JP2016512562A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016512562A5 JP2016512562A5 JP2016501962A JP2016501962A JP2016512562A5 JP 2016512562 A5 JP2016512562 A5 JP 2016512562A5 JP 2016501962 A JP2016501962 A JP 2016501962A JP 2016501962 A JP2016501962 A JP 2016501962A JP 2016512562 A5 JP2016512562 A5 JP 2016512562A5
- Authority
- JP
- Japan
- Prior art keywords
- oil
- api
- pharmaceutical composition
- eye
- pharmaceutical
- 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.)
- Granted
Links
- 239000004530 micro-emulsion Substances 0.000 claims description 91
- 239000004094 surface-active agent Substances 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 81
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000003921 oil Substances 0.000 claims description 59
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 51
- 229920000136 polysorbate Polymers 0.000 claims description 49
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 44
- 239000003937 drug carrier Substances 0.000 claims description 44
- 229960002297 fenofibrate Drugs 0.000 claims description 44
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims description 44
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 39
- 239000008389 polyethoxylated castor oil Substances 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 31
- 229950008882 polysorbate Drugs 0.000 claims description 28
- 229960000701 fenofibric acid Drugs 0.000 claims description 26
- MQOBSOSZFYZQOK-UHFFFAOYSA-N fenofibric acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 MQOBSOSZFYZQOK-UHFFFAOYSA-N 0.000 claims description 26
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 26
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 23
- 238000011200 topical administration Methods 0.000 claims description 22
- 208000030533 eye disease Diseases 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 239000003889 eye drop Substances 0.000 claims description 16
- 229960005150 glycerol Drugs 0.000 claims description 14
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 claims description 11
- 208000022873 Ocular disease Diseases 0.000 claims description 10
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 10
- 208000002780 macular degeneration Diseases 0.000 claims description 10
- 229940057917 medium chain triglycerides Drugs 0.000 claims description 9
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 8
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229940068965 polysorbates Drugs 0.000 claims description 8
- 229960004063 propylene glycol Drugs 0.000 claims description 6
- 208000002691 Choroiditis Diseases 0.000 claims description 5
- 208000001344 Macular Edema Diseases 0.000 claims description 5
- 206010025415 Macular oedema Diseases 0.000 claims description 5
- 201000010183 Papilledema Diseases 0.000 claims description 5
- 208000003971 Posterior uveitis Diseases 0.000 claims description 5
- 206010038886 Retinal oedema Diseases 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 201000010230 macular retinal edema Diseases 0.000 claims description 5
- 201000011195 retinal edema Diseases 0.000 claims description 5
- 208000004644 retinal vein occlusion Diseases 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 claims description 4
- WEBILLRFBZTUIX-BTJKTKAUSA-N 2-(1-adamantyl)ethyl 2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetate;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC(OCC(O)CNC(C)C)=CC=C1CC(=O)OCCC1(C2)CC(C3)CC2CC3C1 WEBILLRFBZTUIX-BTJKTKAUSA-N 0.000 claims description 4
- 229930105110 Cyclosporin A Natural products 0.000 claims description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 4
- 108010036949 Cyclosporine Proteins 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 claims description 4
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 210000004027 cell Anatomy 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- -1 immunoregulator Substances 0.000 claims description 4
- 229960000905 indomethacin Drugs 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 229960002509 miconazole Drugs 0.000 claims description 4
- 229960001416 pilocarpine Drugs 0.000 claims description 4
- 229960002702 piroxicam Drugs 0.000 claims description 4
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002464 receptor antagonist Substances 0.000 claims description 4
- 229940044551 receptor antagonist Drugs 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229960001265 ciclosporin Drugs 0.000 claims description 3
- 210000003630 histaminocyte Anatomy 0.000 claims description 3
- 229940118169 Prostaglandin receptor agonist Drugs 0.000 claims description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 230000001028 anti-proliverative effect Effects 0.000 claims description 2
- 239000000043 antiallergic agent Substances 0.000 claims description 2
- 239000000739 antihistaminic agent Substances 0.000 claims description 2
- 239000002220 antihypertensive agent Substances 0.000 claims description 2
- 229940030600 antihypertensive agent Drugs 0.000 claims description 2
- 229960005475 antiinfective agent Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 2
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940043355 kinase inhibitor Drugs 0.000 claims description 2
- 239000000472 muscarinic agonist Substances 0.000 claims description 2
- 239000004090 neuroprotective agent Substances 0.000 claims description 2
- 239000002522 prostaglandin receptor stimulating agent Substances 0.000 claims description 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 claims description 2
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 claims 1
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 1
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims 1
- 206010027646 Miosis Diseases 0.000 claims 1
- 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 claims 1
- 239000000332 adrenergic beta-1 receptor antagonist Substances 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 230000003547 miosis Effects 0.000 claims 1
- 238000009472 formulation Methods 0.000 description 46
- 235000019198 oils Nutrition 0.000 description 44
- 210000001508 eye Anatomy 0.000 description 40
- 239000007908 nanoemulsion Substances 0.000 description 25
- 239000001087 glyceryl triacetate Substances 0.000 description 13
- 229960002622 triacetin Drugs 0.000 description 13
- 235000011187 glycerol Nutrition 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 210000001525 retina Anatomy 0.000 description 10
- 210000001742 aqueous humor Anatomy 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 229940075495 isopropyl palmitate Drugs 0.000 description 8
- 238000009826 distribution Methods 0.000 description 7
- 229940012356 eye drops Drugs 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 6
- 210000003583 retinal pigment epithelium Anatomy 0.000 description 6
- RROLKYCVTJGMND-UHFFFAOYSA-N 1-acetyl-5-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2C(=O)C RROLKYCVTJGMND-UHFFFAOYSA-N 0.000 description 5
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 210000000695 crystalline len Anatomy 0.000 description 5
- 229940074928 isopropyl myristate Drugs 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 210000003786 sclera Anatomy 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 210000005252 bulbus oculi Anatomy 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000010587 phase diagram Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000007910 systemic administration Methods 0.000 description 3
- 210000004127 vitreous body Anatomy 0.000 description 3
- 208000002177 Cataract Diseases 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- 206010025421 Macule Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 208000000208 Wet Macular Degeneration Diseases 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008499 blood brain barrier function Effects 0.000 description 2
- 210000001218 blood-brain barrier Anatomy 0.000 description 2
- 210000004155 blood-retinal barrier Anatomy 0.000 description 2
- 230000004378 blood-retinal barrier Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 210000003161 choroid Anatomy 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 208000011325 dry age related macular degeneration Diseases 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000000981 epithelium Anatomy 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 210000000554 iris Anatomy 0.000 description 2
