CA2478149A1 - Process for preparing crystalline form i of cabergoline - Google Patents
Process for preparing crystalline form i of cabergoline Download PDFInfo
- Publication number
- CA2478149A1 CA2478149A1 CA002478149A CA2478149A CA2478149A1 CA 2478149 A1 CA2478149 A1 CA 2478149A1 CA 002478149 A CA002478149 A CA 002478149A CA 2478149 A CA2478149 A CA 2478149A CA 2478149 A1 CA2478149 A1 CA 2478149A1
- Authority
- CA
- Canada
- Prior art keywords
- cabergoline
- toluene
- process according
- solvate form
- solvate
- 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
- KORNTPPJEAJQIU-KJXAQDMKSA-N Cabaser Chemical compound C1=CC([C@H]2C[C@H](CN(CC=C)[C@@H]2C2)C(=O)N(CCCN(C)C)C(=O)NCC)=C3C2=CNC3=C1 KORNTPPJEAJQIU-KJXAQDMKSA-N 0.000 title claims abstract description 76
- 229960004596 cabergoline Drugs 0.000 title claims abstract description 67
- 238000004519 manufacturing process Methods 0.000 title description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 132
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000012453 solvate Substances 0.000 claims abstract description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000007614 solvation Methods 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 5
- 238000010791 quenching Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 13
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000005496 eutectics Effects 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 2
- 208000005793 Restless legs syndrome Diseases 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 208000015114 central nervous system disease Diseases 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- 101150049660 DRD2 gene Proteins 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 208000027771 Obstructive airways disease Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000001263 anti-prolactin effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36456702P | 2002-03-15 | 2002-03-15 | |
| US60/364,567 | 2002-03-15 | ||
| US41025302P | 2002-09-12 | 2002-09-12 | |
| US60/410,253 | 2002-09-12 | ||
| PCT/US2003/007138 WO2003078392A2 (en) | 2002-03-15 | 2003-03-10 | Process for preparing crystalline form i of cabergoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2478149A1 true CA2478149A1 (en) | 2003-09-25 |
Family
ID=28045415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002478149A Abandoned CA2478149A1 (en) | 2002-03-15 | 2003-03-10 | Process for preparing crystalline form i of cabergoline |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1507777A4 (sr) |
| JP (1) | JP2005520831A (sr) |
| KR (1) | KR100605794B1 (sr) |
| CN (1) | CN1642953A (sr) |
| AU (1) | AU2003224665A1 (sr) |
| BR (1) | BR0308472A (sr) |
| CA (1) | CA2478149A1 (sr) |
| IL (1) | IL163779A0 (sr) |
| MX (1) | MXPA04008935A (sr) |
| PL (1) | PL372371A1 (sr) |
| RS (1) | RS77704A (sr) |
| RU (1) | RU2277536C2 (sr) |
| TW (1) | TW200306312A (sr) |
| WO (1) | WO2003078392A2 (sr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL155545A (en) | 2003-04-21 | 2009-12-24 | Finetech Pharmaceutical Ltd | Solvate form of cabergoline |
| AU2004238833A1 (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 |
| GB0515430D0 (en) * | 2005-07-27 | 2005-08-31 | Resolution Chemicals Ltd | Preparation of cabergoline |
| EP1953157A1 (en) * | 2007-01-31 | 2008-08-06 | LEK Pharmaceuticals D.D. | New crystal form of cabergoline |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| GB0007308D0 (en) * | 2000-03-24 | 2000-05-17 | Pharmacia & Upjohn Spa | Process for preparing crystalline form | of cabergoline |
| RS81804A (sr) * | 2002-03-15 | 2006-10-27 | Pharmacia Corporation | Postupak za dobijanje kristalnog oblika kabergolina |
-
2003
- 2003-03-10 PL PL03372371A patent/PL372371A1/xx not_active Application Discontinuation
- 2003-03-10 KR KR1020047014429A patent/KR100605794B1/ko not_active Expired - Fee Related
- 2003-03-10 IL IL16377903A patent/IL163779A0/xx unknown
- 2003-03-10 MX MXPA04008935A patent/MXPA04008935A/es not_active Application Discontinuation
- 2003-03-10 RS YU77704A patent/RS77704A/sr unknown
- 2003-03-10 CN CNA038061309A patent/CN1642953A/zh active Pending
- 2003-03-10 AU AU2003224665A patent/AU2003224665A1/en not_active Abandoned
- 2003-03-10 RU RU2004127582/04A patent/RU2277536C2/ru not_active IP Right Cessation
- 2003-03-10 CA CA002478149A patent/CA2478149A1/en not_active Abandoned
- 2003-03-10 JP JP2003576398A patent/JP2005520831A/ja active Pending
- 2003-03-10 WO PCT/US2003/007138 patent/WO2003078392A2/en not_active Ceased
- 2003-03-10 EP EP03721346A patent/EP1507777A4/en not_active Withdrawn
- 2003-03-10 BR BR0308472-8A patent/BR0308472A/pt not_active IP Right Cessation
- 2003-03-13 TW TW092105467A patent/TW200306312A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL163779A0 (en) | 2005-12-18 |
| EP1507777A2 (en) | 2005-02-23 |
| KR100605794B1 (ko) | 2006-08-01 |
| WO2003078392A3 (en) | 2003-12-11 |
| EP1507777A4 (en) | 2007-03-07 |
| CN1642953A (zh) | 2005-07-20 |
| RU2277536C2 (ru) | 2006-06-10 |
| PL372371A1 (en) | 2005-07-25 |
| TW200306312A (en) | 2003-11-16 |
| AU2003224665A1 (en) | 2003-09-29 |
| KR20050002858A (ko) | 2005-01-10 |
| WO2003078392A2 (en) | 2003-09-25 |
| RS77704A (sr) | 2006-10-27 |
| RU2004127582A (ru) | 2006-01-27 |
| MXPA04008935A (es) | 2004-11-26 |
| JP2005520831A (ja) | 2005-07-14 |
| BR0308472A (pt) | 2005-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |