CA2417646A1 - Topical gel delivery system - Google Patents

Topical gel delivery system Download PDF

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Publication number
CA2417646A1
CA2417646A1 CA002417646A CA2417646A CA2417646A1 CA 2417646 A1 CA2417646 A1 CA 2417646A1 CA 002417646 A CA002417646 A CA 002417646A CA 2417646 A CA2417646 A CA 2417646A CA 2417646 A1 CA2417646 A1 CA 2417646A1
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Canada
Prior art keywords
composition
water
treating
disorder
compound
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CA002417646A
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French (fr)
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CA2417646C (en
Inventor
Gordon J. Dow
Robert W. Lathrop
Debra A. Dow
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Bausch Health Ireland Ltd
Original Assignee
Dow Pharmaceutical Sciences
Gordon J. Dow
Robert W. Lathrop
Debra A. Dow
Dow Pharmaceutical Sciences, Inc.
Bausch Health Ireland Limited
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Application filed by Dow Pharmaceutical Sciences, Gordon J. Dow, Robert W. Lathrop, Debra A. Dow, Dow Pharmaceutical Sciences, Inc., Bausch Health Ireland Limited filed Critical Dow Pharmaceutical Sciences
Publication of CA2417646A1 publication Critical patent/CA2417646A1/en
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Publication of CA2417646C publication Critical patent/CA2417646C/en
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    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/7036—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61K47/02—Inorganic compounds
    • 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
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids

Abstract

A topical aqueous gel composition is provided that has a viscosity of less than about 15,000 cP and a pH of about 3.0 to 9.0 for treating a skin disorder in a human subject. The composition consists essentially of (a) a therapeutically-effective amount of at least one compound useful for treating such a disorder, (b) a hydrophilic pharmaceutically-acceptable, polymer material such as a lightly cross-linked polyacrylic acid polymer compatible with the compound, (c) a pharmaceutically-acceptable base to adjust pH, (d) optionally a water miscible solvent, (e) optionally a preservative, (f) water, and (g) optionally an oil phase component and a suitable surfactant. The composition is useful for treating an inflammatory skin disorder, acne, or rosacea. The low viscosity composition has an advantage of being administered more accurately when combined with a container that administers the composition as drops.

Claims (6)

1. A topical aqueous gel composition having a pH of about 3 to about 9 and a viscosity of less than about 15,000 cP for treating a skin disorder in a human subject, which composition consists essentially of (a) a therapeutically-effective amount of at least one compound useful for treating such disorder, (b) a hydrophilic, pharmaceutically-acceptable, lightly cross-linked polyacrylic acid polymer compatible with the compound, (c) a pharmaceutically-acceptable base to adjust pH, (d) optionally a water miscible solvent, (e) optionally a preservative, and (f) water.
2. The composition of Claim 1, wherein the compound is an antibiotic, imidazole, retinoid, corticosteroid, or a non-steroidal anti-inflammatory drug (NSAm).
3. The composition of Claim 2, wherein the compound is an antibiotic alone or in combination with a corticosteroid or a retinoid.
4. The composition of Claim 3, wherein the compound is an antibiotic alone.
5. The composition of Claim 4, wherein the antibiotic is clindamycin phosphate.
6. The composition of Claim 5 having a pH of about 4.0 to 7.0, which composition consists essentially of (a) about 0.5% to about 2.0% w/w clindamycin phosphate, (b) about 0.1% to about 0.4% w/w of the polymer, (c) the base to adjust pH, (d) about 15.0% to about 25.0% w/w of a water miscible solvent, (e) less than about 0.2% w/w of a preservative, and (f) QSAD purified water to 100% w/w.

32.

20. The composition of Claim 19 having a pH of about 4.0 to 7.0, which composition consists essentially of (a) about 0.01% to about 0.1% w/w desonide, (b) about 0.1% to about 0.4% w/w of the polymer, (d) about 3.0% to about 10% w/w of a water miscible solvent, (e) less than about 0.25% w/w of a preservative, and (f) QSAD purified water to 100% w/w.

21. The composition of Claim 19 having a pH of about 5.0 to 6.0, which composition consists essentially of:
(a) about 0.025 to about 0.05% w/w desonide, (b) about 0.3% w/w of the polymer, (c) the base to adjust pH, (d) about 5% w/w propylene glycol, (e) about 0.2 - about 0.25% w/w methylparaben and propylparaben, and (f) QSAD purified water to 100% w/w.

22. The composition of Claim 1 in combination with a container that accurately administers a portion of the composition for topical administration to a patient.

23. The composition of Claim 22 in combination with labeling instructions for use in treating the skin disorder.

24. A method for treating a skin disorder in a human subject, which method comprises topically administering a topical aqueous gel composition having a pH of about 3 to about 9 and a viscosity of less than about 15,000 cP to an affected area of the subject's skin having such disorder in an amount and for a period of time sufficient to improve the skin disorder, wherein the composition consists essentially of 35.

