US20030031705A1 - Pharmaceutical composition comprising fenofibrate - Google Patents
Pharmaceutical composition comprising fenofibrate Download PDFInfo
- Publication number
- US20030031705A1 US20030031705A1 US10/189,009 US18900902A US2003031705A1 US 20030031705 A1 US20030031705 A1 US 20030031705A1 US 18900902 A US18900902 A US 18900902A US 2003031705 A1 US2003031705 A1 US 2003031705A1
- Authority
- US
- United States
- Prior art keywords
- fenofibrate
- disintegrant
- solid dispersion
- pharmaceutical composition
- granules
- 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.)
- Abandoned
Links
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 229960002297 fenofibrate Drugs 0.000 title claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 239000007884 disintegrant Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000007962 solid dispersion Substances 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 238000002844 melting Methods 0.000 claims abstract description 5
- 230000008018 melting Effects 0.000 claims abstract description 5
- 239000002775 capsule Substances 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 229920002785 Croscarmellose sodium Polymers 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical group [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001681 croscarmellose sodium Drugs 0.000 claims description 2
- 229960000913 crospovidone Drugs 0.000 claims description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 claims description 2
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 2
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 2
- 229940079832 sodium starch glycolate Drugs 0.000 claims description 2
- 239000008109 sodium starch glycolate Substances 0.000 claims description 2
- 229920003109 sodium starch glycolate Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005414 inactive ingredient Substances 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
Definitions
- the present invention relates to pharmaceutical compositions for oral administration comprising fenofibrate which enable improve dissolution and bioavailability.
- Fenofibrate is practically insoluble in water. This causes fenofibrate to exhibit a low rate of dissolution in aqueous media (including gastrointestinal fluids), which results in inadequate bioavailability (absorption into systemic circulation) after oral ingestion.
- micronization In this approach, the drug is milled to fine particles, typically having a mean diameter of only a few microns.
- a second approach is to include a surfactant in the composition.
- a composition made according to the invention of U.S. Pat. No. 4,895,726 is sold in Canada as elsewhere under the tradename Lipidil Micro.
- the need for microcomposition and use of a surfactant adds to the cost of capsules containing fenofibrate.
- the rate of dissolution and the bioavailability of fenofibrate can be substantially improved by making a solid dispersion of a disintegrant in the fenofibrate.
- the solid dispersion can be made by heating and melting the fenofibrate, blending the disintegrant into the molten fenofibrate and then cooling and solidifying the mixture.
- Fenofibrate has a melting point of about 80° C. and can be melted without decomposition.
- a disintegrant will be understood to be a substance which is hydrophilic and swells upon absorption of water. Disintegrants are used as excipients (inactive ingredients) in pharmaceutical tablets and capsules so that, when a tablet or capsule is ingested, the disintegrant will cause the tablet or capsule to absorb gastrointestinal fluid and, as a result, to swell and disintegrate, so as to release the active drug for dissolution and absorption
- Disintegrants with very high capacity to absorb water and swell are known as “super-disintegrants”, which include such substances as croscarmellose sodium, sodium starch glycolate and crospovidone.
- a solid dispersion comprising a disintegrant dispersed in the fenofibrate can be made by melting the fenofibrate blending the disintegrant into the molten fenofibrate and then cooling and solidifying the mixture The solid can then be ground into granules for further processing into tablets or capsules.
- each granule or particle of the ground-up solid dispersion will be an approximately uniform mixture of fenofibrate and disintegrant.
- the solid dispersion is thus intrinsically different from a mixture achieved simply by physical mixing of fenofibrate in solid form and disintegrant, because in a physical mix each particle remains either pure fenofibrate or pure disintegrant.
- ingredients other than the fenofibrate and disintegrant may be included in the molten blend and thus incorporated into the solid dispersion.
- Such other ingredients may include, for example, water-soluble or water-insoluble ingredients which serve as surfactant, diluent, or for other purposes.
- This mixture was then filled into 2-piece hard gelatin capsules with a net fill weight of 400 mg per capsule.
- Each capsule thus contained 250 mg of the solid dispersion, which in turn comprised 200 mg of fenofibrate.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
The bioavailability of fenofibrate is improved by making a solid dispersion of a disentegrant in the fenofibrate. Method of making said solid dispersion comprising melting the fenofibrate, blending the disintegrant into the melt, and resolidifying the mixture.
Description
- The present invention relates to pharmaceutical compositions for oral administration comprising fenofibrate which enable improve dissolution and bioavailability.
- Fenofibrate is practically insoluble in water. This causes fenofibrate to exhibit a low rate of dissolution in aqueous media (including gastrointestinal fluids), which results in inadequate bioavailability (absorption into systemic circulation) after oral ingestion.
- In order to make a composition comprising fenofibrate that will enable maximum bioavailability, it is necessary to incorporate into the composition a feature that increases the rate of dissolution of the drug to enable it to dissolve in the gastrointestinal fluids.
- Several ways of increasing the rate of dissolution of drugs having low solubility in water are known in the prior art.
- One approach is micronization. In this approach, the drug is milled to fine particles, typically having a mean diameter of only a few microns. A second approach is to include a surfactant in the composition.
- For the drug fenofibrate, neither micronization alone nor use of a surfactant alone enables maximum bioavailability. U.S. Pat. No. 4,895,726 discloses that the rate of dissolution and the bioavailability of fenofibrate can be maximized by comicronization of fenofibrate. In this process the fenofibrate is first mixed with the surfactant and then the mixture is micronized.
- A composition made according to the invention of U.S. Pat. No. 4,895,726 is sold in Canada as elsewhere under the tradename Lipidil Micro. The need for microcomposition and use of a surfactant adds to the cost of capsules containing fenofibrate.
- In view of the limitations of the prior art, it is an object of the present invention to enable maximum bioavailability of fenofibrate without the need for micronization and without the need for use of a surfactant.
- It has been found the rate of dissolution and the bioavailability of fenofibrate can be substantially improved by making a solid dispersion of a disintegrant in the fenofibrate. The solid dispersion can be made by heating and melting the fenofibrate, blending the disintegrant into the molten fenofibrate and then cooling and solidifying the mixture.
- Fenofibrate has a melting point of about 80° C. and can be melted without decomposition.
- A disintegrant will be understood to be a substance which is hydrophilic and swells upon absorption of water. Disintegrants are used as excipients (inactive ingredients) in pharmaceutical tablets and capsules so that, when a tablet or capsule is ingested, the disintegrant will cause the tablet or capsule to absorb gastrointestinal fluid and, as a result, to swell and disintegrate, so as to release the active drug for dissolution and absorption
- The most commonly used disintegrant is starch.
- Disintegrants with very high capacity to absorb water and swell are known as “super-disintegrants”, which include such substances as croscarmellose sodium, sodium starch glycolate and crospovidone.
- As aforesaid, a solid dispersion comprising a disintegrant dispersed in the fenofibrate can be made by melting the fenofibrate blending the disintegrant into the molten fenofibrate and then cooling and solidifying the mixture The solid can then be ground into granules for further processing into tablets or capsules.
- Because of the very intimate mixing achieved by mixing the disintegrant into the fenofibrate in the molten state, it follows that each granule or particle of the ground-up solid dispersion will be an approximately uniform mixture of fenofibrate and disintegrant.
- The solid dispersion is thus intrinsically different from a mixture achieved simply by physical mixing of fenofibrate in solid form and disintegrant, because in a physical mix each particle remains either pure fenofibrate or pure disintegrant.
- It will be understood that in the process of making a solid dispersion, within the scope of the present invention, ingredients other than the fenofibrate and disintegrant may be included in the molten blend and thus incorporated into the solid dispersion. Such other ingredients may include, for example, water-soluble or water-insoluble ingredients which serve as surfactant, diluent, or for other purposes.
- Alternatively, other ingredients may be mixed with the granules of solid dispersion, and the mix so achieved may be further processed into tablets or capsules.
- The invention will be further illustrated by the following example, which is intended to be illustrative but not limiting of the scope of the invention.
- 4800 g of fenofibrate was placed in a stainless steel pot, which was slowly heated until the fenofibrate was melted. 1200 g of croscamellose sodium was then blended into the molten fenofibrate, and the mix was then poured into trays and allowed to cool and solidify to form a solid dispersion.
- The solid was then removed from the trays and milled through a #10 screen to produce granules.
- 5 kilos of the resulting granules were then mixed with other ingredients as follows:
solid dispersion granules 5.0 kilos lactose monohydrate 2.84 kilos stearic acid 0.14 kilos colloidal silicon dioxide 0.02 kilos 8.00 kilos - This mixture was then filled into 2-piece hard gelatin capsules with a net fill weight of 400 mg per capsule. Each capsule thus contained 250 mg of the solid dispersion, which in turn comprised 200 mg of fenofibrate.
- For these capsules, it was found that the dissolution rate and bioavailability was equivalent to that of commercially available Lipidil Micro capsules containing 200 mg of co-micronized fenofibrate and surfactant.
Claims (4)
1. A solid pharmaceutical composition comprising a solid dispersion of a disintegrant in fenofibrate.
2. A composition as in claim 1 wherein the disintegrant is selected from croscarmellose sodium, sodium starch glycolate and crospovidone.
3. A process of making a composition as in either of claims 1 or 2, which comprises the steps of melting the fenofibrate, blending the disintegrant into the molten fenofibrate, and solidifying the mixture.
4. A process as in claim 3 which further comprises the steps of grinding the resulting solid into granules and further processing the granules into capsules or tablets.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/189,009 US20030031705A1 (en) | 1997-09-19 | 2002-07-05 | Pharmaceutical composition comprising fenofibrate |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002214895A CA2214895C (en) | 1997-09-19 | 1997-09-19 | Improved pharmaceutical composition comprising fenofibrate |
| CA2,214,895 | 1997-09-19 | ||
| US09/154,521 US6444225B1 (en) | 1997-09-19 | 1998-09-16 | Pharmaceutical composition comprising fenofibrate |
| US10/189,009 US20030031705A1 (en) | 1997-09-19 | 2002-07-05 | Pharmaceutical composition comprising fenofibrate |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/154,521 Continuation US6444225B1 (en) | 1997-09-19 | 1998-09-16 | Pharmaceutical composition comprising fenofibrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20030031705A1 true US20030031705A1 (en) | 2003-02-13 |
Family
ID=4161415
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/154,521 Expired - Fee Related US6444225B1 (en) | 1997-09-19 | 1998-09-16 | Pharmaceutical composition comprising fenofibrate |
| US10/189,009 Abandoned US20030031705A1 (en) | 1997-09-19 | 2002-07-05 | Pharmaceutical composition comprising fenofibrate |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/154,521 Expired - Fee Related US6444225B1 (en) | 1997-09-19 | 1998-09-16 | Pharmaceutical composition comprising fenofibrate |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6444225B1 (en) |
| EP (1) | EP0904781A3 (en) |
| JP (1) | JPH11152227A (en) |
| AU (1) | AU731176B2 (en) |
| CA (1) | CA2214895C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030224058A1 (en) * | 2002-05-24 | 2003-12-04 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20040058009A1 (en) * | 2002-05-24 | 2004-03-25 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20070264348A1 (en) * | 2002-05-24 | 2007-11-15 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20080241070A1 (en) * | 2000-09-21 | 2008-10-02 | Elan Pharma International Ltd. | Fenofibrate dosage forms |
| US20090012184A1 (en) * | 2005-02-11 | 2009-01-08 | Abbott Gmbh & Co. Kg | Production of Dosage Forms Comprising a Solid Dispersion of a Microcrystalline Agent |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2758459B1 (en) * | 1997-01-17 | 1999-05-07 | Pharma Pass | FENOFIBRATE PHARMACEUTICAL COMPOSITION HAVING HIGH BIODAVAILABILITY AND PROCESS FOR PREPARING THE SAME |
| HUP0105089A3 (en) | 1998-11-20 | 2002-09-30 | Skyepharma Canada Inc | Compositions containing the active ingredient in form dispersible phospholipid stabilized microparticles |
| CA2270306C (en) * | 1999-04-27 | 2000-09-26 | Bernard Charles Sherman | Pharmaceutical compositions comprising co-micronized fenofibrate |
| US6982281B1 (en) | 2000-11-17 | 2006-01-03 | Lipocine Inc | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
| HK1046644B (en) * | 1999-12-09 | 2006-11-10 | Reckitt Benckiser Healthcare (Uk) Limited | Compressed tablet composition comprising a nsaid |
| US6531158B1 (en) * | 2000-08-09 | 2003-03-11 | Impax Laboratories, Inc. | Drug delivery system for enhanced bioavailability of hydrophobic active ingredients |
| US6982251B2 (en) | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
| FR2819720B1 (en) | 2001-01-22 | 2004-03-12 | Fournier Lab Sa | NEW FENOFIBRATE TABLETS |
| KR100596257B1 (en) | 2001-01-26 | 2006-07-03 | 쉐링 코포레이션 | Compositions comprising a sterol absorption inhibitor, and compositions and combinations comprising a peroxisomal growth factor-activated receptor activator and a sterol absorption inhibitor |
| US7071181B2 (en) | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
| SI1355644T1 (en) | 2001-01-26 | 2006-10-31 | Schering Corp | The use of substituted azetidinone compounds for the treatment of sitosterolemia |
| WO2002069957A1 (en) * | 2001-03-01 | 2002-09-12 | Grelan Pharmaceutical Co., Ltd. | Fenofibrate-containing composition |
| MXPA04002573A (en) | 2001-09-21 | 2004-06-18 | Schering Corp | Treatment of xanthoma with azetidinone derivatives as sterol absorption inhibitors. |
| US7056906B2 (en) | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
| US7053080B2 (en) | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
| CA2504916A1 (en) | 2002-11-06 | 2004-05-27 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| US7459442B2 (en) | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| WO2004081003A1 (en) | 2003-03-07 | 2004-09-23 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholeterolemia |
| CA2517571C (en) | 2003-03-07 | 2011-07-05 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
| WO2004081004A1 (en) | 2003-03-07 | 2004-09-23 | Schering Corporation | Substituted azetidinone compounds, formulations and uses thereof for the treatment of hypercholesterolemia |
| US20080031825A1 (en) * | 2004-08-20 | 2008-02-07 | Yisheng Chen | Pharmaceutical Compositions Comprising Effervescent Agents And Fenofibrate |
| US9180110B2 (en) | 2007-02-26 | 2015-11-10 | Wockhardt Ltd. | Pharmaceutical compositions of fenofibrate |
| US8852635B2 (en) | 2007-02-26 | 2014-10-07 | Wockhardt Ltd | Pharmaceutical compositions of fenofibrate |
| EP2251038B1 (en) * | 2008-03-11 | 2017-05-10 | ASKA Pharmaceutical Co., Ltd. | Solid dispersion, pharmaceutical compositions containing the same, and processes for the production of both |
| US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
| US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9358241B2 (en) | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20120148675A1 (en) | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
| US20170246187A1 (en) | 2014-08-28 | 2017-08-31 | Lipocine Inc. | (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE |
| WO2016033556A1 (en) | 2014-08-28 | 2016-03-03 | Lipocine Inc. | BIOAVAILABLE SOLID STATE (17-β)-HYDROXY-4-ANDROSTEN-3-ONE ESTERS |
| US20160361322A1 (en) | 2015-06-15 | 2016-12-15 | Lipocine Inc. | Composition and method for oral delivery of androgen prodrugs |
| CA3078723A1 (en) | 2016-11-28 | 2018-05-31 | Nachiappan Chidambaram | Oral testosterone undecanoate therapy |
| WO2020018974A1 (en) | 2018-07-20 | 2020-01-23 | Lipocine Inc. | Liver disease |
| MX2022001178A (en) * | 2019-07-31 | 2022-02-22 | Intas Pharmaceuticals Ltd | PHARMACEUTICAL COMPOSITION THAT INCLUDES HMG-COA REDUCTASE INHIBITORS AND FENOFIBRATE. |
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| US4879301A (en) * | 1987-04-28 | 1989-11-07 | Hoei Pharmaceutical Co., Ltd. | Antiallergic and antiinflammatory benzothiazolinone derivatives |
