WO2009129983A1 - Sels d'addition avec des acides de prasugrel et compositions pharmaceutiques les comprenant - Google Patents
Sels d'addition avec des acides de prasugrel et compositions pharmaceutiques les comprenant Download PDFInfo
- Publication number
- WO2009129983A1 WO2009129983A1 PCT/EP2009/002871 EP2009002871W WO2009129983A1 WO 2009129983 A1 WO2009129983 A1 WO 2009129983A1 EP 2009002871 W EP2009002871 W EP 2009002871W WO 2009129983 A1 WO2009129983 A1 WO 2009129983A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- prasugrel
- sulfonic acid
- acid addition
- salt
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 58
- 239000005465 B01AC22 - Prasugrel Substances 0.000 title claims abstract description 56
- 229960004197 prasugrel Drugs 0.000 title claims abstract description 56
- DTGLZDAWLRGWQN-UHFFFAOYSA-N prasugrel Chemical class C1CC=2SC(OC(=O)C)=CC=2CN1C(C=1C(=CC=CC=1)F)C(=O)C1CC1 DTGLZDAWLRGWQN-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 239000002253 acid Substances 0.000 title claims abstract description 48
- 239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 117
- 238000006243 chemical reaction Methods 0.000 claims description 27
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
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- 239000001103 potassium chloride Substances 0.000 description 1
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- WVWZXTJUCNEUAE-UHFFFAOYSA-M potassium;1,2-bis(ethenyl)benzene;2-methylprop-2-enoate Chemical compound [K+].CC(=C)C([O-])=O.C=CC1=CC=CC=C1C=C WVWZXTJUCNEUAE-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Definitions
- EP-A-1 298 132 discloses acid addition salts of Prasugrei, particularly acid addition salts using HCI and maleic acid as acid component. Methane sulfonic acid and p-toluene sulfonic acid are also mentioned.
- Form III is obtained from acetone at a reaction temperature of above 40 0 C, preferably of about 50 0 C to about 60 0 C 1 and in particular at about 56 0 C. It is possible that under these and other reaction conditions mixtures of forms I, Il and/or III are obtained.
- the collected material can be further purified by using recrystallisation techniques, washing with a suitable solvent and/or chromatography.
- the collected precipitate is dried at ambient or elevated temperature between 30 and 100 0 C. The drying process can be improved by using vacuum conditions.
- Attached figure 1 shows the XRPD of the crystalline salt of Prasugrel with benzene sulfonic acid.
- a sample of the besylate salt was stored for 108 day at ambient temperature in a closed bottle and the purity of the sample decreased only from 100% to 99.8% within this time.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention porte sur des sels d'addition avec des acides de Prasugrel, sur un procédé pour leur fabrication et sur des compositions pharmaceutiques les comprenant. En particulier, l'invention porte sur des sels de Prasugrel avec des acides benzènesulfonique et naphtalènesulfonique.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN975/CHE/2008 | 2008-04-21 | ||
| IN975CH2008 | 2008-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009129983A1 true WO2009129983A1 (fr) | 2009-10-29 |
Family
ID=40904043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2009/002871 WO2009129983A1 (fr) | 2008-04-21 | 2009-04-20 | Sels d'addition avec des acides de prasugrel et compositions pharmaceutiques les comprenant |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2009129983A1 (fr) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2469883A (en) * | 2009-04-30 | 2010-11-03 | Sandoz Ag | Novel crystalline form of Prasugrel hydrogensulphate |
| WO2011127300A1 (fr) | 2010-04-08 | 2011-10-13 | Teva Pharmaceutical Industries Ltd. | Formes cristallines de sels de prasugrel |
| EP2377520A1 (fr) | 2010-03-24 | 2011-10-19 | Ratiopharm GmbH | Composition pharmaceutique du prasugrel |
| CZ302796B6 (cs) * | 2009-11-16 | 2011-11-16 | Zentiva, K. S. | Cyklamát 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jeho výroby |
| US8193358B2 (en) | 2006-04-06 | 2012-06-05 | Daiichi Sankyo Company, Limited | Process for producing high-purity prasugrel and acid addition salt thereof |
| CN102532161A (zh) * | 2012-02-27 | 2012-07-04 | 扬州市星斗药业有限公司 | 普拉格雷苯磺酸盐及其制备方法 |
| WO2013010502A1 (fr) * | 2011-07-21 | 2013-01-24 | 四川海思科制药有限公司 | Sel d'addition d'acide de prasugrel, son procédé de préparation et utilisation |
| CN103304577A (zh) * | 2012-03-07 | 2013-09-18 | 辽宁亿灵科创生物医药科技有限公司 | 普拉格雷酸加成盐及其制备方法和药物应用 |
