EA005928B1 - Способ получения кристаллической формы i каберголина - Google Patents
Способ получения кристаллической формы i каберголина Download PDFInfo
- Publication number
- EA005928B1 EA005928B1 EA200201016A EA200201016A EA005928B1 EA 005928 B1 EA005928 B1 EA 005928B1 EA 200201016 A EA200201016 A EA 200201016A EA 200201016 A EA200201016 A EA 200201016A EA 005928 B1 EA005928 B1 EA 005928B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- cabergoline
- mixture
- toluene
- diethyl ether
- solvate
- Prior art date
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 47
- 229960004596 cabergoline Drugs 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 238000002425 crystallisation Methods 0.000 claims abstract description 4
- 230000008025 crystallization Effects 0.000 claims abstract description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- 239000007790 solid phase Substances 0.000 description 8
- 238000004566 IR spectroscopy Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 description 2
- 229940097325 prolactin Drugs 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010021082 Hypoprolactinaemia Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001263 anti-prolactin effect Effects 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000000414 obstructive effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002076 thermal analysis method 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007308.0A GB0007308D0 (en) | 2000-03-24 | 2000-03-24 | Process for preparing crystalline form | of cabergoline |
| PCT/EP2001/003099 WO2001070740A1 (en) | 2000-03-24 | 2001-03-19 | Process for preparing crystalline form i of cabergoline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200201016A1 EA200201016A1 (ru) | 2003-02-27 |
| EA005928B1 true EA005928B1 (ru) | 2005-08-25 |
Family
ID=9888433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200201016A EA005928B1 (ru) | 2000-03-24 | 2001-03-19 | Способ получения кристаллической формы i каберголина |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6727363B2 (enExample) |
| EP (1) | EP1272489B1 (enExample) |
| JP (1) | JP4184666B2 (enExample) |
| KR (1) | KR100827558B1 (enExample) |
| CN (1) | CN1188412C (enExample) |
| AR (1) | AR032449A1 (enExample) |
| AT (1) | ATE250601T1 (enExample) |
| AU (2) | AU780747B2 (enExample) |
| BR (1) | BR0109507A (enExample) |
| CA (1) | CA2402836A1 (enExample) |
| CZ (1) | CZ20023176A3 (enExample) |
| DE (1) | DE60100858T2 (enExample) |
| DK (1) | DK1272489T3 (enExample) |
| EA (1) | EA005928B1 (enExample) |
| EE (1) | EE05088B1 (enExample) |
| ES (1) | ES2208602T3 (enExample) |
| GB (1) | GB0007308D0 (enExample) |
| HK (1) | HK1052348B (enExample) |
| HU (1) | HUP0300591A3 (enExample) |
| IL (2) | IL150985A0 (enExample) |
| MX (1) | MXPA02009283A (enExample) |
| MY (1) | MY134189A (enExample) |
| NO (1) | NO20024321L (enExample) |
| NZ (1) | NZ521316A (enExample) |
| PE (1) | PE20011140A1 (enExample) |
| PL (1) | PL358253A1 (enExample) |
| PT (1) | PT1272489E (enExample) |
| SI (1) | SI1272489T1 (enExample) |
| SK (1) | SK13582002A3 (enExample) |
| WO (1) | WO2001070740A1 (enExample) |
| ZA (1) | ZA200206045B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE10043321B4 (de) * | 2000-08-24 | 2005-07-28 | Neurobiotec Gmbh | Verwendung eines transdermalen therapeutischen Systems zur Behandlung der Parkinsonschen Krankheit, zur Behandlung und Prävention des prämenstruellen Syndroms und zur Lactationshemmung |
| DE10053397A1 (de) * | 2000-10-20 | 2002-05-02 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| DE10064453A1 (de) * | 2000-12-16 | 2002-07-04 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| MXPA04008935A (es) * | 2002-03-15 | 2004-11-26 | Pharmacia Corp | Procedimiento para la preparacion de la forma i cristalina de la cabergolina. |
| US20060281777A1 (en) * | 2002-03-15 | 2006-12-14 | Pfizer Inc. | Process for preparing crystalline form I of cabergoline |
| IL155545A (en) | 2003-04-21 | 2009-12-24 | Finetech Pharmaceutical Ltd | Solvate form of cabergoline |
| KR20060028761A (ko) * | 2003-05-08 | 2006-04-03 | 아이박스 파마슈티컬스 에스.알.오. | 다형의 카베르골린 |
| GB0409785D0 (en) * | 2004-04-30 | 2004-06-09 | 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 |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | 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 |
| EP2185169A2 (en) * | 2007-08-29 | 2010-05-19 | Max Zeller Söhne AG | Use of vitex agnus castus extracts for preparing a medicament |
| EP4074552B1 (en) * | 2021-04-16 | 2024-04-03 | Thermo King LLC | Electrical connection unit |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3019322A1 (de) | 1980-05-21 | 1981-12-03 | Merck Patent Gmbh, 6100 Darmstadt | Psychopharmakon sowie verwendung von adenosinderivaten |
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| GB2103603B (en) * | 1981-08-11 | 1985-04-11 | Erba Farmitalia | Ergoline derivatives |
| GB9205439D0 (en) * | 1992-03-12 | 1992-04-22 | Erba Carlo Spa | Process for the synthesis of ergoline derivatives |
| AU680539B2 (en) | 1993-08-18 | 1997-07-31 | Alcon Laboratories, Inc. | Use of ergoline derivatives for the treatment of glaucoma |
| WO1999036095A1 (en) | 1998-01-13 | 1999-07-22 | Astrazeneca Uk Limited | PHARMACEUTICAL COMPOSITIONS COMPRISING A COMPOUND HAVING DOPAMINE (D2) RECEPTOR AGONIST ACTIVITY AND A COMPOUND (B) HAVING β2-ADRENORECEPTOR AGONIST ACTIVITY |
| EP1066038B1 (en) | 1998-03-27 | 2005-12-21 | Pharmacia & Upjohn Company LLC | Use of cabergoline in the treatment of restless legs syndrome |
| 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 |
| GB0007309D0 (en) | 2000-03-24 | 2000-05-17 | Pharmacia & Upjohn Spa | Crystalline form V|| of cabergoline |
-
2000
- 2000-03-24 GB GBGB0007308.0A patent/GB0007308D0/en not_active Ceased
-
2001
- 2001-03-13 PE PE2001000237A patent/PE20011140A1/es not_active Application Discontinuation
- 2001-03-19 CA CA002402836A patent/CA2402836A1/en not_active Withdrawn
- 2001-03-19 SK SK1358-2002A patent/SK13582002A3/sk unknown
- 2001-03-19 HU HU0300591A patent/HUP0300591A3/hu unknown
- 2001-03-19 NZ NZ521316A patent/NZ521316A/en unknown
- 2001-03-19 MX MXPA02009283A patent/MXPA02009283A/es active IP Right Grant
- 2001-03-19 WO PCT/EP2001/003099 patent/WO2001070740A1/en not_active Ceased
- 2001-03-19 ES ES01936098T patent/ES2208602T3/es not_active Expired - Lifetime
- 2001-03-19 EA EA200201016A patent/EA005928B1/ru unknown
- 2001-03-19 SI SI200130045T patent/SI1272489T1/xx unknown
- 2001-03-19 CN CNB018070051A patent/CN1188412C/zh not_active Expired - Fee Related
- 2001-03-19 AR ARP010101263A patent/AR032449A1/es unknown
- 2001-03-19 EE EEP200200545A patent/EE05088B1/xx not_active IP Right Cessation
- 2001-03-19 HK HK03104554.7A patent/HK1052348B/zh not_active IP Right Cessation
- 2001-03-19 AU AU62110/01A patent/AU780747B2/en not_active Ceased
- 2001-03-19 JP JP2001568941A patent/JP4184666B2/ja not_active Expired - Fee Related
- 2001-03-19 PT PT01936098T patent/PT1272489E/pt unknown
- 2001-03-19 PL PL01358253A patent/PL358253A1/xx not_active Application Discontinuation
- 2001-03-19 IL IL15098501A patent/IL150985A0/xx active IP Right Grant
- 2001-03-19 BR BR0109507-2A patent/BR0109507A/pt not_active Application Discontinuation
- 2001-03-19 US US10/239,636 patent/US6727363B2/en not_active Expired - Fee Related
- 2001-03-19 DE DE60100858T patent/DE60100858T2/de not_active Expired - Fee Related
- 2001-03-19 DK DK01936098T patent/DK1272489T3/da active
- 2001-03-19 AT AT01936098T patent/ATE250601T1/de not_active IP Right Cessation
- 2001-03-19 KR KR1020027012590A patent/KR100827558B1/ko not_active Expired - Fee Related
- 2001-03-19 CZ CZ20023176A patent/CZ20023176A3/cs unknown
- 2001-03-19 EP EP01936098A patent/EP1272489B1/en not_active Expired - Lifetime
- 2001-03-22 MY MYPI20011364A patent/MY134189A/en unknown
-
2002
- 2002-07-29 ZA ZA200206045A patent/ZA200206045B/xx unknown
- 2002-07-30 IL IL150985A patent/IL150985A/en not_active IP Right Cessation
- 2002-09-10 NO NO20024321A patent/NO20024321L/no not_active Application Discontinuation
-
2003
- 2003-10-31 US US10/698,737 patent/US6953854B2/en not_active Expired - Fee Related
-
2005
- 2005-07-14 AU AU2005203071A patent/AU2005203071B2/en not_active Ceased
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