CN103830201A - Dutasteride liquid soft capsules - Google Patents
Dutasteride liquid soft capsules Download PDFInfo
- Publication number
- CN103830201A CN103830201A CN201210469454.4A CN201210469454A CN103830201A CN 103830201 A CN103830201 A CN 103830201A CN 201210469454 A CN201210469454 A CN 201210469454A CN 103830201 A CN103830201 A CN 103830201A
- Authority
- CN
- China
- Prior art keywords
- dutasteride
- soft capsule
- chain triglyceride
- capmul mcm
- bht
- 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
- JWJOTENAMICLJG-QWBYCMEYSA-N dutasteride Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)N[C@@H]4CC3)C)CC[C@@]21C)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F JWJOTENAMICLJG-QWBYCMEYSA-N 0.000 title claims abstract description 82
- 229960004199 dutasteride Drugs 0.000 title claims abstract description 76
- 239000007901 soft capsule Substances 0.000 title claims abstract description 64
- 239000007788 liquid Substances 0.000 title claims abstract description 14
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims abstract description 29
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002775 capsule Substances 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims description 12
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 abstract description 18
- 238000004090 dissolution Methods 0.000 abstract description 15
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 abstract 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 20
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 20
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 20
- 229940054749 avodart Drugs 0.000 description 6
- 239000004530 micro-emulsion Substances 0.000 description 4
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940049654 glyceryl behenate Drugs 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 description 2
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 231100000360 alopecia Toxicity 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 (trifluoromethyl) phenyl Chemical group 0.000 description 1
- 229940123407 Androgen receptor antagonist Drugs 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003936 androgen receptor antagonist Substances 0.000 description 1
- 206010068168 androgenetic alopecia Diseases 0.000 description 1
- 230000001826 anti-prostatic effect Effects 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000012395 formulation development Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to dutasteride liquid soft capsules and a preparation method thereof. The soft capsules comprise a capsule shell and contents, wherein the contents mainly comprise, by weight, 0.05-0.3% of dutasteride, 19.8-94.8% of medium chain triglyceride, and 5-80% of mono-caprylin glycerate. The soft capsules have characteristics of rapid dissolution, simple preparation process and the like.
Description
Technical field
The invention belongs to field of pharmaceutical preparations, be specifically related to a kind of dutasteride's liquid soft capsule, this soft capsule comprises capsule shells and content, wherein, content is mainly by dutasteride 0.05%-0.3%, median chain triglyceride oil 19.8%-94%, Capmul MCM C8 5%-80%, and antioxidant 0.005%-0.2% composition.
Technical background
Dutasteride's chemical name: (5 α, 17 β)-(two (trifluoromethyl) phenyl of 2,5-)-3-oxygen-4-azepine-androstane-1-alkene-17-Methanamide, its chemical structural formula is:
Dutasteride is 2nd generation 5 alpha-reductase depressants, researched and developed by Ge Lansu company, l0 Yue10You FDA Food and Drug Administration (FDA) in 2002 approval is in U.S.'s listing, and trade name Avodart, is called Avolve at the commodity of European market.Be mainly used in clinically the treatment of prostate hyperplasia, male pattern baldness, seborrheic alopecia, hereditary alopecia, that current the first is also unique a kind of medicine that simultaneously suppresses I type and II type 5 alpha-reductases, compared with other 5α-reductase inhibitor, it is useful that dutasteride's dual function is proved to be clinically.In China, 5α-reductase inhibitor and androgen receptor antagonist have approximately occupied the share of half in anti-prostatic hyperplasia market.However, because dutasteride is water-soluble hardly, limited by its physicochemical property, its preparation bioavailability is not high, and therefore dutasteride's preparation of development of new is very necessary.
Dutasteride's dosage form of listing is soft capsule, and commodity are called AVODART, is dutasteride is dissolved in sad list/bis-glyceride and the mixture of butylated hydroxytoluene, then is filled in soft capsule and obtains.But its dissolution is not high or In Vitro Dissolution line is undesirable.
Prior art adopts self-microemulsion technology can improve preferably the dissolution of dutasteride's oral formulations, as patent KR100962447, disclose a kind of solid state Emulsion of self emulsifying, patent KR101055412 discloses hardening composition (tablet) of a kind of dutasteride's self-emulsifying drug delivery etc. and all improves dutasteride's result of extraction.In self-microemulsion prescription, need to add more than 50% surfactant, because surfactant easily causes the side effect such as digestive tract hemorrhage in oral administration, therefore self-microemulsion technology is subject to many limitations in oral administration, in addition self-microemulsion technology because of prescription constituent contain more surfactant, and exist with oily liquids form, prepare oral formulations, as the aspect such as soft capsule, tablet exists many restrictions, bringing restriction to formulation development and application.Patent CN102319228A discloses employing caprylic/capric glyceride and Glyceryl Behenate is single or mixture is that oil phase is applied to and prepares liquid hard capsule, its dissolution listing product improves a lot, " pharmaceutic adjuvant handbook " the 4th edition 303 pages of records that Zheng Jun democracy is translated: Glyceryl Behenate is white or off-white powder or hard wax piece, in chloroform, dissolve, almost insoluble in water or ethanol, fusing point is 65-77 DEG C, property analysis is difficult to melting under 37 DEG C of conditions as the capsule of an oil preparation accordingly, known dutasteride is difficult to stripping under this condition.Document 437-438 page is also recorded this product and is colourless or light yellow oily liquid, water insoluble, can infer that dutasteride is difficult to stripping under this condition.Therefore, meaningless to improving dutasteride's dissolubility taking Glyceryl Behenate or caprylic/capric glyceride as solvent separately.
The present invention adopts caprylin and median chain triglyceride oil mixed solution to prepare soft capsule as oil item, can improve preferably dutasteride's dissolution and stability, particularly can improve period before stripping as the dissolution rate of first 35 minutes, thereby improve dutasteride's bioavailability, accelerate drug absorption.
Summary of the invention
The invention provides a kind of dutasteride's liquid soft capsule, comprise capsule shells and content, wherein content is mainly made up of the component of following weight percent: dutasteride 0.05%-0.3%, median chain triglyceride oil 19.8%-94.8%, Capmul MCM C8 5%-80% and antioxidant 0.005%-0.2%, wherein, antioxidant is selected from butylated hydroxyarisol (BHA), BHT (BHT) and the mixture of the two.
Dutasteride's liquid soft capsule of the invention described above, wherein, capsule shells is conventional soft capsule material, be known in the art, as gelatin etc.
Dutasteride's liquid soft capsule of the invention described above, dutasteride's content is preferably 5mg.
Another object of the present invention is also to provide a kind of method of the dutasteride's of preparation liquid soft capsule, the method comprises dutasteride and BHT, optionally antioxidant is dissolved in the Capmul MCM C8 that is heated to 35-70 DEG C, in the mixed liquor of median chain triglyceride oil, after stirring, embedding is in soft capsule, make dutasteride's soft capsule, wherein said dutasteride's liquid soft capsule, comprise capsule shells and content, wherein content is mainly made up of the component of following weight percent: dutasteride 0.05%-0.3%, median chain triglyceride oil 19.8%-94.8%, Capmul MCM C8 5%-80%, with antioxidant 0.005%-0.2%, wherein, antioxidant is selected from butylated hydroxyarisol (BHA), BHT (BHT) and the mixture of the two.Capsule shells is conventional soft capsule material, for knowing in ability field, as gelatin etc.
Dutasteride's pharmaceutical composition tool of the present invention has the following advantages:
1, can significantly improve dutasteride's dissolution;
2, preparation technology is simple, stable and controllable for quality;
3, can significantly improve in dutasteride's dissolution rate and body and absorb.
brief description of the drawings
fig. 1: embodiment 1-6 soft capsule, comparing embodiment 1-2 soft capsule andthe accumulation stripping curve figure of AVODART soft capsule.
Detailed description of the invention
Following examples are used for further explaining and understanding the present invention, but do not limit the scope of the invention.
Embodiment 1
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 19.885g
Capmul MCM C8 80g
BHT 0.005g
Preparation method: take recipe quantity dutasteride, BHT and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 70 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules.
Embodiment 2
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 94.647g
Capmul MCM C8 5g
BHT 0.2g
Preparation method: take recipe quantity dutasteride, BHT and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 35 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules.
Embodiment 3
Prescription:
Dutasteride 0.05g
Median chain triglyceride oil 49.94g
Capmul MCM C8 50g
BHT 0.01g
Preparation method: take recipe quantity dutasteride, BHT and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 60 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 100 of soft capsules.
Embodiment 4
Prescription:
Dutasteride 0.3g
Median chain triglyceride oil 69.69g
Capmul MCM C8 30g
BHA 0.01g
Preparation method: take recipe quantity dutasteride, BHA and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 45 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 600 of soft capsules.
Embodiment 5
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 84.647g
Capmul MCM C8 15g
BHA 0.2g
Preparation method: take recipe quantity dutasteride, BHA and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 45 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules.
Embodiment 6
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 39.797g
Capmul MCM C8 60g
BHT 0.025g
BHA 0.025g
Preparation method: take recipe quantity dutasteride, BHT and BHA mixing antioxidant and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 55 DEG C and median chain triglyceride oil, after stirring, embedding is in soft capsule, make dutasteride's soft capsule, make altogether 306 of soft capsules.
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 4.797g
Capmul MCM C8 95g
BHT 0.05g
Preparation method: take recipe quantity dutasteride, BHT and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 55 DEG C and median chain triglyceride oil, after stirring, embedding is in soft capsule, make dutasteride's soft capsule, make altogether 270 of soft capsules.
Embodiment 8
Prescription:
Dutasteride 0.153g
Median chain triglyceride oil 4.842g
Capmul MCM C8 95g
BHA 0.005g
Preparation method: take recipe quantity dutasteride, BHA and be dissolved in the mixed liquor that is heated to the Capmul MCM C8 of 60 DEG C and median chain triglyceride oil, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules.
Comparing embodiment 1
Dutasteride 0.153g
Capmul MCM C8 99.84g
BHT 0.01g
Preparation method: take recipe quantity dutasteride, BHT is dissolved in the Capmul MCM C8 that is heated to 70 DEG C, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules.
Comparing embodiment 2
Dutasteride 0.153g
Median chain triglyceride oil 99.84g
BHT 0.01g
Preparation method: take recipe quantity dutasteride, BHT is dissolved in the Capmul MCM C8 that is heated to 45 DEG C, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule, makes altogether 306 of soft capsules
Embodiment 9 dissolution determinations
Relatively make the stripping behavior of embodiment 1-7 dutasteride soft capsule, comparing embodiment 1, comparing embodiment 2 and the dutasteride's soft capsule (trade name: AVODART) that goes on the market by oneself.
Table 1 sample accumulation dissolution (%)
| Sample point/min | AVODART | Comparing embodiment 1 | Comparing embodiment 2 | Embodiment 1 | Embodiment 2 |
| 0 | 0 | 0 | 0 | 0 | 0 |
| 10 | 20.25 | 1.24 | 0.03 | 91.38 | 31.23 |
| 15 | 34.61 | 3.61 | 0.31 | 93.74 | 44.79 |
| 25 | 62.23 | 6.23 | 0.84 | 94.92 | 72.97 |
| 35 | 78.68 | 8.68 | 1.08 | 96.89 | 82.50 |
| 45 | 85.86 | 15.86 | 1.14 | 97.52 | 86.07 |
| 60 | 93.20 | 17.20 | 2.41 | 98.42 | 94.11 |
Table 2 sample accumulation dissolution (%)
| Sample point/min | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | |
| 0 | 0 | 0 | 0 | 0 | 0 |
| 10 | 82.38 | 65.38 | 41.23 | 90.38 | 17.24 |
| 15 | 92.04 | 80.74 | 53.79 | 92.74 | 24.61 |
| 25 | 97.92 | 93.92 | 77.97 | 95.92 | 46.23 |
| 35 | 97.89 | 97.89 | 89.50 | 98.89 | 68.68 |
| 45 | 99.52 | 98.52 | 95.07 | 98.52 | 73.86 |
| 60 | 100.42 | 99.42 | 97.11 | 99.42 | 87.20 |
The result of table 1-2 shows, each sample point dissolution preparation of dutasteride's soft capsule (trade name: AVODART) and comparing embodiment 1,2 that is all better than going on the market, all can not reach satisfied result of extraction by the known simple employing Capmul MCM C8 of comparing embodiment or medium chain triglycerides simultaneously before dutasteride's soft capsule of the present invention (embodiment 1-6) 45min.Inventor also finds that Capmul MCM C8 consumption brings up to a certain degree, can cause dissolution to decline, from embodiment 7.From above-mentioned experimental result, dutasteride's soft capsule of the present invention can effectively improve dutasteride's dissolution.