| US5545628A (en) * | 1995-01-10 | 1996-08-13 | Galephar P.R. Inc. | Pharmaceutical composition containing fenofibrate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2627696B1 (en) * | 1988-02-26 | 1991-09-13 | Fournier Innovation Synergie | NEW GALENIC FORM OF FENOFIBRATE |
| US5190970A (en) * | 1990-10-19 | 1993-03-02 | E. R. Squibb & Sons, Inc. | Method for preventing onset of or treating Type II diabetes employing a cholesterol lowering drug alone or in combination with an ace inhibitor |
| DE69222182T2 (en) * | 1991-12-18 | 1998-02-26 | Warner Lambert Co | METHOD FOR PRODUCING A SOLID DISPERSION |
| US5948438A (en) * | 1995-01-09 | 1999-09-07 | Edward Mendell Co., Inc. | Pharmaceutical formulations having improved disintegration and/or absorptivity |
| NZ286451A (en) * | 1996-04-24 | 1998-04-27 | Bernard Charles Sherman | Controlled release pharmaceutical composition containing granules comprising drug, water-insoluble polymer and meltable carrier |
| US5883109A (en) * | 1996-07-24 | 1999-03-16 | Bristol-Myers Squibb Company | Method for lowering serum lipid levels employing an MTP inhibitor in combination with another cholesterol lowering drug |
-
1997
- 1997-09-19 CA CA002214895A patent/CA2214895C/en not_active Expired - Fee Related
-
1998
- 1998-09-16 US US09/154,521 patent/US6444225B1/en not_active Expired - Fee Related
- 1998-09-17 EP EP98307588A patent/EP0904781A3/en not_active Withdrawn
- 1998-09-18 JP JP10264722A patent/JPH11152227A/en active Pending
- 1998-09-21 AU AU86073/98A patent/AU731176B2/en not_active Ceased
-
2002
- 2002-07-05 US US10/189,009 patent/US20030031705A1/en not_active Abandoned
Patent Citations (7)
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080241070A1 (en) * | 2000-09-21 | 2008-10-02 | Elan Pharma International Ltd. | Fenofibrate dosage forms |
| US20070298115A1 (en) * | 2002-05-24 | 2007-12-27 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20080095851A1 (en) * | 2002-05-24 | 2008-04-24 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20050276974A1 (en) * | 2002-05-24 | 2005-12-15 | Elan Pharma Internationl, Ltd. | Nanoparticulate fibrate formulations |
| US7276249B2 (en) | 2002-05-24 | 2007-10-02 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20070264348A1 (en) * | 2002-05-24 | 2007-11-15 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20030224058A1 (en) * | 2002-05-24 | 2003-12-04 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US7320802B2 (en) | 2002-05-24 | 2008-01-22 | Elan Pharma International, Ltd. | Methods of treatment using nanoparticulate fenofibrate compositions |
| US20040087656A1 (en) * | 2002-05-24 | 2004-05-06 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20080138424A1 (en) * | 2002-05-24 | 2008-06-12 | Elan Pharma Internationa, Ltd. | Nanoparticulate fibrate formulations |
| US20040058009A1 (en) * | 2002-05-24 | 2004-03-25 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US7931917B2 (en) | 2002-05-24 | 2011-04-26 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US7927627B2 (en) | 2002-05-24 | 2011-04-19 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
| US20090012184A1 (en) * | 2005-02-11 | 2009-01-08 | Abbott Gmbh & Co. Kg | Production of Dosage Forms Comprising a Solid Dispersion of a Microcrystalline Agent |
| US10653625B2 (en) * | 2005-02-11 | 2020-05-19 | AbbVie Deutschland GmbH & Co. KG | Production of dosage forms comprising a solid dispersion of a microcrystalline agent |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0904781A3 (en) | 1999-11-03 |
| JPH11152227A (en) | 1999-06-08 |
| AU8607398A (en) | 1999-04-15 |
| CA2214895A1 (en) | 1998-11-27 |
| CA2214895C (en) | 1999-04-20 |
| US6444225B1 (en) | 2002-09-03 |
| AU731176B2 (en) | 2001-03-22 |
| EP0904781A2 (en) | 1999-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |