CN102793680A - Azilsartan solid dispersion and preparation method and medicinal composition thereof - Google Patents
Azilsartan solid dispersion and preparation method and medicinal composition thereof Download PDFInfo
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- CN102793680A CN102793680A CN2011101344667A CN201110134466A CN102793680A CN 102793680 A CN102793680 A CN 102793680A CN 2011101344667 A CN2011101344667 A CN 2011101344667A CN 201110134466 A CN201110134466 A CN 201110134466A CN 102793680 A CN102793680 A CN 102793680A
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Abstract
The invention relates to an azilsartan solid dispersion and a preparation method and medicinal composition thereof. A solid dispersion system is prepared from azilsartan and pharmaceutically acceptable carrier materials of azilsartan. According to the invention, the problem of poor water solubility of asilsartan can be solved, the pH dependence of azilsartan dissolubility can be weakened, and azilsartan can achieve an ideal dissolving effect in different pH media.
Description
Technical field
The pharmaceutical composition that the present invention relates to a kind of A Qishatan solid dispersion, its preparation method and comprise it, and the purposes in the preparation antihypertensive drug.。
Background technology
Drug products need have effectiveness and safety.Effectiveness and safety in order to ensure drug products; The not only effectiveness of active ingredient itself and safety; And, all be very important such as the stability of active ingredient in preparation, the dissolution characteristic of medicine from preparation etc. from the character of preparation medicament aspect.For example, even preparation satisfies the quality of certain level after preparation just, if the active ingredient in preparation decomposes in time, effectiveness and the safety said preparation according to drug products is problematic so.For the dissolution characteristic of medicine from preparation, when medicine when stripping is too slow from preparation, this medicine may not reach valid density and may not realize desired effect in blood.
A Qishatan (English name Azilsartan) is a kind of angiotensin ii receptor antagonist medicine that is in the treatment vascular hypertension in the research and development; Through of the vasoconstrictive effect that combine block Angiotensin II of selective exclusion Angiotensin II with vascular smooth muscle AT1 receptor; Be used to treat vascular hypertension, also be at present unique clinical angiotensin ii receptor antagonist in latter stage (husky smooth type) medicine that is in more.
CN 101528262A provides a kind of solid composite medicament that is intended to improve the medicine dissolution rate, but the dissolution rate of this solid composite is still not satisfactory, and its dissolubility has special pH dependency, in different pH media, changes bigger.This has bad influence to effective ingredient absorption in vivo and bioavailability.
Summary of the invention
The present invention aims to provide a kind of have better A Qishatan dissolubility and dissolution, and the solid dispersion of compressibility, good fluidity weakens the pH dependency of its dissolubility.
The present invention aims to provide the solid dispersion of a kind of A Qishatan, wherein contains A Qishatan and carrier material as active component.
Said carrier material is selected from polyvidone, poloxamer, Polyethylene Glycol, hydroxypropyl cellulose, polyethylene glycol oxide etc.Preferred polyvidone and hydroxypropyl cellulose, more preferably polyvidone.
The povidone selected from povidone K-17, povidone K-25, povidone K-30, povidone K-90; hydroxypropyl cellulose selected, for example under the trade name
LF,
JF,
-EF,
-EXF like.
The quality ratio range of active component A Qishatan and carrier material is 1 among the present invention: 0.5-1: 20, be preferably 1: 0.75-1: 15, more preferably 1: 1-1: and 10, most preferably be 1: 2-1: 5.
Another object of the present invention is to provide a kind of method for preparing above-mentioned A Qishatan solid dispersion, comprise solvent method, fusion method and polishing, be preferably solvent method.
Wherein solvent method may further comprise the steps:
1. active component and carrier material are dissolved in the organic solvent;
2. organic solvent is removed.
Wherein, the solvent that in step 1, uses is selected from one or more of methanol, ethanol, acetone, oxolane, chloroform, dichloromethane, particular methanol.As the weight of the A Qishatan of active component and carrier and with the mass ratio of organic solvent be 1: 5-1: 50, be preferably 1: 10-1: 30.
The method of in step 2, removing organic solvent is selected from and removes under reduced pressure, drying under reduced pressure, vacuum drying, lyophilization, spray drying, fluid bed drying, heating, drying, preferred drying under reduced pressure or spray drying.
