WO2010039251A1 - Stabilized composition for treating psoriasis - Google Patents
Stabilized composition for treating psoriasis Download PDFInfo
- Publication number
- WO2010039251A1 WO2010039251A1 PCT/US2009/005426 US2009005426W WO2010039251A1 WO 2010039251 A1 WO2010039251 A1 WO 2010039251A1 US 2009005426 W US2009005426 W US 2009005426W WO 2010039251 A1 WO2010039251 A1 WO 2010039251A1
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- WO
- WIPO (PCT)
- Prior art keywords
- composition
- percent
- weight
- alkyl
- ddaip
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/221—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having an amino group, e.g. acetylcholine, acetylcarnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
- A61K31/355—Tocopherols, e.g. vitamin E
-
- 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
- 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
-
- 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
-
- 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
- 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
-
- 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
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- This application relates to room temperature-stable, non-aqueous ointment compositions containing a vitamin D compound and a corticosteroid useful for treating psoriasis.
- Psoriasis is a noncontagious disease that affects the skin and joints.
- the disease is accompanied by red scaly patches on the skin, called psoriatic plaques, which are areas of inflammation and excessive skin production.
- psoriatic plaques are areas of inflammation and excessive skin production.
- psoriatic arthritis As many as 7.5 million Americans have psoriasis, according to the National Institutes of Health. It has been estimated that about 10 percent to 30 percent of people with psoriasis will also develop a joint disease known as psoriatic arthritis, which causes joint pain, stiffness and swelling.
- Psoriasis is a chronic recurring condition, which can vary significantly in severity. Some sufferers exhibit minor localised patches of psoriatic plaques, while others have plaque overage over almost every area of the body. Fingernails and toenails are often affected.
- psoriasis The cause of psoriasis is not known, but it may have a genetic component. Stress, excessive alcohol consumption, and smoking have been known to aggravate the condition. In addition to the obvious physical manifestations, individuals with psoriasis may also suffer from depression and loss of self-esteem. There are many topical medications that have been utilized to treat psoriasis. For example, vitamin D-3 (calcipotriene), coal tar, corticosteroids (e.g., clobetasol, fluocinolone, and betamethasone), tree bark extract (e.g., anthralin), and retinoids (e.g., tazarotene).
- vitamin D-3 calcipotriene
- coal tar tar
- corticosteroids e.g., clobetasol, fluocinolone, and betamethasone
- tree bark extract e.g., anthralin
- retinoids e.g., taza
- compositions for treating psoriasis that include both vitamin D compounds and corticosteroids have also been described (see U.S. Patent No. 6,753,013).
- Combinations of vitamin D compounds and corticosteroids can be unstable, since the corticosteroids tend to favor acidic conditions, whereas vitamin D compounds are more stable in alkaline conditions.
- TACLONEX® topical ointment is a combination product, which includes both calcipotriene and betamethasone dipropionate, and is stabilized by a polyoxyalkylene ether-type so 1 vent.
- a storage stable ointment of the present invention comprises a vitamin D compound, a corticosteroid, and an N,N-di(C,-C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester a (C,-C 4 )-alkyl (C 8 -C 22 ) carboxylic ester, in a petrolatum carrier, and optionally containing mineral oil, tocopherol, or both.
- the vitamin D compound comprises calcipotriene.
- the corticosteroid preferably is a pharmaceutically acceptable salt of clobetasol or a pharmaceutical acceptable salt of betamethasone.
- a preferred N,N-di(C, -C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester is dodecyl 2-(N 5 N- dimethylamino)-propionate (DDAIP).
- compositions of the present invention have storage stabilities comparable to commercial TACLONEX® topical ointment, while providing for surprisingly enhanced skin penetration of calcipotriene compared to the commercial product.
- FIG. 1 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus time on the skin from a standard assay of skin permeation performed on compositions of the present invention containing calcipotriene, betamethasone dipropionate, and various amounts of DDAIP, compared to a composition containing no DDAIP, and TACLONEX® ointment.
- FIG. 1 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus time on the skin from a standard assay of skin permeation performed on compositions of the present invention containing calcipotriene, betamethasone dipropionate, and various amounts of DDAIP, compared to a composition containing no DDAIP, and TACLONEX® ointment.
- FIG. 1 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus time on the skin from a standard assay of skin permeation performed
- FIG. 2 depicts a graph of cumulative permeation of betamethasone through pig ear skin versus time on the skin from a standard assay of skin permeation performed on compositions of the present invention containing calcipotriene, betamethasone dipropionate, and various amounts of DDAIP, compared to a composition containing no DDAIP, and TACLONEX® ointment.
- FIG. 3 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus time on the skin from a standard assay of skin permeation performed on compositions of the present invention containing calcipotriene, clobetasol propionate, and various amounts of DDAIP, compared to a composition containing no DDAIP.
- FIG. 4 depicts a graph of cumulative permeation of clobetasol through pig ear skin versus time on the skin from a standard assay of skin permeation performed on compositions of the present invention containing calcipotriene, clobetasol propionate, and various amounts of DDAIP, compared to a composition containing no DDAIP.
- the present invention provides a storage stable ointment useful for treatment of psoriasis.
- the compositions of the invention comprise a vitamin D compound, a corticosteroid, and an N,N-di(C,-C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C , 8 ) carboxylic ester a (C,-C 4 )-alkyl (C 8 -C 22 ) carboxylic ester, in a petrolatum (e.g., white petrolatum) carrier, and optionally containing mineral oil, tocopherol (vitamin E), or both mineral oil and tocopherol.
- a petrolatum e.g., white petrolatum
- Suitable vitamin D compounds for use in the compositions of the present invention include calcipotriene (also known as calcipotriol), calcitriol, tacalcitol, maxacalcitol, and l(S),3(R)-dihydroxy-20(R)-[((3(2-hydroxy-2- ⁇ ropyl)- phenyl)-methoxy)-methyl]-9,10-seco-pregna-5(Z),7(E),10(19)-triene, as well as combinations of two or more thereof.
- a preferred vitamin D compound is calcipotriene, which is (IR 5 SS)-S-P-[OR 5 BaRJaS)-I-[ ⁇ S)-S-CyCIoPrOPyI-
- the vitamin D compound preferably is present in the composition at a concentration in the range of about 0.001 to about 0.01 percent by weight.
- Suitable corticosteroids for use in the compositions of the present invention include hydrocortisone, desonide, flumethasone pivalate, fluocinolone acetonide, triamcinolone acetonide, alclometasone dipropionate, hydrocortisone valerate, prednicarbate, clocortolone pivalate, fluticasone propionate, mometasone furoate, betamethasone, betamethasone dipropionate, amcinonide, desoximetasone, diflorason, fluocinonide, halcinonide, halobetasol propionate, clobetasol propionate, and combinations of two or more thereof.
- Particularly preferred corticosteroids are clobetasol propionate and betamethasone dipropionate.
- the corticosteroid is present in the composition at a concentration in the range of about 0.01 to about 0.1 percent by weight.
- Tocopherol is also preferably included in the compositions of the present invention, e.g., at a concentration in the range of about 0.001 to 0.01 percent by weight.
- compositions of the present invention include a N 5 N- di(C,-C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester, e.g., as a solvent and a skin penetration enhancer, preferably at a concentration in the range of about 0.1 to about 5 percent by weight.
- N,N-di(Ci-C 8 ) alkylamino substituted in reference to a (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester means that either the alcohol portion or the carboxylic acid portion from which the ester is prepared bears an amino substituent NR x R y , wherein R x and R 7 are each independently a (C 1 -C 8 ) alkyl group.
- R x and R y are both methyl groups.
