CA2867749A1 - Vesicular formulations - Google Patents
Vesicular formulations Download PDFInfo
- Publication number
- CA2867749A1 CA2867749A1 CA2867749A CA2867749A CA2867749A1 CA 2867749 A1 CA2867749 A1 CA 2867749A1 CA 2867749 A CA2867749 A CA 2867749A CA 2867749 A CA2867749 A CA 2867749A CA 2867749 A1 CA2867749 A1 CA 2867749A1
- Authority
- CA
- Canada
- Prior art keywords
- formulation
- surfactant
- lipid
- buffer
- glycerol
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 406
- 238000009472 formulation Methods 0.000 title claims abstract description 400
- 201000004700 rosacea Diseases 0.000 claims abstract description 51
- 241001303601 Rosacea Species 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims description 188
- -1 phospho Chemical class 0.000 claims description 106
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 94
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 29
- 229920000053 polysorbate 80 Polymers 0.000 claims description 29
- 206010015150 Erythema Diseases 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 231100000321 erythema Toxicity 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 5
- 210000003462 vein Anatomy 0.000 claims description 5
- 239000006071 cream Substances 0.000 claims description 4
- 239000010408 film Substances 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- 239000006210 lotion Substances 0.000 claims description 4
- 229940068968 polysorbate 80 Drugs 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical class CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 324
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 315
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 303
- 150000002632 lipids Chemical class 0.000 description 202
- 239000000872 buffer Substances 0.000 description 138
- 239000003963 antioxidant agent Substances 0.000 description 135
- 235000006708 antioxidants Nutrition 0.000 description 135
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 130
- 239000002738 chelating agent Substances 0.000 description 122
- 239000004599 antimicrobial Substances 0.000 description 118
- 235000019445 benzyl alcohol Nutrition 0.000 description 105
- 229960004217 benzyl alcohol Drugs 0.000 description 105
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 104
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 103
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 103
- 229940034794 benzylparaben Drugs 0.000 description 103
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 103
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 103
- 235000011187 glycerol Nutrition 0.000 description 102
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 84
- 235000010262 sodium metabisulphite Nutrition 0.000 description 84
- 229940001584 sodium metabisulfite Drugs 0.000 description 83
- 230000000845 anti-microbial effect Effects 0.000 description 71
- 229910019142 PO4 Inorganic materials 0.000 description 70
- 239000010452 phosphate Substances 0.000 description 70
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 68
- 229920000136 polysorbate Polymers 0.000 description 52
- 230000003078 antioxidant effect Effects 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 45
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 38
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 38
- 125000000217 alkyl group Chemical group 0.000 description 21
- 150000003904 phospholipids Chemical class 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000008389 polyethoxylated castor oil Substances 0.000 description 14
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 150000008104 phosphatidylethanolamines Chemical group 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 12
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 11
- 230000002354 daily effect Effects 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 229940033663 thimerosal Drugs 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 238000011010 flushing procedure Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000013543 active substance Substances 0.000 description 9
