Compositions and methods for improved delivery of lipid regulating agents
First Claim
Patent Images
1. A pharmaceutical composition comprising:
- (a) a hydrophobic therapeutic agent; and
(b) a carrier,
said carrier comprising;
(i) at least one hydrophilic surfactant; and
(ii) at least one hydrophobic surfactant,
said hydrophilic and hydrophobic surfactants being present in amounts such that upon mixing with an aqueous solution the carrier forms a clear aqueous dispersion of the hydrophilic and hydrophobic surfactants containing the hydrophobic therapeutic agent, said composition being substantially free of triglycerides.
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Abstract
The present invention relates to triglyceride-free pharmaceutical compositions for delivery of hydrophobic therapeutic agents. Compositions of the present invention include a hydrophobic therapeutic agent and a carrier, where the carrier is formed from a combination of a hydrophilic surfactant and a hydrophobic surfactant. Upon dilution with an aqueous solvent, the composition forms a clear, aqueous dispersion of the surfactants containing the therapeutic agent. The invention also provides methods of treatment with hydrophobic therapeutic agents using these compositions.
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Citations
140 Claims
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1. A pharmaceutical composition comprising:
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(a) a hydrophobic therapeutic agent; and
(b) a carrier,
said carrier comprising;
(i) at least one hydrophilic surfactant; and
(ii) at least one hydrophobic surfactant,
said hydrophilic and hydrophobic surfactants being present in amounts such that upon mixing with an aqueous solution the carrier forms a clear aqueous dispersion of the hydrophilic and hydrophobic surfactants containing the hydrophobic therapeutic agent,said composition being substantially free of triglycerides. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 63, 64, 65, 66, 67, 68, 69, 70)
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2. The pharmaceutical composition of claim 1, wherein the hydrophobic surfactant is present in an amount of less than about 200% by weight, relative to the amount of the hydrophilic surfactant.
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3. The pharmaceutical composition of claim 2, wherein the hydrophobic surfactant is present in an amount of less than about 100% by weight, relative to the amount of the hydrophilic surfactant.
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4. The pharmaceutical composition of claim 3, wherein the hydrophobic surfactant is present in an amount of less than about 60% by weight, relative to the amount of the hydrophilic surfactant.
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5. The pharmaceutical composition of claim 1, wherein the hydrophilic surfactant comprises at least one non-ionic hydrophilic surfactant having an HLB value greater than or equal to about 10.
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6. The pharmaceutical composition of claim 1, wherein the hydrophilic surfactant comprises at least one ionic surfactant.
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7. The pharmaceutical composition of claim 5, which further comprises at least one ionic surfactant.
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8. The pharmaceutical composition of claim 5, wherein the non-ionic surfactant is selected from the group consisting of alkylglucosides;
- alkylmaltosides;
alkylthioglucosides;
lauryl macrogolglycerides;
polyoxyethylene alkyl ethers;
polyoxyethylene alkylphenols;
polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyglycerol fatty acid esters;
polyoxyethylene glycerides;
polyoxyethylene sterols, derivatives, and analogues thereof;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols;
sugar esters, sugar ethers;
sucroglycerides; and
mixtures thereof.
- alkylmaltosides;
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9. The pharmaceutical composition of claim 5, wherein the non-ionic hydrophilic surfactant is selected from the group consisting of polyoxyethylene alkylethers;
- polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyglycerol fatty acid esters;
polyoxyethylene glycerides;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- polyethylene glycol fatty acids esters;
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10. The pharmaceutical composition of claim 9, wherein the glyceride is a monoglyceride, diglyceride, triglyceride, or a mixture thereof.
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11. The pharmaceutical composition of claim 9, wherein the reaction mixture comprises the transesterification products of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
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12. The pharmaceutical composition of claim 9, wherein the polyol is glycerol, ethylene glycol, polyethylene glycol, sorbitol, propylene glycol, pentaerythritol or a mixture thereof.
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13. The pharmaceutical composition of claim 5, wherein the hydrophilic surfactant is PEG-10 laurate, PEG-12 laurate, PEG-20 laurate, PEG-32 laurate, PEG-32 dilaurate, PEG-12 oleate, PEG-15 oleate, PEG-20 oleate, PEG-20 dioleate, PEG-32 oleate, PEG-200 oleate, PEG400 oleate, PEG-15 stearate, PEG-32 distearate, PEG-40 stearate, PEG-100 stearate, PEG-20 dilaurate, PEG-25 glyceryl trioleate, PEG-32 dioleate, PEG-20 glyceryl laurate, PEG-30 glyceryl laurate, PEG-20 glyceryl stearate, PEG-20 glyceryl oleate, PEG-30 glyceryl oleate, PEG-30 glyceryl laurate, PEG-40 glyceryl laurate, PEG-40 palm kernel oil, PEG-50 hydrogenated castor oil, PEG-40 castor oil, PEG-35 castor oil, PEG-60 castor oil, PEG-40 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-60 corn oil, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polyglyceryl-10 laurate, PEG-30 cholesterol, PEG-25 phyto sterol, PEG-30 soya sterol, PEG-20 trioleate, PEG-40 sorbitan oleate, PEG-80 sorbitan laurate, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, POE-20 oleyl ether, POE-20 stearyl ether, tocopheryl PEG-100 succinate, PEG-24 cholesterol, polyglyceryl-10 oleate, Tween 40, Tween 60, sucrose monostearate, sucrose monolaurate, sucrose monopalmitate, PEG 10-100 nonyl phenol series, PEG 15-100 octyl phenol series, a poloxamer, or a mixture thereof.
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14. The pharmaceutical composition of claim 5, wherein the hydrophilic surfactant is PEG-20 laurate, PEG-20 oleate, PEG-35 castor oil, PEG-40 palm kernel oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, polyglyceryl-10 laurate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, PEG-30 cholesterol, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, PEG-24 cholesterol, sucrose monostearate, sucrose monolaurate, a poloxamer, or a mixture thereof.
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15. The pharmaceutical composition of claim 5, wherein the hydrophilic surfactant is PEG-35 castor oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polysorbate 20, polysorbate 80, tocopheryl PEG-1000 succinate, PEG-24 cholesterol, a poloxamer, or a mixture thereof.
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16. The pharmaceutical composition of claim 6, wherein the ionic surfactant is selected from the group consisting of alkyl ammonium salts;
- bile acids and salts, analogues, and derivatives thereof;
fatty acid derivatives of amino acids, oligopeptides, and polypeptides;
glyceride derivatives of amino acids, oligopeptides, and polypeptides;
acyl lactylates;
mono-,diacetylated tartaric acid esters of mono-,diglycerides;
succinylated monoglycerides;
citric acid esters of mono-,diglycerides;
alginate salts;
propylene glycol alginate;
lecithins and hydrogenated lecithins;
lysolecithin and hydrogenated lysolecithins;
lysophospholipids and derivatives thereof;
phospholipids and derivatives thereof;
salts of alkylsulfates;
salts of fatty acids;
sodium docusate; and
mixtures thereof.
