WO2000072825A1 - Novel formulations comprising lipid-regulating agents - Google Patents
Novel formulations comprising lipid-regulating agents Download PDFInfo
- Publication number
- WO2000072825A1 WO2000072825A1 PCT/US2000/014106 US0014106W WO0072825A1 WO 2000072825 A1 WO2000072825 A1 WO 2000072825A1 US 0014106 W US0014106 W US 0014106W WO 0072825 A1 WO0072825 A1 WO 0072825A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- lipid
- regulating agent
- hydrophilic
- fenofibrate
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- 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
- 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
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Definitions
- the present invention relates to novel formulations comprising lipid-regulating agents.
- 2- [4- (4-chlorobenzoyl) phenoxy] -2-methyl-propanoic acid, 1-methylethylester, also known as fenofibrate, is representative of a broad class of compounds having pharmaceutical utility as lipid regulating agents. More specifically, this compound is part of a lipid-regulating agent class of compounds commonly known as fibrates, and is disclosed in U.S. Patent No. 4,058,552.
- Fenofibrate has been prepared in several different formulations, c.f., U.S. Patent No. 4,800,079 and U.S. Patent No. 4,895,726.
- U.S. Patent No. 4,895,726 discloses a co-micronized formulation of fenofibrate and a solid surfactant .
- U.S. Patent No. 4,961,890 discloses a process for preparing a controlled release formulation containing fenofibrate in an intermediate layer in the form of crystalline microparticles included within pores of an inert matrix.
- the formulation is prepared by a process involving the sequential steps of dampening said inert core with a solution based on said binder, then projecting said fenofibrate microparticles in a single layer onto said dampened core, and thereafter drying, before said solution based on said binder dissolves said fenofibrate microparticles, and repeating said three steps in sequence until said intermediate layer is formed.
- EP0793958A2 discloses a process for producing a fenofibrate solid dosage form utilizing fenofibrate, a surface active agent and polyvinyl pyrrolidone in which the fenofibrate particles are mixed with a polyvinyl pyrrolidone solution. The thus obtained mixture is granulated with an aqueous solution of one or more surface active agents, and the granules thus produced are dried.
- PCT Publication No. WO 82/01649 discloses a fenofibrate formulation having granules that are comprised of a neutral core that is a mixture of saccharose and starch.
- the neutral core is covered with a first layer of fenofibrate, admixed with an excipient and with a second microporous outer layer of an edible polymer.
- U.S. Patent No. 5,645,856 describes the use of a carrier for hydrophobic drugs, including fenofibrate, and pharmaceutical compositions based thereon.
- the carrier comprises a digestible oil and a pharmaceutically-acceptable surfactant component for dispersing the oil in vivo upon administration of the carrier, which comprises a hydrophilic surfactant, said surfactant component being such as not to substantially inhibit the in vivo lipolysis of the digestible oil .
- Gemfibrozil is another member of the fibrate class of lipid-regulating agents.
- U.S. Patent No. 4,927,639 discloses a disintegratable formulation of gemfibrozil providing both immediate and sustained release, comprising a tablet compressed from a mixture of a first and second granulation, and a disintegration excipient operable to effect partial or complete disintegration in the stomach.
- the first granulation comprises finely divided particles of pure gemfibrozil granulated with at least one cellulose derivative
- the second granulation comprises finely divided particles of pure gemfibrozil granulated with a pharmaceutically-acceptable water soluble or insoluble polymer which are then uniformly coated with a pharmaceutically-acceptable (meth) acrylate copolymer prior to admixture with the first granulation.
- the first and second granulations are present in the final composition in a ratio of from about 10:1 to about 1:10.
- U.S. Patent 4,925,676 discloses a disintegratable gemfibrozil tablet providing both immediate and enteric release, which is compressed from a mixture of a first granulation of gemfibrozil with at least one acid- disintegratable binder, and a second granulation formed from the first granulation, but regranulated or coated with an alkali-disintegratable formulation of at least one substantially alkali-soluble and substantially acid- insoluble polymer.
- statins Another class of lipid-regulating agents are commonly known as statins, of which pravastatin and atorvastatin are members.
- U.S. Patents 5,030,447 and 5,180,589 describe stable pharmaceutical compositions, which when dispersed in water have a pH of at least 9, and include a medicament which is sensitive to a low pH environment, such as prevastatin, one or more fillers such as lactose and/or macrocrystalline cellulose, one or more binders, such as macrocrystalline cellulose (dry binder) or polyvinylpyrrolidone (wet binder) , one or more disintegrating agents such as croscarmellose sodium, one or more lubricants such as magnesium stearate and one or more basifying agents such as magnesium oxide.
