WO2009125415A1 - Forme amorphe de citrate de sildénafil - Google Patents
Forme amorphe de citrate de sildénafil Download PDFInfo
- Publication number
- WO2009125415A1 WO2009125415A1 PCT/IN2008/000226 IN2008000226W WO2009125415A1 WO 2009125415 A1 WO2009125415 A1 WO 2009125415A1 IN 2008000226 W IN2008000226 W IN 2008000226W WO 2009125415 A1 WO2009125415 A1 WO 2009125415A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sildenafil citrate
- amorphous form
- amorphous
- sildenafil
- citrate
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Definitions
- the invention relates to a novel amorphous form of sildenafil citrate, to a process for the preparation thereof and to a composition comprising thereof.
- Sildenafil citrate is known by the chemical name 1-[[3-(4,7-Dihydro-1- methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl] -4-methylpiperazine citrate.
- Sildenafil citrate is an antihypertensive agent having a treatment of male erectile dysfunction.
- Sildenafil citrate is represented by the following structure:
- Sildenafil and its citrate salt may be prepared using the procedures described in Eur. Pat. No. 00463756 and WO 2005/067936 A2.
- U.S. pat. App. No. 2004/0235857 A1 discloses crystalline forms of sildenafil citrate Anhydrous Form, Hydrated Form and Hydrated forms of sildenafil hemicitrate.
- sildenafil citrate in substantially amorphous form has higher bioavailability than when in crystalline form and that moreover the amorphous form of Sildenafil citrate has adequate chemical stability upon storage and therefore can be used in pharmaceutical formulation.
- the object of present invention is to provide a novel amorphous form of sildenafil citrate (herein after referred to as amorphous sildenafil citrate), process for preparation thereof and a pharmaceutical composition containing it.
- amorphous sildenafil citrate a novel amorphous form of sildenafil citrate
- amorphous sildenafil citrate substantially amorphous form.
- the amorphous form of sildenafil citrate present invention is characterized by powder x-ray diffraction pattern as shown in fig.1 and FTIR spectrum as shown in fig.2.
- the amorphous sildenafil citrate according to the invention is prepared by a process which constitutes a further feature of the present invention and which comprises recovering sildenafil citrate from an aqueous solution of sildenafil citrate thereof under conditions whereby a substantially amorphous product is obtained.
- Substantial amorphous sildenafil citrate refers to amorphous form having less than 5% crystallinity as measured by X-RD techniques.
- Techniques which are employed to recover amorphous sildenafil citrate from the solution thereof include those wherein water is removed from an aqueous solution of sildenafil citrate and the product deposited. Methods involving the use of these procedures include spray drying and vacuum drying.
- a pharmaceutical composition comprising amorphous sildenafil citrate and a pharmaceutically acceptable excipient.
- Preferable pharmaceutical composition of amorphous sildenafil citrate is a solid oral dosage form, comprising amorphous sildenafil citrate.
- Figure 1 is X-ray powder diffraction spectrum of amorphous sildenafil citrate.
- Figure 2 is FTIR spectrum of amorphous sildenafil citrate.
- X-ray powder diffraction spectrum was measured on a bruker axs D8 advance X-ray powder diffractometer having a copper-K ⁇ radiation. Approximately 1gm of sample was gently flattered on a sample holder and scanned from 2 to 50 degrees two-theta, at 0.03 degrees to theta per step and a step of 0.5 seconds. The sample was simply placed on the sample holder. The sample was rotated at 30 rpm at a voltage 40 KV and current 35 mA.
- Crystalline sildenafil citrate (5 gm) is dissolved in water (800 ml). The solution is subjected to vacuum drying at 80 0 C for 10 hours to give quantative yield of amorphous sildenafil citrate.
- Crystalline sildenafil citrate (5 gm) is dissolved in water (800 ml) and heated to 50 - 6O 0 C and the solution is subjected to spray drying at 80 0 C for 30 minutes to give quantative yield of amorphous sildenafil citrate.