- 239000002537 cosmetic Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 150000003905 phosphatidylinositols Chemical class 0.000 description 9
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 8
- ATMNQRRJNBCQJO-UHFFFAOYSA-N 4-hexoxy-2,3,6-trimethylphenol Chemical compound CCCCCCOC1=CC(C)=C(O)C(C)=C1C ATMNQRRJNBCQJO-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 208000002874 Acne Vulgaris Diseases 0.000 description 7
- 206010000496 acne Diseases 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000002736 nonionic surfactant Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 7
- 230000001052 transient effect Effects 0.000 description 7
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 6
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 6
- 239000003974 emollient agent Substances 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 230000003641 microbiacidal effect Effects 0.000 description 6
- 229940124561 microbicide Drugs 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000000232 Lipid Bilayer Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 230000001815 facial effect Effects 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 229940049964 oleate Drugs 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
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- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- 125000006413 ring segment Chemical group 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
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- LRYZPFWEZHSTHD-HEFFAWAOSA-O 2-[[(e,2s,3r)-2-formamido-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical class CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](NC=O)COP(O)(=O)OCC[N+](C)(C)C LRYZPFWEZHSTHD-HEFFAWAOSA-O 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 206010016260 Fatty acid deficiency Diseases 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
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- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 239000004098 Tetracycline Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
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- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
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- QRYRORQUOLYVBU-VBKZILBWSA-N carnosic acid Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C(O)=O)C1=C2C=C(C(C)C)C(O)=C1O QRYRORQUOLYVBU-VBKZILBWSA-N 0.000 description 3
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
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- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 description 3
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 2
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- WJXSWCUQABXPFS-UHFFFAOYSA-N 3-hydroxyanthranilic acid Chemical compound NC1=C(O)C=CC=C1C(O)=O WJXSWCUQABXPFS-UHFFFAOYSA-N 0.000 description 2
- VCKPUUFAIGNJHC-UHFFFAOYSA-N 3-hydroxykynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(O)=C1N VCKPUUFAIGNJHC-UHFFFAOYSA-N 0.000 description 2
- FUYCAQNCWDAOLQ-UHFFFAOYSA-N 4,8,12-trimethyltridecanoic acid Chemical compound CC(C)CCCC(C)CCCC(C)CCC(O)=O FUYCAQNCWDAOLQ-UHFFFAOYSA-N 0.000 description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
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- 125000001536 trans-vaccenoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
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- A61K31/66—Phosphorus compounds
- A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K31/688—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols both hydroxy compounds having nitrogen atoms, e.g. sphingomyelins
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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- 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