- prevastatin one or more fillers such as lactose and/or macrocrystalline cellulose
- binders such as macrocrystalline cellulose (dry binder) or polyvinylpyrrolidone (wet binder)
- the present invention is directed to a solid formulation comprising the lipid-regulating agent dispersed in a hydrophilic, amorphous polymer in which said lipid- regulating agent is present as a metastable, amorphous phase.
- the size reduction obtained through the preparation of a dispersion is usually difficult to obtain.
- any technique that results in the dispersion of the lipid-regulating agent in an amorphous polymer such as, for example, solvent evaporation or fusion, results in an increase in the dissolution rate and oral bioavailability of the said lipid-regulating agent.
- the formulation may be administered directly, diluted into an appropriate vehicle for administration, encapsulated into hard gelatin shells or capsules, or compressed into tablets, for administration, or administered by other means obvious to those skilled in the art.
- Figure 1 is a graph showing the plasma concentration in fed dogs of the formulation of Example 1 and a reference compound .
- the bulk lipid-regulating agent may be prepared by any available method, as for example the compound fenofibrate may be prepared by the procedure disclosed in U.S. Patent No. 4,058,552, or the procedure disclosed in U.S. Patent No. 4,739,101, both herein incorporated by reference.
- composition comprising the lipid-regulating agent is prepared by dissolving or dispersing the lipid-regulating agent and hydrophilic, amorphous polymer in a sufficient amount of solvent.
- the solvent is evaporated to yield a solid mass which is ground, sized and optionally formulated into an appropriate delivery system.
- Other techniques known in the art, such as for example fusion or fusion- evaporation, may also be used.
- the delivery system of the present invention results in increased solubility and bioavailability, and improved dissolution rate of the lipid-regulating agent.
- suitable solvents include, for example, lower alkyl alcohols such as methanol, ethanol, or any other pharmaceutically-acceptable organic solvent in which the lipid-regulating agent and the polymers have appreciable solubility.
- Suitable hydrophilic, amorphous polymers include, for example, polyvinylpyrrolidone (PVP) , hydroxypropylmethylcellulose (HPMC) , or other pharmaceutically-acceptable hydrophilic, amorphous polymers such as for example, Eudragits ® .
- Suitable excipients include, for example, lactose, starch, magnesium stearate, or other pharmaceutically-acceptable fillers, diluents, lubricants, disintegrants, etc., that might be needed to prepare a capsule or tablet.
- the resulting composition comprising the lipid-regulating agent may be dosed directly for oral administration, diluted into an appropriate vehicle for oral administration, filled into capsules, or made into tablets for oral administration, or delivered by some other means obvious to those skilled in the art.
- the said composition can be used to improve the oral bioavailability and solubility of said lipid-regulating agent.
- a mixture (3 g) of statin and PVP (PF 17) in a ratio of 15:85 is dissolved in sufficient ethanol.
- the ethanol is evaporated under vacuum at 85°C.
- the resulting dry solid is then ground and sized through a 60-100 mesh screen.
- the solid is then filled in capsules to obtain the desired unit dose .
- the plasma concentrations of fenofibric acid were determined by HPLC. Concentrations were normalized to a 6.7 mg/kg dose in each dog.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA01012162A MXPA01012162A (en) | 1999-05-29 | 2000-05-23 | Novel formulations comprising lipid-regulating agents. |
EP00932706A EP1183012A1 (en) | 1999-05-29 | 2000-05-23 | Novel formulations comprising lipid-regulating agents |
JP2000620937A JP2003500437A (en) | 1999-05-29 | 2000-05-23 | Novel formulations containing lipid modulators |
CA002374288A CA2374288A1 (en) | 1999-05-29 | 2000-05-23 | Novel formulations comprising lipid-regulating agents |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/320,188 | 1999-05-29 | ||
US09/320,188 US6465011B2 (en) | 1999-05-29 | 1999-05-29 | Formulations comprising lipid-regulating agents |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000072825A1 true WO2000072825A1 (en) | 2000-12-07 |
Family
ID=23245274
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/014106 WO2000072825A1 (en) | 1999-05-29 | 2000-05-23 | Novel formulations comprising lipid-regulating agents |
