CA2406930A1 - Preparation of aqueous clear solution dosage forms with bile acids - Google Patents
Preparation of aqueous clear solution dosage forms with bile acids Download PDFInfo
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- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
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- 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
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
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- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- 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
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- 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
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
Abstract
Compositions for pharmaceutical and other uses comprising clear aqueous solutions of bile acids which do not form any detectable precipitates over selected ranges of pH values of the aqueous solution and methods of making such solutions. The compositions of the invention comprise water; a bile aci d in the form of a bile acid, bile acid salt, or a bile acid conjugated with a n amine by an amide linkage; and either or both an aqueous soluble starch conversion product and a aqueous soluble non-starch polysaccharide. The composition remains in solution without forming a precipitate over a range o f pH values and, according to one embodiment, remains in solution for all pH values obtainable in an aqueous system. The composition, according to some embodiments, may further contain a pharmaceutical compound in a pharmaceutically effective amount. Non-limiting examples of pharmaceutical compounds include insulin, heparin, bismuth compounds, amantadine and rimantadine.
Claims (87)
1. A method for treating gastritis and peptic ulcer disease comprising:
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
2. The method of Claim 1 wherein the dosage form is selected from the group consisting of a syrup, a thick syrup, and a paste.
3. The method of Claim 1 wherein the oral liquid dosage form additionally comprises a bismuth compound in a pharmaceutically effective amount.
4. The method of Claim 3 wherein the bismuth compound comprises an aqueous soluble reaction product between a bismuth ion and a chelator.
5. The method of Claim 4 wherein the chelator is selected from the group consisting of citric acid, tartaric acid, malic acid, lactic acid and eidetic acid and alkalies.
6. The method of Claim 5 wherein the bismuth compound is selected from the group consisting of an ammonium salt of bismuth sulphate, an ammonium salt of bismuth citrate, and bismuth sodium tartrate.
7. The method of Claim 1 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
8. The method of Claim 1 wherein the second material is selected from the group consisting of maltodextrin, dextrin, corn syrup corn syrup solid, soluble starch, and dextrans.
9. The method of Claim 1 wherein the the oral liquid dosage form comprises one or more additional bile acids, aqueous soluble derivatives of bile acid, bile acid salts, and amine-conjugated bile acids conjugated by an amide linkage.
10. The method of Claim 1 wherein the the oral liquid dosage form additionally comprises a least one emulsifying agent.
11. The method of Claim 10 wherein the emulsifying agent is selected from the group consisting of guar gum, pectin, acacia, carrageenan, carboxymethyl cellulose sodium, hydroxymethyl cellulose, hydroxypropyl cellulose, methyl cellulose, polyvinyl alcohol, povidone, tragacanth gum, xanthan gum, and sorbitan ester.
12. The method of Claim 1 wherein the oral liquid dosage form additionally comprises at least one pharmaceutical in a pharmaceutically effective amount.
13. The method of Claim 12 wherein the pharmaceutical is selected from the group consisting of antibiotics, H2-receptor antagonists, and antiprotozoal drugs.
14. The method of Claim 12 wherein the pharmaceutical is selected from the group consisting of ampicillin, amoxicillin, cefaclor, cefadroxyl, azithromycin, clarithromycin, demeclocycline.cndot.HCl, doxycycline, minocycline.cndot.HCl, tetracycline, oxytetracycline, cimetidine, famotidine, nizatidine, ranitidine, sucralfate, metronidazole, atovaquone, and pentamidine.cndot.isethionate.
15. A method for treating a liver disease comprising:
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
16. The method of Claim 15 wherein the dosage form is selected from the group consisting of a syrup, a thick syrup, and a paste.
17. The method of Claim 15 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
18. The method of Claim 15 wherein the second material is selected from the group consisting of maltodextrin, dextrin, corn syrup corn syrup solid, soluble starch, and dextrans.
19. The method of Claim 15 wherein the oral liquid dosage form additionally comprises at least one pharmaceutical in a pharmaceutically effective amount.
20. The method of Claim 19 wherein the pharmaceutical is selected from the group consisting of acyclovir, amantadine.cndot.HCl, rimantidine.cndot.HCl, cidofovir, delavirdine mesylate, didanosine, famciclovir, forscarnet, sodium gancyclovir, idoxuridine, lamivudine, nevirapine, penciclovir, ribavirin, stavudine, trifluridine, valacyclovir.cndot.HCl, zalcitabine, zidovudine, indinavir.cndot.H2SO4, ritonavir, nelfinavir.cndot.CH3SO3H, saquinavir.cndot.CH3SO3H, interferons, branched chain amino acid, betamethasone, budesonide, dexamethasone, fludrocortisone.cndot.CH3COOH, flunisolide, prednisone, prednisolone, methyl prednisolone, hydrocortisone, trameinolone, chlorambucil, azathioprine, azacitidine, fluorouracil, mercaptopurine, methotrexate, trientine.cndot.2HCl, and catechin.