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Public Health (AREA)
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- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Materials For Medical Uses (AREA)
- Fodder In General (AREA)
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| PCT/EP2013/056694 WO2013144289A1 (en) | 2012-03-29 | 2013-03-28 | Vesicular formulations |
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| CA2867749A1 true CA2867749A1 (en) | 2013-10-03 |
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| JP (1) | JP2015511618A (https=) |
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| CA (1) | CA2867749A1 (https=) |
| CL (1) | CL2014002547A1 (https=) |
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| EA (1) | EA038899B1 (https=) |
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| PH (1) | PH12014502065A1 (https=) |
| SG (1) | SG11201406144TA (https=) |
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| BR112012003834A2 (pt) | 2009-08-21 | 2017-08-08 | Targeted Delivery Tech Limited | métodos para tratamento de distúrbios e para tratamentos de deficiências em ácidos graxos, hipertrigliceridemia ou hipercolesterolemia e pacote |
| WO2016102683A1 (en) * | 2014-12-23 | 2016-06-30 | Camurus Ab | Controlled-release formulations |
| PL3316856T3 (pl) | 2015-06-30 | 2021-10-25 | Sequessome Technology Holdings Limited | Zmieszane formulacje |
| EP3681479B1 (en) | 2017-09-15 | 2024-01-31 | Dyve Biosciences, Inc. | Sodium bicarbonate for use in the treatment of gout and related disorders |
| US20240299378A1 (en) * | 2021-02-25 | 2024-09-12 | Exinov | Emulsion for use in the treatment of rosacea |
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| JPS60136511A (ja) | 1983-12-26 | 1985-07-20 | Eisai Co Ltd | 高尿酸血症治療剤 |
| WO1987001938A1 (en) | 1985-09-27 | 1987-04-09 | The Regents Of The University Of California | Liposome transdermal drug delivery system |
| JPS6295134A (ja) | 1985-10-21 | 1987-05-01 | Nippon Saafuakutanto Kogyo Kk | リポソ−ムの製造法 |
| US5015483A (en) | 1989-02-09 | 1991-05-14 | Nabisco Brands, Inc. | Liposome composition for the stabilization of oxidizable substances |
| US5498607A (en) | 1990-07-30 | 1996-03-12 | University Of Miami | Treatment for hypercholesterolemia |
| US6165500A (en) | 1990-08-24 | 2000-12-26 | Idea Ag | Preparation for the application of agents in mini-droplets |
| JP3765579B2 (ja) | 1990-08-24 | 2006-04-12 | イーデーエーアー アーゲー | 作用物質投与用超微小滴状調剤 |
| US5498420A (en) | 1991-04-12 | 1996-03-12 | Merz & Co. Gmbh & Co. | Stable small particle liposome preparations, their production and use in topical cosmetic, and pharmaceutical compositions |
| EP0648114B1 (de) | 1992-07-08 | 1997-09-17 | DIANORM G. Maierhofer GmbH | Liposomen, verfahren zu ihrer herstellung und ihre verwendung zur herstellung eines arzneimittels |
| FR2714382B1 (fr) | 1993-12-27 | 1996-02-02 | Roussel Uclaf | Phospholipides vecteur de molécule active, leur préparation et leur utilisation dans des compositions cosmétiques ou dermatologiques. |
| DE4447287C1 (de) | 1994-12-30 | 1996-11-07 | Cevc Gregor | Präparat zum Wirkstofftransport durch Barrieren |
| US5902604A (en) | 1995-06-06 | 1999-05-11 | Board Of Regents, The University Of Texas System | Submicron liposome suspensions obtained from preliposome lyophilizates |
| FR2767691B1 (fr) | 1997-08-27 | 2000-02-18 | Oreal | Utilisation d'une dispersion a base de vehicules lipidiques comme composition anti-inflammatoire |
| ATE210438T1 (de) * | 1997-11-19 | 2001-12-15 | Schering Ag | Zusammensetzung mit azelainsäure |
| US6165997A (en) | 1997-11-20 | 2000-12-26 | Statens Serum Institut | Phospholipids having antimicrobial activity with or without the presence of antimicrobials |
| MXPA01002149A (es) | 1998-09-01 | 2003-03-27 | Idea Ag | Transporte electricamente controlado de penetrantes cargados a traves de barreras. |
| JP2002533379A (ja) | 1998-12-23 | 2002-10-08 | イデア アクチェンゲゼルシャフト | 生体内における局所的に非侵襲性である用途のための改善された製剤 |