Country Status (6)
Country | Link |
---|---|
US (1) | US6465011B2 (en) |
EP (1) | EP1183012A1 (en) |
JP (1) | JP2003500437A (en) |
CA (1) | CA2374288A1 (en) |
MX (1) | MXPA01012162A (en) |
WO (1) | WO2000072825A1 (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
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GB2355194A (en) * | 1999-08-31 | 2001-04-18 | Bradford Particle Design Plc | Stable amorphous active component containing composition |
JP2005533802A (en) * | 2002-06-25 | 2005-11-10 | セエルエル ファルマ | Solid pharmaceutical composition containing lipophilic active ingredient and method for producing the same |
US6982281B1 (en) | 2000-11-17 | 2006-01-03 | Lipocine Inc | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
US7115279B2 (en) | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
EP1785133A1 (en) | 2005-11-10 | 2007-05-16 | Laboratoires Fournier S.A. | Use of fenofibrate or a derivative thereof for preventing diabetic retinopathy |
US7235259B2 (en) | 2000-08-03 | 2007-06-26 | Pfizer Inc | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
WO2008104852A2 (en) * | 2007-02-26 | 2008-09-04 | Wockhardt Research Centre | Pharmaceutical compositions comprising adsorbate of fenofibrate |
WO2009013633A2 (en) * | 2007-07-20 | 2009-01-29 | Actavis Group Ptc Ehf | Amorphous coprecipitates of atorvastatin pharmaceutically acceptable salts |
US7655692B2 (en) | 2003-06-12 | 2010-02-02 | Pfizer Inc. | Process for forming amorphous atorvastatin |
US7790197B2 (en) | 2003-06-09 | 2010-09-07 | Warner-Lambert Company Llc | Pharmaceutical compositions of atorvastatin |
US7887840B2 (en) | 2001-06-22 | 2011-02-15 | Bend Research, Inc. | Pharmaceutical compositions comprising drug and concentration-enhancing polymers |
EP1274401B2 (en) † | 2000-04-10 | 2014-08-13 | Teva Pharmaceutical Industries Ltd. | Stable pharmaceutical compositions containing 7-substituted-3,5-dihydroxyheptanoic acids or 7-substituted-3,5-dihydroxyheptenoic acids |
US8865695B2 (en) | 2009-01-08 | 2014-10-21 | Lipocine Inc. | Steroidal 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 |
US9498485B2 (en) | 2014-08-28 | 2016-11-22 | Lipocine Inc. | Bioavailable solid state (17-β)-hydroxy-4-androsten-3-one esters |
US10561615B2 (en) | 2010-12-10 | 2020-02-18 | Lipocine Inc. | Testosterone undecanoate compositions |
US11559530B2 (en) | 2016-11-28 | 2023-01-24 | Lipocine Inc. | Oral testosterone undecanoate therapy |
US11707467B2 (en) | 2014-08-28 | 2023-07-25 | Lipocine Inc. | (17-ß)-3-oxoandrost-4-en-17YL tridecanoate compositions and methods of their preparation and use |
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WO2001034119A2 (en) | 1999-11-12 | 2001-05-17 | Abbott Laboratories | Inhibitors of crystallization in a solid dispersion |
US7364752B1 (en) | 1999-11-12 | 2008-04-29 | Abbott Laboratories | Solid dispersion pharamaceutical formulations |
DE10026698A1 (en) | 2000-05-30 | 2001-12-06 | Basf Ag | Self-emulsifying active ingredient formulation and use of this formulation |
US7276249B2 (en) * | 2002-05-24 | 2007-10-02 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
US20030224058A1 (en) * | 2002-05-24 | 2003-12-04 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
US20080241070A1 (en) * | 2000-09-21 | 2008-10-02 | Elan Pharma International Ltd. | Fenofibrate dosage forms |
US20070264348A1 (en) * | 2002-05-24 | 2007-11-15 | Elan Pharma International, Ltd. | Nanoparticulate fibrate formulations |
US7259186B2 (en) * | 2002-12-17 | 2007-08-21 | Abbott Laboratories | Salts of fenofibric acid and pharmaceutical formulations thereof |
EP1572190B1 (en) * | 2002-12-17 | 2007-04-18 | Abbott GmbH & Co. KG | Formulation comprising fenofibric acid, a physiologically acceptable salt or derivative thereof |
EP1829541A1 (en) * | 2002-12-17 | 2007-09-05 | Abbott GmbH & Co. KG | Formulation comprising fenofibric acid or a physiologically acceptable salt thereof |
US20080051411A1 (en) * | 2002-12-17 | 2008-02-28 | Cink Russell D | Salts of Fenofibric Acid and Pharmaceutical Formulations Thereof |
US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
US20080152714A1 (en) * | 2005-04-08 | 2008-06-26 | Yi Gao | Pharmaceutical Formulations |
US7872560B2 (en) * | 2007-03-19 | 2011-01-18 | Abc Taiwan Electronics Corp. | Independent planar transformer |
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WO2009085766A2 (en) * | 2007-12-19 | 2009-07-09 | Mutual Pharmaceutical Company, Inc. | Fenofibric acid amorphous dispersion; method of making; and method of use thereof |