- DDAIP dodecyl-2-(N,N-dimethylamino)- propionate
- DDAA dodecyl-2-(N,N-dimethylamino)-acetate
- DAIPD 1-(N 5 N- dimethylamino)-2-propyl dodecanoate
- DAIPM l-(N,N-dimethylamino)-2- propyl myristate
- DAIPO l-(N,N-dimethylamino)-2-propyl oleate
- compositions of the present invention can include up to about 10 percent by weight (e.g., 1 to 10 percent) of mineral oil.
- the composition includes about 1 to about 5 percent by weight of mineral oil.
- a composition of the invention comprises about 0.001 to about 0.01 percent by weight of a vitamin D compound; about 0.01 to about 0.1 percent by weight of a corticosteroid; about 0.001 to about 0.01 percent by weight of tocopherol; and about 0.1 to about 5 percent by weight of an N,N- di(C ] -C 8 ) alkylamino substituted, (C 4 -C , 8 ) alkyl (C 2 -C 18 ) carboxylic ester a (C 1 -C 4 )- alkyl (C 8 -C 22 ) carboxylic ester; in a petrolatum carrier, and optionally contains mineral oil.
- the vitamin D compound comprises calcipotriene
- the corticosteroid is selected from the group consisting of clobetasol propionate and betamethasone dipropionate
- the N,N-di(C,-C 8 ) alkylamino substituted, (C 4 -C 18 ) alkyl (C 2 -C 18 ) carboxylic ester is DDAIP , CAS Reg. No. 224297-43-2.
- One such preferred embodiment comprises about 0.001 to about 0.01 percent by weight of a calcipotriene; about 0.01 to about 0.1 percent by weight of a corticosteroid selected from clobetasol propionate and betamethasone dipropionate; about 0.001 to about 0.01 percent by weight of tocopherol; up to about 10 percent by weight mineral oil, and about 0.1 to about 5 percent by weight of an N,N-di(C,-C 8 ) alkylamino substituted, (C 4 -C , g ) alkyl (C 2 -C 18 ) carboxylic ester a (C,-C 4 )-alkyl (C 8 -C 22 ) carboxylic ester; in a petrolatum carrier.
- compositions of the present invention were prepared.
- the formulations of the compositions are described in Tables 1 and 2.
- CAL refers to calcipotriene
- BET-D refers to betamethasone dipropionate
- CLO-P refers to clobetasol propionate.
- Stability data of the combination compositions of Example 1 are described in Table 3.
- the reference standard was TACLONEX® ointment (a commercial product containing calcipotriene and betamethasone dipropionate, stabilized with a poly(alkylene oxide) ester solvent), which is known to be a stable product.
- the compositions of Example 1 and TACLONEX® ointment were stored at the indicated temperatures show in Table 3, and analyzed by high performance liquid chromatography for the indicated API (active pharmaceutical ingredient).
- the number entries in Table 3 are percentages of the indicated active ingredient based on the known formulations of the compositions, from analyses of samples taken at the indicated the storage times and temperatures. Table 3.
- compositions of the invention were also evaluated for their permeation through pig ear skin.
- Pig ear skin is commonly used to evaluate the permeation of topical products due to its permeation proximity to that of human skin.
- Compositions of the invention containing 0.005 wt. % calcipotriene, 0.002 wt. % tocopherol, 3 wt. % mineral oil, and either 0.05 wt. % clobetasol propionate or 0.064 wt. % betamethasone dipropionate, in a white petrolatum carrier, containing varying concentrations of DDAIP (1, 1.5, 2, and 2.5 wt.
- FIG. 1 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus the amount of time the composition was on the skin, for the calcipotriene/betamethasone-containing compositions and TACLONEX® ointment.
- FIG. 2 depicts a graph of cumulative permeation of betamethasone through pig ear skin versus the amount of time the compositions were on the skin for the calcipotriene/betamethasone-containing compositions, and TACLONEX® ointment.
- FIG. 3 depicts a graph of cumulative permeation of calcipotriene through pig ear skin versus the amount of time the compositions were on the skin for the calcipotriene/clobetasol-containing compositions.
- FIG. 4 depicts a graph of cumulative permeation of clobetasol through pig ear skin versus the amount of time the compositions were on the skin for the calcipotriene/clobetasol-containing compositions. Table 4.
- composition containing 1 % DDAIP also showed a surprising enhancement in calcipotriene penetration in the 24 to 96 hour evaluations compared to the composition with no DDAIP and to TACLONEX® ointment.
- the composition containing 2 % DDAIP exhibited about 7.1 times higher calcipotriene penetration compared to the composition with no DDAIP, and 1.9 times higher penetration than TACLONEX® ointment.
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Abstract
Description
Claims
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ592300A NZ592300A (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
BRPI0920728-7A BRPI0920728A2 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for psoriasis treatment |
JP2011530054A JP5667060B2 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
CN2009801396130A CN102202509A (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
EP09818111.8A EP2343978A4 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
CA2739376A CA2739376A1 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
MX2011003568A MX2011003568A (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis. |
AU2009300331A AU2009300331A1 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
RU2011117230/15A RU2526162C2 (en) | 2008-10-03 | 2009-10-02 | Stabilised composition for treating psoriasis |
US12/998,261 US9220701B2 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
IL212062A IL212062A0 (en) | 2008-10-03 | 2011-03-31 | Stabilized composition for treating psoriasis |
ZA2011/03061A ZA201103061B (en) | 2008-10-03 | 2011-04-21 | Stabilized composition for treating psoriasis |
US14/941,390 US20160067266A1 (en) | 2008-10-03 | 2015-11-13 | Stabilized composition for treating psoriasis |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US19512608P | 2008-10-03 | 2008-10-03 | |
US61/195,126 | 2008-10-03 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/998,261 A-371-Of-International US9220701B2 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
US14/941,390 Continuation US20160067266A1 (en) | 2008-10-03 | 2015-11-13 | Stabilized composition for treating psoriasis |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010039251A1 true WO2010039251A1 (en) | 2010-04-08 |
Family
ID=42073781
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2009/005426 WO2010039251A1 (en) | 2008-10-03 | 2009-10-02 | Stabilized composition for treating psoriasis |
Country Status (18)
Country | Link |
---|---|
US (2) | US9220701B2 (en) |
EP (1) | EP2343978A4 (en) |
JP (1) | JP5667060B2 (en) |
KR (1) | KR20110067145A (en) |
CN (1) | CN102202509A (en) |
AU (1) | AU2009300331A1 (en) |
BR (1) | BRPI0920728A2 (en) |
CA (1) | CA2739376A1 (en) |
CL (1) | CL2011000722A1 (en) |
CR (1) | CR20110225A (en) |
EC (1) | ECSP11011022A (en) |
IL (1) | IL212062A0 (en) |
MX (1) | MX2011003568A (en) |
NZ (1) | NZ592300A (en) |
PE (1) | PE20110849A1 (en) |
RU (1) | RU2526162C2 (en) |
WO (1) | WO2010039251A1 (en) |