Claims (4)
1. dutasteride's liquid soft capsule, comprises capsule shells and content, and wherein, content is mainly by dutasteride 0.05%-0.3%, median chain triglyceride oil 19.8%-94.8%, Capmul MCM C8 5%-80%.
2. soft capsule as claimed in claim 1, also further comprises that percentage by weight is the antioxidant of 0.005%-0.2%.
3. soft capsule as claimed in claim 2, described antioxidant is butylated hydroxyarisol (BHA), BHT (BHT) or the two mixture.
4. prepare the method for the arbitrary dutasteride's liquid soft capsule of claim 1-3 for one kind, it is characterized in that: dutasteride, antioxidant are dissolved in the mixed liquor of the Capmul MCM C8, the median chain triglyceride oil that are heated to 35-70 DEG C, after stirring, embedding, in soft capsule, makes dutasteride's soft capsule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210469454.4A CN103830201A (en) | 2012-11-20 | 2012-11-20 | Dutasteride liquid soft capsules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210469454.4A CN103830201A (en) | 2012-11-20 | 2012-11-20 | Dutasteride liquid soft capsules |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103830201A true CN103830201A (en) | 2014-06-04 |
Family
ID=50794309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210469454.4A Pending CN103830201A (en) | 2012-11-20 | 2012-11-20 | Dutasteride liquid soft capsules |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103830201A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104069084A (en) * | 2013-03-25 | 2014-10-01 | 重庆华邦制药有限公司 | Dutasteride soft capsule with stable quality |
| CN105395517A (en) * | 2015-12-11 | 2016-03-16 | 成都华宇制药有限公司 | Dutasteride soft capsule preparation and preparation process thereof |
| CN109394723A (en) * | 2017-08-17 | 2019-03-01 | 海南皇隆制药股份有限公司 | A kind of dutasteride's soft capsule and preparation method thereof |
| CN109674762A (en) * | 2019-03-05 | 2019-04-26 | 南京正大天晴制药有限公司 | A kind of composition capsule of dutasteride and hair growth |
| CN110613695A (en) * | 2019-10-23 | 2019-12-27 | 人福普克药业（武汉）有限公司 | Dutasteride soft capsule and preparation method thereof |
| CN110960496A (en) * | 2018-09-28 | 2020-04-07 | 华宇药品股份有限公司 | Solid pharmaceutical composition of dutasteride and preparation method thereof |
| CN115887407A (en) * | 2022-12-29 | 2023-04-04 | 深圳市泰力生物医药有限公司 | Sirolimus soft capsule and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1263466A (en) * | 1997-08-19 | 2000-08-16 | 葛兰素集团有限公司 | Solutions containing azasteroids |
| WO2006055659A2 (en) * | 2004-11-15 | 2006-05-26 | Smithkline Beecham Corporation | Fixed dose combination op dutasteride and tamsulosin |
| CN102319228A (en) * | 2011-08-12 | 2012-01-18 | 福格森（武汉）生物科技有限公司 | Dutasteride's liquid hard capsule and preparation method thereof |
-
2012
- 2012-11-20 CN CN201210469454.4A patent/CN103830201A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1263466A (en) * | 1997-08-19 | 2000-08-16 | 葛兰素集团有限公司 | Solutions containing azasteroids |
| WO2006055659A2 (en) * | 2004-11-15 | 2006-05-26 | Smithkline Beecham Corporation | Fixed dose combination op dutasteride and tamsulosin |
| CN102319228A (en) * | 2011-08-12 | 2012-01-18 | 福格森（武汉）生物科技有限公司 | Dutasteride's liquid hard capsule and preparation method thereof |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104069084A (en) * | 2013-03-25 | 2014-10-01 | 重庆华邦制药有限公司 | Dutasteride soft capsule with stable quality |
| CN104069084B (en) * | 2013-03-25 | 2019-06-25 | 重庆华邦制药有限公司 | A kind of dutasteride's soft capsule that quality is stable |
| CN105395517A (en) * | 2015-12-11 | 2016-03-16 | 成都华宇制药有限公司 | Dutasteride soft capsule preparation and preparation process thereof |
| CN105395517B (en) * | 2015-12-11 | 2018-04-06 | 成都华宇制药有限公司 | A kind of dutasteride's soft capsule preparation and its preparation technology |
| CN109394723A (en) * | 2017-08-17 | 2019-03-01 | 海南皇隆制药股份有限公司 | A kind of dutasteride's soft capsule and preparation method thereof |
| CN109394723B (en) * | 2017-08-17 | 2020-11-24 | 海南皇隆制药股份有限公司 | Dutasteride soft capsule and preparation method thereof |