KR101202994B1 (en) * | 2010-04-12 | 2012-11-21 | 한미사이언스 주식회사 | Oral pharmaceutical composition comprising fenofibric acid and an alkalifying agent |
US9107983B2 (en) | 2010-10-27 | 2015-08-18 | Warsaw Orthopedic, Inc. | Osteoconductive matrices comprising statins |
US8877221B2 (en) | 2010-10-27 | 2014-11-04 | Warsaw Orthopedic, Inc. | Osteoconductive matrices comprising calcium phosphate particles and statins and methods of using the same |
WO2012170417A2 (en) | 2011-06-06 | 2012-12-13 | Warsaw Orthopedic, Inc. | Methods and compositions to enhance bone growth comprising a statin |
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EP0462066A1 (en) * | 1990-06-15 | 1991-12-18 | Warner-Lambert Company | Amorphous gemfibrozil |
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1999
- 1999-05-29 US US09/320,188 patent/US6465011B2/en not_active Expired - Fee Related
-
2000
- 2000-05-23 EP EP00932706A patent/EP1183012A1/en not_active Withdrawn
- 2000-05-23 WO PCT/US2000/014106 patent/WO2000072825A1/en not_active Application Discontinuation
- 2000-05-23 CA CA002374288A patent/CA2374288A1/en not_active Abandoned
- 2000-05-23 JP JP2000620937A patent/JP2003500437A/en not_active Withdrawn
- 2000-05-23 MX MXPA01012162A patent/MXPA01012162A/en active IP Right Grant
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Cited By (39)
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GB2355194B (en) * | 1999-08-31 | 2003-01-08 | Bradford Particle Design Plc | Coformulation methods and their products |
GB2355194A (en) * | 1999-08-31 | 2001-04-18 | Bradford Particle Design Plc | Stable amorphous active component containing composition |
EP1274401B2 (en) † | 2000-04-10 | 2014-08-13 | Teva Pharmaceutical Industries Ltd. | Stable pharmaceutical compositions containing 7-substituted-3,5-dihydroxyheptanoic acids or 7-substituted-3,5-dihydroxyheptenoic acids |
US7115279B2 (en) | 2000-08-03 | 2006-10-03 | Curatolo William J | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
US7235259B2 (en) | 2000-08-03 | 2007-06-26 | Pfizer Inc | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
US8389011B2 (en) | 2000-08-03 | 2013-03-05 | Bend Research, Inc. | Pharmaceutical compositions of cholesteryl ester transfer protein inhibitors |
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US6982281B1 (en) | 2000-11-17 | 2006-01-03 | Lipocine Inc | Pharmaceutical compositions and dosage forms for administration of hydrophobic drugs |
US7887840B2 (en) | 2001-06-22 | 2011-02-15 | Bend Research, Inc. | Pharmaceutical compositions comprising drug and concentration-enhancing polymers |
JP2005533802A (en) * | 2002-06-25 | 2005-11-10 | セエルエル ファルマ | Solid pharmaceutical composition containing lipophilic active ingredient and method for producing the same |
US7790197B2 (en) | 2003-06-09 | 2010-09-07 | Warner-Lambert Company Llc | Pharmaceutical compositions of atorvastatin |
US7655692B2 (en) | 2003-06-12 | 2010-02-02 | Pfizer Inc. | Process for forming amorphous atorvastatin |
EP3167882A1 (en) | 2005-11-10 | 2017-05-17 | BGP Products Operations GmbH | Use of fenofibrate or a derivative thereof for preventing diabetic retinopathy |
EP1785133A1 (en) | 2005-11-10 | 2007-05-16 | Laboratoires Fournier S.A. | Use of fenofibrate or a derivative thereof for preventing diabetic retinopathy |
WO2008104852A3 (en) * | 2007-02-26 | 2009-03-26 | Wockhardt Research Center | Pharmaceutical compositions comprising adsorbate of fenofibrate |
WO2008104852A2 (en) * | 2007-02-26 | 2008-09-04 | Wockhardt Research Centre | Pharmaceutical compositions comprising adsorbate of fenofibrate |
WO2009013633A3 (en) * | 2007-07-20 | 2009-05-14 | Actavis Group Ptc Ehf | Amorphous coprecipitates of atorvastatin pharmaceutically acceptable salts |
WO2009013633A2 (en) * | 2007-07-20 | 2009-01-29 | Actavis Group Ptc Ehf | Amorphous coprecipitates of atorvastatin pharmaceutically acceptable salts |
US8865695B2 (en) | 2009-01-08 | 2014-10-21 | Lipocine Inc. | Steroidal compositions |
US11052096B2 (en) | 2009-01-08 | 2021-07-06 | Lipocine Inc. | Steroidal compositions |
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Also Published As
Publication number | Publication date |
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US20010006662A1 (en) | 2001-07-05 |
US6465011B2 (en) | 2002-10-15 |
EP1183012A1 (en) | 2002-03-06 |
MXPA01012162A (en) | 2002-07-22 |
JP2003500437A (en) | 2003-01-07 |
CA2374288A1 (en) | 2000-12-07 |
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