21. The method of Claim 15 wherein the oral liquid dosage form additionally comprises a a branched chain amino acid.
22. The method of Claim 21 wherein the branched chain amino acid is selected from the group consisting of leucine, isoleucine, and valine.
23. A method for treating gall stones comprising:
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(b) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (c) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(b) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (c) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
24. The method of Claim 23 wherein the dosage form is selected from the group consisting of a syrup, a thick syrup, and a paste.
25. The method of Claim 23 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
26. The method of Claim 23 wherein the second material is selected from the group consisting of maltodextrin, dextrin, corn syrup corn syrup solid, soluble starch, and dextrans.
27. The method of Claim 23 wherein the the oral liquid dosage form comprises one or more additional bile acids, aqueous soluble derivatives of bile acid, bile acid salts, and amine-conjugated bile acids conjugated by an amide linkage.
28. A method for treating or preventing colorectal adenoma comprising:
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
29. The method of Claim 28 wherein the dosage form is selected from the group consisting of a syrup, a thick syrup, and a paste.
30. The method of Claim 28 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
31. The method of Claim 28 wherein the second material is selected from the group consisting of maltodextrin, dextrin, corn syrup corn syrup solid, soluble starch, and dextrans.
32. The method of Claim 28 wherein the the oral liquid dosage form comprises one or more additional bile acids, aqueous soluble derivatives of bile acid, bile acid salts, and amine-conjugated bile acids conjugated by an amide linkage.
33. The method of Claim 28 wherein the the oral liquid dosage form additionally comprises a least one emulsifying agent.
34. The method of Claim 33 wherein the emulsifying agent is selected from the group consisting of guar gum, pectin, acacia, carrageenan, carboxymethyl cellulose sodium, hydroxymethyl cellulose, hydroxypropyl cellulose, methyl cellulose, polyvinyl alcohol, povidone, tragacanth gum, xanthan gum, and sorbitan ester.
35. The method of Claim 28 wherein the oral liquid dosage form additionally comprises at least one pharmaceutical in a pharmaceutically effective amount.
36. The method of Claim 35 wherein the pharmaceutical is selected from the group consisting of colchicine, sulfinpyrazone, allopurinol, piroxicam, tolmetin-sodium, idomethacin, ibuprofen, diflunisal, mefenamic acid, and mesalamine.
37. A method for treating hyperlipidemia comprising:
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) administration of an oral liquid dosage form comprising:
(i) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, a bile acid conjugated with an amine by an amide linkage, and combinations thereof ;
(ii) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (iii) water, wherein the first and second materials both remain in solution for all pH
values of the solution within a selected range of pH values.
38. The method of Claim 37 wherein the dosage form is selected from the group consisting of a syrup, a thick syrup, and a paste.
39. The method of Claim 37 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
40. The method of Claim 37 wherein the second material is selected from the group consisting of maltodextrin, dextrin, corn syrup corn syrup solid, soluble starch, and dextrans.
41. The method of Claim 37 wherein the the oral liquid dosage form comprises one or more additional bile acids, aqueous soluble derivatives of bile acid, bile acid salts, and amine-conjugated bile acids conjugated by an amide linkage.
42. The method of Claim 37 wherein the the oral liquid dosage form additionally comprises a least one emulsifying agent.
43. The method of Claim 38 wherein the emulsifying agent is selected from the group consisting of guar gum, pectin, acacia, carrageenan, carboxymethyl cellulose sodium, hydroxymethyl cellulose, hydroxypropyl cellulose, methyl cellulose, polyvinyl alcohol, povidone, tragacanth gum, xanthan gum, and sorbitan ester.
44. The method of Claim 37 wherein the oral liquid dosage form additionally comprises at least one pharmaceutical in a pharmaceutically effective amount.
45. The method of Claim 44 wherein the pharmaceutical is selected from the group consisting of atorvastatin-calcium, cerivastatin sodium, fluvastatin sodium, lovastatin, pravastatin sodium, and simvastatin.
46. The method of Claim 37 wherein the oral liquid dosage form additionally comprises a dietary fiber.
47. The method of Claim 46 wherein the dietary fiber is selected from the group consisting of psyllium, oat gum, soybean fiber, oat bran, corn bran, cellulose and wheat bran.
48. A clear aqueous solution comprising:
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) an aqueous soluble non-starch polysaccharide; and (c) water, wherein the first material and the polysaccharide both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) an aqueous soluble non-starch polysaccharide; and (c) water, wherein the first material and the polysaccharide both remain in solution for all pH
values of the solution within a selected range of pH values.
49. The aqueous solution of Claim 48 wherein the first material is present in a pharmaceutically effective amount.
50. The aqueous solution of Claim 48 wherein the solution additionally comprises a pharmaceutically effective amount of a pharmaceutical compound and the pharmaceutical compound remains in solution for all pH values within the selected range.
51. The aqueous solution of Claim 50 wherein the pharmaceutical compound is selected from the group consisting of insulin, heparin, calcitonin, ampicillin, amantadine~HCl, rimantadine~HCl, proinsulin, insoluble insulins, and amino acids.
52. The aqueous solution of Claim 50 wherein the pharmaceutical compound is selected from the group consisting of octreotide, sildenafil citrate, calcitriol, dihydrotachysterol, ampomorphine, yohimbin, trazodone, acyclovir, cidofovir, delavirdine~mesylate, didanosine, famciclovir, forscarnet sodium, fluorouracil, ganciclovir sodium, idoxuridine, interferon-.alpha., lamivudine, nevirapine, penciclovir, ribavirin, stavudine, trifluridine, valacyclovir HCl, zalcitabine, zidovudine, indinavir H2SO4, ritonavir, nelfinavir CH3SO3H, saquinavir CH3SO3H, d-penicillamine, chloroquine, hydroxychloroquine, aurothioglucose, gold sodium thiomalate, auranofin levamisole, DTC, isoprinosine, methyl inosine monophosphate, muramyl dipeptide, diazoxide, hydralazine HCl, minoxidil, dipyridamole, isoxsuprine~HCl, niacin, nylidrin~HCl, phentolamine, doxazosin~CH3SO3H, prazosin~HCl, terazocin~HCl, clonidine~HCl, nifedipine, molsidomine, amiodarone, acetylsalicylic acid, verapamil, diltiazem, nisoldipine, isradipine, bepridil, isosorbide~dinitrate, pentaerythrytol~tetranitrate, nitroglycerin, cimetidine, famotidine, nizatidine, ranitidine, lansoprazole, omeprazole, misoprostol, sucralfate, metoclopramide~HCl, erythromycin, alprostadil, albuterol, pirbuterol, terbutaline~H2SO4, salmetrol, aminophylline, dyphylline, ephedrine, ethylnorepinephrine, isoetharine, isoproterenol, metaproterenol, n~docromil, oxy triphylline, theophylline, bitolterol, fenoterol, budesonide, flunisolide, beclomethasone~dipropionate, fluticasone~propionate, codeine, codeine sulfate, codeine phosphate, dextromethorpham~HBr, triamcinolone~acetonide, montelukast sodium, zafirlukast, zileuton, cromolyn sodium, ipratropium bromide, nedocromil sodium benzonate, diphenhydramine~HCl, hydrocodone~bitartarate, methadone~HCl, morphine sulfate, acetylcysteine, guaifenesin, ammonium carbonate, ammonium chloride, antimony potassium tartarate, glycerin, terpimhydrate, colfosceril palmitate, atorvastatin~calcium, cervastatin~sodium, fluvastatin~sodium, lovastatin, pravastatin~sodium, simvastatin, picrorrhazia kurrva, andrographis paniculata, moringa oleifera, albizzia lebeck, adhata vasica, curcuma Tonga, momordica charantia, gymnema sylvestre, terminalia arjuna, azadirachta indica, tinosporia cordifolia, metronidazole, amphotericin B, clotrimazole, fluconazole, haloprogin, ketoconazole, griseofulvin, itraconazole, terbinafi~HCl, econazole~HNO3, miconazole, nystatin, oxiconazole~HNO3, sulconazole~HNO3, cetirizine~2HCl, dexamethasone, hydrocortisone, prednisolone, cortisone, catechin and its derivatives, glycyrrhizin, glycyrrhizic acid, betamethasone, ludrocortisone~acetate, flunisolide, fluticasone~propionate, methyl prednisolone, somatostatin, lispro, glucagon, acarbose, chlorpropamide, glipizide, glyburide, metformin~HCl, repaglinide, tolbutamide, colchicine, sulfinpyrazone, allopurinol, piroxicam, tolmetin sodium, indomethacin, ibuprofen, diflunisal, mefenamic acid, naproxen, and trientine.