(a) a therapeutically-effective amount of at least one compound useful for treating such disorder, (b) a hydrophilic pharmaceutically-acceptable lightly cross-linked polyacrylic acid polymer compatible with the pharmaceutical active material, (c) a pharmaceutically-acceptable base to adjust pH
(d) optionally a water miscible solvent, (e) optionally a preservative, and (f) water.

25. A method of preparing a topical aqueous gel composition having a viscosity of less than about 15,000.cP and a pH of about 3 to 9 useful for treating a skin disorder in a human subject, which method comprises (a) combining water with a therapeutically-effective amount of at least one compound useful for treating such disorder and a hydrophilic pharmaceutically-acceptable, lightly cross-linked polyacrylic acid polymer compatible with the compound, (b) adjusting the pH to about 3 to 9, and (c) optionally combining a water-miscible solvent, and a preservative, to form the composition.

26. The method of Claim 25, wherein the compound is an antibiotic, imidazole, retinoid, corticosteroid, or a nonsteroidal anti-inflammatory drug (NSAID).

27. The method of Claim 26, wherein the compound is an antibiotic alone or in combination with a corticosteroid or a retinoid.

28. The method of Claim 27, wherein the compound is an antibiotic alone.

29. The method of Claim 28, wherein the antibiotic is clindamycin phosphate.

30. The method of Claim 29, wherein the composition has a pH of about 4 to 7, and consists essentially of 36.

48. The composition of Claim 6, wherein the corticosteroid is desonide.

49. The composition of Claim 48, wherein the desonide is present at about 0.01 % w/w to about 1.0 % w/w.

50. The method of Claim 40, wherein the corticosteroid is desonide.

51. The method of Claim 50, wherein the desonide is present at about 0.01 % w/w to about 1.0% w/w.

52. A topical aqueous gel composition having a pH of about 3 to about 9 and a viscosity of less than about 15,000 cP for treating a skin disorder in a human subject, which composition consists essentially of (a) a therapeutically-effective amount of at least one compound useful for treating such disorder, (b) a hydrophilic pharmaceutically-acceptable, polymeric material compatible with the compound, (c) a pharmaceutically-acceptable base to adjust pH, (d) optionally a water miscible solvent, (e) optionally a preservative, and (f) water.

53. The composition of Claim 52 having a pH of about 4.0 to about 7.0, which composition consists essentially of (a) about 0.5% to about 2.0% w/w clindamycin phosphate, (b) about 0.05% to about 1.0% w/w of the polymeric material, (c) the base to adjust pH, (d) 0.0% to about 40% w/w of a water miscible solvent, (e) less than about 0.2% w/w of a preservative, and (f) purified water in a quantity sufficient to make (QSAD) 100% w/w.

54. The composition of Claim 52 having a pH of about 4 to about 7, which composition is a gel consisting essentially of (a) (i) about 0.5% to about 2% w/w clindamycin phosphate, and (ii) about 0.01% to about 0.05% w/w tretinoin;
(b) about 0.05% to about 1% w/w of the polymeric material, (c) the base to adjust pH;
(d) 0% to about 40% w/w of a water-miscible solvent;
(e) less than about 0.2% of a preservative; and (f) QSAD purified water 100% w/w.

55. A method for treating a skin disorder in a human subject, which method comprises topically administering the composition of claim 52, 53, or 54 to an affected area of the subject's skin having such disorder in an amount and for a period of time sufficient to improve the skin disorder.

56. A method of preparing the composition of claim 52, 53, or 54, which method comprises (a) combining water with a therapeutically-effective amount of at least one compound useful for treating such disorder and the polymeric material, (b) adjusting the pH to about 3 to about 9, and (c) optionally combining a water-miscible solvent and a preservative to form the composition.

57. A topical aqueous gel composition having a pH of about 3 to about 9 and a viscosity of less than about 15,000 cP for treating a skin disorder in a human subject, which comprises (a) a therapeutically-effective amount of clindamycin phosphate and tretinoin useful for treating such disorder, (b) a hydrophilic pharmaceutically-acceptable, lightly cross-linked polyacrylic acid polymer compatible with the compound, (c) a pharmaceutically-acceptable base to adjust pH, (d) optionally a water miscible solvent, (e) optionally a preservative, and (f) water, wherein the clindamycin phosphate is dissolved and the tretinoin is suspended.

41.

58. The composition of Claim 57 having a pH of about 4 to about 7, which composition is a gel consisting essentially of (a) (i) about 0.5% to about 2% w/w clindamycin phosphate, and (ii) about 0.01% to about 0.05% w/w tretinoin;
(b) about 0.05% to about 1% w/w of the polymer;
(c) the base to adjust pH;
(d) 0% to about 40% w/w of a water-miscible solvent;
(e) about 0.01 to about 1% w/w of a preservative; and (f) QSAD purified water 100% w/w.