ZA (1) | ZA201103061B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012087443A1 (en) * | 2010-11-22 | 2012-06-28 | Dow Pharmaceutical Sciences, Inc. | Pharmaceutical formulations containing corticosteroids for topical administration |
WO2020044223A1 (en) * | 2018-08-28 | 2020-03-05 | Glenmark Pharmaceuticals Limited | Container system and pharmaceutical foam composition comprising betamethasone |
US11839656B2 (en) | 2010-11-22 | 2023-12-12 | Bausch Health Ireland Limited | Pharmaceutical formulations containing corticosteroids for topical administration |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ592300A (en) * | 2008-10-03 | 2013-01-25 | Nexmed Holdings Inc | Stabilized composition for treating psoriasis |
WO2014028780A2 (en) * | 2012-08-15 | 2014-02-20 | Nexmed Holdings, Inc. | Antifungal compounds and methods of use |
CN105784902A (en) * | 2016-03-11 | 2016-07-20 | 重庆华邦制药有限公司 | Detection method for low-concentration clobetasone butyrate |
EP3456314A1 (en) | 2017-09-14 | 2019-03-20 | Tiofarma B.V. | Topical formulation comprising 17-ketolic corticosteroid |
Citations (3)
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US20060057075A1 (en) * | 2004-08-02 | 2006-03-16 | Moshe Arkin | Pharmaceutical and cosmeceutical wash-off mousse shampoo compositions, processes for preparing the same and uses thereof |
US20060067898A1 (en) * | 2003-03-21 | 2006-03-30 | Kepka Stanley W | Antifungal nail coat and method of use |
US20080069779A1 (en) * | 2003-08-04 | 2008-03-20 | Foamix Ltd. | Foamable vehicle and vitamin and flavonoid pharmaceutical compositions thereof |
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US4980378A (en) * | 1988-06-01 | 1990-12-25 | Odontex, Inc. | Biodegradable absorption enhancers |
US6046244A (en) | 1997-11-05 | 2000-04-04 | Nexmed Holdings, Inc. | Topical compositions for prostaglandin E1 delivery |
US6414028B1 (en) | 1997-11-05 | 2002-07-02 | Nexmed Holdings, Inc. | Topical compositions containing prostaglandin E1 |
US8263580B2 (en) * | 1998-09-11 | 2012-09-11 | Stiefel Research Australia Pty Ltd | Vitamin formulation |
TR200101790T2 (en) | 1998-12-23 | 2001-10-22 | Idea Ag. | Formula developed for uncommon in vivo topical applications |
HU230045B1 (en) | 1999-04-23 | 2015-06-29 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Pharmaceutical composition for dermal use |
JP2006511545A (en) | 2002-12-17 | 2006-04-06 | ガルデルマ・ソシエテ・アノニム | Pharmaceutical composition comprising a combination of calcitriol and clobetasol propionate |
FR2871696B1 (en) * | 2004-06-17 | 2006-11-10 | Galderma Sa | TOPICAL COMPOSITION FOR THE TREATMENT OF PSORIASIS |
CA2633489C (en) * | 2005-12-14 | 2013-09-24 | Zars Pharma, Inc. | Compositions and methods for treating dermatological conditions |
US7560489B2 (en) | 2006-10-11 | 2009-07-14 | Nexmed Holdings, Inc. | Stabilized prostaglandin E composition |
NZ592300A (en) * | 2008-10-03 | 2013-01-25 | Nexmed Holdings Inc | Stabilized composition for treating psoriasis |
-
2009
- 2009-10-02 NZ NZ592300A patent/NZ592300A/en not_active IP Right Cessation
- 2009-10-02 AU AU2009300331A patent/AU2009300331A1/en not_active Abandoned
- 2009-10-02 CN CN2009801396130A patent/CN102202509A/en active Pending
- 2009-10-02 EP EP09818111.8A patent/EP2343978A4/en not_active Withdrawn
- 2009-10-02 JP JP2011530054A patent/JP5667060B2/en not_active Expired - Fee Related
- 2009-10-02 CA CA2739376A patent/CA2739376A1/en not_active Abandoned
- 2009-10-02 PE PE2011000834A patent/PE20110849A1/en not_active Application Discontinuation
