JP6463902B2 - 眼科薬送達のための安定したリポソーム製剤 - Google Patents
眼科薬送達のための安定したリポソーム製剤 Download PDFInfo
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- JP6463902B2 JP6463902B2 JP2014094096A JP2014094096A JP6463902B2 JP 6463902 B2 JP6463902 B2 JP 6463902B2 JP 2014094096 A JP2014094096 A JP 2014094096A JP 2014094096 A JP2014094096 A JP 2014094096A JP 6463902 B2 JP6463902 B2 JP 6463902B2
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- latanoprost
- liposome
- popc
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- liposomes
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- 238000009472 formulation Methods 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title claims description 27
- 238000012377 drug delivery Methods 0.000 title description 3
- 239000003732 agents acting on the eye Substances 0.000 title description 2
- 229940023490 ophthalmic product Drugs 0.000 title description 2
- 239000002502 liposome Substances 0.000 claims description 52
- 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 38
- 239000003814 drug Substances 0.000 claims description 37
- GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 claims description 35
- 229960001160 latanoprost Drugs 0.000 claims description 35
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 12
- 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 description 11
- 208000010412 Glaucoma Diseases 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 238000012384 transportation and delivery Methods 0.000 claims description 7
- 206010030043 Ocular hypertension Diseases 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 229960002470 bimatoprost Drugs 0.000 claims description 2
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 claims description 2
- DLJKPYFALUEJCK-MRVZPHNRSA-N carboprost Chemical compound CCCCC[C@](C)(O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O DLJKPYFALUEJCK-MRVZPHNRSA-N 0.000 claims description 2
- 229960003395 carboprost Drugs 0.000 claims description 2
- 229960002368 travoprost Drugs 0.000 claims description 2
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 claims description 2
- 208000022873 Ocular disease Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 description 30
- 230000004410 intraocular pressure Effects 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 7
- 239000003889 eye drop Substances 0.000 description 7
- 208000030533 eye disease Diseases 0.000 description 6
- 229940012356 eye drops Drugs 0.000 description 6
- 241000282567 Macaca fascicularis Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000002969 egg yolk Anatomy 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000002322 Egg Proteins Human genes 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 235000013345 egg yolk Nutrition 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000007726 management method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 2
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- 239000000232 Lipid Bilayer Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229960003299 ketamine Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 229940072358 xylocaine Drugs 0.000 description 2
- FQRHOOHLUYHMGG-BTJKTKAUSA-N 3-(2-acetylphenothiazin-10-yl)propyl-dimethylazanium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound OC(=O)\C=C/C(O)=O.C1=C(C(C)=O)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 FQRHOOHLUYHMGG-BTJKTKAUSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000446313 Lamella Species 0.000 description 1
