CA2565440A1 - Preparation of cabergoline form i from a solvate of cabergoline and ethylbenzene - Google Patents
Preparation of cabergoline form i from a solvate of cabergoline and ethylbenzene Download PDFInfo
- Publication number
- CA2565440A1 CA2565440A1 CA002565440A CA2565440A CA2565440A1 CA 2565440 A1 CA2565440 A1 CA 2565440A1 CA 002565440 A CA002565440 A CA 002565440A CA 2565440 A CA2565440 A CA 2565440A CA 2565440 A1 CA2565440 A1 CA 2565440A1
- Authority
- CA
- Canada
- Prior art keywords
- cabergoline
- solvent
- solvate
- ethylbenzene
- inert gas
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
- C07D457/06—Lysergic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Secondary Cells (AREA)
Abstract
The present invention discloses a method for preparing cabergoline form I by combining cabergoline and a solvent comprising ethylbenzene to form a solvate and obtaining form I from the solvate. Also disclosed in a method for preparing cabergoline form I by combining cabergoline and a fist solvent to form a solution and additionally including a second solvent to the solution, followed by crystallisation to form cabergoline form I. Further disclosed is a solvate form of cabergoline comprising cabergoline and ethylbenzene and, optionally, n-heptane.
Claims (30)
1. A method of preparing of cabergoline form I, comprising forming a solvate including cabergoline and ethylbenzene, and obtaining form I from the solvate.
2. The method of claim 1, wherein the cabergoline form I is obtained from the solvate by drying.
3. The method of claim 2, wherein the drying is performed at a pressure of 900 mbar or less.
4. The method of claim 2, wherein the drying occurs at a temperature of 50°
C or higher.
C or higher.
5. The method of claim 2, wherein the drying occurs in an inert gas atmosphere.
6. The method of claim 5, wherein the inert gas is selected from the group consisting of nitrogen or argon gas.
7. The method of claim 5, wherein the inert gas atmosphere comprises a gas mixture including 80% inert gas.
8. The method of claim 5, wherein the inert gas atmosphere comprises 5% or less oxygen.
9. A method according to claim 1, wherein the solvate is formed by dissolving cabergoline in a solvent.
10. The method of claim 9, wherein the solvent comprises ethylbenzene.
11. The method of claim 9, wherein the solvent comprises at least 75% by volume ethylbenzene.
12. The method of claim 10, wherein the solvate is cooled to a temperature of -5° C or below.
13. A method of preparing cabergoline form I, comprising dissolving cabergoline in a first solvent comprising ethylbenzene to form a solution, and obtaining form I from the solution.
14. The method of claim 13, further comprising adding a second solvent to the solution.
15. The method of claim 14, wherein the second solvent is selected from the group consisting of hexane, heptane, diethylether, isopropylether, tetrabutylmethylether, and mixtures thereof.
16. The method of claim 14, wherein the second solvent is heptane.
17. The method of claim 14, wherein the second solvent is n-heptane.
18. The method of claim 14, further comprising the step of drying the solution to obtain cabergoline form I.
19. The method of claim 18, wherein the step of drying is performed at a pressure of 900 mbar or less.
20. The method of claim 18, wherein the step of drying occurs at a temperature of 50° C or higher.
21. The method of claim 18, wherein the step of drying occurs in an inert gas atmosphere.
22. The method of claim 21, wherein the inert gas is selected from the group consisting of nitrogen and argon.
23. The method of claim 21, wherein the inert gas atmosphere comprises a gas mixture including 80% inert gas.
24. The method of claim 21, wherein the inert gas atmosphere comprises 5%
or less oxygen.
or less oxygen.
25. A method of preparing cabergoline form I, comprising a) dissolving cabergoline in a first solvent to form a solution; and b) adding a second solvent to the solution to obtain cabergoline form I.
26. A method of preparing cabergoline form I, comprising a) dissolving cabergoline in a first solvent comprising ethylbenzene to form a solution; and b) adding a second solvent comprising n-heptane to the solution to obtain cabergoline form I.
27. Cabergoline form I, obtained by a method according to claim 1.
28. Cabergoline form I, obtained by a method according to claim 13.
29. A solvate form of cabergoline, comprising cabergoline and ethylbenzene.
30. The solvate form of claim 29, further comprising n-heptane.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0409785.3A GB0409785D0 (en) | 2004-04-30 | 2004-04-30 | Preparation of cabergoline |
| GB0409785.3 | 2004-04-30 | ||
| PCT/GB2005/001649 WO2005105796A1 (en) | 2004-04-30 | 2005-04-29 | Preparation of cabergoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2565440A1 true CA2565440A1 (en) | 2005-11-10 |
| CA2565440C CA2565440C (en) | 2011-09-20 |
Family
ID=32482531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2565440A Expired - Fee Related CA2565440C (en) | 2004-04-30 | 2005-04-29 | Preparation of cabergoline form i from a solvate of cabergoline and ethylbenzene |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7186837B2 (en) |
| EP (1) | EP1591445B1 (en) |
| JP (1) | JP2007535526A (en) |
| AT (1) | ATE394397T1 (en) |
| AU (1) | AU2005238276B2 (en) |
| CA (1) | CA2565440C (en) |
| CY (1) | CY1108244T1 (en) |
| DE (1) | DE602005006465D1 (en) |
| DK (1) | DK1591445T3 (en) |
| ES (1) | ES2304670T3 (en) |
| GB (1) | GB0409785D0 (en) |
| HR (1) | HRP20080292T3 (en) |
| NZ (1) | NZ550925A (en) |
| PL (1) | PL1591445T3 (en) |
| PT (1) | PT1591445E (en) |
| RS (1) | RS50655B (en) |
| SI (1) | SI1591445T1 (en) |
| WO (1) | WO2005105796A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60236600D1 (en) | 2001-08-13 | 2010-07-15 | Du Pont | SUBSTITUTED 1H-DIHYDROPYRAZOLE, THEIR PREPARATION AND USE |
| CA2525104A1 (en) * | 2003-05-08 | 2004-11-25 | Ivax Pharmaceuticals S.R.O. | Polymorphs of cabergoline |
| GB0409785D0 (en) | 2004-04-30 | 2004-06-09 | Resolution Chemicals Ltd | Preparation of cabergoline |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | Resolution Chemicals, Ltd. | Preparation of cabergoline |
| GB0505965D0 (en) | 2005-03-23 | 2005-04-27 | Resolution Chemicals Ltd | Preparation of cabergoline |
| EP1925616A1 (en) * | 2006-10-26 | 2008-05-28 | LEK Pharmaceuticals D.D. | Process for the preparation of crystal forms of cabergoline via stable solvates of cabergoline |
| EP1953157A1 (en) | 2007-01-31 | 2008-08-06 | LEK Pharmaceuticals D.D. | New crystal form of cabergoline |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH535235A (en) | 1970-06-19 | 1973-03-31 | Sandoz Ag | 6-nor-6-cyano-lysergic acid derivs - withpharmacological activity |
| CH535236A (en) | 1970-06-19 | 1973-03-31 | Sandoz Ag | 6-nor-lysergic acid derivs - with pharmacological activity |
| US3920664A (en) * | 1972-07-21 | 1975-11-18 | Lilly Co Eli | D-2-halo-6-alkyl-8-substituted ergolines and related compounds |
| PH11140A (en) | 1973-11-28 | 1977-10-27 | Lilly Co Eli | D-6-alkyl-2,8-disubstituted ergolines and a process for inhibiting the secretion of prolactin in mammals |
| CH587858A5 (en) * | 1973-11-28 | 1977-05-13 | Sandoz Ag | |
| DE2525962A1 (en) | 1974-06-21 | 1976-01-08 | Sandoz Ag | NEW HETEROCYCLIC COMPOUNDS, THEIR PRODUCTION AND USE |
| US4180582A (en) * | 1978-02-08 | 1979-12-25 | Eli Lilly And Company | 6-n-Propyl-8-methoxy-methyl or methylmercaptomethylergolines and related compounds as prolactin inhibitors and to treat Parkinson's syndrome |
| US4166182A (en) | 1978-02-08 | 1979-08-28 | Eli Lilly And Company | 6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4202979A (en) * | 1979-01-11 | 1980-05-13 | Eli Lilly And Company | 6-Ethyl(or allyl)-8-methoxymethyl or methylmercaptomethylergolines and related compounds |
| US4246265A (en) * | 1979-10-01 | 1981-01-20 | Eli Lilly And Company | 6-n-Propyl-8α-methoxymethyl or methylmercaptomethylergolines and related compounds |
