NO20074558L - Krystallisasjon og rensing av glykopyrroniumbromid - Google Patents
Krystallisasjon og rensing av glykopyrroniumbromidInfo
- Publication number
- NO20074558L NO20074558L NO20074558A NO20074558A NO20074558L NO 20074558 L NO20074558 L NO 20074558L NO 20074558 A NO20074558 A NO 20074558A NO 20074558 A NO20074558 A NO 20074558A NO 20074558 L NO20074558 L NO 20074558L
- Authority
- NO
- Norway
- Prior art keywords
- diastereoisomers
- crystallization
- purification
- glycopyrronium bromide
- solvent
- Prior art date
Links
- 229960002462 glycopyrronium bromide Drugs 0.000 title abstract 3
- 238000002425 crystallisation Methods 0.000 title abstract 2
- 230000008025 crystallization Effects 0.000 title abstract 2
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- ANGKOCUUWGHLCE-UHFFFAOYSA-N 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (1,1-dimethyl-3-pyrrolidin-1-iumyl) ester Chemical compound C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 ANGKOCUUWGHLCE-UHFFFAOYSA-N 0.000 abstract 1
- ANGKOCUUWGHLCE-HKUYNNGSSA-N [(3s)-1,1-dimethylpyrrolidin-1-ium-3-yl] (2r)-2-cyclopentyl-2-hydroxy-2-phenylacetate Chemical compound C1[N+](C)(C)CC[C@@H]1OC(=O)[C@](O)(C=1C=CC=CC=1)C1CCCC1 ANGKOCUUWGHLCE-HKUYNNGSSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229940102396 methyl bromide Drugs 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or 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 to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Medicinal Preparation (AREA)
Abstract
KRYSTALLISASJON OG RENSNING AV GLYKOPYRRONIUMBROMID En metode for fremstilling av krystallinsk glyk opyrroniumbromid, omfatter reaksjonen av glykopyrroniumbase med metylbromid i et løsningsmiddel, hvor løsningsmidlet er valgt slik at det diastereoisomere forhold av produktet favoriserer R,S og S,R diastereoisomerer over R,R, og S,S diastereoisomerer og separerer de ønskede diastereoisomerer gjennom én eller flere kontrollerte krystallisasjonstrinn. Denne metoden gir et produkt som har en partikkelstørrelse med smal fordeling.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0504463.1A GB0504463D0 (en) | 2005-03-03 | 2005-03-03 | Method of crystallisation and purification |
| PCT/GB2006/000770 WO2006092617A1 (en) | 2005-03-03 | 2006-03-03 | Crystallisation and purification of glycopyrronium bromide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20074558L true NO20074558L (no) | 2007-09-28 |
| NO340220B1 NO340220B1 (no) | 2017-03-20 |
Family
ID=34451780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20074558A NO340220B1 (no) | 2005-03-03 | 2007-09-10 | Krystallinsk glykopyrroniumbromid |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8846954B2 (no) |
| EP (1) | EP1856041B1 (no) |
| JP (1) | JP5319119B2 (no) |
| KR (1) | KR101267108B1 (no) |
| CN (1) | CN101133021B (no) |
| AT (1) | ATE431337T1 (no) |
| AU (1) | AU2006219727B2 (no) |
| BR (1) | BRPI0609057A2 (no) |
| CA (1) | CA2601129C (no) |
| DE (1) | DE602006006808D1 (no) |
| DK (1) | DK1856041T3 (no) |
| ES (1) | ES2326132T3 (no) |
| GB (1) | GB0504463D0 (no) |
| IL (1) | IL185576A (no) |
| MX (1) | MX2007010729A (no) |
| NO (1) | NO340220B1 (no) |
| NZ (1) | NZ561293A (no) |
| PT (1) | PT1856041E (no) |
| WO (1) | WO2006092617A1 (no) |
| ZA (1) | ZA200707512B (no) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090005577A1 (en) * | 2007-06-29 | 2009-01-01 | Nikolai Kraiouchkine | Method of producing 1-substituted 3-pyrrolates |
| JP5902612B2 (ja) * | 2009-04-09 | 2016-04-13 | ノバルティス アーゲー | ピロリジニウム塩の調製方法 |
| ES2528957T3 (es) * | 2010-06-14 | 2015-02-13 | Chiesi Farmaceutici S.P.A. | Forma cristalina del cloruro de glicopirronio |
| CN103159659A (zh) * | 2011-12-19 | 2013-06-19 | 沈阳药科大学 | 一种毒蕈碱受体拮抗剂格隆溴铵的制备方法 |
| CN102627595A (zh) * | 2012-03-09 | 2012-08-08 | 徐奎 | 一种制备格隆溴铵的方法 |
| ES2699257T3 (es) | 2013-02-28 | 2019-02-08 | Dermira Inc | Sales de glicopirrolato |
| US9006462B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Glycopyrrolate salts |
| US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
| CN103553996B (zh) * | 2013-11-13 | 2016-01-20 | 北京三泉医药技术有限公司 | 抗胆碱药物组合物 |