- 206010023332 keratitis Diseases 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 210000001328 optic nerve Anatomy 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229940068977 polysorbate 20 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 210000001210 retinal vessel Anatomy 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 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 2
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- XLMXUUQMSMKFMH-UZRURVBFSA-N 2-hydroxyethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCO XLMXUUQMSMKFMH-UZRURVBFSA-N 0.000 description 1
- 108700028490 CAP protocol 2 Proteins 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000005590 Choroidal Neovascularization Diseases 0.000 description 1
- 206010060823 Choroidal neovascularisation Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010010996 Corneal degeneration Diseases 0.000 description 1
- 206010055665 Corneal neovascularisation Diseases 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 208000005100 Herpetic Keratitis Diseases 0.000 description 1
- 201000002287 Keratoconus Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010073938 Ophthalmic herpes simplex Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 241000282485 Vulpes vulpes Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 description 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 102000016967 beta-1 Adrenergic Receptors Human genes 0.000 description 1
- 108010014494 beta-1 Adrenergic Receptors Proteins 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 201000000159 corneal neovascularization Diseases 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009513 drug distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- 229960002143 fluorescein Drugs 0.000 description 1
- 238000013534 fluorescein angiography Methods 0.000 description 1
- 229940020947 fluorescein sodium Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 201000010884 herpes simplex virus keratitis Diseases 0.000 description 1
- 210000004276 hyalin Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 229940124644 immune regulator Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000004410 intraocular pressure Effects 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 201000010666 keratoconjunctivitis Diseases 0.000 description 1
- 208000029515 lens disease Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361784005P | 2013-03-14 | 2013-03-14 | |
| US61/784,005 | 2013-03-14 | ||
| PCT/US2014/025773 WO2014160079A1 (en) | 2013-03-14 | 2014-03-13 | Microemulsion topical delivery platform |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016512562A JP2016512562A (ja) | 2016-04-28 |
| JP2016512562A5 true JP2016512562A5 (enExample) | 2017-02-23 |
| JP6348567B2 JP6348567B2 (ja) | 2018-06-27 |
Family
ID=50628949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016501962A Active JP6348567B2 (ja) | 2013-03-14 | 2014-03-13 | マイクロエマルジョン局所送達プラットフォーム |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8968775B2 (enExample) |
| EP (1) | EP2968139B1 (enExample) |
| JP (1) | JP6348567B2 (enExample) |
| CN (1) | CN105451718B (enExample) |
| AU (1) | AU2014244154B2 (enExample) |
| CA (1) | CA2905023C (enExample) |
| DK (1) | DK2968139T3 (enExample) |
| ES (1) | ES2673009T3 (enExample) |
| PL (1) | PL2968139T3 (enExample) |
| PT (1) | PT2968139T (enExample) |
| TR (1) | TR201808197T4 (enExample) |
| WO (1) | WO2014160079A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2007272839B2 (en) | 2006-07-13 | 2012-05-24 | Achillion Pharmaceuticals, Inc. | 4-amino-4-oxobutanoyl peptides as inhibitors of viral replication |
| ES2584534B1 (es) * | 2015-03-27 | 2017-03-13 | Retinset, S.L. | Formulación tópica oftálmica de bosentan |
| EP3405183A4 (en) | 2016-01-18 | 2019-12-11 | Arisan Therapeutics Inc. | ADAMATE DERIVATIVES FOR TREATING A FILOVIRUS INFECTION |
| ES2706535T3 (es) * | 2016-07-07 | 2019-03-29 | Salvat Lab Sa | Composiciones oftálmicas que comprenden aceite de ricino y triglicéridos de cadena media |
