WO2006008354A1 - Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis - Google Patents
Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis Download PDFInfo
- Publication number
- WO2006008354A1 WO2006008354A1 PCT/FR2005/001348 FR2005001348W WO2006008354A1 WO 2006008354 A1 WO2006008354 A1 WO 2006008354A1 FR 2005001348 W FR2005001348 W FR 2005001348W WO 2006008354 A1 WO2006008354 A1 WO 2006008354A1
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- WO
- WIPO (PCT)
- Prior art keywords
- clobetasol propionate
- calcitriol
- composition
- per gram
- psoriasis
- Prior art date
Links
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 title claims abstract description 73
- 229960004703 clobetasol propionate Drugs 0.000 title claims abstract description 70
- 229960005084 calcitriol Drugs 0.000 title claims abstract description 55
- 235000020964 calcitriol Nutrition 0.000 title claims abstract description 55
- 239000011612 calcitriol Substances 0.000 title claims abstract description 55
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 title claims abstract description 55
- 201000004681 Psoriasis Diseases 0.000 title claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 92
- 239000003814 drug Substances 0.000 claims description 12
- 239000002674 ointment Substances 0.000 claims description 12
- 239000006071 cream Substances 0.000 claims description 9
- 230000000699 topical effect Effects 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims 2
- CNXNMLQATFFYLX-ICTDYHGOSA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5s)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol;[2-[(8s,9r,10s,11s,13s,14s,16s,17r)-9-fluoro-11-hydroxy-10,13,16-trime Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CNXNMLQATFFYLX-ICTDYHGOSA-N 0.000 description 9
- 239000003246 corticosteroid Substances 0.000 description 7
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 description 5
- 229930003316 Vitamin D Natural products 0.000 description 4
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 4
- 239000010432 diamond Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 230000008595 infiltration Effects 0.000 description 4
- 238000001764 infiltration Methods 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 235000019166 vitamin D Nutrition 0.000 description 4
- 239000011710 vitamin D Substances 0.000 description 4
- 150000003710 vitamin D derivatives Chemical class 0.000 description 4
- 229940046008 vitamin d Drugs 0.000 description 4
- 206010015150 Erythema Diseases 0.000 description 3
- 206010040844 Skin exfoliation Diseases 0.000 description 3
- 229960002882 calcipotriol Drugs 0.000 description 3
- LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 description 3
- 230000035618 desquamation Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 235000019489 Almond oil Nutrition 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 239000004264 Petrolatum Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000008168 almond oil Substances 0.000 description 2
- 229960002537 betamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 229940066842 petrolatum Drugs 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 206010006956 Calcium deficiency Diseases 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 1
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000010162 Tukey test Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013103 analytical ultracentrifugation Methods 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 229960001102 betamethasone dipropionate Drugs 0.000 description 1
- CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 231100000749 chronicity Toxicity 0.000 description 1
- 229960002842 clobetasol Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 208000028659 discharge Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 210000001513 elbow Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 210000002414 leg Anatomy 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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
- A61K31/56—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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to a pharmaceutical composition
- a pharmaceutical composition comprising, in a pharmaceutically acceptable medium, calcitriol and clobetasol propionate, and to the use of this composition for the preparation of a medicament for the treatment of psoriasis.
- Psoriasis is a chronic inflammatory skin disease affecting about 3% of the French population. This disease is manifested by red patches covered with whitish scales that detach from the skin. Psoriasis plaques are often located on the elbows, knees, scalp and lower back, but can reach all other parts of the body such as the face, hands, feet, wrinkles, nails. Psoriasis can occur at any age, but the first outbreaks occur most of the time in the second or third decade. It is a chronic disease whose evolution is unpredictable: in phases of recurrence succeeds phases of remission. Although this disease rarely endangers the life of a person, it has a strong impact on its quality of life, given its unsightly appearance and chronicity. In psoriasis, some people suffer from a single plaque of psoriasis located in a specific area of the body while others are prone to extensive psoriasis throughout the body.
- the invention relates to a pharmaceutical composition
- a pharmaceutical composition comprising calcitriol and clobetasol propionate in a given ratio, so that a synergistic effect between the two active ingredients is observed in the treatment of psoriasis.
- Calcitriol is the natural and active form of vitamin D. It is particularly used for calcium deficiencies and regulate its homeostasis in the body.