53. The aqueous solution of Claim 50 wherein the first material is ursodeoxycholic acid and the pharmaceutical compound is selected from the group consisting of metformin HCl, ranitidine HCI, cimetidine, lamivudine, cetrizine 2HC1, amantadine, rimantadine, sildenafil, apomorphine, yohimbine, trazodone, ribavirin, dexamethasone, hydrocortisone, prednisolone, triamcinolone, cortisone, niacin, catechin and its derivatives, taurine, vitamins, naturally occurring amino acids, and glycyrrhiza extract.
54. The aqueous solution of Claim 48 wherein the selected pH
range is between approximately 1 and approximately 10 inclusive.
range is between approximately 1 and approximately 10 inclusive.
55. The aqueous solution of Claim 48 wherein the selected pH
range is the range spanned by the prevailing pH values found in the mouth, stomach, and intestines of a mammal.
range is the range spanned by the prevailing pH values found in the mouth, stomach, and intestines of a mammal.
56. The aqueous solution of Claim 48 wherein the selected pH
range is the range spanned by the prevailing pH values found in the mouth, stomach, and intestines of a human being.
range is the range spanned by the prevailing pH values found in the mouth, stomach, and intestines of a human being.
57. The aqueous solution of Claim 48 wherein the selected pH
range is a range of pH values obtainable in an aqueous system encountered by the solution during preparation, administration and until absorption in the body to which the solution is administered.
range is a range of pH values obtainable in an aqueous system encountered by the solution during preparation, administration and until absorption in the body to which the solution is administered.
58. The aqueous solution of Claim 48 wherein the selected pH
range spans all obtainable pH values in an aqueous system.
range spans all obtainable pH values in an aqueous system.
59. The aqueous solution of Claim 48 wherein the first material is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, lithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus, their salts, or their conjugates with amines.
60. The aqueous solution of Claim 48 wherein the bile acid salt is a product of the reaction of a bile acid and an amine.
61. The aqueous solution of Claim 60 wherein the bile acid is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, and their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus.
62. The aqueous solution of Claim 60 wherein the amine is selected from the group consisting of an aliphatic free amine, trientine, diethylene triamine, tetraethylene pentamine, a basic amino acid, arginine, lysine, ornithine, ammonia, an amino sugar, D-glucamine, N-alkylglucamines, a quaternary ammonium derivative, choline, an heterocyclic amine, piperazine, N-alkylpiperazine, piperidine, N-alkylpiperidine, morpholine, N-alkylmorphline, pyrrolidine, triethanolamine, and trimethanolamine.
63. The aqueous solution of Claim 48 wherein the bile acid salt is a soluble metal salt of a bile acid, an inclusion compound between the bile acid and cyclodextrin and its derivatives, or an aqueous soluble O-sulfonated bile acid.
64. The aqueous solution of Claim 50 wherein the first material is an adjuvant.
65. The aqueous solution of Claim 50 wherein the first material is a carrier of the pharmaceutical compound.
66. The aqueous solution of Claim 48 wherein the solution further comprises a micelle forming material.
67. The aqueous solution of Claim 48 wherein the solution is comprised in a preparation for oral consumption.
68. The aqueous solution of Claim 48 wherein the solution is comprised in an enema.
69. The aqueous solution of Claim 48 wherein the solution is comprised in a mouthwash.
70. The aqueous solution of Claim 48 wherein the solution is comprised in a gargle.
71. The aqueous solution of Claim 48 wherein the solution is comprised in a preparation for nasal administration.
72. The aqueous solution of Claim 48 wherein the solution is comprised in a preparation for otic administration.
73. The aqueous solution of Claim 48 wherein the solution is comprised in an injection.
74. The aqueous solution of Claim 48 wherein the solution is comprised in a douche.
75. The aqueous solution of Claim 48 wherein the solution is comprised in a topical skin preparation.
76. The aqueous solution of Claim 48 wherein the solution is comprised in a cosmetic preparation.
77. The aqueous solution of Claim 48 wherein the solution is comprised in a dosage form selected from the group consisting of a syrup, a thick syrup, and a paste.