59. The composition of Claim 57 in combination with a container that accurately administers a portion of the composition for topical administration to a patient.

60. The composition of Claim 59 in combination with labeling instructions for use in treating the skin disorder.

61. A method for treating a skin disorder in a human subject, which method comprises topically administering the composition of claim 57 or 58 to an affected area of the subject's skin having such disorder in an amount and for a period of time sufficient to improve the skin disorder.

62. The method of Claim 61, wherein the skin disorder is an inflammatory skin disorder, acne, or rosacea.

63. The method of Claim 62, wherein the composition is administered once a day for the period of time sufficient to improve the skin disorder.

64. The method of Claim 62, wherein the skin disorder is acne.

65. A topical aqueous gel composition having a pH of about 3 to about 9 and a viscosity of less than about 15,000 cP for treating a skin disorder in a human subject, which composition consists essentially of (a) a corticosteroid at a level of about 0.01% w/w/ to about 1% w/w, (b) a hydrophilic pharmaceutically-acceptable, lightly cross-linked polyacrylic acid polymer compatible with the compound, (c) a pharmaceutically-acceptable base to adjust pH, (d) optionally a water miscible solvent, (e) optionally a preservative, and (f) water.

66. The composition of Claim 65, wherein the corticosteroid is desonide at a level of about 0.05% w/w to about 0.1% w/w and the polymeric material is present at a level of about 0.05% w/w to about 1% w/w.

67. The composition of Claim 65, wherein the corticosteroid is halobetasol propionate and the polymeric material is present art a level of about 0.05%
w/w to about 1% w/w.

68. A method for treating a skin disorder in a human subject, which method comprises topically administering the composition of claim 65, 66, or 67 to an affected area of the subject's skin having such disorder in an amount and for a period of time sufficient to improve the skin disorder.

69. A method of preparing the composition of claim 65, 66, or 67, which method comprises (a) combining water with a therapeutically-effective amount of the corticosteroid and the polymer, (b) adjusting the pH to about 3 to about 9, and (c) optionally combining the water-miscible solvent and the preservative to form the composition.

43.
CA2417646A 2000-08-03 2001-07-24 Topical gel delivery system Expired - Lifetime CA2417646C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US09/632,508 US6387383B1 (en) 2000-08-03 2000-08-03 Topical low-viscosity gel composition
US09/632,508 2000-08-03
PCT/US2001/023341 WO2002011683A1 (en) 2000-08-03 2001-07-24 Topical gel delivery system

Publications (2)

Publication Number Publication Date
CA2417646A1 true CA2417646A1 (en) 2002-02-14
CA2417646C CA2417646C (en) 2010-05-04

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US (2) US6387383B1 (en)
EP (2) EP1304992B1 (en)
JP (1) JP4988129B2 (en)
KR (2) KR20080036246A (en)
CN (2) CN101305982B (en)
AR (1) AR030093A1 (en)
AT (1) ATE429922T1 (en)
AU (2) AU7900201A (en)
BE (1) BE2013C060I2 (en)
BR (1) BR0113247A (en)
CA (1) CA2417646C (en)
CY (3) CY1109189T1 (en)
DE (1) DE60138549D1 (en)
DK (2) DK2052714T3 (en)
ES (2) ES2437321T3 (en)
FR (1) FR14C0053I1 (en)
HK (1) HK1125847A1 (en)
LU (1) LU92401I2 (en)
MX (1) MXPA03001006A (en)
PL (1) PL213237B1 (en)
PT (2) PT2052714E (en)
RU (1) RU2251410C2 (en)
SI (2) SI2052714T1 (en)
WO (1) WO2002011683A1 (en)
ZA (1) ZA200301037B (en)

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WO2020097211A1 (en) * 2018-11-06 2020-05-14 Cote Tim Topical compositions comprising pentoxifylline and methods of treatment using the same

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US20020048596A1 (en) * 1994-12-30 2002-04-25 Gregor Cevc Preparation for the transport of an active substance across barriers
AUPN814496A0 (en) * 1996-02-19 1996-03-14 Monash University Dermal penetration enhancer
KR100638150B1 (en) 1998-12-23 2006-10-26 이데아 악티엔게젤샤프트 Improved formulation for topical non-invasive application in vivo
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EP1304992B1 (en) 2009-04-29
JP2004505900A (en) 2004-02-26
MXPA03001006A (en) 2005-02-25
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HK1125847A1 (en) 2009-08-21
LU92401I2 (en) 2014-05-19
EP1304992A1 (en) 2003-05-02
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US6387383B1 (en) 2002-05-14
PL360589A1 (en) 2004-09-06
DK2052714T3 (en) 2013-10-14
SI2052714T1 (en) 2013-11-29
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ZA200301037B (en) 2004-02-09
FR14C0053I1 (en) 2014-08-08
AR030093A1 (en) 2003-08-13
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CY2014005I2 (en) 2015-12-09
CA2417646C (en) 2010-05-04
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