JP2007524565A5 - - Google Patents
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- Publication number
- JP2007524565A5 JP2007524565A5 JP2004560470A JP2004560470A JP2007524565A5 JP 2007524565 A5 JP2007524565 A5 JP 2007524565A5 JP 2004560470 A JP2004560470 A JP 2004560470A JP 2004560470 A JP2004560470 A JP 2004560470A JP 2007524565 A5 JP2007524565 A5 JP 2007524565A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- glycopyrronium
- stereoisomer
- quaternization
- solvent
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 claims description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- 238000005956 quaternization reaction Methods 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 24
- 229960002462 glycopyrronium bromide Drugs 0.000 claims 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 12
- 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 claims 11
- 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 claims 10
- 238000006243 chemical reaction Methods 0.000 claims 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- 239000000039 congener Substances 0.000 claims 4
- 238000004090 dissolution Methods 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000001953 recrystallisation Methods 0.000 claims 3
- 241000162682 Heterogen Species 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical group [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940015042 glycopyrrolate Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0189602A AT412088B (de) | 2002-12-18 | 2002-12-18 | Verfahren zur herstellung der r,r oder s,s konfigurierten glycopyrronium-isomere |
| PCT/EP2003/014432 WO2004054971A1 (de) | 2002-12-18 | 2003-12-18 | Verfaren zur herstellung des r,r (oder s,s) konfugurierten glycopyrronium-stereoisomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007524565A JP2007524565A (ja) | 2007-08-30 |
| JP2007524565A5 true JP2007524565A5 (https=) | 2010-09-16 |
Family
ID=31192804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004560470A Pending JP2007524565A (ja) | 2002-12-18 | 2003-12-18 | Ｒ，ｒ（又はｓ，ｓ）配置されたグリコピロニウム−立体異性体の製造方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7569598B2 (https=) |
| EP (1) | EP1572641B1 (https=) |
| JP (1) | JP2007524565A (https=) |
| CN (1) | CN100349867C (https=) |
| AT (2) | AT412088B (https=) |
| AU (1) | AU2003290075B2 (https=) |
| CA (1) | CA2510280C (https=) |
| DK (1) | DK1572641T3 (https=) |
| ES (1) | ES2383799T3 (https=) |
| NO (1) | NO330851B1 (https=) |
| NZ (1) | NZ541098A (https=) |
| PL (1) | PL214802B1 (https=) |
| PT (1) | PT1572641E (https=) |
| RU (1) | RU2337096C2 (https=) |
| WO (1) | WO2004054971A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0504463D0 (en) * | 2005-03-03 | 2005-04-13 | Arakis Ltd | Method of crystallisation and purification |
| WO2010115937A1 (en) * | 2009-04-09 | 2010-10-14 | Novartis Ag | Process for preparing pyrrolidinium salts |
| 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 |
| RS55996B1 (sr) * | 2011-12-22 | 2017-09-29 | Cerbios-Pharma S A | Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina |
| CN102627595A (zh) * | 2012-03-09 | 2012-08-08 | 徐奎 | 一种制备格隆溴铵的方法 |
| US8558008B2 (en) | 2013-02-28 | 2013-10-15 | Dermira, Inc. | Crystalline glycopyrrolate tosylate |
| EP3473615B1 (en) | 2013-02-28 | 2022-01-19 | Journey Medical Corporation | Glycopyrrolate salts |
| US9006462B2 (en) | 2013-02-28 | 2015-04-14 | Dermira, Inc. | Glycopyrrolate salts |
| CN104586841A (zh) * | 2013-10-30 | 2015-05-06 | 中国药科大学 | (3r,2’r)-格隆溴铵作为m3毒蕈碱性受体拮抗剂在制药中的用途 |
| CN107304178B (zh) * | 2016-04-21 | 2020-03-27 | 辽宁药联制药有限公司 | 一种毒蕈碱受体拮抗剂格隆溴铵手性对映体的制备方法 |
| 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 |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0937041T3 (da) * | 1996-11-11 | 2003-08-11 | Christian R Noe | Anvendelse af et farmaceutisk egnet salt af (3R,2'R)-3-[(cyclopentil-hydroxyphenylacetyl)oxyl]-1,1-dimethyl-pyrrolidinium til fremstilling af et lægemiddel |
-
2002
- 2002-12-18 AT AT0189602A patent/AT412088B/de not_active IP Right Cessation
-
2003
- 2003-12-18 EP EP03782435A patent/EP1572641B1/de not_active Expired - Lifetime
- 2003-12-18 NZ NZ541098A patent/NZ541098A/en not_active IP Right Cessation
- 2003-12-18 DK DK03782435.6T patent/DK1572641T3/da active
- 2003-12-18 WO PCT/EP2003/014432 patent/WO2004054971A1/de not_active Ceased
- 2003-12-18 PT PT03782435T patent/PT1572641E/pt unknown
- 2003-12-18 ES ES03782435T patent/ES2383799T3/es not_active Expired - Lifetime
- 2003-12-18 US US10/540,187 patent/US7569598B2/en not_active Expired - Lifetime
- 2003-12-18 CN CNB2003801098187A patent/CN100349867C/zh not_active Expired - Fee Related
- 2003-12-18 JP JP2004560470A patent/JP2007524565A/ja active Pending
- 2003-12-18 AU AU2003290075A patent/AU2003290075B2/en not_active Ceased
- 2003-12-18 AT AT03782435T patent/ATE548348T1/de active
- 2003-12-18 CA CA2510280A patent/CA2510280C/en not_active Expired - Fee Related
- 2003-12-18 PL PL377441A patent/PL214802B1/pl unknown
- 2003-12-18 RU RU2005122497/04A patent/RU2337096C2/ru active
-
2005
- 2005-07-15 NO NO20053473A patent/NO330851B1/no not_active IP Right Cessation
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