- 2009-10-02 RU RU2011117230/15A patent/RU2526162C2/en not_active IP Right Cessation
- 2009-10-02 BR BRPI0920728-7A patent/BRPI0920728A2/en not_active IP Right Cessation
- 2009-10-02 MX MX2011003568A patent/MX2011003568A/en active IP Right Grant
- 2009-10-02 KR KR1020117010072A patent/KR20110067145A/en not_active Application Discontinuation
- 2009-10-02 WO PCT/US2009/005426 patent/WO2010039251A1/en active Application Filing
- 2009-10-02 US US12/998,261 patent/US9220701B2/en not_active Expired - Fee Related
-
2011
- 2011-03-31 IL IL212062A patent/IL212062A0/en unknown
- 2011-04-01 CL CL2011000722A patent/CL2011000722A1/en unknown
- 2011-04-21 ZA ZA2011/03061A patent/ZA201103061B/en unknown
- 2011-04-29 CR CR20110225A patent/CR20110225A/en unknown
- 2011-05-03 EC EC2011011022A patent/ECSP11011022A/en unknown
-
2015
- 2015-11-13 US US14/941,390 patent/US20160067266A1/en not_active Abandoned
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US20060067898A1 (en) * | 2003-03-21 | 2006-03-30 | Kepka Stanley W | Antifungal nail coat and method of use |
US20080069779A1 (en) * | 2003-08-04 | 2008-03-20 | Foamix Ltd. | Foamable vehicle and vitamin and flavonoid pharmaceutical compositions thereof |
US20060057075A1 (en) * | 2004-08-02 | 2006-03-16 | Moshe Arkin | Pharmaceutical and cosmeceutical wash-off mousse shampoo compositions, processes for preparing the same and uses thereof |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012087443A1 (en) * | 2010-11-22 | 2012-06-28 | Dow Pharmaceutical Sciences, Inc. | Pharmaceutical formulations containing corticosteroids for topical administration |
AU2011345240B2 (en) * | 2010-11-22 | 2016-11-17 | Dow Pharmaceutical Sciences, Inc. | Pharmaceutical formulations containing corticosteroids for topical administration |
US10478502B2 (en) | 2010-11-22 | 2019-11-19 | Dow Pharmaceutical Sciences, Inc. | Pharmaceutical formulations containing corticosteroids for topical administration |
US11213587B2 (en) | 2010-11-22 | 2022-01-04 | Bausch Health Ireland Limited | Pharmaceutical formulations containing corticosteroids for topical administration |
US11839656B2 (en) | 2010-11-22 | 2023-12-12 | Bausch Health Ireland Limited | Pharmaceutical formulations containing corticosteroids for topical administration |
US11957753B2 (en) | 2010-11-22 | 2024-04-16 | Bausch Health Ireland Limited | Pharmaceutical formulations containing corticosteroids for topical administration |
WO2020044223A1 (en) * | 2018-08-28 | 2020-03-05 | Glenmark Pharmaceuticals Limited | Container system and pharmaceutical foam composition comprising betamethasone |
Also Published As
Publication number | Publication date |
---|---|
CL2011000722A1 (en) | 2012-01-20 |
ZA201103061B (en) | 2012-04-25 |
RU2011117230A (en) | 2012-11-10 |
US20110237558A1 (en) | 2011-09-29 |
US9220701B2 (en) | 2015-12-29 |
CR20110225A (en) | 2011-07-18 |
KR20110067145A (en) | 2011-06-21 |
NZ592300A (en) | 2013-01-25 |
ECSP11011022A (en) | 2011-06-30 |
BRPI0920728A2 (en) | 2015-08-18 |
JP2012504607A (en) | 2012-02-23 |
US20160067266A1 (en) | 2016-03-10 |
PE20110849A1 (en) | 2011-12-02 |
CN102202509A (en) | 2011-09-28 |
AU2009300331A1 (en) | 2010-04-08 |
IL212062A0 (en) | 2011-06-30 |
RU2526162C2 (en) | 2014-08-20 |
EP2343978A1 (en) | 2011-07-20 |
CA2739376A1 (en) | 2010-04-08 |
MX2011003568A (en) | 2011-06-09 |
EP2343978A4 (en) | 2013-11-27 |
JP5667060B2 (en) | 2015-02-12 |
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