| CN110960496A (en) * | 2018-09-28 | 2020-04-07 | 华宇药品股份有限公司 | Solid pharmaceutical composition of dutasteride and preparation method thereof |
| CN109674762A (en) * | 2019-03-05 | 2019-04-26 | 南京正大天晴制药有限公司 | A kind of composition capsule of dutasteride and hair growth |
| CN110613695A (en) * | 2019-10-23 | 2019-12-27 | 人福普克药业（武汉）有限公司 | Dutasteride soft capsule and preparation method thereof |
| CN115887407A (en) * | 2022-12-29 | 2023-04-04 | 深圳市泰力生物医药有限公司 | Sirolimus soft capsule and preparation method thereof |
| CN115887407B (en) * | 2022-12-29 | 2023-08-18 | 深圳市泰力生物医药有限公司 | Sirolimus soft capsule and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103830201A (en) | Dutasteride liquid soft capsules | |
| US12357643B2 (en) | Emulsion formulations | |
| JP5847730B2 (en) | Modulation of lipophilic drug solubility, stability, absorbability, metabolism, and pharmacokinetic profile by sterols | |
| JP5753157B2 (en) | Self-microemulsifying oral pharmaceutical composition of hydrophilic drug and preparation method thereof | |
| Perlman et al. | Development of a self-emulsifying formulation that reduces the food effect for torcetrapib | |
| TWI654981B (en) | Medicinal composition comprising dutasteride and propylene glycol monolaurate and preparation method thereof | |
| KR20220080205A (en) | Natural combination hormone replacement formulations and therapies | |
| US20110263552A1 (en) | Modulation of side effect profile of 5-alpha reductase inhibitor therapy | |
| CN103479595B (en) | A kind of soft capsule containing dutasteride | |
| TWI660730B (en) | Pharmaceutical composition including dutasteride and capsule formulation comprising the same | |
| RS55504A (en) | Pharmaceutical compositions based on azetidine derivatives | |
| CN105640961A (en) | A pharmaceutical composition containing ibrutinib | |
| US20200368221A1 (en) | Solid particle, preparation method therefor, and pharmaceutical composition containing solid particle | |
| CN106692051A (en) | Preparation of 17-(3-pyridine)-androst-4, 6-diene-3-one | |
| TW201821065A (en) | Oral capsule composite formulation of dutasteride and tadalafil | |
| Strickley | An Overview of Lipid Excipients Currently Available: Strengths, Weaknesses and Opportunity Gaps: The Options for the Formulator | |
| CN103705462A (en) | Oral testosterone ester preparation and method for treating testosterone deficiency comprising oral testosterone ester preparation | |
| CHIANG et al. | Commentary: Liquid-filled Formulations | |
| CN103784395B (en) | A kind of sufentanil gel preparation and preparation method thereof | |
| RU2642244C2 (en) | Oral pharmaceutical compositions of testosterone esters and method for testosterone shortage treatment with their use | |
| Biyani | Selecting excipients for liquid-filled Hard capsules | |
| EP4181908A2 (en) | Compositions comprising gardos channel antagonists and their uses | |
| CN103830245A (en) | Oral testosterone ester formulation and application of same in preparation of drug used for treating testosterone deficiency | |
| JP2015134803A (en) | Oral testosterone ester combination and method for treating testosterone deficiency containing the same | |
| HK1193359A (en) | Modulation of solubility, stability, absorption, metabolism, and pharmacokinetic profile of lipophilic drugs by sterols |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: SHENYANG HONGQI PHARMACEUTICAL CO., LTD. Effective date: 20150410 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20150410 Address after: 400061 No. 565, Tu Shan Road, Nan'an District, Chongqing Applicant after: Chongqing Pharmaceutical Research Institute Co., Ltd. Applicant after: Shenyang Hongqi Pharmaceutical Co., Ltd. Address before: 400061 No. 565, Tu Shan Road, Nan'an District, Chongqing Applicant before: Chongqing Pharmaceutical Research Institute Co., Ltd. |
|
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140604 |
|
| WD01 | Invention patent application deemed withdrawn after publication |