- Clobetasol propionate or 17-propionant of clobetasol, is a corticosteroid.
- the mechanism of action of corticosteroids is attributed to their inhibition of inflammatory processes (Lange K et al., Skin Pharmacol Appl. Skin Physiol 13 (2): 93-103 (2000)).
- clobetasol propionate and 17-clobetasol propionate will be used interchangeably.
- compositions for topical application in the treatment of dermatological diseases such as for example psoriasis, including calcitriol.
- These compositions may further contain a corticosteroid such as for example hydrocortisone or dexamethasone.
- WO 00/64450 discloses a pharmaceutical composition for dermal use containing a vitamin D analogue and a corticosteroid. The examples given relate more particularly to compositions comprising calcipotriol (vitamin D analogue) and betamethasone (corticosteroid).
- the subject of the present invention is therefore a pharmaceutical composition intended for the treatment of psoriasis, characterized in that it comprises clobetasol propionate and calcitriol in an amount suitable for application once a day to the part or parts of the skin affected ( s) by psoriasis.
- the composition is more particularly characterized in that it comprises from 100 to 700 ⁇ g of clobetasol propionate per gram of composition, more particularly from 150 to 500 ⁇ g per gram of composition, and preferably 250 ⁇ g of clobetasol propionate per gram of composition.
- the composition is more particularly characterized in that it comprises from 0.5 to 10 ⁇ g of calcitriol per gram of composition, more particularly from 1.5 to 9 ⁇ g per gram of composition, and preferably 3 ⁇ g of calcitriol per gram of composition.
- a preferred composition of the invention comprises 3 ⁇ g of calcitriol per gram of composition and 250 ⁇ g of clobetasol propionate per gram of composition.
- composition of the invention further comprises one or more pharmaceutical excipients adapted for topical application.
- the composition of the invention is in the form of a gel, a cream, an ointment, a lotion or a solution.
- the creams may preferably be formulated from a mixture of mineral oil, or a mixture of beeswax and water which is emulsified instantaneously, in which calcitriol and clobetasol propionate are added, dissolve in a small amount of oil such as almond oil.
- the lotions can be prepared by dissolving calcitriol and clobetasol propionate in a high molecular weight alcohol, such as polyethylene glycol.
- a high molecular weight alcohol such as polyethylene glycol.
- the ointments can be formulated by mixing a solution of calcitriol and clobetasol propionate in an oil such as almond oil in heated paraffin and then allowing the mixture to cool.
- the gels can be prepared preferably by dispersing or dissolving calcitriol and clobetasol propionate in a suitable ratio in a carbomer, poloxamer or cellulosic type gel.
- Other ingredients may be added to the topical composition, such as preservatives, for example DL-alpha-tocopherol, or perfumes, if necessary.
- the present invention also relates to the use of a combination of clobetasol propionate and calcitriol for the manufacture of a medicament for the treatment of psoriasis, said medicament containing an appropriate amount of clobetasol propionate and calcitriol to be applied. once a day on the part (s) of skin affected by psoriasis.
- the drug comprises one or more pharmaceutical excipients adapted for topical application, and is in the form of a gel, a cream, an ointment, a lotion or a solution.
- Figures 1 and 2 represent the average of the TSS as a function of time of the seven compositions tested and described in Example 1 below.
- Figures 3 and 4 show the number of subjects whose lesion was healed as a function of time of the seven compositions tested and described in Example 1 below.
- compositions that are the subject of the invention are the following:
- composition comprising, respectively, 250 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition, namely more particularly a cream comprising 250 ⁇ g / g of clobetasol propionate in combination with an ointment comprising 9 ⁇ g / g of calcitriol;
- composition comprising respectively 250 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition, namely more particularly a cream comprising 250 ⁇ g / g of clobetasol propionate in combination with an ointment comprising 3 ⁇ g / g of calcitriol (Silkis® );
- composition comprising, respectively, 500 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition, namely more particularly a cream comprising 500 ⁇ g / g of clobetasol propionate (Dermoval®) in combination with an ointment comprising 9 ⁇ g / g of calcitriol;
- composition comprising, respectively, 500 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition, namely more particularly a cream comprising 500 ⁇ g / g of clobetasol propionate; (Dermoval ®) in combination with an ointment comprising
- compositions not of the invention are the following: - composition sold under the name "Daivobet ®", consisting of an ointment of the combinaion 500 mcg / g betamethasone dipropionate
- composition comprising 250 ⁇ g of clobetasol propionate per gram of composition in combination with the Silkis vehicle (ointment combining petrolatum and paraffin oil);
- composition comprising 500 ⁇ g of clobetasol propionate per gram of composition (Dermoval®) in combination with a Silkis vehicle (petrolatum / paraffin oil ointment).
