CA2737255A1 - Modified release emulsions for application to skin or vaginal mucosa - Google Patents
Modified release emulsions for application to skin or vaginal mucosa Download PDFInfo
- Publication number
- CA2737255A1 CA2737255A1 CA2737255A CA2737255A CA2737255A1 CA 2737255 A1 CA2737255 A1 CA 2737255A1 CA 2737255 A CA2737255 A CA 2737255A CA 2737255 A CA2737255 A CA 2737255A CA 2737255 A1 CA2737255 A1 CA 2737255A1
- Authority
- CA
- Canada
- Prior art keywords
- emulsion according
- weight
- amounts
- water
- emulsion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 53
- 210000004877 mucosa Anatomy 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 14
- 229940079593 drug Drugs 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 51
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 17
- 239000000499 gel Substances 0.000 claims description 14
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000007764 o/w emulsion Substances 0.000 claims description 10
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 claims description 7
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical group ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 claims description 7
- 239000006071 cream Substances 0.000 claims description 7
- 239000006210 lotion Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229960003749 ciclopirox Drugs 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
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- SRQKTCXJCCHINN-NYYWCZLTSA-N nifuratel Chemical compound O=C1OC(CSC)CN1\N=C\C1=CC=C([N+]([O-])=O)O1 SRQKTCXJCCHINN-NYYWCZLTSA-N 0.000 claims description 4
- 229960002136 nifuratel Drugs 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 229920003086 cellulose ether Polymers 0.000 claims description 3
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 3
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 3
- 229920000609 methyl cellulose Polymers 0.000 claims description 3
- 239000001923 methylcellulose Substances 0.000 claims description 3
- 230000003232 mucoadhesive effect Effects 0.000 claims description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 2
- 229960004150 aciclovir Drugs 0.000 claims description 2
- 229920013820 alkyl cellulose Polymers 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 claims description 2
- 229960004022 clotrimazole Drugs 0.000 claims description 2
- 229920006037 cross link polymer Polymers 0.000 claims description 2
- 229960005309 estradiol Drugs 0.000 claims description 2
- 229930182833 estradiol Natural products 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 2
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 claims description 2
- 229960002751 imiquimod Drugs 0.000 claims description 2
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 claims description 2
- 229960000282 metronidazole Drugs 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
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- 206010046914 Vaginal infection Diseases 0.000 claims 2
- 230000000063 preceeding effect Effects 0.000 claims 2
- 208000032159 Vaginal inflammation Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 claims 1
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- 229940124350 antibacterial drug Drugs 0.000 claims 1
- 239000003904 antiprotozoal agent Substances 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
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- 230000002538 fungal effect Effects 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 25
- 229920000642 polymer Polymers 0.000 abstract description 5
- 238000013508 migration Methods 0.000 abstract description 3
- 230000005012 migration Effects 0.000 abstract description 3
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 33
- 238000009472 formulation Methods 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 19
- -1 alkyl methacrylate Chemical compound 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- 229920001983 poloxamer Polymers 0.000 description 5
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 4
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
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- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000003623 enhancer Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- MBRHNTMUYWQHMR-UHFFFAOYSA-N 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one Chemical compound NCCO.ON1C(=O)C=C(C)C=C1C1CCCCC1 MBRHNTMUYWQHMR-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
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- 229960004375 ciclopirox olamine Drugs 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
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- 238000001595 flow curve Methods 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008308 lipophilic cream Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000000399 optical microscopy Methods 0.000 description 2
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- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001587 sorbitan monostearate Substances 0.000 description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 description 2
- 229940035048 sorbitan monostearate Drugs 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 229920000148 Polycarbophil calcium Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
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- 239000008168 almond oil Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 229940043348 myristyl alcohol Drugs 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/345—Nitrofurans
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Reproductive Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gynecology & Obstetrics (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Oncology (AREA)
- Pregnancy & Childbirth (AREA)
- Tropical Medicine & Parasitology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Colloid Chemistry (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08166058.1 | 2008-10-08 | ||
| EP08166058A EP2174650A1 (en) | 2008-10-08 | 2008-10-08 | Modified release emulsions for application to skin or vaginal mucosa |
| PCT/EP2009/062190 WO2010040632A1 (en) | 2008-10-08 | 2009-09-21 | Modified release emulsions for application to skin or vaginal mucosa |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2737255A1 true CA2737255A1 (en) | 2010-04-15 |
Family
ID=40340663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2737255A Abandoned CA2737255A1 (en) | 2008-10-08 | 2009-09-21 | Modified release emulsions for application to skin or vaginal mucosa |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20110195944A1 (https=) |
| EP (2) | EP2174650A1 (https=) |
| JP (1) | JP2012505171A (https=) |
| KR (1) | KR20110067115A (https=) |
| CN (1) | CN102170862A (https=) |
| AR (1) | AR073801A1 (https=) |
| AU (1) | AU2009301275A1 (https=) |
| BR (1) | BRPI0920565A2 (https=) |
| CA (1) | CA2737255A1 (https=) |
| CL (1) | CL2011000767A1 (https=) |
| CO (1) | CO6361898A2 (https=) |
| EA (1) | EA201170555A1 (https=) |
| IL (1) | IL211681A0 (https=) |
| MA (1) | MA32687B1 (https=) |
| MX (1) | MX2011003696A (https=) |
| NZ (1) | NZ591919A (https=) |
| PE (1) | PE20110449A1 (https=) |
| WO (1) | WO2010040632A1 (https=) |
| ZA (1) | ZA201101818B (https=) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10286056B2 (en) * | 2011-01-27 | 2019-05-14 | Glaxosmithkline Biologicals S.A. | Adjuvant nanoemulsions with crystallisation inhibitors |
| US9056137B2 (en) | 2011-04-01 | 2015-06-16 | University Of Florida Research Foundation, Incorporated | Thermo-sensitive, mucoadhesive or dermoadhesive, and penetration-enhancing formulations for topical delivery of therapeutics |
| DE102011076869A1 (de) * | 2011-06-01 | 2012-12-06 | Beiersdorf Ag | Emulsionszubereitungen mit verbesserten rheologischen Eigenschaften |
| BR112014012444B1 (pt) | 2011-11-23 | 2021-12-14 | Therapeuticsmd, Inc | Composição farmacêutica compreendendo estradiol solubilizado, progesterona e um agente de solubilização, bem como usos desta para tratar um sintoma relacionado à menopausa em uma mulher |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| CN110075310A (zh) | 2011-12-20 | 2019-08-02 | 维奥姆治疗有限公司 | 用于治疗真菌感染的局部油组合物 |
| US20130338122A1 (en) | 2012-06-18 | 2013-12-19 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| WO2014167554A2 (en) * | 2013-04-12 | 2014-10-16 | Vyome Biosciences Pvt. Ltd. | Composition and formulation of antimicrobial agents, processes thereof and methods for treating microbial infections |
| CA2942345C (en) * | 2014-03-12 | 2020-12-01 | Warner Chilcott Company, Llc | Low-dose estradiol cream |
| RU2016143081A (ru) | 2014-05-22 | 2018-06-26 | Терапьютиксмд, Инк. | Натуральные комбинированные гормонозаместительные составы и терапии |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| US10286077B2 (en) | 2016-04-01 | 2019-05-14 | Therapeuticsmd, Inc. | Steroid hormone compositions in medium chain oils |
| US9931349B2 (en) | 2016-04-01 | 2018-04-03 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical composition |
| CA3040422A1 (en) * | 2016-10-13 | 2018-04-19 | Catalent U.K. Swindon Zydis Limited | Lyophilized pharmaceutical compositions for vaginal delivery |
| KR20200019735A (ko) * | 2017-06-22 | 2020-02-24 | 비라말 리미티드 | 약물 전달을 위한 조성물 및 그의 사용 방법 |
| WO2019213473A1 (en) | 2018-05-04 | 2019-11-07 | The Procter & Gamble Company | Compositions and methods for treating vaginal dryness |
| BR112021007877A2 (pt) | 2018-10-26 | 2021-08-03 | Viramal Limited | composição em gel mucoadesiva |
| EP3659583B1 (en) | 2018-11-30 | 2023-06-07 | Viramal Limited | A method of preparing a gelling agent, the gelling agent obtained thereby, and the use of said gelling agent |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE414511T1 (de) * | 2000-12-05 | 2008-12-15 | Los Angeles Childrens Hospital | Pharmazeutische zusammensetzungen von fenretinid mit erhöhter bioverfügbarkeit und verfahren zu deren verwendung |
| US20030228340A1 (en) * | 2002-04-04 | 2003-12-11 | Gans Eugene H. | Methods for treating rosacea with pyridones |
| US20060018937A1 (en) * | 2002-10-25 | 2006-01-26 | Foamix Ltd. | Steroid kit and foamable composition and uses thereof |
| US20060233721A1 (en) * | 2002-10-25 | 2006-10-19 | Foamix Ltd. | Foam containing unique oil globules |
| US20040087564A1 (en) * | 2002-10-31 | 2004-05-06 | Wright D. Craig | Delivery composition and method |
| CA2611577A1 (en) * | 2005-06-07 | 2007-09-07 | Foamix Ltd. | Antibiotic kit and composition and uses thereof |
| US20070071705A1 (en) * | 2005-09-29 | 2007-03-29 | De Oliveira Monica A M | Topical anti-microbial compositions |
| US20080075745A1 (en) * | 2006-09-21 | 2008-03-27 | Glenmark Pharmaceuticals Limited | Topical pharmaceutical compositions containing ciclopirox or a pharmaceutically acceptable salt thereof |
-
2008
- 2008-10-08 EP EP08166058A patent/EP2174650A1/en not_active Withdrawn
-
2009
- 2009-09-21 US US12/998,331 patent/US20110195944A1/en not_active Abandoned
- 2009-09-21 AU AU2009301275A patent/AU2009301275A1/en not_active Abandoned
- 2009-09-21 JP JP2011530445A patent/JP2012505171A/ja not_active Withdrawn
- 2009-09-21 BR BRPI0920565A patent/BRPI0920565A2/pt not_active IP Right Cessation
- 2009-09-21 KR KR1020117007601A patent/KR20110067115A/ko not_active Withdrawn
- 2009-09-21 NZ NZ591919A patent/NZ591919A/xx not_active IP Right Cessation
- 2009-09-21 EP EP09818802A patent/EP2331065A1/en not_active Withdrawn
- 2009-09-21 PE PE2011000670A patent/PE20110449A1/es not_active Application Discontinuation
- 2009-09-21 CN CN2009801391796A patent/CN102170862A/zh active Pending
- 2009-09-21 MX MX2011003696A patent/MX2011003696A/es unknown
- 2009-09-21 EA EA201170555A patent/EA201170555A1/ru unknown
- 2009-09-21 CA CA2737255A patent/CA2737255A1/en not_active Abandoned
- 2009-09-21 WO PCT/EP2009/062190 patent/WO2010040632A1/en not_active Ceased
- 2009-10-08 AR ARP090103886A patent/AR073801A1/es unknown
-
2011
- 2011-03-09 ZA ZA2011/01818A patent/ZA201101818B/en unknown
- 2011-03-10 IL IL211681A patent/IL211681A0/en unknown
- 2011-04-01 MA MA33736A patent/MA32687B1/fr unknown
- 2011-04-06 CL CL2011000767A patent/CL2011000767A1/es unknown
- 2011-04-07 CO CO11043013A patent/CO6361898A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2331065A1 (en) | 2011-06-15 |
| PE20110449A1 (es) | 2011-07-07 |
| JP2012505171A (ja) | 2012-03-01 |
| AR073801A1 (es) | 2010-12-01 |
| MX2011003696A (es) | 2011-06-20 |
| US20110195944A1 (en) | 2011-08-11 |
| AU2009301275A2 (en) | 2011-04-28 |
| CN102170862A (zh) | 2011-08-31 |
| NZ591919A (en) | 2012-09-28 |
| CL2011000767A1 (es) | 2011-06-17 |
| ZA201101818B (en) | 2012-05-30 |
| WO2010040632A1 (en) | 2010-04-15 |
| BRPI0920565A2 (pt) | 2015-12-29 |
| MA32687B1 (fr) | 2011-10-02 |
| IL211681A0 (en) | 2011-06-30 |
| KR20110067115A (ko) | 2011-06-21 |
| EA201170555A1 (ru) | 2011-12-30 |
| AU2009301275A1 (en) | 2010-04-15 |
| EP2174650A1 (en) | 2010-04-14 |
| CO6361898A2 (es) | 2012-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140923 |