- bile acids and salts, analogues, and derivatives thereof;
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17. The pharmaceutical composition of claim 6, wherein the ionic surfactant is selected from the group consisting of bile acids and salts, analogues, and derivatives thereof;
- lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof;
salts of alkylsulfates;
salts of fatty acids;
sodium docusate;
acyl lactylates;
mono-,diacetylated tartaric acid esters of mono-,diglycerides;
succinylated monoglycerides;
citric acid esters of mono-,diglycerides; and
mixtures thereof.
- lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof;
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18. The pharmaceutical composition of claim 6, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, phosphatidylserine, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylglycerol, lysophosphatidic acid, lysophosphatidylserine, PEG-phosphatidylethanolamine, PVP-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, chenodeoxycholate, glycodeoxycholate, glycochenodeoxycholate, taurochenodeoxycholate, ursodeoxycholate, tauroursodeoxycholate, glycoursodeoxycholate, cholylsarcosine, N-methyl taurocholate, caproate, caprylate, caprate, laurate, myristate, palmitate, oleate, ricinoleate, linoleate, linolenate, stearate, lauryl sulfate, teracecyl sulfate, docusate, and salts and mixtures thereof.
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19. The pharmaceutical composition of claim 6, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, lysophosphatidylcholine, PEG-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, glycodeoxycholate, cholylsarcosine, caproate, caprylate, caprate, laurate, oleate, lauryl sulfate, docusate, and salts and mixtures thereof.
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20. The pharmaceutical composition of claim 6, wherein the ionic surfactant is selected from the group consisting of lecithin, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, taurocholate, caprylate, caprate, oleate, lauryl sulfate, docusate, and salts and mixtures thereof.
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21. The pharmaceutical composition of claim 1 wherein the hydrophobic surfactant is a compound or mixture of compounds having an HLB value less than about 10.
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22. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is selected from the group consisting of alcohols;
- polyoxyethylene alkylethers;
fatty acids;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lower alcohol fatty acids esters;
polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters;
polyoxyethylene glycerides;
lactic acid derivatives of mono/diglycerides;
propylene glycol diglycerides;
sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
transesterified vegetable oils;
sterols;
sterol derivatives;
sugar esters;
sugar ethers;
sucroglycerides;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- polyoxyethylene alkylethers;
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23. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is selected from the group consisting of fatty acids;
- lower alcohol fatty acid esters;
polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters;
polyoxyethylene glycerides;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lactic acid derivatives of mono/diglycerides;
sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- lower alcohol fatty acid esters;
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24. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is selected from the group consisting of lower alcohol fatty acids esters;
- polypropylene glycol fatty acid esters;
propylene glycol fatty acid esters;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lactic acid derivatives of mono/diglycerides;
sorbitan fatty acid esters;
polyoxyethylene vegetable oils; and
mixtures thereof.
- polypropylene glycol fatty acid esters;
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25. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is a glycerol fatty acid ester, an acetylated glycerol fatty acid ester, or a mixture thereof.
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26. The pharmaceutical composition of claim 25, wherein the glycerol fatty acid ester is a monoglyceride, diglyceride, or a mixture thereof.
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27. The pharmaceutical composition of claim 26, wherein the fatty acid of the glycerol fatty acid ester is a C6 to C20 fatty acid or a mixture thereof.
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28. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is a reaction mixture of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
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29. The pharmaceutical composition of claim 28, wherein the reaction mixture is a transesterification product of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
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30. The pharmaceutical composition of claim 28, wherein the polyol is polyethylene glycol, sorbitol, propylene glycol, pentaerythritol or a mixture thereof.
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31. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is selected from the group consisting of myristic acid;
- oleic acid;
lauric acid;
stearic acid;
palmitic acid;
PEG 1-4 stearate;
PEG 2-4 oleate;
PEG-4 dilaurate;
PEG-4 dioleate;
PEG-4 distearate;
PEG-6 dioleate;
PEG-6 distearate;
PEG-8 dioleate;
PEG 3-16 castor oil;
PEG 5-10 hydrogenated castor oil;
PEG 6-20 corn oil;
PEG 6-20 almond oil;
PEG-6 olive oil;
PEG-6 peanut oil;
PEG-6 palm kernel oil;
PEG-6 hydrogenated palm kernel oil;
PEG-4 capric/caprylic triglyceride, mono, di, tri, tetra esters of vegetable oil and sorbitol;
pentaerythrityl di, tetra stearate, isostearate, oleate, caprylate, or caprate;
polyglyceryl 2-4 oleate, stearate, or isostearate;
polyglyceryl 4-10 pentaoleate;
polyglyceryl-3 dioleate;
polyglyceryl-6 dioleate;
polyglyceryl-10 trioleate;
polyglyceryl-3 distearate;
propylene glycol mono- or diesters of a C6 to C20 fatty acid;
monoglycerides of a C6 to C20 fatty acid;
acetylated monoglycerides of C6 to C20 fatty acid;
diglycerides of C6 to C20 fatty acids;
lactic acid derivatives of monoglycerides;
lactic acid derivatives of diglycerides;
cholesterol;
phytosterol;
PEG 5-20 soya sterol;
PEG-6 sorbitan tetra, hexastearate;
PEG-6 sorbitan tetraoleate;
sorbitan monolaurate;
sorbitan monopalmitate;
sorbitan mono, trioleate;
sorbitan mono, tristearate;
sorbitan monoisostearate;
sorbitan sesquioleate;
sorbitan sesquistearate;
PEG 2-5 oleyl ether;
POE 2-4 lauryl ether;
PEG-2 cetyl ether;
PEG-2 stearyl ether;
sucrose distearate;
sucrose dipalmitate;
ethyl oleate;
isopropyl myristate;
isopropyl palmitate;
ethyl linoleate;
isopropyl linoleate;
poloxamers; and
mixtures thereof.
- oleic acid;
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32. The pharmaceutical composition of claim 21, wherein the hydrophobic surfactant is selected from the group consisting of oleic acid;
- lauric acid;
glyceryl monocaprate;
glyceryl monocaprylate;
glyceryl monolaurate;
glyceryl monooleate;
glyceryl dicaprate;
glyceryl dicaprylate;
glyceryl dilaurate;
glyceryl dioleate;
acetylated monoglycerides;
propylene glycol oleate;
propylene glycol laurate;
polyglyceryl-3 oleate;
polyglyceryl-6 dioleate;
PEG-6 corn oil;
PEG-20 corn oil;
PEG-20 almond oil;
sorbitan monooleate;
sorbitan monolaurate;
POE-4 lauryl ether;
POE-3 oleyl ether;
ethyl oleate;
poloxamers; and
mixtures thereof.
- lauric acid;
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33. The pharmaceutical composition of claim 1, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 100 nm.
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34. The pharmaceutical composition of claim 33, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 50 nm.
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35. The pharmaceutical composition of claim 33, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 20 nm.
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36. The pharmaceutical composition of claim 1, wherein the clear aqueous dispersion has an absorbance of less than about 0.1 at about 400 nm when the carrier is diluted with an aqueous solution in an aqueous solution to carrier ratio of 100:
- 1 by weight.
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37. The pharmaceutical composition of claim 36, wherein the absorbance is less than about 0.01.
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38. The pharmaceutical composition of claim 1, wherein the hydrophobic therapeutic agent has an intrinsic water solubility of less than about 1% by weight at 25°
- C.
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39. The pharmaceutical composition of claim 38, wherein the intrinsic water solubility is less than about 0.1% by weight at 25°
- C.
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40. The pharmaceutical composition of claim 39, wherein the intrinsic water solubility is less than about 0.01% by weight at 25°
- C.
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41. The pharmaceutical composition of claim 1, wherein the therapeutic agent is a drug, a vitamin, a nutritional supplement, a cosmeceutical, or a mixture thereof.
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42. The pharmaceutical composition of claim 43, wherein the therapeutic agent is a polyfunctional hydrophobic drug, a lipophilic drug, a pharmaceutically acceptable salt, isomer or derivative thereof, or a mixture thereof.
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43. The pharmaceutical composition of claim 41, wherein the therapeutic agent is selected from the group consisting of analgesics, anti-inflammatory agents, anthelmintics, anti-arrhythmic agents, anti-bacterial agents, anti-viral agents, anti-coagulants, anti-depressants, anti-diabetics, anti-epileptics, anti-fungal agents, anti-gout agents, anti-hypertensive agents, anti-malarials, anti-migraine agents, anti-muscarinic agents, anti-neoplastic agents, erectile dysfunction improvement agents, immunosuppressants, anti-protozoal agents, anti-thyroid agents, anxiolytic agents, sedatives, hypnotics, neuroleptics, β
- -Blockers, cardiac inotropic agents, corticosteroids, diuretics, anti-parkinsonian agents, gastro-intestinal agents, histamine H,-receptor antagonists, keratolytics, lipid regulating agents, anti-anginal agents, nutritional agents, opioid analgesics, sex hormones, stimulants, muscle relaxants, anti-osteoporosis agents, anti-obesity agents, cognition enhancers, anti-urinary incontinence agents, nutritional oils, anti-benign prostate hypertrophy agents, essential fatty acids, non-essential fatty acids, and mixtures thereof.
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44. The pharmaceutical composition of claim 41, wherein the therapeutic agent is tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, albendazole, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, azithromycin, ciprofloxacin, clarithromycin, dirithromycin, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, dicoumarol, tirofibran, cilostazol, ticlidopine, clopidrogel, oprevelkin, paroxetine, sertraline, venlafaxine, bupropion, clomipramine, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, amphotericin B, butenafine, terbinafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, griseofulvin, nitrofurantoin, spironolactone, lisinopril, benezepril, nifedipine, nilsolidipine, telmisartan, irbesartan, eposartan, valsartan, candesartan, minoxidil, terzosin, halofantrine, mefloquine, dihydroergotamine, ergotamine, frovatriptan, pizofetin, sumatriptan, zolmitriptan, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, pseudo-ephedrine, toremifene, atovaquone, metronidazole, furazolidone, paricalcitol, benzonatate, midazolam, zolpidem, gabapentin, zopiclone, digoxin, beclomethsone, budesonide, betamethasone, prednisolone, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecalciferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, gemfibrozil, cerivistatin, pravastatin, simvastatin, fluvastatin, atorvastatin, tizanidine, dantrolene, isosorbide dinatrate, a carotene, dihydrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, an essential fatty acid source, codeine, fentanyl, methadone, nalbuphine, pentazocine, clomiphene, danazol, dihydro epiandrosterone, medroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, amphetamine, L-thryroxine, tamsulosin, methoxsalen, tacrine, donepezil, raloxifene, vertoporfin, sibutramine, pyridostigmine, a pharmaceutically acceptable salt, isomer, or derivative thereof, or a mixture thereof.
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45. The pharmaceutical composition of claim 1, wherein the hydrophobic therapeutic agent is selected from the group consisting of tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, albendazole, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, azithromycin, ciprofloxacin, clarithromycin, dirithromycin, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, amphotericin B, butenafine, terbinafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, griseofulvin, nitrofurantoin, spironolactone, halofantrine, mefloquine, dihydroergotamine, ergotamine, frovatriptan, pizofetin, sumatriptan, zolmitriptan, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, pseudo-ephedrine, toremifene, atovaquone, metronidazole, furzolidone, paricalcitol, benzonatate, midazolam, zolpidem, gabapentin, zopiclone, digoxin, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecaliferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, gemfibrozil, cerivistatin, pravastatin, simvastatin, fluvastatin, atorvastatin, tizanidine, dantrolene, carotenes, dihyrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, essential fatty acid sources, codeine, fentanyl, methdone, nalbuphine, pentazocine, clomiphene, danazol, dihydro epiandrosterone, mmedroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, amphetamine, L-thryroxine, tamsulosin, methoxsalen, tacrine, donepezil, raloxifene, vertoporfin, sibutramine, pyridostigmine, pharmaceutically acceptable salts, isomers and derivatives thereof, and mixtures thereof.
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46. The pharmaceutical composition of claim 1, wherein the therapeutic agent is selected from the group consisting of tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, terbenafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, nitrofurantoin, dihydroergotamine, ergotamine, frovatriptan, pizofetin, zolmitriptan, pseudo-ephedrine, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, toremifene, atovaquone, metronidazole, furzolidone, paricalcitol, benzonatate, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecaliferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, simvastatin, atorvastatin, tizanidine, dantrolene, carotenes, dihyrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, essential fatty acid sources, danazol, dihydro epiandrosterone, medroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, raloxifene, L-thryroxine, tamsulosin, methoxsalen, pharmaceutically acceptable salts, isomers and derivative thereof, and mixtures thereof.
-
47. The pharmaceutical composition of claim 1, wherein the hydrophobic therapeutic agent is selected from the group consisting of sildenafil citrate, amlodipine, tramadol, celecoxib, refocoxib, oxaprozin, nabumetone, ibuprofen, terbenafine, itraconazole, zileuton, zafirlukast, cisapride, fenofibrate, tizanidine, nizatidine, fexofenadine, loratadine, famotidine, paricalcitol, atovaquone, nabumetone, tetrahydrocannabinol, megesterol acetate, repaglinide, progesterone, rimexolone, cyclosporine, tacrolimus, sirolimus, teniposide, paclitaxel, pseudo-ephedrine, troglitazone, rosiglitazone, finasteride, vitamin A, vitamin D, vitamin E, pharmaceutically acceptable salts, isomers and derivatives thereof, and mixtures thereof.
-
48. The pharmaceutical composition of claim 1, wherein the hydrophobic therapeutic agent is progesterone or cyclosporin.
-
49. The pharmaceutical composition of claim 1, which further comprises a solubilizer.
-
50. The pharmaceutical composition of claim 49, wherein the solubilizer is selected from the group consisting of alcohols, polyols, amides, esters, propylene glycol ethers and mixtures thereof.
-
51. The pharmaceutical composition of claim 50, wherein the alcohol or polyol is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediols and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, and mixtures thereof.
-
52. The pharmaceutical composition of claim 50, wherein the amide is selected from the group consisting of 2-pyrrolidone, 2-piperidone, ε
- -caprolactam, N-alkylpyrrolidone, N-hydroxyalkylpyrrolidone, N-alkylpiperidone, N-alkylcaprolactam, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
-
53. The pharmaceutical composition of claim 50, wherein the ester is selected from the group consisting of ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol monoacetate, propylene glycol diacetate, ε
- -caprolactone and isomers thereof, δ
-valerolactone and isomers thereof, β
-butyrolactone and isomers thereof, and mixtures thereof.
- -caprolactone and isomers thereof, δ
-
54. The pharmaceutical composition of claim 49, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediol and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins, clodextrins and derivatives thereof, ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol diacetate, ε
- -caprolactone and isomers thereof, δ
-valerolactone and isomers thereof, β
-butyrolactone and isomers thereof, 2-pyrrolidone, 2-2 piperidone, ε
-caprolactam, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethyl pyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, glycofurol, methoxy PEG, and mixtures thereof.
- -caprolactone and isomers thereof, δ
-
55. The pharmaceutical composition of claim 49, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, 1,3-butanediol, glycerol, pentaerythritol, sorbitol, glycofurol, transcutol, dimethyl isosorbide, polyethylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose, methylcellulose, ethylcellulose, hydroxypropylcyclodextrins, sulfobutyl ether derivatives of cyclodextrins, ethyl propionate, tributylcitrate, triethylcitrate, ethyl oleate, ethyl caprylate, triacetin, β
- -butyrolactone and isomers thereof, 2-pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethylpyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
-
56. The pharmaceutical composition of claim 49, wherein the solubilizer is triacetin, triethylcitrate, ethyl oleate, ethyl caprylate, dimethylacetamide, N-methylpyrrolidone, N-hydroxyethylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl methylcellulose, hydroxypropyl cyclodextrins, ethanol, polyethylene glycol 200-600, glycofurol, transcutol, propylene glycol, dimethyl isosorbide, or a mixture thereof.
-
57. The pharmaceutical composition of claim 49, wherein the solubilizer is triacetin, ethanol, polyethylene glycol 400, glycofurol, propylene glycol or a mixture thereof.
-
58. The pharmaceutical composition of claim 49, wherein the solubilizer is present in the composition in an amount of about 400% or less by weight, based on the total weight of the surfactants.
-
59. The pharmaceutical composition of claim 58, wherein the solubilizer is present in the composition in an amount of about 200% or less by weight, based on the total weight of the surfactants.
-
60. The pharmaceutical composition of claim 59, wherein the solubilizer is present in the composition in an amount of about 100% or less by weight, based on the total weight of the surfactants.
-
63. The pharmaceutical composition of claim 1, which further comprises an antioxidant, a preservative, a chelating agent, a viscomodulator, a tonicifier, a flavorant, a colorant, an odorant, an opacifier, a suspending agent, a binder, or a mixture thereof.
-
64. The pharmaceutical composition of claim 1 in the form of a preconcentrate, a diluted preconcentrate, a semi-solid dispersion, a solid dispersion, or a sprayable solution.
-
65. A dosage form comprising a capsule filled with the pharmaceutical composition of claim 1.
-
66. A dosage form comprising a multiparticulate carrier coated with the pharmaceutical composition of claim 1.
-
67. A dosage form comprising the pharmaceutical composition of claim 1 formulated as a solution, a cream, a lotion, an ointment, a suppository, a spray, an aerosol, a paste or a gel.
-
68. The dosage form of claim 65, wherein the capsule is a hard gelatin capsule, a soft gelatin capsule, a starch capsule or an enteric coated capsule.
-
69. The pharmaceutical composition of claim 1, which further comprises water or an aqueous buffer.
-
70. The pharmaceutical composition of claim 1, which further comprises an additional amount of a hydrophobic therapeutic agent, said additional amount not solubilized in the carrier.
-
2. The pharmaceutical composition of claim 1, wherein the hydrophobic surfactant is present in an amount of less than about 200% by weight, relative to the amount of the hydrophilic surfactant.
-
-
62. The pharmaceutical composition of claim 60, wherein the solubilizer is present in the composition in an amount of about 50% or less by weight, based on the total weight of the surfactants.
-
62-1. The pharmaceutical composition of claim 61, wherein the solubilizer is present in the composition in an amount about 25% or less by weight, based on the total weight of the surfactants.
-
71. A pharmaceutical composition comprising:
-
(a) at least one hydrophilic surfactant;
(b) at least one hydrophobic surfactant; and
(c) a hydrophobic therapeutic agent, said pharmaceutical composition being in the form of a clear, aqueous dispersion which is substantially free of triglycerides. - View Dependent Claims (72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134)
-
72. The pharmaceutical composition of claim 71, wherein the hydrophobic surfactant is present in an amount of less than about 200% by weight, relative to the amount of the hydrophilic surfactant.
-
73. The pharmaceutical composition of claim 72, wherein the hydrophobic surfactant is present in an amount of less than about 100% by weight, relative to the amount of the hydrophilic surfactant.
-
74. The pharmaceutical composition of claim 73, wherein the hydrophobic surfactant is present in an amount of less than about 60% by weight, relative to the amount of the hydrophilic surfactant.
-
75. The pharmaceutical composition of claim 71, wherein the hydrophilic surfactant comprises at least one non-ionic hydrophilic surfactant having an HLB value greater than or equal to about 10.
-
76. The pharmaceutical composition of claim 71, wherein the hydrophilic surfactant comprises at least one ionic surfactant.
-
77. The pharmaceutical composition of claim 75, which further comprises at least one ionic surfactant.
-
78. The pharmaceutical composition of claim 75, wherein the non-ionic surfactant is selected from the group consisting of alkylglucosides;
- alkylmaltosides;
alkylthioglucosides;
lauryl macrogolglycerides;
polyoxyethylene alkylethers;
polyoxyethylene alkylphenols;
polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyglycerol fatty acid esters;
polyoxyethylene glycerides;
polyoxyethylene sterols, derivatives, and analogues thereof;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols;
sugar esters, sugar ethers;
sucroglycerides; and
mixtures thereof.
- alkylmaltosides;
-
79. The pharmaceutical composition of claim 75, wherein the non-ionic hydrophilic surfactant is selected from the group consisting of polyoxyethylene alkylethers;
- polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyglycerol fatty acid esters;
polyoxyethylene glycerides;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- polyethylene glycol fatty acids esters;
-
80. The pharmaceutical composition of claim 79, wherein the glyceride is a monoglyceride, diglyceride, triglyceride, or a mixture thereof.