| US11548893B2 (en) | 2017-07-15 | 2023-01-10 | Arisan Therapeutics Inc. | Enantiomerically pure adamantane carboxamides for the treatment of filovirus infection |
| EP3672587A4 (en) * | 2017-08-27 | 2021-05-19 | Rhodes Technologies | PHARMACEUTICAL COMPOSITIONS INTENDED FOR THE TREATMENT OF OPHTHALMIC DISORDERS |
| US11583497B2 (en) | 2017-11-14 | 2023-02-21 | The Schepens Eye Research Institute, Inc. | Nano-emulsion of CBFß-RUNX1 inhibitor for ocular drug delivery |
| CN114245737A (zh) | 2019-06-11 | 2022-03-25 | 司斐股份有限公司 | 微乳剂组合物 |
| EP3998063A4 (en) * | 2019-07-08 | 2023-03-15 | MORESCO Corporation | Compositions for preparing microemulsion, microemulsion, method for producing composition and microemulsion, and use of microemulsion |
| US20240415796A1 (en) * | 2020-11-19 | 2024-12-19 | Nihon University | Eyedrops for ameliorating or preventing retinal circulation disorder and retinal neurovascular coupling disorder |
| ES3032065T3 (en) * | 2021-10-01 | 2025-07-15 | Univ South Africa | A nano emulsified phyto-drug for transdermal treatment of diabetes |
| CN119789854A (zh) * | 2023-08-04 | 2025-04-08 | Ads医疗有限责任公司 | 用于递送眼科活性物的组合物和方法 |
| WO2025090133A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Compositions and methods for use of cannabinol compounds in neuroprotection |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI398261B (zh) * | 2003-12-17 | 2013-06-11 | Alcon Inc | 血清類澱粉ａ基因於診斷及治療青光眼及鑑定抗青光眼劑上之用途 |
| US7569612B1 (en) * | 2006-08-21 | 2009-08-04 | Mutual Pharmaceutical Company, Inc. | Methods of use of fenofibric acid |
| US20090082470A1 (en) * | 2007-09-24 | 2009-03-26 | Rafal Farjo | Stat3 inhibiting compositions and methods |
| US8652443B2 (en) * | 2008-02-14 | 2014-02-18 | Precision Dermatology, Inc. | Foamable microemulsion compositions for topical administration |
| CA2827082A1 (en) * | 2011-02-11 | 2012-08-16 | Psivida Us, Inc. | Methods of treating macular edema using antiedema therapeutics |
| WO2013049621A1 (en) * | 2011-09-29 | 2013-04-04 | The Board Of Regents Of The University Of Oklahoma | Ophthalmic compositions comprising ppar-alpha agonists and methods of production and use thereof |
-
2014
- 2014-03-13 DK DK14720786.4T patent/DK2968139T3/en active
- 2014-03-13 JP JP2016501962A patent/JP6348567B2/ja active Active
- 2014-03-13 WO PCT/US2014/025773 patent/WO2014160079A1/en not_active Ceased
- 2014-03-13 TR TR2018/08197T patent/TR201808197T4/tr unknown
- 2014-03-13 AU AU2014244154A patent/AU2014244154B2/en active Active
- 2014-03-13 PT PT147207864T patent/PT2968139T/pt unknown
- 2014-03-13 CN CN201480027477.7A patent/CN105451718B/zh active Active
- 2014-03-13 EP EP14720786.4A patent/EP2968139B1/en active Active
- 2014-03-13 CA CA2905023A patent/CA2905023C/en active Active
- 2014-03-13 PL PL14720786T patent/PL2968139T3/pl unknown
- 2014-03-13 ES ES14720786.4T patent/ES2673009T3/es active Active
- 2014-03-14 US US14/212,675 patent/US8968775B2/en active Active - Reinstated
-
2015
- 2015-02-24 US US14/630,073 patent/US9149453B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6348567B2 (ja) | マイクロエマルジョン局所送達プラットフォーム | |
| JP2016512562A5 (enExample) | ||
| JP7547411B2 (ja) | 局所用シクロスポリン含有製剤およびその使用 | |
| JP5441058B2 (ja) | 四級アンモニウム化合物を含む組成物 | |
| JP7496778B2 (ja) | チモロールを含む医薬組成物 | |
| JP7353292B2 (ja) | ネビボロールを含む医薬組成物 | |
| US20210085603A1 (en) | Microemulsion for opthalmic drug delivery | |
| KR101587412B1 (ko) | 사이클로스포린 및 트레할로스를 포함하는 안과용 조성물 | |
| JP7669326B2 (ja) | 局所製剤およびその使用 | |
| JP2017519813A (ja) | 局所製剤およびその使用 | |
| JP2018532809A5 (enExample) | ||
| KR20150000405A (ko) | 난용성 의약품의 수중유적형 에멀젼 조성물 및 이의 제조방법 | |
| CN116898800A (zh) | 无防腐剂的眼科药物乳剂及其应用 | |
| Ansari | Self-Nano Emulsifying Drug delivery system (SNEEDS) for Ocular Administration | |
| KR101151235B1 (ko) | 나노에멀젼 형태의 안과용 조성물 | |
| US20140302099A1 (en) | Ophthalmic Composition Containing Cyclosporine And method For Preparing Same | |
| Acharya | Development and Evaluation of Liquid Crystalline Cubogel for Ocular Delivery of Anti-glaucoma Agents | |
| HK40044057A (en) | Pharmaceutical compositions comprising nebivolol | |
| HK40044057B (zh) | 包含奈必洛尔的药物组合物 | |
| Khodakiya | Formulation Design and Optimization of topical Microemulsion in Situ Gelling System: Drug Delivery to Posterior Segment of the Eye |