| WO2013150322A1 (fr) | 2012-04-02 | 2013-10-10 | Egis Pharmaceuticals Public Limited Company | Compositions pharmaceutiques orales stables à libération immédiate et contenant du prasugrel |
| CN103772408A (zh) * | 2012-10-26 | 2014-05-07 | 江苏先声药物研究有限公司 | 普拉格雷-1,5-萘二磺酸盐的结晶 |
| CN103848844A (zh) * | 2012-12-07 | 2014-06-11 | 天津市汉康医药生物技术有限公司 | 普拉格雷成盐化合物及其制备方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0542411A2 (fr) * | 1991-09-09 | 1993-05-19 | Sankyo Company Limited | Dérivés de tétrahydrothieno-, und Pyrrolopyridinderivate, ihre Herstellung und Verwendung als Blutplättchen-Aggregation-Inhibitoren |
| EP1298132A1 (fr) * | 2000-07-06 | 2003-04-02 | Sankyo Company, Limited | Sels d'addition acides de d riv s hydropyridine |
| WO2007114526A1 (fr) * | 2006-04-06 | 2007-10-11 | Daiichi Sankyo Company, Limited | Procede de production de prasugrel de grande purete et sel d'addition d'acide de celui-ci |
| WO2009062044A2 (fr) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Procédés de préparation de prasugrel et ses sels et polymorphes |
| WO2009066326A2 (fr) * | 2007-11-19 | 2009-05-28 | Msn Laboratories Limited | Procédé amélioré pour la préparation de prasugrel et de ses sels pharmaceutiquement acceptables |
-
2009
- 2009-04-20 WO PCT/EP2009/002871 patent/WO2009129983A1/fr active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0542411A2 (fr) * | 1991-09-09 | 1993-05-19 | Sankyo Company Limited | Dérivés de tétrahydrothieno-, und Pyrrolopyridinderivate, ihre Herstellung und Verwendung als Blutplättchen-Aggregation-Inhibitoren |
| EP1298132A1 (fr) * | 2000-07-06 | 2003-04-02 | Sankyo Company, Limited | Sels d'addition acides de d riv s hydropyridine |
| WO2007114526A1 (fr) * | 2006-04-06 | 2007-10-11 | Daiichi Sankyo Company, Limited | Procede de production de prasugrel de grande purete et sel d'addition d'acide de celui-ci |
| EP2003136A1 (fr) * | 2006-04-06 | 2008-12-17 | Daiichi Sankyo Company, Limited | Procede de production de prasugrel de grande purete et sel d'addition d'acide de celui-ci |
| WO2009062044A2 (fr) * | 2007-11-09 | 2009-05-14 | Dr. Reddy's Laboratories Ltd. | Procédés de préparation de prasugrel et ses sels et polymorphes |
| WO2009066326A2 (fr) * | 2007-11-19 | 2009-05-28 | Msn Laboratories Limited | Procédé amélioré pour la préparation de prasugrel et de ses sels pharmaceutiquement acceptables |
Non-Patent Citations (1)
| Title |
|---|
| BASTIN R J ET AL: "Salt Selection and Optimisation for Pharmaceutical New Chemical Entities", ORGANIC PROCESS RESEARCH AND DEVELOPMENT, CAMBRIDGE, GB, vol. 4, no. 5, 1 January 2000 (2000-01-01), pages 427 - 435, XP002228592 * |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8193358B2 (en) | 2006-04-06 | 2012-06-05 | Daiichi Sankyo Company, Limited | Process for producing high-purity prasugrel and acid addition salt thereof |
| GB2469883A (en) * | 2009-04-30 | 2010-11-03 | Sandoz Ag | Novel crystalline form of Prasugrel hydrogensulphate |
| CZ302796B6 (cs) * | 2009-11-16 | 2011-11-16 | Zentiva, K. S. | Cyklamát 5-[2-cyklopropyl-1-(2-fluorfenyl)-2-oxoethyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetátu známého pod nechráneným názvem prasugrel a zpusob jeho výroby |
| EP2377520A1 (fr) | 2010-03-24 | 2011-10-19 | Ratiopharm GmbH | Composition pharmaceutique du prasugrel |
| US8802854B2 (en) | 2010-04-08 | 2014-08-12 | Teva Pharmaceutical Industries Ltd. | Crystalline forms of Prasugrel salts |
| WO2011127300A1 (fr) | 2010-04-08 | 2011-10-13 | Teva Pharmaceutical Industries Ltd. | Formes cristallines de sels de prasugrel |
| EP2883877A1 (fr) | 2010-04-08 | 2015-06-17 | Teva Pharmaceutical Industries, Ltd. | Formes cristallines de sels de prasugrel |
| US9012641B2 (en) | 2010-04-08 | 2015-04-21 | Teva Pharmaceuticals Industries Ltd. | Crystalline forms of Prasugrel salts |
| WO2013010502A1 (fr) * | 2011-07-21 | 2013-01-24 | 四川海思科制药有限公司 | Sel d'addition d'acide de prasugrel, son procédé de préparation et utilisation |
| CN102532161A (zh) * | 2012-02-27 | 2012-07-04 | 扬州市星斗药业有限公司 | 普拉格雷苯磺酸盐及其制备方法 |
| CN103304577A (zh) * | 2012-03-07 | 2013-09-18 | 辽宁亿灵科创生物医药科技有限公司 | 普拉格雷酸加成盐及其制备方法和药物应用 |
| US8603537B2 (en) | 2012-04-02 | 2013-12-10 | Egis Pharmaceuticals Plc | Prasugrel containing quickly released stable oral pharmaceutical compositions |
| WO2013150322A1 (fr) | 2012-04-02 | 2013-10-10 | Egis Pharmaceuticals Public Limited Company | Compositions pharmaceutiques orales stables à libération immédiate et contenant du prasugrel |
| CN103772408A (zh) * | 2012-10-26 | 2014-05-07 | 江苏先声药物研究有限公司 | 普拉格雷-1,5-萘二磺酸盐的结晶 |
| CN103848844A (zh) * | 2012-12-07 | 2014-06-11 | 天津市汉康医药生物技术有限公司 | 普拉格雷成盐化合物及其制备方法 |
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