- Spray dryer conditions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention porte sur une nouvelle forme amorphe de citrate de sildénafil, sur un procédé pour la fabrication de celle-ci et sur une composition la contenant.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IN2008/000226 WO2009125415A1 (fr) | 2008-04-07 | 2008-04-07 | Forme amorphe de citrate de sildénafil |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IN2008/000226 WO2009125415A1 (fr) | 2008-04-07 | 2008-04-07 | Forme amorphe de citrate de sildénafil |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009125415A1 true WO2009125415A1 (fr) | 2009-10-15 |
Family
ID=41161591
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IN2008/000226 WO2009125415A1 (fr) | 2008-04-07 | 2008-04-07 | Forme amorphe de citrate de sildénafil |
Country Status (1)
Country | Link |
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WO (1) | WO2009125415A1 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107722019A (zh) * | 2015-07-23 | 2018-02-23 | 青岛华之草医药科技有限公司 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
US9968609B2 (en) | 2014-03-19 | 2018-05-15 | Vigorous Solutions Ltd. | Sildenafil solutions and methods of making and using same |
CN109867677A (zh) * | 2017-12-04 | 2019-06-11 | 广州白云山医药集团股份有限公司白云山化学制药厂 | 一种回收制备西地那非的方法 |
CN112618508A (zh) * | 2021-01-15 | 2021-04-09 | 遂成药业股份有限公司 | 一种稳定无定型的枸橼酸西地那非片及其生产工艺 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040235857A1 (en) * | 2003-02-11 | 2004-11-25 | Pfizer Inc | Crystalline therapeutic agent |
WO2005067936A2 (fr) * | 2004-01-05 | 2005-07-28 | Teva Pharmaceutical Industries Ltd. | Procedes de fabrication de sildenafil base et de son sel citrate |
WO2005115330A2 (fr) * | 2004-05-28 | 2005-12-08 | Pfizer Products Inc. | Compositions pharmaceutiques aux performances accrues |
EP1779852A2 (fr) * | 2004-01-05 | 2007-05-02 | Teva Pharmaceutical Industries Ltd. | Procédés de production d'une base de sildenafil et de sel de citrate |
-
2008
- 2008-04-07 WO PCT/IN2008/000226 patent/WO2009125415A1/fr active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040235857A1 (en) * | 2003-02-11 | 2004-11-25 | Pfizer Inc | Crystalline therapeutic agent |
WO2005067936A2 (fr) * | 2004-01-05 | 2005-07-28 | Teva Pharmaceutical Industries Ltd. | Procedes de fabrication de sildenafil base et de son sel citrate |
EP1779852A2 (fr) * | 2004-01-05 | 2007-05-02 | Teva Pharmaceutical Industries Ltd. | Procédés de production d'une base de sildenafil et de sel de citrate |
WO2005115330A2 (fr) * | 2004-05-28 | 2005-12-08 | Pfizer Products Inc. | Compositions pharmaceutiques aux performances accrues |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9968609B2 (en) | 2014-03-19 | 2018-05-15 | Vigorous Solutions Ltd. | Sildenafil solutions and methods of making and using same |
US10211534B2 (en) | 2014-03-19 | 2019-02-19 | Vigorous Solutions Ltd. | Sildenafil solutions and methods of making and using same |
CN107722019A (zh) * | 2015-07-23 | 2018-02-23 | 青岛华之草医药科技有限公司 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN107722018A (zh) * | 2015-07-23 | 2018-02-23 | 青岛华之草医药科技有限公司 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN107722020A (zh) * | 2015-07-23 | 2018-02-23 | 青岛华之草医药科技有限公司 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN107827895A (zh) * | 2015-07-23 | 2018-03-23 | 青岛华之草医药科技有限公司 | 一种制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN107880047A (zh) * | 2015-07-23 | 2018-04-06 | 青岛华之草医药科技有限公司 | 一种枸橼酸西地那非化合物 |
CN107880048A (zh) * | 2015-07-23 | 2018-04-06 | 青岛华之草医药科技有限公司 | 一种枸橼酸西地那非化合物 |
CN107903270A (zh) * | 2015-07-23 | 2018-04-13 | 青岛华之草医药科技有限公司 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN109867677A (zh) * | 2017-12-04 | 2019-06-11 | 广州白云山医药集团股份有限公司白云山化学制药厂 | 一种回收制备西地那非的方法 |
CN112618508A (zh) * | 2021-01-15 | 2021-04-09 | 遂成药业股份有限公司 | 一种稳定无定型的枸橼酸西地那非片及其生产工艺 |
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