-
81. The pharmaceutical composition of claim 79, wherein the reaction mixture comprises the transesterification products of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
-
82. The pharmaceutical composition of claim 79, wherein the polyol is glycerol, ethylene glycol, polyethylene glycol, sorbitol, propylene glycol, pentaerythritol or a mixture thereof.
-
83. The pharmaceutical composition of claim 75, wherein the hydrophilic surfactant is PEG-10 laurate, PEG-12 laurate, PEG-20 laurate, PEG-32 laurate, PEG-32 dilaurate, PEG-12 oleate, PEG-15 oleate, PEG-20 oleate, PEG-20 dioleate, PEG-32 oleate, PEG-200 oleate, PEG-400 oleate, PEG-15 stearate, PEG-32 distearate, PEG-40 stearate, PEG-100 stearate, PEG-20 dilaurate, PEG-25 glyceryl trioleate, PEG-32 dioleate, PEG-20 glyceryl laurate, PEG-30 glyceryl laurate, PEG-20 glyceryl stearate, PEG-20 glyceryl oleate, PEG-30 glyceryl oleate, PEG-30 glyceryl laurate, PEG-40 glyceryl laurate, PEG-40 palm kernel oil, PEG-50 hydrogenated castor oil, PEG-40 castor oil, PEG-35 castor oil, PEG-60 castor oil, PEG40 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-60 corn oil, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polyglyceryl-10 laurate, PEG-30 cholesterol, PEG-25 phyto sterol, PEG-30 soya sterol, PEG-20 trioleate, PEG-40 sorbitan oleate, PEG-80 sorbitan laurate, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, POE-20 oleyl ether, POE-20 stearyl ether, tocopheryl PEG-100 succinate, PEG-24 cholesterol, polyglyceryl-10 oleate, Tween 40, Tween 60, sucrose monostearate, sucrose monolaurate, sucrose monopalmitate, PEG 10-100 nonyl phenol series, PEG 15-100 octyl phenol series, a poloxamer, or a mixture thereof.
-
84. The pharmaceutical composition of claim 75, wherein the hydrophilic surfactant is PEG-20 laurate, PEG-20 oleate, PEG-35 castor oil, PEG-40 palm kernel oil, PEG-40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, polyglyceryl-10 laurate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, PEG-30 cholesterol, polysorbate 20, polysorbate 80, POE-9 lauryl ether, POE-23 lauryl ether, POE-10 oleyl ether, PEG-24 cholesterol, sucrose monostearate, sucrose monolaurate, a poloxamer, or a mixture thereof.
-
85. The pharmaceutical composition of claim 75, wherein the hydrophilic surfactant is PEG-35 castor oil, PEG40 hydrogenated castor oil, PEG-60 corn oil, PEG-25 glyceryl trioleate, PEG-6 caprate/caprylate glycerides, PEG-8 caprate/caprylate glycerides, polysorbate 20, polysorbate 80, tocopheryl PEG-1000 succinate, PEG-24 cholesterol, a poloxamer, or a mixture thereof.
-
86. The pharmaceutical composition of claim 76, wherein the ionic surfactant is selected from the group consisting of alkyl ammonium salts;
- bile acids and salts, analogues, and derivatives thereof;
fatty acid derivatives of amino acids, oligopeptides, and polypeptides;
glyceride derivatives of amino acids, oligopeptides, and polypeptides;
acyl lactylates;
mono-,diacetylated tartaric acid esters of mono-,diglycerides;
succinylated monoglycerides;
citric acid esters of mono-,diglycerides;
alginate salts;
propylene glycol alginate;
lecithins and hydrogenated lecithins;
lysolecithin and hydrogenated lysolecithins;
lysophospholipids and derivatives thereof;
phospholipids and derivatives thereof;
salts of alkylsulfates;
salts of fatty acids;
sodium docusate; and
mixtures thereof.
- bile acids and salts, analogues, and derivatives thereof;
-
87. The pharmaceutical composition of claim 76, wherein the ionic surfactant is selected from the group consisting of bile acids and salts, analogues, and derivatives thereof;
- lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof;
salts of alkylsulfates;
salts of fatty acids;
sodium docusate;
acyl lactylates;
mono-,diacetylated tartaric acid esters of mono-,diglycerides;
succinylated monoglycerides;
citric acid esters of mono-,diglycerides; and
mixtures thereof.
- lecithins, lysolecithin, phospholipids, lysophospholipids and derivatives thereof;
-
88. The pharmaceutical composition of claim 76, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, phosphatidic acid, phosphatidylserine, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylglycerol, lysophosphatidic acid, lysophosphatidylserine, PEG-phosphatidylethanolamine, PVP-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, chenodeoxycholate, glycodeoxycholate, glycochenodeoxycholate, taurochenodeoxycholate, ursodeoxycholate, tauroursodeoxycholate, glycoursodeoxycholate, cholylsarcosine, N-methyl taurocholate, caproate, caprylate, caprate, laurate, myristate, palmitate, oleate, ricinoleate, linoleate, linolenate, stearate, lauryl sulfate, teracecyl sulfate, docusate, and salts and mixtures thereof.
-
89. The pharmaceutical composition of claim 76, wherein the ionic surfactant is selected from the group consisting of lecithin, lysolecithin, phosphatidylcholine, phosphatidylethanolamine, phosphatidylglycerol, lysophosphatidylcholine, PEG-phosphatidylethanolamine, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, cholate, taurocholate, glycocholate, deoxycholate, taurodeoxycholate, glycodeoxycholate, cholylsarcosine, caproate, caprylate, caprate, laurate, oleate, lauryl sulfate, docusate, and salts and mixtures thereof.
-
90. The pharmaceutical composition of claim 76, wherein the ionic surfactant is selected from the group consisting of lecithin, lactylic esters of fatty acids, stearoyl-2-lactylate, stearoyl lactylate, succinylated monoglycerides, mono/diacetylated tartaric acid esters of mono/diglycerides, citric acid esters of mono/diglycerides, taurocholate, caprylate, caprate, oleate, lauryl sulfate, docusate, and salts and mixtures thereof.
-
91. The pharmaceutical composition of claim 71 wherein the hydrophobic surfactant is a compound or mixture of compounds having an HLB value less than about 10.
-
92. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is selected from the group consisting of alcohols;
- polyoxyethylene alkylethers;
fatty acids;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lower alcohol fatty acids esters;
polyethylene glycol fatty acids esters;
polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters;
polyoxyethylene glycerides;
lactic acid derivatives of mono/diglycerides;
propylene glycol diglycerides;
sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
transesterified vegetable oils;
sterols;
sterol derivatives;
sugar esters;
sugar ethers;
sucroglycerides;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- polyoxyethylene alkylethers;
-
93. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is selected from the group consisting of fatty acids;
- lower alcohol fatty acid esters;
polyethylene glycol glycerol fatty acid esters;
polypropylene glycol fatty acid esters;
polyoxyethylene glycerides;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lactic acid derivatives of mono/diglycerides;
sorbitan fatty acid esters;
polyoxyethylene sorbitan fatty acid esters;
polyoxyethylene-polyoxypropylene block copolymers;
polyoxyethylene vegetable oils;
polyoxyethylene hydrogenated vegetable oils;
reaction mixtures of polyols and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols; and
mixtures thereof.
