备方法 |
| US12472156B2 (en) | 2020-06-05 | 2025-11-18 | Antecip Bioventures Ii Llc | Compounds and combinations thereof for treating neurological and psychiatric conditions |
| US12433884B2 (en) | 2020-06-05 | 2025-10-07 | Antecip Bioventures Ii Llc | Compounds and combinations thereof for treating neurological and psychiatric conditions |
| JP2023553393A (ja) | 2020-12-01 | 2023-12-21 | アンテシップ バイオベンチャーズ トゥー エルエルシー | うつ病患者の自殺リスク低減のためのブプロピオンおよびデキストロメトルファン |
| US12036191B1 (en) | 2022-06-30 | 2024-07-16 | Antecip Bioventures Ii Llc | Treatment of poor metabolizers of dextromethorphan with a combination of bupropion and dextromethorphan |
| US12156914B2 (en) | 2022-06-30 | 2024-12-03 | Axsome Therapeutics, Inc. | Pharmaceutical compositions comprising bupropion and cysteine |
| US11717518B1 (en) | 2022-06-30 | 2023-08-08 | Antecip Bioventures Ii Llc | Bupropion dosage forms with reduced food and alcohol dosing effects |
| US20240000729A1 (en) * | 2022-06-30 | 2024-01-04 | Axsome Therapeutics, Inc. | Microparticles containing bupropion |
| US11730706B1 (en) | 2022-07-07 | 2023-08-22 | Antecip Bioventures Ii Llc | Treatment of depression in certain patient populations |
| US12194036B2 (en) | 2022-07-07 | 2025-01-14 | Antecip Bioventures Ii Llc | Combination of dextromethorphan and bupropion for treating depression |
| US11844797B1 (en) | 2023-04-20 | 2023-12-19 | Antecip Bioventures Ii Llc | Combination of dextromethorphan and bupropion for treating depression |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE759838A (fr) * | 1969-12-04 | 1971-06-03 | Wellcome Found | Cetones a activite biologique |
| US6238697B1 (en) * | 1998-12-21 | 2001-05-29 | Pharmalogix, Inc. | Methods and formulations for making bupropion hydrochloride tablets using direct compression |
| US6306436B1 (en) * | 2000-04-28 | 2001-10-23 | Teva Pharmaceuticals Usa, Inc. | Stabilized, acid-free formulation for sustained release of bupropion hydrochloride |
-
2003
- 2003-04-11 IT ITMI20030762 patent/ITMI20030762A1/it unknown
-
2004
- 2004-04-09 WO PCT/EP2004/050495 patent/WO2004089873A1/fr not_active Ceased
- 2004-04-09 CA CA002549350A patent/CA2549350A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI20030762A1 (it) | 2004-10-12 |
| WO2004089873A1 (fr) | 2004-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |