CZ20023176A3 - Způsob výroby krystalické formy i kabergolinu a solvatované formy v kabergolinu - Google Patents
Způsob výroby krystalické formy i kabergolinu a solvatované formy v kabergolinu Download PDFInfo
- Publication number
- CZ20023176A3 CZ20023176A3 CZ20023176A CZ20023176A CZ20023176A3 CZ 20023176 A3 CZ20023176 A3 CZ 20023176A3 CZ 20023176 A CZ20023176 A CZ 20023176A CZ 20023176 A CZ20023176 A CZ 20023176A CZ 20023176 A3 CZ20023176 A3 CZ 20023176A3
- Authority
- CZ
- Czechia
- Prior art keywords
- cabergoline
- toluene
- diethyl ether
- solvated
- ether mixture
- 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 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000012453 solvate Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 7
- 238000002425 crystallisation Methods 0.000 claims abstract description 5
- 230000008025 crystallization Effects 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000428 dust Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 238000003828 vacuum filtration Methods 0.000 claims description 2
- 238000001144 powder X-ray diffraction data Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 description 8
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000004566 IR spectroscopy Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 208000001089 Multiple system atrophy Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 208000018737 Parkinson disease Diseases 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 1
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 208000027771 Obstructive airways disease Diseases 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 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
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 238000005388 cross polarization Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000985 reflectance spectrum Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0007308.0A GB0007308D0 (en) | 2000-03-24 | 2000-03-24 | Process for preparing crystalline form | of cabergoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20023176A3 true CZ20023176A3 (cs) | 2003-02-12 |
Family
ID=9888433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20023176A CZ20023176A3 (cs) | 2000-03-24 | 2001-03-19 | Způsob výroby krystalické formy i kabergolinu a solvatované formy v kabergolinu |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US6727363B2 (https=) |
| EP (1) | EP1272489B1 (https=) |
| JP (1) | JP4184666B2 (https=) |
| KR (1) | KR100827558B1 (https=) |
| CN (1) | CN1188412C (https=) |
| AR (1) | AR032449A1 (https=) |
| AT (1) | ATE250601T1 (https=) |
| AU (2) | AU780747B2 (https=) |
| BR (1) | BR0109507A (https=) |
| CA (1) | CA2402836A1 (https=) |
| CZ (1) | CZ20023176A3 (https=) |
| DE (1) | DE60100858T2 (https=) |
| DK (1) | DK1272489T3 (https=) |
| EA (1) | EA005928B1 (https=) |
| EE (1) | EE05088B1 (https=) |
| ES (1) | ES2208602T3 (https=) |
| GB (1) | GB0007308D0 (https=) |
| HK (1) | HK1052348B (https=) |
| HU (1) | HUP0300591A3 (https=) |
| IL (2) | IL150985A0 (https=) |
| MX (1) | MXPA02009283A (https=) |
| MY (1) | MY134189A (https=) |
| NO (1) | NO20024321D0 (https=) |
| NZ (1) | NZ521316A (https=) |
| PE (1) | PE20011140A1 (https=) |
| PL (1) | PL358253A1 (https=) |
| PT (1) | PT1272489E (https=) |
| SI (1) | SI1272489T1 (https=) |
| SK (1) | SK13582002A3 (https=) |
| WO (1) | WO2001070740A1 (https=) |
| ZA (1) | ZA200206045B (https=) |
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 |
| DE10053397A1 (de) * | 2000-10-20 | 2002-05-02 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| 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 |
| DE10064453A1 (de) * | 2000-12-16 | 2002-07-04 | Schering Ag | Verwendung eines dopaminergen Wirkstoffes zur Behandlung von dopaminerg behandelbaren Erkrankungen |
| IL163779A0 (en) * | 2002-03-15 | 2005-12-18 | Pharmacia Corp | Process for preparing crystalline form i of cabergoline |
| PL374503A1 (en) * | 2002-03-15 | 2005-10-31 | Pharmacia Corporation | 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 |
| US7339060B2 (en) | 2005-03-23 | 2008-03-04 | Resolution Chemicals, Ltd. | Preparation of cabergoline |
| GB0515430D0 (en) * | 2005-07-27 | 2005-08-31 | 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 |
| US8637099B2 (en) * | 2007-08-29 | 2014-01-28 | Max Zeller Sohne 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 |
| WO1995005176A1 (en) | 1993-08-18 | 1995-02-23 | Alcon Laboratories, Inc. | Use of ergoline derivatives for the treatment of glaucoma |
| JP2002509119A (ja) | 1998-01-13 | 2002-03-26 | アストラゼネカ ユーケイ リミテッド | ドーパミン（Ｄ２）レセプターアゴニスト活性を有する化合物およびβ２−アドレナリンレセプターアゴニスト活性を有する化合物（Ｂ）を含有する薬学的組成物 |
| JP2002507562A (ja) | 1998-03-27 | 2002-03-12 | ファルマシア・アンド・アップジョン・カンパニー | レストレスレッグ症候群の治療におけるカベルゴリンの使用 |
| 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 |
-
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 PL PL01358253A patent/PL358253A1/xx not_active Application Discontinuation
- 2001-03-19 ES ES01936098T patent/ES2208602T3/es not_active Expired - Lifetime
- 2001-03-19 HK HK03104554.7A patent/HK1052348B/zh not_active IP Right Cessation
- 2001-03-19 WO PCT/EP2001/003099 patent/WO2001070740A1/en not_active Ceased
- 2001-03-19 EP EP01936098A patent/EP1272489B1/en not_active Expired - Lifetime
- 2001-03-19 EA EA200201016A patent/EA005928B1/ru unknown
- 2001-03-19 MX MXPA02009283A patent/MXPA02009283A/es active IP Right Grant
- 2001-03-19 CA CA002402836A patent/CA2402836A1/en not_active Withdrawn
- 2001-03-19 SK SK1358-2002A patent/SK13582002A3/sk unknown
- 2001-03-19 KR KR1020027012590A patent/KR100827558B1/ko 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 IL IL15098501A patent/IL150985A0/xx active IP Right Grant
- 2001-03-19 AR ARP010101263A patent/AR032449A1/es unknown
- 2001-03-19 CZ CZ20023176A patent/CZ20023176A3/cs unknown
- 2001-03-19 BR BR0109507-2A patent/BR0109507A/pt not_active Application Discontinuation
- 2001-03-19 AU AU62110/01A patent/AU780747B2/en not_active Ceased
- 2001-03-19 SI SI200130045T patent/SI1272489T1/xx unknown
- 2001-03-19 EE EEP200200545A patent/EE05088B1/xx not_active IP Right Cessation
- 2001-03-19 PT PT01936098T patent/PT1272489E/pt unknown
- 2001-03-19 US US10/239,636 patent/US6727363B2/en not_active Expired - Fee Related
- 2001-03-19 JP JP2001568941A patent/JP4184666B2/ja not_active Expired - Fee Related
- 2001-03-19 NZ NZ521316A patent/NZ521316A/en unknown
- 2001-03-19 CN CNB018070051A patent/CN1188412C/zh not_active Expired - Fee Related
- 2001-03-19 HU HU0300591A patent/HUP0300591A3/hu unknown
- 2001-03-19 AT AT01936098T patent/ATE250601T1/de not_active IP Right Cessation
- 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/NO20024321D0/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
Also Published As
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