Another object of the present invention is to provide a kind of pharmaceutical composition that comprises said A Qishatan solid dispersion and pharmaceutically acceptable, suitable pharmaceutic adjuvant.
Said pharmaceutical composition can be prepared into tablet, capsule, drop pill, granule, pellet, is preferably tablet
The purposes of the pharmaceutical composition that another object of the present invention also is said A Qishatan solid dispersion to be provided and to contain this solid dispersion in the preparation antihypertensive drug.
A Qishatan solid dispersion through the present invention's preparation compared with prior art has the following advantages:
1. the present invention has significantly improved the dissolubility of A Qishatan, has weakened the pH dependency of A Qishatan dissolubility.
2. the A Qishatan solid dispersion of the present invention's preparation makes A Qishatan that ideal stripping all arranged in different pH medium.Its stripping in pH4.5 acetate salt buffer medium is apparently higher than prior art (CN 101528262A).
3.X-after the presentation of results A Qishatan of x ray diffraction and carrier formed solid dispersion, the crystal diffraction peak of A Qishatan disappeared, solid dispersion exists with amorphous or molecularity.
4. the A Qishatan solid dispersion powder compressibility, the good fluidity that make.
Description of drawings
Fig. 1 is that the embodiment of the invention 16 and the stripping of patent CN 101528262A embodiment 2 in pH 6.8 are compared.
Fig. 2 is that the embodiment of the invention 16 and the stripping of patent CN 101528262A embodiment 2 in pH 4.5 are compared.
Fig. 3 is the x-ray diffraction pattern of A Qishatan crude drug.
Fig. 4 is the x-ray diffraction pattern of A Qishatan-PVP solid dispersion.
Fig. 5 is the x-ray diffraction pattern of PVP carrier.
The specific embodiment
The present invention does further to set forth through following examples, but does not really want to come by any way invention is limited with it.Wherein embodiment 1-11 is the preparation of solid dispersion; Embodiment 12-17 is the solid dispersion preparation of drug combination.
Embodiment 1
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 10g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 15g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 17.5g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 4
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 20g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 5
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 25g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 6
Take by weighing the A Qishatan of 5g and the PVP-K25 of 15g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 7
Take by weighing the A Qishatan of 5g and the PVP-K90 of 15g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 8
Take by weighing the A Qishatan of 5g and the HPC-EF of 15g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 9
Take by weighing the A Qishatan of 5g and the poloxamer 188 of 25g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion
Take by weighing the A Qishatan of 5g and the Polyethylene Glycol PEG4000 of 25g, add 400mL methanol and be stirred to dissolving, it is changed in the vacuum drying oven, keep 40 ℃, pulverize behind the drying under reduced pressure 24h, cross 60 mesh sieves, promptly obtain the A Qishatan solid dispersion.
Embodiment 11
Take by weighing the A Qishatan of 5g and the polyvidone PVP-K30 of 20g, add 400mL methanol and be stirred to dissolving.This solution is carried out spray drying.Its entrance and exit temperature of spray drying maintains 90 ℃ and 50 ℃ respectively, and collecting sample is the De Aqishatan solid dispersion.
Embodiment 12
Method for preparing: claim the solid dispersion of recipe quantity and the adjuvant except that magnesium stearate.Behind the mix homogeneously, cross 30 mesh sieves, mix the back once more and add the recipe quantity magnesium stearate.Adopt the 8.5mm punch die behind the mix homogeneously, with weight 250mg, pressure 7～9kg is with the mixture tabletting.
Embodiment 13
Method for preparing: claim the solid dispersion of recipe quantity and the adjuvant except that magnesium stearate.Behind the mix homogeneously, cross 30 mesh sieves, mix the back once more and add the recipe quantity magnesium stearate, adopt the 8.5mm punch die behind the mix homogeneously, with weight 250mg, pressure 7～9kg is with the mixture tabletting.
Embodiment 14
Method for preparing: claim the solid dispersion of recipe quantity and the adjuvant except that magnesium stearate.Behind the mix homogeneously, cross 30 mesh sieves, mix the back once more and add recipe quantity magnesium stearate (with preceding mistake 60 mesh sieves).Adopt the 8.5mm punch die behind the mix homogeneously, with weight 250mg, pressure 7～9kg is with the mixture tabletting.