| ATE216875T1 (de) | 1999-01-27 | 2002-05-15 | Idea Ag | Nichtinvasive impfung durch die haut |
| US6294192B1 (en) | 1999-02-26 | 2001-09-25 | Lipocine, Inc. | Triglyceride-free compositions and methods for improved delivery of hydrophobic therapeutic agents |
| WO2001001962A1 (en) | 1999-07-05 | 2001-01-11 | Idea Ag. | A method for the improvement of transport across adaptable semi-permeable barriers |
| US6248728B1 (en) | 2000-03-10 | 2001-06-19 | Kansas State University Research Foundation | Phosphatidylcholine compositions and methods for lowering intestinal absorption and plasma levels of cholesterol |
| US6191121B1 (en) * | 2000-04-06 | 2001-02-20 | Nicholas V. Perricone | Treatment of skin damage using polyenylphosphatidylcholine |
| ES2270991T3 (es) | 2000-04-12 | 2007-04-16 | Liplasome Pharma A/S | Sistemas basados en lipidos para el direccionado de agentes de diagnostico. |
| TWI281407B (en) | 2000-09-18 | 2007-05-21 | Vasogen Ireland Ltd | Apoptosis-mimicking synthetic entities and use thereof in medical treatment |
| US20030064948A1 (en) | 2001-02-08 | 2003-04-03 | Alfred Fahr | Invasomes for therapy of disorders, their preparation and use |
| KR20040033286A (ko) | 2001-05-31 | 2004-04-21 | 파마시아 코포레이션 | 선택적인 사이클로옥시게나제-2 억제제 및 1가 알콜을포함하는 피부-침투성 조성물 |
| CA2451245A1 (en) | 2001-06-25 | 2003-01-03 | Depuy International Limited | Liposomal encapsulation of glycosaminoglycans for the treatment of arthritic joints |
| CA2368656A1 (en) | 2002-01-21 | 2003-07-21 | Vasogen Ireland Limited | Receptor-ligand pairing for anti-inflammatory response |
| AU2003233396B2 (en) | 2002-03-13 | 2007-05-24 | Thomas Skold | Water-based delivery systems |
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| US20040105881A1 (en) | 2002-10-11 | 2004-06-03 | Gregor Cevc | Aggregates with increased deformability, comprising at least three amphipats, for improved transport through semi-permeable barriers and for the non-invasive drug application in vivo, especially through the skin |
| AU2003273977B2 (en) | 2002-10-11 | 2007-07-12 | Idea Ag | Aggregate with increased deformability, comprising at least three amphipats, for improved transport through semi-permeable barriers and for the non-invasive drug application in vivo, especially through the skin |
| JP2004131432A (ja) | 2002-10-11 | 2004-04-30 | Kumamoto Technology & Industry Foundation | 悪性腫瘍抑制剤 |
| WO2004098524A2 (en) | 2003-05-02 | 2004-11-18 | Aronex Pharmaceuticals, Inc. | Lipid platinum complexes and methods of use thereof |
| AU2004257375A1 (en) | 2003-07-21 | 2005-01-27 | Vasogen Ireland Limited | Liposomes containing phosphate glycerol groups for treating acute inflammatory condition |
| JP2005179313A (ja) * | 2003-12-24 | 2005-07-07 | Shu Uemura:Kk | 皮膚化粧料用基剤の製造方法および皮膚化粧料 |
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| CA2634139C (en) | 2005-12-20 | 2015-06-23 | Cenestra, Llc. | Omega 3 fatty acid formulations |
| JP5009547B2 (ja) * | 2006-03-31 | 2012-08-22 | 株式会社コーセー | 顔料とリポソームを含む化粧料 |
| US7544375B1 (en) | 2006-06-12 | 2009-06-09 | Swiss Skin Repair, Inc. | Composition |
| ES2599630T3 (es) | 2006-09-28 | 2017-02-02 | Hadasit Medical Research Services & Development Limited | Uso de glicerofosfolípidos para lubricación de las articulaciones |
| JP4732307B2 (ja) * | 2006-11-20 | 2011-07-27 | 株式会社アンズコーポレーション | ナノエマルション及びそれを配合した化粧料 |
| US20100130611A1 (en) | 2006-12-20 | 2010-05-27 | Cenestra Llc | Omega 3 fatty acid formulations |
| EP1938801A1 (en) | 2006-12-22 | 2008-07-02 | Biofrontera Bioscience GmbH | Nanoemulsion |
| US9511016B2 (en) | 2007-06-12 | 2016-12-06 | Epicentrx, Inc. | Topical composition for treating pain |
| ITVR20080006A1 (it) | 2008-01-23 | 2009-07-24 | David Ceretta | Apparato per la realizzazione di elementi d'impasto |
| ES2335636B1 (es) | 2008-02-29 | 2011-05-11 | Lipotec, S.A. | Composicion cosmetica o dermofarmaceutica de micelas mixtas. |
| JP2009256331A (ja) | 2008-03-25 | 2009-11-05 | Nagase Chemtex Corp | 高尿酸血症、又は痛風の予防、改善、又は治療剤 |