78. A method of preparing an aqueous solution wherein the solution forms no detectable precipitate at any pH value of the solution within a selected range of pH values comprising the steps of:
(a) dissolving a bile acid, bile acid salt, or bile acid-amine conjugate in water to form a clear solution;
(b) adding at least one aqueous soluble non-starch polysaccharide to the clear solution and allowing it to dissolve to form a clear solution; and (c) optionally adding a pharmaceutically effective amount of a pharmaceutical compound.
(a) dissolving a bile acid, bile acid salt, or bile acid-amine conjugate in water to form a clear solution;
(b) adding at least one aqueous soluble non-starch polysaccharide to the clear solution and allowing it to dissolve to form a clear solution; and (c) optionally adding a pharmaceutically effective amount of a pharmaceutical compound.
79. The method of Claim 78 wherein the selected range is all pH
values obtainable in an aqueous system.
values obtainable in an aqueous system.
80. The method of Claim 78 wherein the selected range is between approximately pH 1 and approximately pH 10.
81. A clear aqueous solution comprising:
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) a polysaccharide having at least one reducing end and one at least one non-reducing end; and (c) water, wherein the first material and the polysaccharide both remain in solution for all pH
values of the solution within a selected range of pH values.
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) a polysaccharide having at least one reducing end and one at least one non-reducing end; and (c) water, wherein the first material and the polysaccharide both remain in solution for all pH
values of the solution within a selected range of pH values.
82. A clear aqueous solution comprising:
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (c) a third material comprising an aqueous soluble bismuth compound; and (d) water, wherein the first, second, and third materials all remain in solution for all pH values of the solution within a selected range of pH values.
(a) a first material selected from the group consisting of a bile acid, an aqueous soluble derivative of a bile acid, a bile acid salt, and a bile acid conjugated with an amine by an amide linkage;
(b) a second material selected from the group consisting of an aqueous soluble starch conversion product and an aqueous soluble non-starch polysaccharide; and (c) a third material comprising an aqueous soluble bismuth compound; and (d) water, wherein the first, second, and third materials all remain in solution for all pH values of the solution within a selected range of pH values.
83. The aqueous solution of Claim 82 wherein the bile acid is selected from the group consisting of ursodeoxycholic acid, chenodeoxycholic acid, cholic acid, hyodeoxycholic acid, deoxycholic acid, 7-oxolithocholic acid, iododeoxycholic acid, iocholic acid, tauroursodeoxycholic acid, taurochenodeoxycholic acid, taurodeoxycholic acid, glycoursodeoxycholic acid, taurocholic acid, glycocholic acid, and their derivatives at a hydroxyl or carboxylic acid group on the steroid nucleus.
84. The aqueous solution of Claim 82 wherein the pH range is selected from about 2 to about 9.
85. The aqueous solution of Claim 82 wherein the bismuth compound comprises an aqueous soluble reaction product between a bismuth ion and a chelator.
86. The aqueous solution of Claim 85 wherein the chelator is selected from the group consisting of citric acid, tartaric acid, malic acid, lactic acid and eidetic acid and alkalies.
87. The aqueous solution of Claim 85 wherein the bismuth compound is selected from the group consisting of an ammonium salt of bismuth sulphate, an ammonium salt of bismuth citrate, and bismuth sodium tartrate.
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US18026800P | 2000-02-04 | 2000-02-04 | |
US60/180,268 | 2000-02-04 | ||
PCT/US2001/003745 WO2001056547A2 (en) | 2000-02-04 | 2001-02-05 | Preparation of aqueous clear solution dosage forms with bile acids |
Publications (2)
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CA2406930A1 true CA2406930A1 (en) | 2001-08-09 |
CA2406930C CA2406930C (en) | 2011-02-15 |
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US (1) | US7166299B2 (en) |
EP (1) | EP1255566A2 (en) |
JP (1) | JP2004500378A (en) |
KR (1) | KR100848344B1 (en) |
CN (1) | CN100558407C (en) |
AU (2) | AU2001236685B2 (en) |
BR (1) | BR0108080A (en) |
CA (1) | CA2406930C (en) |
IL (2) | IL150952A0 (en) |
RU (1) | RU2277913C2 (en) |
WO (1) | WO2001056547A2 (en) |
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IL150952A (en) | 2010-11-30 |
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CN100558407C (en) | 2009-11-11 |
WO2001056547B1 (en) | 2003-02-20 |
IL150952A0 (en) | 2003-02-12 |
AU2001236685B2 (en) | 2006-05-18 |
AU3668501A (en) | 2001-08-14 |
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