Embodiment 15
Method for preparing: claim the solid dispersion of recipe quantity and the adjuvant except that magnesium stearate.Behind the mix homogeneously, cross 30 mesh sieves, mix the back once more and add the recipe quantity magnesium stearate.Adopt the 10.5mm punch die behind the mix homogeneously, with weight 500mg, pressure 7～9kg is with the mixture tabletting.
Embodiment 16
Method for preparing: claim the solid dispersion of recipe quantity and the adjuvant except that magnesium stearate.Behind the mix homogeneously, cross 30 mesh sieves, mix the back once more and add the recipe quantity magnesium stearate, adopt the 9.5mm punch die behind the mix homogeneously, with weight 350mg, pressure 7～9kg is with the mixture tabletting.
Embodiment 17
Method for preparing 1:, preceding four kinds of pressed powder mixings are crossed 30 mesh sieves by above prescription.Hydroxypropyl cellulose aqueous solution with 5% is granulated as binding agent.After wet granular is crossed 20 mesh sieves, be positioned in 40 ℃ of baking ovens and dry.Granule is taken out in the oven dry back, crosses 20 mesh sieves.Add recipe quantity cross-linked pvp and magnesium stearate then, mix homogeneously.Adopt the 8.5mm punch die, with weight 250mg, pressure 7～9kg is with the mixture tabletting.
Method for preparing 2: with the A Qishatan in the above-mentioned prescription-polyvidone PVP-K30 solid dispersion, mannitol, microcrystalline Cellulose, cross 30 mesh sieves behind the mix homogeneously, carry out dry granulation.Add recipe quantity cross-linked pvp and magnesium stearate again, behind the mix homogeneously, adopt the 8.5mm punch die, with weight 250mg, pressure 7～9kg is with the mixture tabletting.
Test case 1: dissolution test
Respectively the embodiment of the invention 16 is compared with the dissolution that patent CN 101528262A embodiment 2 carries out different dissolution mediums.
Fig. 1 is the embodiment of the invention 16 and the stripping of patent CN 101528262A embodiment 2 in pH6.8.
Fig. 2. be the embodiment of the invention 16 and the stripping of patent CN 101528262A embodiment 2 in pH4.5.
Visible by figure, the embodiment of the invention 16 all has ideal stripping with patent CN 101528262A embodiment 2 in pH 6.8.But in pH4.5 patent CN 101528262A embodiment 2 only stripping about 10%, and the present invention still keeps ideal stripping.Because A Qishatan has higher dissolubility (893.6 μ g/mL) in pH 6.8, and the dissolubility in pH 4.5 very low (49.45 μ g/mL).This has caused the difference of CN 101528262A embodiment 2 dissolution in different medium.And the present invention combines to form solid dispersion with A Qishatan with carrier, thereby has weakened the pH dependency of A Qishatan dissolubility, makes A Qishatan in different medium, all keep good stripping.This has great significance to promoting A Qishatan absorption in vivo and the bioavailability that improves A Qishatan.
Test case 2: powder x-ray diffraction test (PXRD)
Fig. 3 is the x-ray diffraction pattern of A Qishatan crude drug.
Fig. 4 is the x-ray diffraction pattern of A Qishatan-PVP solid dispersion.
Fig. 5. be PVP carrier x-ray diffraction pattern.
Visible by figure, after A Qishatan and carrier had formed solid dispersion, the crystal diffraction peak of A Qishatan disappeared, and solid dispersion exists with amorphous or molecularity.
Claims (14)
1. the solid dispersion of Yi Zhong A Qishatan contains A Qishatan and carrier material as active component.
2. solid dispersion as claimed in claim 1 is characterized in that said carrier material is selected from one or more in polyvidone, poloxamer, Polyethylene Glycol, hydroxypropyl cellulose, the polyethylene glycol oxide.
3. solid dispersion as claimed in claim 1; It is characterized in that said carrier material is selected from one or more among 30 POVIDONE K 30 BP/USP-17,30 POVIDONE K 30 BP/USP-25,30 POVIDONE K 30 BP/USP-30,30 POVIDONE K 30 BP/USP-90, poloxamer 188, Macrogol 4000, polyethylene glycol 6000,
LF,
JF,
EF,
EXF, the PEO-N80.