| NL189462C (en) | 1980-04-03 | 1993-04-16 | Erba Carlo Spa | ERGOLINE DERIVATIVES WITH ANTIPROLACTINIC AND / OR ANTIHYPERTENSIVE PROPERTIES AND PHARMACEUTICAL PREPARATION THEREOF. |
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| AU553809B2 (en) * | 1981-07-21 | 1986-07-31 | Farmitalia Carlo Erba S.P.A. | Ergoline derivatives |
| GB2103603B (en) | 1981-08-11 | 1985-04-11 | Erba Farmitalia | Ergoline derivatives |
| US4782152A (en) * | 1985-08-16 | 1988-11-01 | Eli Lilly And Company | Decyanation of pergolide intermediate |
| GB9205439D0 (en) * | 1992-03-12 | 1992-04-22 | Erba Carlo Spa | Process for the synthesis of ergoline derivatives |
| CZ287176B6 (en) | 1997-10-03 | 2000-10-11 | Galena A. S. | Process for preparing ergoline derivatives |
| IT1307934B1 (en) * | 1999-01-27 | 2001-11-29 | Poli Ind Chimica Spa | PROCESS FOR THE PREPARATION OF ALCHEMERCAPTOMETHYLERGOLINIC DERIVATIVES. |
| GB0007309D0 (en) | 2000-03-24 | 2000-05-17 | Pharmacia & Upjohn Spa | Crystalline form V|| of cabergoline |
| GB0007307D0 (en) | 2000-03-24 | 2000-05-17 | Pharmacia & Upjohn Spa | Crystalline form || of cabergoline |
| GB0007308D0 (en) | 2000-03-24 | 2000-05-17 | Pharmacia & Upjohn Spa | Process for preparing crystalline form | of cabergoline |
| JP2005520831A (en) | 2002-03-15 | 2005-07-14 | ファルマシア・コーポレーション | Method for producing crystalline form I of cabergoline |
| IL163520A0 (en) | 2002-03-15 | 2005-12-18 | Pharmacia Italia Spa | Process for preparing crystalline form i of cabergoline |
| CA2525104A1 (en) * | 2003-05-08 | 2004-11-25 | Ivax Pharmaceuticals S.R.O. | Polymorphs of cabergoline |
| GB0409785D0 (en) | 2004-04-30 | 2004-06-09 | Resolution Chemicals Ltd | Preparation of cabergoline |
-
2004
- 2004-04-30 GB GBGB0409785.3A patent/GB0409785D0/en not_active Ceased
-
2005
- 2005-02-18 US US11/060,991 patent/US7186837B2/en not_active Expired - Fee Related
- 2005-04-29 ES ES05252709T patent/ES2304670T3/en active Active
- 2005-04-29 NZ NZ550925A patent/NZ550925A/en not_active IP Right Cessation
- 2005-04-29 DE DE602005006465T patent/DE602005006465D1/en active Active
- 2005-04-29 DK DK05252709T patent/DK1591445T3/en active
- 2005-04-29 AU AU2005238276A patent/AU2005238276B2/en not_active Ceased
- 2005-04-29 AT AT05252709T patent/ATE394397T1/en active
- 2005-04-29 JP JP2007510117A patent/JP2007535526A/en active Pending
- 2005-04-29 RS RSP-2008/0265A patent/RS50655B/en unknown
- 2005-04-29 WO PCT/GB2005/001649 patent/WO2005105796A1/en active Application Filing
- 2005-04-29 EP EP05252709A patent/EP1591445B1/en not_active Revoked
- 2005-04-29 PT PT05252709T patent/PT1591445E/en unknown
- 2005-04-29 PL PL05252709T patent/PL1591445T3/en unknown
- 2005-04-29 SI SI200530276T patent/SI1591445T1/en unknown
- 2005-04-29 CA CA2565440A patent/CA2565440C/en not_active Expired - Fee Related
-
2008
- 2008-06-23 HR HR20080292T patent/HRP20080292T3/en unknown
- 2008-08-06 CY CY20081100830T patent/CY1108244T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005105796A1 (en) | 2005-11-10 |
| DE602005006465D1 (en) | 2008-06-19 |
| JP2007535526A (en) | 2007-12-06 |
| US20050245560A1 (en) | 2005-11-03 |
| EP1591445B1 (en) | 2008-05-07 |
| HRP20080292T3 (en) | 2008-07-31 |
| CY1108244T1 (en) | 2014-02-12 |
| AU2005238276B2 (en) | 2011-08-18 |
| GB0409785D0 (en) | 2004-06-09 |
| EP1591445A1 (en) | 2005-11-02 |
| AU2005238276A1 (en) | 2005-11-10 |
| DK1591445T3 (en) | 2008-08-11 |
| SI1591445T1 (en) | 2008-08-31 |
| CA2565440C (en) | 2011-09-20 |
| ATE394397T1 (en) | 2008-05-15 |
| PL1591445T3 (en) | 2008-09-30 |
| RS50655B (en) | 2010-06-30 |
| NZ550925A (en) | 2010-02-26 |
| US7186837B2 (en) | 2007-03-06 |
| PT1591445E (en) | 2008-06-02 |
| ES2304670T3 (en) | 2008-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150429 |