- lower alcohol fatty acid esters;
-
94. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is selected from the group consisting of lower alcohol fatty acids esters;
- polypropylene glycol fatty acid esters;
propylene glycol fatty acid esters;
glycerol fatty acid esters;
acetylated glycerol fatty acid esters;
lactic acid derivatives of mono/diglycerides;
sorbitan fatty acid esters;
polyoxyethylene vegetable oils; and
mixtures thereof.
- polypropylene glycol fatty acid esters;
-
95. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is a glycerol fatty acid ester, an acetylated glycerol fatty acid ester, or a mixture thereof.
-
96. The pharmaceutical composition of claim 95, wherein the glycerol fatty acid ester is a monoglyceride, diglyceride, or a mixture thereof.
-
97. The pharmaceutical composition of claim 96, wherein the fatty acid of the glycerol fatty acid ester is a C6 to C20 fatty acid or a mixture thereof.
-
98. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is a reaction mixture of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
-
99. The pharmaceutical composition of claim 98, wherein the reaction mixture is a transesterification product of a polyol and at least one member of the group consisting of fatty acids, glycerides, vegetable oils, hydrogenated vegetable oils, and sterols.
-
100. The pharmaceutical composition of claim 98, wherein the polyol is polyethylene glycol, sorbitol, propylene glycol, pentaerythritol or a mixture thereof.
-
101. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is selected from the group consisting of myristic acid;
- oleic acid;
lauric acid;
stearic acid;
palmitic acid;
PEG 1-4 stearate;
PEG 2-4 oleate;
PEG-4 dilaurate;
PEG-4 dioleate;
PEG-4 distearate;
PEG-6 dioleate;
PEG-6 distearate;
PEG-8 dioleate;
PEG 3-16 castor oil;
PEG 5-10 hydrogenated castor oil;
PEG 6-20 corn oil;
PEG 6-20 almond oil;
PEG-6 olive oil;
PEG-6 peanut oil;
PEG-6 palm kernel oil;
PEG-6 hydrogenated palm kernel oil;
PEG-4 capric/caprylic triglyceride, mono, di, tri, tetra esters of vegetable oil and sorbitol;
pentaerythrityl di, tetra stearate, isostearate, oleate, caprylate, or caprate;
polyglyceryl 2-4 oleate, stearate, or isostearate;
polyglyceryl 4-10 pentaoleate;
polyglyceryl-3 dioleate;
polyglyceryl-6 dioleate;
polyglyceryl-10 trioleate;
polyglyceryl-3 distearate;
propylene glycol mono- or diesters of a C6 to C20 fatty acid;
monoglycerides of a C6 to C20 fatty acid;
acetylated monoglycerides of C6 to C20 fatty acid;
diglycerides of C6 to C20 fatty acids;
lactic acid derivatives of monoglycerides;
lactic acid derivatives of diglycerides;
cholesterol;
phytosterol;
PEG 5-20 soya sterol;
PEG-6 sorbitan tetra, hexastearate;
PEG-6 sorbitan tetraoleate;
sorbitan monolaurate;
sorbitan monopalmitate;
sorbitan mono, trioleate;
sorbitan mono, tristearate;
sorbitan monoisostearate;
sorbitan sesquioleate;
sorbitan sesquistearate;
PEG 2-5 oleyl ether;
POE 2-4 lauryl ether;
PEG-2 cetyl ether;
PEG-2 stearyl ether;
sucrose distearate;
sucrose dipalmitate;
ethyl oleate;
isopropyl myristate;
isopropyl palmitate;
ethyl linoleate;
isopropyl linoleate;
poloxamers; and
mixtures thereof.
- oleic acid;
-
102. The pharmaceutical composition of claim 91, wherein the hydrophobic surfactant is selected from the group consisting of oleic acid;
- lauric acid;
glyceryl monocaprate;
glyceryl monocaprylate;
glyceryl monolaurate;
glyceryl monooleate;
glyceryl dicaprate;
glyceryl dicaprylate;
glyceryl dilaurate;
glyceryl dioleate;
acetylated monoglycerides;
propylene glycol oleate;
propylene glycol laurate;
polyglyceryl-3 oleate;
polyglyceryl-6 dioleate;
PEG-6 corn oil;
PEG-20 corn oil;
PEG-20 almond oil;
sorbitan monooleate;
sorbitan monolaurate;
POE-4 lauryl ether;
POE-3 oleyl ether;
ethyl oleate;
poloxamers; and
mixtures thereof.
- lauric acid;
-
103. The pharmaceutical composition of claim 71, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 100 nm.
-
104. The pharmaceutical composition of claim 103, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 50 nm.
-
105. The pharmaceutical composition of claim 103, wherein the clear aqueous dispersion has a particle size distribution having an average particle size of less than about 20 nm.
-
106. The pharmaceutical composition of claim 71, wherein the clear aqueous dispersion has an absorbance of less than about 0.1 at 400 nm when the ratio of the weight of water to the total weight of the hydrophilic surfactant, the hydrophobic surfactant and the therapeutic agent is 100:
- 1.
-
107. The pharmaceutical composition of claim 106, wherein the absorbance is less than about 0.01.
-
108. The pharmaceutical composition of claim 71, wherein the hydrophobic therapeutic agent has an intrinsic water solubility of less than about 1% by weight at 25°
- C.
-
109. The pharmaceutical composition of claim 108, wherein the intrinsic water solubility is less than about 0.1% by weight at 25°
- C.
-
110. The pharmaceutical composition of claim 109, wherein the intrinsic water solubility is less than about 0.01% by weight at 25°
- C.
-
111. The pharmaceutical composition of claim 71, wherein the therapeutic agent is a drug, a vitamin, a nutritional supplement, a cosmeceutical, or a mixture thereof.
-
112. The pharmaceutical composition of claim 111, wherein the therapeutic agent is a polyfunctional hydrophobic drug, a lipophilic drug, a pharmaceutically acceptable salt, isomer or derivative thereof, or a mixture thereof.
-
113. The pharmaceutical composition of claim 111, wherein the therapeutic agent is selected from the group consisting of analgesics, anti-inflammatory agents, anthelmintics, anti-arrhythmic agents, anti-bacterial agents, anti-viral agents, anti-coagulants, anti-depressants, anti-diabetics, anti-epileptics, anti-fungal agents, anti-gout agents, anti-hypertensive agents, anti-malarials, anti-migraine agents, anti-muscarinic agents, anti-neoplastic agents, erectile dysfunction improvement agents, immunosuppressants, anti-protozoal agents, anti-thyroid agents, anxiolytic agents, sedatives, hypnotics, neuroleptics, β
- -Blockers, cardiac inotropic agents, corticosteroids, diuretics, anti-parkinsonian agents, gastro-intestinal agents, histamine H,-receptor antagonists, keratolytics, lipid regulating agents, anti-anginal agents, nutritional agents, opioid analgesics, sex hormones, stimulants, muscle relaxants, anti-osteoporosis agents, anti-obesity agents, cognition enhancers, anti-urinary incontinence agents, nutritional oils, anti-benign prostate hypertrophy agents, essential fatty acids, non-essential fatty acids, and mixtures thereof.