4. solid dispersion as claimed in claim 3 is characterized in that, said carrier material is selected from one or more of 30 POVIDONE K 30 BP/USP-17,30 POVIDONE K 30 BP/USP-25,30 POVIDONE K 30 BP/USP 30,30 POVIDONE K 30 BP/USP-90.
5. solid dispersion as claimed in claim 4 is characterized in that, said carrier material is a 30 POVIDONE K 30 BP/USP-30.
6. like any described solid dispersion of claim 1-5; It is characterized in that the quality ratio range of said A Qishatan and carrier material is 1: 0.5-1: 20, be preferably 1: 0.75-1: 15; More preferably 1: 1-1: 10, most preferably be 1: 2-1: 5.
7. method for preparing like the arbitrary described A Qishatan solid dispersion of right 1-6, this method is selected from solvent method, fusion method, polishing, the preferred solvent method.
8. the method for preparing of A Qishatan solid dispersion as claimed in claim 7 is characterized in that, this method may further comprise the steps:
(1) A Qishatan and carrier are dissolved in the solvent, stir to A Qishatan and carrier and all dissolve;
(2), pulverizing also dry except that desolvating obtains solid dispersion.
9. the method for preparing of A Qishatan solid dispersion as claimed in claim 8 is characterized in that, said solvent is selected from one or more of methanol, ethanol, acetone, oxolane, chloroform, dichloromethane, particular methanol.
10. like the method for preparing of the arbitrary described A Qishatan solid dispersion of claim 8-9, it is characterized in that, the weight of A Qishatan and carrier and with the weight ratio of solvent be 1: 5-1: 50, be preferably 1: 10-1: 30.
11. method for preparing like the arbitrary described A Qishatan solid dispersion of claim 8-10; It is characterized in that; Remove the method desolvate be selected from remove under reduced pressure, drying under reduced pressure, vacuum drying, lyophilization, spray drying, fluid bed drying, heating, drying one or more, be preferably drying under reduced pressure or spray drying.
12. a pharmaceutical composition, it comprises arbitrary described A Qishatan solid dispersion of right 1-6 and pharmaceutically acceptable, suitable pharmaceutic adjuvant.
13. pharmaceutical composition as claimed in claim 12 is characterized in that, said composition can be prepared into tablet, capsule, drop pill, granule, pellet, is preferably tablet.
14. like any described solid dispersion of claim 1-6 or the purposes of any described pharmaceutical composition of claim 12-13 in the preparation antihypertensive drug.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101344667A CN102793680A (en) | 2011-05-23 | 2011-05-23 | Azilsartan solid dispersion and preparation method and medicinal composition thereof |
| CN201280003292.3A CN103260605B (en) | 2011-05-23 | 2012-04-17 | Azilsartan solid dispersion, preparation method and pharmaceutical compositions thereof |
| PCT/CN2012/074162 WO2012159511A1 (en) | 2011-05-23 | 2012-04-17 | Azilsartan solid dispersion, preparation method and pharmaceutical compositions thereof |
| TW101114351A TW201247201A (en) | 2011-05-23 | 2012-04-23 | Azilsartan solid dispersion, its preparation method and pharmaceutical composition thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101344667A CN102793680A (en) | 2011-05-23 | 2011-05-23 | Azilsartan solid dispersion and preparation method and medicinal composition thereof |
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|---|---|
| CN102793680A true CN102793680A (en) | 2012-11-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2011101344667A Pending CN102793680A (en) | 2011-05-23 | 2011-05-23 | Azilsartan solid dispersion and preparation method and medicinal composition thereof |
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| Country | Link |
|---|---|