| US20100105139A1 (en) | 2008-10-27 | 2010-04-29 | Remco Alexander Spanjaard | Ligand Targeted Nanocapsules for the delivery of RNAi and other Agents |
| MX2011008204A (es) | 2009-02-05 | 2011-12-06 | Targeted Delivery Technologies Ltd | Metodos para reducir la proliferacion y viabilidad de los agentes microbianos. |
| MX349417B (es) | 2009-06-03 | 2017-07-28 | Charles Mayo John | Formulaciones para el tratamiento de dolor de tejido profundo. |
| BR112012003834A2 (pt) | 2009-08-21 | 2017-08-08 | Targeted Delivery Tech Limited | métodos para tratamento de distúrbios e para tratamentos de deficiências em ácidos graxos, hipertrigliceridemia ou hipercolesterolemia e pacote |
| EP2382994A1 (en) | 2010-04-26 | 2011-11-02 | Maurizio Victor Cattaneo | Ligand targeted nanocapsules for the delivery of RNAi and other agents |
| WO2011162802A1 (en) | 2010-06-21 | 2011-12-29 | Virun, Inc. | Compositions containing non-polar compounds |
| US20120045405A1 (en) | 2010-08-18 | 2012-02-23 | Gilman Miles E | Under eye cream |
| GB201206486D0 (en) | 2012-04-12 | 2012-05-30 | Sequessome Technology Holdings Ltd | Vesicular formulations and uses thereof |
| GB201208384D0 (en) | 2012-05-14 | 2012-06-27 | Sequessome Technology Holdings Ltd | Vesicular formulations, uses and methods |
| GB201208409D0 (en) | 2012-05-14 | 2012-06-27 | Sequessome Technology Holdings Ltd | Vesicular formulations, kits and uses |
| CN114949237A (zh) | 2013-07-31 | 2022-08-30 | 斯昆申技术控股有限责任公司 | 囊泡 |
-
2012
- 2012-03-29 GB GBGB1205642.0A patent/GB201205642D0/en not_active Ceased
-
2013
- 2013-03-28 MX MX2014011516A patent/MX2014011516A/es unknown
- 2013-03-28 EP EP13712801.3A patent/EP2830630A1/en not_active Ceased
- 2013-03-28 US US14/388,469 patent/US9555051B2/en not_active Expired - Fee Related
- 2013-03-28 AU AU2013241701A patent/AU2013241701A1/en not_active Abandoned
- 2013-03-28 JP JP2015502351A patent/JP2015511618A/ja active Pending
- 2013-03-28 CA CA2867749A patent/CA2867749A1/en not_active Abandoned
- 2013-03-28 SG SG11201406144TA patent/SG11201406144TA/en unknown
- 2013-03-28 IN IN7913DEN2014 patent/IN2014DN07913A/en unknown
- 2013-03-28 WO PCT/EP2013/056694 patent/WO2013144289A1/en not_active Ceased
- 2013-03-28 GB GB1419075.5A patent/GB2515440B/en not_active Expired - Fee Related
- 2013-03-28 CN CN201380027033.9A patent/CN104349782A/zh active Pending
- 2013-03-28 BR BR112014024033A patent/BR112014024033A8/pt not_active IP Right Cessation
- 2013-03-28 NZ NZ700472A patent/NZ700472A/en not_active IP Right Cessation
- 2013-03-28 KR KR1020147027498A patent/KR20150004798A/ko not_active Withdrawn
- 2013-03-28 EA EA201491581A patent/EA038899B1/ru unknown
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2014
- 2014-09-17 PH PH12014502065A patent/PH12014502065A1/en unknown
- 2014-09-18 IL IL234747A patent/IL234747A0/en unknown
- 2014-09-25 CL CL2014002547A patent/CL2014002547A1/es unknown
- 2014-10-28 CO CO14238690A patent/CO7121334A2/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CL2014002547A1 (es) | 2015-03-27 |
| GB2515440A (en) | 2014-12-24 |
| JP2015511618A (ja) | 2015-04-20 |
| EA038899B1 (ru) | 2021-11-03 |
| IL234747A0 (en) | 2014-11-30 |
| BR112014024033A2 (https=) | 2017-06-20 |
| MX2014011516A (es) | 2015-04-08 |
| US20150057249A1 (en) | 2015-02-26 |
| NZ700472A (en) | 2016-02-26 |
| GB201205642D0 (en) | 2012-05-16 |
| GB2515440B (en) | 2017-02-08 |
| KR20150004798A (ko) | 2015-01-13 |
| BR112014024033A8 (pt) | 2017-07-25 |
| EP2830630A1 (en) | 2015-02-04 |
| IN2014DN07913A (https=) | 2015-04-24 |
| WO2013144289A1 (en) | 2013-10-03 |
| CO7121334A2 (es) | 2014-11-20 |
| CN104349782A (zh) | 2015-02-11 |
| AU2013241701A1 (en) | 2014-10-16 |
| US9555051B2 (en) | 2017-01-31 |
| EA201491581A1 (ru) | 2015-02-27 |
| SG11201406144TA (en) | 2014-10-30 |
| PH12014502065A1 (en) | 2014-12-10 |
| GB201419075D0 (en) | 2014-12-10 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
Effective date: 20190328 |