-
114. The pharmaceutical composition of claim 111, wherein the therapeutic agent is tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, albendazole, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, azithromycin, ciprofloxacin, clarithromycin, dirithromycin, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, dicoumarol, tirofibran, cilostazol, ticlidopine, clopidrogel, oprevelkin, paroxetine, sertraline, venlafaxine, bupropion, clomipramine, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, amphotericin B, butenafine, terbinafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, griseofulvin, nitrofurantoin, spironolactone, lisinopril, benezepril, nifedipine, nilsolidipine, telmisartan, irbesartan, eposartan, valsartan, candesartan, minoxidil, terzosin, halofantrine, mefloquine, dihydroergotamine, ergotamine, frovatriptan, pizofetin, sumatriptan, zolmitriptan, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, ephedrine, toremifene, atovaquone, metronidazole, furazolidone, paricalcitol, benzonatate, midazolam, zolpidem, gabapentin, zopiclone, digoxin, beclomethsone, budesonide, betamethasone, prednisolone, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecalciferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, gemfibrozil, cerivistatin, pravastatin, simvastatin, fluvastatin, atorvastatin, tizanidine, dantrolene, isosorbide dinatrate, a carotene, dihydrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, an essential fatty acid source, codeine, fentanyl, methadone, nalbuphine, pentazocine, clomiphene, danazol, dihydro epiandrosterone, medroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, amphetamine, L-thryroxine, tamsulosin, methoxsalen, tacrine, donepezil, raloxifene, vertoporfin, sibutramine, pyridostigmine, a pharmaceutically acceptable salt, isomer, or derivative thereof, or a mixture thereof.
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115. The pharmaceutical composition of claim 71, wherein the hydrophobic therapeutic agent is selected from the group consisting of tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, albendazole, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, azithromycin, ciprofloxacin, clarithromycin, dirithromycin, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, amphotericin B, butenafine, terbinafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, griseofulvin, nitrofurantoin, spironolactone, halofantrine, mefloquine, dihydroergotamine, ergotamine, frovatriptan, pizofetin, sumatriptan, zolmitriptan, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, pseudo-ephedrine, toremifene, atovaquone, metronidazole, furzolidone, paricalcitol, benzonatate, midazolam, zolpidem, gabapentin, zopiclone, digoxin, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecaliferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, gemfibrozil, cerivistatin, pravastatin, simvastatin, fluvastatin, atorvastatin, tizanidine, dantrolene, carotenes, dihyrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, essential fatty acid sources, codeine, fentanyl, methdone, nalbuphine, pentazocine, clomiphene, danazol, dihydro epiandrosterone, mmedroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, amphetamine, L-thryroxine, tamsulosin, methoxsalen, tacrine, donepezil, raloxifene, vertoporfin, sibutramine, pyridostigmine, pharmaceutically acceptable salts, isomers and derivatives thereof, and mixtures thereof.
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116. The pharmaceutical composition of claim 71, wherein the therapeutic agent is selected from the group consisting of tramadol, celecoxib, etodolac, refocoxib, oxaprozin, leflunomide, diclofenac, nabumetone, ibuprofen, flurbiprofen, tetrahydrocannabinol, capsaicin, ketorolac, ivermectin, amiodarone, zileuton, zafirlukast, albuterol, montelukast, rifabutine, rifapentine, trovafloxacin, baclofen, ritanovir, saquinavir, nelfinavir, efavirenz, miglitol, repaglinide, glymepride, pioglitazone, rosigiltazone, troglitazone, glyburide, glipizide, glibenclamide, carbamezepine, fosphenytion, tiagabine, topiramate, lamotrigine, vigabatrin, terbenafine, itraconazole, flucanazole, miconazole, ketoconazole, metronidazole, nitrofurantoin, dihydroergotamine, ergotamine, frovatriptan, pizofetin, zolmitriptan, pseudo-ephedrine, naratiptan, rizatriptan, aminogluthemide, busulphan, cyclosporine, mitoxantrone, irinotecan, etoposide, teniposide, paclitaxel, tacrolimus, sirolimus, tamoxifen, camptothecan, topotecan, nilutanide, bicalutanide, toremifene, atovaquone, metronidazole, furzolidone, paricalcitol, benzonatate, cisapride, cimetidine, loperamide, famotidine, lanosprazole, rabeprazole, nizatidine, omeprazole, citrizine, cinnarizine, dexchlopheniramine, loratadine, clemastine, fexofenadine, chlorpheniramine, acutretin, tazarotene, calciprotiene, calcitriol, targretin, ergocalciferol, cholecaliferol, isotreinoin, tretinoin, calcifediol, fenofibrate, probucol, simvastatin, atorvastatin, tizanidine, dantrolene, carotenes, dihyrotachysterol, vitamin A, vitamin D, vitamin E, vitamin K, essential fatty acid sources, danazol, dihydro epiandrosterone, medroxyprogesterone, progesterone, rimexolone, megesterol acetate, osteradiol, finasteride, mefepristone, raloxifene, L-thryroxine, tamsulosin, methoxsalen, pharmaceutically acceptable salts, isomers and derivative thereof, and mixtures thereof.
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117. The pharmaceutical composition of claim 71, wherein the hydrophobic therapeutic agent is selected from the group consisting of sildenafil citrate, amlodipine, tramadol, celecoxib, refocoxib, oxaprozin, nabumetone, ibuprofen, terbenafine, itraconazole, zileuton, zafirlukast, cisapride, fenofibrate, tizanidine, nizatidine, fexofenadine, loratadine, famotidine, paricalcitol, atovaquone, nabumetone, tetrahydrocannabinol, megesterol acetate, repaglinide, progesterone, rimexolone, cyclosporine, tacrolimus, sirolimus, teniposide, paclitaxel, pseudo-ephedrine, troglitazone, rosiglitazone, finasteride, vitamin A, vitamin D, vitamin E, pharmaceutically acceptable salts, isomers and derivatives thereof, and mixtures thereof.
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118. The pharmaceutical composition of claim 71, wherein the hydrophobic therapeutic agent is progesterone or cyclosporin.
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119. The pharmaceutical composition of claim 71, which further comprises a solubilizer.
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120. The pharmaceutical composition of claim 119, wherein the solubilizer is selected from the group consisting of alcohols, polyols, amides, esters, polyethylene glycol ethers and mixtures thereof.
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121. The pharmaceutical composition of claim 120, wherein the alcohol or polyol is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediols and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins and cyclodextrin derivatives, and mixtures thereof.