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014102628A1 (en) * | 2012-12-31 | 2014-07-03 | Ranbaxy Laboratories Limited | Stable pharmaceutical composition comprising azilsartan medoxomil |
| CN104490835A (en) * | 2014-12-23 | 2015-04-08 | 广东东阳光药业有限公司 | Azilsartan medoxomil tablets and preparation method thereof |
| CN104523632A (en) * | 2015-02-03 | 2015-04-22 | 山东新时代药业有限公司 | Azilsartan tablet |
| CN104546770A (en) * | 2015-01-07 | 2015-04-29 | 万特制药(海南)有限公司 | Azilsartan orally-disintegrating tablet and preparation method thereof |
| CN104721147A (en) * | 2015-04-03 | 2015-06-24 | 海南海力制药有限公司 | Azilsartan solid dispersion as well as preparation method and medicament composition thereof |
| WO2015176655A1 (en) * | 2014-05-23 | 2015-11-26 | 深圳信立泰药业股份有限公司 | Allisartan isoproxil solid dispersion and pharmaceutical composition thereof |
| CN106109420A (en) * | 2016-08-11 | 2016-11-16 | 吴启旸 | Eplerenone solid dispersion and preparation thereof |
| CN106214649A (en) * | 2016-08-30 | 2016-12-14 | 佛山市弘泰药物研发有限公司 | A kind of Azilsartan potassium salt solid dispersion preparation and preparation method thereof |
| CN106913538A (en) * | 2015-12-25 | 2017-07-04 | 山东新时代药业有限公司 | A kind of Abiraterone acetate sublingual tablets and preparation method thereof |
| CN108096195A (en) * | 2018-01-08 | 2018-06-01 | 中国药科大学 | The method that Supercritical anti-solvent prepares azilsartan solid dispersion |
| CN111417386A (en) * | 2017-11-30 | 2020-07-14 | 保宁制药株式会社 | Solid dispersion containing fimasartan |
| CN111643461A (en) * | 2019-03-04 | 2020-09-11 | 鲁南制药集团股份有限公司 | Tablet for treating hypertension and preparation method thereof |
-
2011
- 2011-05-23 CN CN2011101344667A patent/CN102793680A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014102628A1 (en) * | 2012-12-31 | 2014-07-03 | Ranbaxy Laboratories Limited | Stable pharmaceutical composition comprising azilsartan medoxomil |
| WO2015176655A1 (en) * | 2014-05-23 | 2015-11-26 | 深圳信立泰药业股份有限公司 | Allisartan isoproxil solid dispersion and pharmaceutical composition thereof |
| CN104490835A (en) * | 2014-12-23 | 2015-04-08 | 广东东阳光药业有限公司 | Azilsartan medoxomil tablets and preparation method thereof |
| CN104546770A (en) * | 2015-01-07 | 2015-04-29 | 万特制药(海南)有限公司 | Azilsartan orally-disintegrating tablet and preparation method thereof |
| CN104523632A (en) * | 2015-02-03 | 2015-04-22 | 山东新时代药业有限公司 | Azilsartan tablet |
| CN104523632B (en) * | 2015-02-03 | 2017-09-29 | 山东新时代药业有限公司 | A kind of Azilsartan tablet |
| CN104721147A (en) * | 2015-04-03 | 2015-06-24 | 海南海力制药有限公司 | Azilsartan solid dispersion as well as preparation method and medicament composition thereof |
| CN106913538A (en) * | 2015-12-25 | 2017-07-04 | 山东新时代药业有限公司 | A kind of Abiraterone acetate sublingual tablets and preparation method thereof |
| CN106913538B (en) * | 2015-12-25 | 2020-06-16 | 山东新时代药业有限公司 | Abiraterone acetate sublingual tablet and preparation method thereof |
| CN106109420A (en) * | 2016-08-11 | 2016-11-16 | 吴启旸 | Eplerenone solid dispersion and preparation thereof |
| CN106109420B (en) * | 2016-08-11 | 2018-07-06 | 吴启旸 | Eplerenone solid dispersions and its preparation |
| CN106214649A (en) * | 2016-08-30 | 2016-12-14 | 佛山市弘泰药物研发有限公司 | A kind of Azilsartan potassium salt solid dispersion preparation and preparation method thereof |
| CN111417386A (en) * | 2017-11-30 | 2020-07-14 | 保宁制药株式会社 | Solid dispersion containing fimasartan |
| CN108096195A (en) * | 2018-01-08 | 2018-06-01 | 中国药科大学 | The method that Supercritical anti-solvent prepares azilsartan solid dispersion |
| CN111643461A (en) * | 2019-03-04 | 2020-09-11 | 鲁南制药集团股份有限公司 | Tablet for treating hypertension and preparation method thereof |
| CN111643461B (en) * | 2019-03-04 | 2022-09-13 | 鲁南制药集团股份有限公司 | Tablet for treating hypertension and preparation method thereof |
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Application publication date: 20121128 |