| US9926270B2 (en) | 2014-08-20 | 2018-03-27 | Dermira, Inc. | Process for production of glycopyrronium tosylate |
| CZ2014680A3 (cs) | 2014-10-06 | 2016-04-13 | Zentiva, K.S. | Způsob přípravy glykopyrronium bromidu |
| US9925168B2 (en) * | 2016-01-22 | 2018-03-27 | Chiesi Farmaceutici S.P.A. | Preparation of micronized particles of an antimuscarinic compound by hydrodynamic cavitation |
| CN107345945B (zh) * | 2016-05-05 | 2019-12-17 | 辽宁药联制药有限公司 | 一种拆分格隆溴铵对映体及杂质检查的高效液相色谱方法 |
| PT109445B (pt) | 2016-06-08 | 2018-11-06 | Hovione Farm Sa | Co-cristais farmacêuticos cristalinos de brometo de glicopirrónio com lactose |
| CN107915666A (zh) * | 2016-10-09 | 2018-04-17 | 四川海思科制药有限公司 | 一种格隆溴铵化合物 |
| WO2022079194A1 (en) | 2020-10-14 | 2022-04-21 | Pcas | Process for the production of glycopyrronium tosylate |
| CN113234003B (zh) * | 2021-04-23 | 2024-02-02 | 广东嘉博制药有限公司 | 一种格隆溴铵及其制备方法 |
| CN114428131B (zh) * | 2021-12-27 | 2023-09-15 | 山东泰合医药科技有限公司 | 一种拆分格隆溴铵中间体的非对映异构体的检测方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956062A (en) * | 1959-02-26 | 1960-10-11 | Robins Co Inc A H | Esters of amino alcohols |
| EP0937041B1 (de) * | 1996-11-11 | 2003-04-23 | Christian R. Noe | Verwendung eines pharmazeutisch geeigneten Salzes von (3R,2'R)-3-[(Cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium zur Herstellung eines Arzneimittels |
| AT412088B (de) | 2002-12-18 | 2004-09-27 | Pharmacon Forschung & Beratung Gmbh | Verfahren zur herstellung der r,r oder s,s konfigurierten glycopyrronium-isomere |
-
2005
- 2005-03-03 GB GBGB0504463.1A patent/GB0504463D0/en not_active Ceased
-
2006
- 2006-03-03 CN CN2006800069015A patent/CN101133021B/zh not_active Expired - Lifetime
- 2006-03-03 BR BRPI0609057-5A patent/BRPI0609057A2/pt not_active Application Discontinuation
- 2006-03-03 JP JP2007557594A patent/JP5319119B2/ja not_active Expired - Lifetime
- 2006-03-03 EP EP06709993A patent/EP1856041B1/en not_active Expired - Lifetime
- 2006-03-03 ZA ZA200707512A patent/ZA200707512B/xx unknown
- 2006-03-03 NZ NZ561293A patent/NZ561293A/en not_active IP Right Cessation
- 2006-03-03 CA CA2601129A patent/CA2601129C/en not_active Expired - Lifetime
- 2006-03-03 PT PT06709993T patent/PT1856041E/pt unknown
- 2006-03-03 KR KR1020077022077A patent/KR101267108B1/ko not_active Expired - Lifetime
- 2006-03-03 ES ES06709993T patent/ES2326132T3/es not_active Expired - Lifetime
- 2006-03-03 DK DK06709993T patent/DK1856041T3/da active
- 2006-03-03 US US11/817,166 patent/US8846954B2/en active Active
- 2006-03-03 DE DE602006006808T patent/DE602006006808D1/de not_active Expired - Lifetime
- 2006-03-03 MX MX2007010729A patent/MX2007010729A/es active IP Right Grant
- 2006-03-03 AT AT06709993T patent/ATE431337T1/de active
- 2006-03-03 WO PCT/GB2006/000770 patent/WO2006092617A1/en not_active Ceased
- 2006-03-03 AU AU2006219727A patent/AU2006219727B2/en not_active Expired
-
2007
- 2007-08-29 IL IL185576A patent/IL185576A/en active IP Right Grant
- 2007-09-10 NO NO20074558A patent/NO340220B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20080227988A1 (en) | 2008-09-18 |
| NO340220B1 (no) | 2017-03-20 |
| ATE431337T1 (de) | 2009-05-15 |
| KR101267108B1 (ko) | 2013-05-23 |
| KR20070113263A (ko) | 2007-11-28 |
| PT1856041E (pt) | 2009-07-21 |
| GB0504463D0 (en) | 2005-04-13 |
| ZA200707512B (en) | 2008-11-26 |
| DK1856041T3 (da) | 2009-08-24 |
| NZ561293A (en) | 2010-05-28 |
| IL185576A0 (en) | 2008-01-06 |
| EP1856041B1 (en) | 2009-05-13 |
| CN101133021A (zh) | 2008-02-27 |
| AU2006219727A1 (en) | 2006-09-08 |
| BRPI0609057A2 (pt) | 2010-02-17 |
| JP5319119B2 (ja) | 2013-10-16 |
| CA2601129A1 (en) | 2006-09-08 |
| MX2007010729A (es) | 2007-11-08 |
| HK1104817A1 (en) | 2008-01-25 |
| IL185576A (en) | 2011-11-30 |
| ES2326132T3 (es) | 2009-10-01 |
| AU2006219727B2 (en) | 2010-03-04 |
| WO2006092617A1 (en) | 2006-09-08 |
| EP1856041A1 (en) | 2007-11-21 |
| CN101133021B (zh) | 2011-01-19 |
| CA2601129C (en) | 2013-04-30 |
| JP2008531674A (ja) | 2008-08-14 |
| DE602006006808D1 (de) | 2009-06-25 |
| US8846954B2 (en) | 2014-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: SOSEI R&D LTD., GB |
|
| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: HEPTARES THERAPEUTICS LIMITED, GB |