- the objective of the study is to identify and select the concentrations of calcitriol and clobetasol propionate which, after 21 days of treatment, have been applied to 29 subjects with psoriasis (65.5% men and 34 5% female), an efficacy profile superior to those of a composition of Daivobet ® and compositions comprising only clobetasol propionate, clobetasol propionate said being present in the same concentration as that of a composition comprising a combination of clobetasol propionate and calcitriol.
- compositions tested were randomly applied to seven locations on one or more psoriatic plaques of identical severity located on the legs (anterior aspect of the tibia excluded), on the trunk or on the arms.
- the different compositions were applied under normal conditions of use ie without occlusion, once a day, except Sunday, for a total of 18 times in all (21 days of experimentation).
- compositions are carried out in the following manner: clobetasol propionate is applied initially only, and when the latter has completely penetrated, the calcitriol or the Silkis vehicle is applied under the same conditions without any latency period between them. two applications.
- AUC Area Under Curve
- Total sum score addition of individual scores for erythema, desquamation and infiltration
- the curve connected by black diamonds corresponds to the treatment with a composition "Daivobet®”.
- the curve connected by dark gray squares corresponds to treatment with a composition comprising 250 ⁇ g of clobetasol propionate per gram of composition.
- the curve connected by white triangles corresponds to treatment with a composition of the invention comprising respectively 250 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition.
- the curve connected by black crosses corresponds to the treatment with a composition of the invention comprising respectively 250 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition.
- the curve connected by dark gray squares corresponds to treatment with a composition comprising 500 ⁇ g of clobetasol propionate per gram of composition.
- the curve connected by white triangles corresponds to the treatment with a composition of the invention comprising respectively 500 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition.
- the curve connected by black crosses corresponds to the treatment with a composition of the invention comprising respectively 500 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition.
- Figures 3 and 4 show the number of subjects whose lesion was healed as a function of time of seven different compositions objects or not of the invention and described in this example.
- the curve connected by black diamonds corresponds to the treatment with a composition "Daivobet®”.
- the curve connected by dark gray squares corresponds to treatment with a composition comprising 250 ⁇ g of clobetasol propionate per gram of composition.
- the curve connected by white triangles corresponds to treatment with a composition of the invention comprising respectively 250 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition.
- the curve connected by black crosses corresponds to the treatment with a composition of the invention comprising respectively 250 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition.
- the curve connected by dark gray squares corresponds to treatment with a composition comprising 500 ⁇ g of clobetasol propionate per gram of composition.
- the curve connected by white triangles corresponds to the treatment with a composition of the invention comprising respectively 500 ⁇ g of clobetasol propionate and 3 ⁇ g of calcitriol per gram of composition.
- the curve connected by black crosses corresponds to the treatment with a composition of the invention comprising respectively 500 ⁇ g of clobetasol propionate and 9 ⁇ g of calcitriol per gram of composition.
- TSS AUCs are shown in Table 1 below.
- a composition comprising 250 ⁇ g / g of clobetasol propionate and 3 ⁇ g / g of Calcitriol showed significantly better efficacy results than clobetasol propionate 250 ⁇ g / g alone and Daivobet ® .
- this combination showed similar efficacy results to clobetasol propionate 500 ⁇ g / g alone ( Figures 1 and 2).