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122. The pharmaceutical composition of claim 120, wherein the amide is selected from the group consisting of 2-pyrrolidone, 2-piperidone, ε
- -caprolactam, N-alkylpyrrolidone, N-hydroxyalkylpyrrolidone, N-alkylpiperidone, N-alkylcaprolactam, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
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123. The pharmaceutical composition of claim 120, wherein the ester is selected from the group consisting of ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol monoacetate, propylene glycol diacetate, ε
- -caprolactone and isomers thereof, δ
-valerolactone and isomers thereof, β
-butyrolactone and isomers thereof, and mixtures thereof.
- -caprolactone and isomers thereof, δ
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124. The pharmaceutical composition of claim 119, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, butanediol and isomers thereof, glycerol, pentaerythritol, sorbitol, mannitol, transcutol, dimethyl isosorbide, polyethylene glycol, polypropylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose and other cellulose derivatives, cyclodextrins, clodextrins and derivatives thereof, ethyl propionate, tributylcitrate, acetyl triethylcitrate, acetyl tributyl citrate, triethylcitrate, ethyl oleate, ethyl caprylate, ethyl butyrate, triacetin, propylene glycol diacetate, ε
- -caprolactone and isomers thereof, δ
-valerolactone and isomers thereof, β
-butyrolactone and isomers thereof, 2-pyrrolidone, 2-piperidone, ε
-caprolactam, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethyl pyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, glycofurol, methoxy PEG, and mixtures thereof.
- -caprolactone and isomers thereof, δ
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125. The pharmaceutical composition of claim 119, wherein the solubilizer is selected from the group consisting of ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, 1,3-butanediol, glycerol, pentaerythritol, sorbitol, glycofurol, transcutol, dimethyl isosorbide, polyethylene glycol, polyvinylalcohol, hydroxypropyl methylcellulose, methylcellulose, ethylcellulose, hydroxypropylcyclodextrins, sulfobutyl ether derivatives of cyclodextrins, ethyl propionate, tributylcitrate, triethylcitrate, ethyl oleate, ethyl caprylate, triacetin, β
- -butyrolactone and isomers thereof, 2-pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, N-hydroxyethylpyrrolidone, N-octylpyrrolidone, N-laurylpyrrolidone, dimethylacetamide, polyvinylpyrrolidone, and mixtures thereof.
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126. The pharmaceutical composition of claim 119, wherein the solubilizer is triacetin, triethylcitrate, ethyl oleate, ethyl caprylate, dimethylacetamide, N-methylpyrrolidone, N-hydroxyethylpyrrolidone, polyvinylpyrrolidone, hydroxypropyl methylcellulose, hydroxypropyl cyclodextrins, ethanol, polyethylene glycol 200-600, glycofurol, transcutol, propylene glycol, dimethyl isosorbide, or a mixture thereof.
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127. The pharmaceutical composition of claim 119, wherein the solubilizer is triacetin, ethanol, polyethylene glycol 400, glycofurol, propylene glycol or a mixture thereof.
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128. The pharmaceutical composition of claim 119, wherein the solubilizer is present in the composition in an amount of about 400% or less by weight, based on the total weight of the surfactants.
-
129. The pharmaceutical composition of claim 128, wherein the solubilizer is present in the composition in an amount of about 200% or less by weight, based on the total weight of the surfactants.
-
130. The pharmaceutical composition of claim 129, wherein the solubilizer is present in the composition in an amount of about 100% or less by weight, based on the total weight of the surfactants.
-
131. The pharmaceutical composition of claim 130, wherein the solubilizer is present in the composition in an amount of about 50% or less by weight, based on the total weight of the surfactants.
-
132. The pharmaceutical composition of claim 131, wherein the solubilizer is present in the composition in an amount about 25% or less by weight, based on the total weight of the surfactants.
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133. The pharmaceutical composition of claim 71, which further comprises an antioxidant, a preservative, a chelating agent, a viscomodulator, a tonicifier, a flavorant, a colorant, an odorant, an opacifier or a mixture thereof.
-
134. The pharmaceutical composition of claim 71, which further comprises an additional amount of a hydrophobic therapeutic agent, said additional amount not solubilized in the carrier.
-
72. The pharmaceutical composition of claim 71, wherein the hydrophobic surfactant is present in an amount of less than about 200% by weight, relative to the amount of the hydrophilic surfactant.
-
-
135. A pharmaceutical composition comprising:
-
(a) a carrier,
said carrier comprising;
(i) at least one hydrophilic surfactant; and
(ii) at least one hydrophobic surfactant,
said hydrophilic and hydrophobic surfactants being present in amounts such that upon mixing with an aqueous solution the carrier forms a clear aqueous dispersion of the hydrophilic and hydrophobic surfactants;
(b) a first amount of a hydrophobic therapeutic agent, said first amount being solubilized in the carrier; and
(c) a second amount of a hydrophobic therapeutic agent, said second amount not solubilized in the clear aqueous dispersion, said composition being substantially free of triglycerides.
-
-
136. A method of treating an animal with a hydrophobic therapeutic agent, the method comprising:
-
providing a dosage form of a pharmaceutical composition comprising;
a hydrophobic therapeutic agent; and
a carrier,
said carrier comprising;
at least one hydrophilic surfactant; and
at least one hydrophobic surfactant,
said hydrophilic and hydrophobic surfactants being present in amounts such that upon mixing with an aqueous solution the carrier forms a clear aqueous dispersion of the hydrophilic and hydrophobic surfactants containing the hydrophobic therapeutic agent,said composition being substantially free of triglycerides; and
administering said dosage form to said animal. - View Dependent Claims (137, 138, 139, 140)
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137. The method of claim 136, wherein the dosage form is a capsule, a cream, a lotion, an ointment, a suppository, a paste or a gel.
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138. The method of claim 136, wherein the dosage form is administered by an oral, parenteral, topical, transdermal, ocular, pulmonary, vaginal, rectal or transmucosal route.
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139. The method of claim 136, wherein the animal is a mammal.
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140. The method of claim 139, wherein the mammal is a human.
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137. The method of claim 136, wherein the dosage form is a capsule, a cream, a lotion, an ointment, a suppository, a paste or a gel.
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Specification
- Resources
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Current AssigneeLipocine Inc.
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Original AssigneeLipocine Inc.
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InventorsChen, Feng-Jing, Patel, Mahesh V.
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Granted Patent
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Time in Patent OfficeDays
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Field of Search
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US Class Current424/400
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CPC Class CodesA61K 31/57 substituted in position 17 ...A61K 38/13 CyclosporinsA61K 9/4808 characterised by the form o...A61K 9/4858 Organic compoundsA61P 15/00 Drugs for genital or sexual...A61P 15/06 Antiabortive agents; Labour...A61P 37/06 Immunosuppressants, e.g. dr...A61P 5/24 of the sex hormonesA61P 5/26 AndrogensB82Y 5/00 Nanobiotechnology or nanome...