- composition comprising 250 ⁇ g / g of clobetasol propionate and 3 ⁇ g / g of calcitriol showed better results in terms of healing (see FIGS. 3 and 4) with respect to:
- compositions respectively comprising an association:
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA06014410A MXPA06014410A (es) | 2004-06-17 | 2005-06-01 | Uso de una composicion farmaceutica que comprende calcitriol y propionato de clobetasol para el tratamiento de la psoriasis. |
AT05775762T ATE480242T1 (de) | 2004-06-17 | 2005-06-01 | Verwendung einer pharmazeutischen zusammensetzung mit calcitriol und clobetasolpropionat zur behandlung von schuppenflechte |
EP05775762A EP1758587B1 (fr) | 2004-06-17 | 2005-06-01 | Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis |
JP2007515980A JP2008502659A (ja) | 2004-06-17 | 2005-06-01 | 乾癬の治療のための、クロベタゾールプロピオネートとカルシトリオールとを含む製薬組成物の使用 |
DE602005023452T DE602005023452D1 (de) | 2004-06-17 | 2005-06-01 | Mit calcitriol und clobetasolpropionat zur behandlung von schuppenflechte |
BRPI0511209-5A BRPI0511209A (pt) | 2004-06-17 | 2005-06-01 | composição farmacêutica e uso de uma associação de propionato de clobetasol e de calcitriol |
CA002568753A CA2568753A1 (fr) | 2004-06-17 | 2005-06-01 | Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0406608 | 2004-06-17 | ||
FR0406608A FR2871693B1 (fr) | 2004-06-17 | 2004-06-17 | Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006008354A1 true WO2006008354A1 (fr) | 2006-01-26 |
Family
ID=34946514
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2005/001348 WO2006008354A1 (fr) | 2004-06-17 | 2005-06-01 | Utilisation d'une composition pharmaceutique comprenant du calcitriol et du propionate de clobetasol pour le traitement du psoriasis |
Country Status (16)
Country | Link |
---|---|
US (1) | US20050282792A1 (fr) |
EP (1) | EP1758587B1 (fr) |
JP (1) | JP2008502659A (fr) |
CN (1) | CN1968702A (fr) |
AR (1) | AR049517A1 (fr) |
AT (1) | ATE480242T1 (fr) |
AU (1) | AU2005263804A1 (fr) |
BR (1) | BRPI0511209A (fr) |
CA (1) | CA2568753A1 (fr) |
DE (1) | DE602005023452D1 (fr) |
ES (1) | ES2351045T3 (fr) |
FR (1) | FR2871693B1 (fr) |
MX (1) | MXPA06014410A (fr) |
RU (1) | RU2007101538A (fr) |
WO (1) | WO2006008354A1 (fr) |
ZA (1) | ZA200700233B (fr) |
Cited By (2)
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FR2912655A1 (fr) * | 2007-02-15 | 2008-08-22 | Galderma Sa | Produit de soin cutane a double compartiment comprenant du calcitriol et du propionate de clobetasol, et son utilisation |
EP2070533A1 (fr) | 2007-12-11 | 2009-06-17 | Apoteknos Para La Piel, s.l. | Utilisation d'un composant dérivé de l'acide propionique P-hydroxyphényl pour le traitement de la psoriasis |
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EP1970048A1 (fr) * | 2007-03-15 | 2008-09-17 | Drug Delivery Solutions Limited | Composition topique de type polyaphron avec de la vitamine D |
US10265265B2 (en) * | 2007-03-15 | 2019-04-23 | Drug Delivery Solutions Limited | Topical composition |
EP2008651A1 (fr) | 2007-06-26 | 2008-12-31 | Drug Delivery Solutions Limited | Patch bioérodable |
CN103533962B (zh) | 2011-03-14 | 2018-05-18 | 药品配送方案有限公司 | 一种眼用组合物 |
JP6371312B2 (ja) | 2013-01-29 | 2018-08-08 | アヴェクシン エーエス | 坑炎症および抗腫瘍2−オキソチアゾール化合物ならびに2−オキソチオフェン化合物 |
CN103142466B (zh) * | 2013-03-21 | 2015-04-22 | 青岛正大海尔制药有限公司 | 骨化三醇凝胶及其制备方法 |
GB201413695D0 (en) | 2014-08-01 | 2014-09-17 | Avexxin As | Compound |
GB201604316D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
GB201604318D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
US11351127B2 (en) | 2016-09-21 | 2022-06-07 | Avexxin As | Pharmaceutical composition |
KR102619458B1 (ko) | 2017-06-16 | 2023-12-29 | 학교법인 도시샤 | mTOR 인히비터를 포함하는, 눈의 증상, 장해 또는 질환을 치료 또는 예방하기 위한 의약 및 그 응용 |
EP3639855A4 (fr) * | 2017-06-16 | 2021-03-17 | The Doshisha | Composés ayant une activité inhibitrice de caspase, agent pharmaceutique les contenant pour le traitement ou la prévention des symptômes, troubles ou maladies de l'endothélium cornéen, et application dudit agent pharmaceutique |
EP3542788A1 (fr) | 2018-03-19 | 2019-09-25 | MC2 Therapeutics Limited | Composition topique comprenant calcipotriol et dipropionate de bétaméthasone |
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2004
- 2004-06-17 FR FR0406608A patent/FR2871693B1/fr not_active Expired - Fee Related
- 2004-09-17 US US10/942,997 patent/US20050282792A1/en not_active Abandoned
-
2005
- 2005-06-01 CN CNA2005800200384A patent/CN1968702A/zh active Pending
- 2005-06-01 DE DE602005023452T patent/DE602005023452D1/de active Active
- 2005-06-01 AT AT05775762T patent/ATE480242T1/de not_active IP Right Cessation
- 2005-06-01 CA CA002568753A patent/CA2568753A1/fr not_active Abandoned
- 2005-06-01 RU RU2007101538/15A patent/RU2007101538A/ru unknown
- 2005-06-01 WO PCT/FR2005/001348 patent/WO2006008354A1/fr active Application Filing
- 2005-06-01 BR BRPI0511209-5A patent/BRPI0511209A/pt not_active IP Right Cessation
- 2005-06-01 EP EP05775762A patent/EP1758587B1/fr active Active
- 2005-06-01 ES ES05775762T patent/ES2351045T3/es active Active
- 2005-06-01 AU AU2005263804A patent/AU2005263804A1/en not_active Abandoned
- 2005-06-01 JP JP2007515980A patent/JP2008502659A/ja not_active Ceased
- 2005-06-01 MX MXPA06014410A patent/MXPA06014410A/es not_active Application Discontinuation
- 2005-06-16 AR ARP050102465A patent/AR049517A1/es unknown
-
2007
- 2007-01-09 ZA ZA200700233A patent/ZA200700233B/en unknown
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WO2000064450A1 (fr) * | 1999-04-23 | 2000-11-02 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | Composition pharmaceutique |
WO2002034235A1 (fr) * | 2000-10-27 | 2002-05-02 | Leo Pharma A/S | Composition topique contenant au moins une vitamine d ou un analogue de vitamine d et au moins un corticosteroide |
FR2848454A1 (fr) * | 2002-12-17 | 2004-06-18 | Galderma Res & Dev | Composition pharmaceutique comprenant une association de calcitriol et d'un corticosteroide |
WO2004054588A1 (fr) * | 2002-12-17 | 2004-07-01 | Galderma Sa | Compositions pharmaceutiques comprenant une combinaison de calcitriol et d'un clobetasol propionate |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2912655A1 (fr) * | 2007-02-15 | 2008-08-22 | Galderma Sa | Produit de soin cutane a double compartiment comprenant du calcitriol et du propionate de clobetasol, et son utilisation |
EP2070533A1 (fr) | 2007-12-11 | 2009-06-17 | Apoteknos Para La Piel, s.l. | Utilisation d'un composant dérivé de l'acide propionique P-hydroxyphényl pour le traitement de la psoriasis |
Also Published As
Publication number | Publication date |
---|---|
EP1758587A1 (fr) | 2007-03-07 |
MXPA06014410A (es) | 2007-02-19 |
ES2351045T3 (es) | 2011-01-31 |
US20050282792A1 (en) | 2005-12-22 |
FR2871693A1 (fr) | 2005-12-23 |
FR2871693B1 (fr) | 2006-08-25 |
CA2568753A1 (fr) | 2006-01-26 |
JP2008502659A (ja) | 2008-01-31 |
RU2007101538A (ru) | 2008-07-27 |
BRPI0511209A (pt) | 2007-11-27 |
AU2005263804A1 (en) | 2006-01-26 |
ATE480242T1 (de) | 2010-09-15 |
ZA200700233B (en) | 2007-12-27 |
DE602005023452D1 (de) | 2010-10-21 |
CN1968702A (zh) | 2007-05-23 |
EP1758587B1 (fr) | 2010-09-08 |
AR049517A1 (es) | 2006-08-09 |
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