- 208000023715 Ocular surface disease Diseases 0.000 description 1
- 206010061323 Optic neuropathy Diseases 0.000 description 1
- BGDKAVGWHJFAGW-UHFFFAOYSA-N Tropicamide Chemical compound C=1C=CC=CC=1C(CO)C(=O)N(CC)CC1=CC=NC=C1 BGDKAVGWHJFAGW-UHFFFAOYSA-N 0.000 description 1
- 206010047571 Visual impairment Diseases 0.000 description 1
- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
- 229960001946 acepromazine maleate Drugs 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001384 anti-glaucoma Effects 0.000 description 1
- 229960002028 atropine sulfate Drugs 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 210000004240 ciliary body Anatomy 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003560 epithelium corneal Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000001328 optic nerve Anatomy 0.000 description 1
- 208000020911 optic nerve disease Diseases 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229960003733 phenylephrine hydrochloride Drugs 0.000 description 1
- OCYSGIYOVXAGKQ-FVGYRXGTSA-N phenylephrine hydrochloride Chemical compound [H+].[Cl-].CNC[C@H](O)C1=CC=CC(O)=C1 OCYSGIYOVXAGKQ-FVGYRXGTSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000013439 planning Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 238000011277 treatment modality Methods 0.000 description 1
- 229960004791 tropicamide Drugs 0.000 description 1
- 239000002691 unilamellar liposome Substances 0.000 description 1
- 208000029257 vision disease Diseases 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- 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
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- 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
- A61K9/0048—Eye, e.g. artificial tears
-
- 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
- A61K9/127—Liposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Dispersion Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
薄膜水和技術(thin film hydration technique)を使用して、薬剤放出研究のためのラタノプロスト含有POPCリポソームを作製した。簡潔に言うと、POPCを計量し、クロロホルム:メタノール(2:1 v/v)溶媒混合液に溶解した。ラタノプロスト(アセトニトリル中の保存溶液、2mg/ml)を薬剤:脂質が0.175:1のモル比である脂質溶媒混合液へ加え、40℃で放置した。溶媒混合液を40℃に保たれた水浴に結合したロータリー・エバポレーター中の丸底フラスコへ加えた。前記フラスコを、1時間、減圧下100rpmで回転して溶媒を除去し、薄い薬剤を含有した脂質膜を形成した。等張リン酸緩衝塩類溶液(PBS;150mM、pH5.5)をこの膜へ加え、多層状の小胞(multilamellar vesicles (MLV))を形成した。MLVはポリカーボネートフィルター(0.2μm〜0.08μm)を通して、10回押し出した。押し出し加工によって直径0.09〜0.12μmの粒度分布を有するLUVが形成された。
安定性の研究の目的で、薬剤を含有したLUVをも作製した。POPCをpH6.7のPBS中に溶解し、2時間室温で一定にかき混ぜ、MLVを形成した。MLVをベンチ・トップ押出機(bench top extruder)上で、積層された3つの80nmサイズのポリカーボネート膜を使用して3〜5回押し出して、POPC LUVを形成した。ラタノプロストをエタノール中に溶解し、その溶液を水浴中50℃で丸底フラスコ中に保持し、窒素ガスのガス流下で乾燥して、薄い薬剤の膜を形成した。薬剤の膜は、油滴がフラスコの側面に観察されなくなるまで、2〜3時間、室温でPOPC LUVで水和した。ラタノプロスト:POPCは0.175:1のモル比で、薬剤を含有したLUVの作製に用いた。ラタノプロスト含有POPC LUVは、0.2μm注射器フィルタ(syringe filter)を用いて室温でろ過し、分析されるまで4℃で保存した。同様の方法で、ラタノプロスト含有卵PCリポソーム(egg PC liposome)の作製のために用いた。
薬剤放出研究は、pH7.4のPBSに対して上記の実施例1で述べられたように作製したラタノプロスト含有POPCリポソームを透析によって分離し、さらにHPLCにより放出されたラタノプロストの量を測定することによって実施した。結果は図1に示した。28日の間、ラタノプロストのおおよそ65%が、時間依存的な様式でラタノプロスト含有POPCリポソームから放出された。
上述のラタノプロストリポソーム製剤の効能は緑内障のモデル動物、すなわち、IOP>18mmHgとして定義される高眼圧症のカニクイザル(Macaca fascicularis)で検証した。動物実験は、視覚と眼科学研究協会会議(ARVO)によって承認された目および視力の研究における動物の使用のための生命に従って実行した。更に、国際実験動物管理公認協会のためのシングヘルス(Singhealth)シンガポール協会の動物倫理委員会のガイドラインも適用した。
この明細書で明らかにされる特徴のすべては、どんな組み合わせによっても組合すことができる。明細書中に開示されたそれぞれの特徴は、同様であるか、等しいか、類似した選択的な特徴によって取り換えることができる。この様、明示的に別段の定めをした場合を除き、明らかにされるそれぞれの特徴は、等しいまたは類似した特徴の一般的な一連の実施例のみである。
Claims (8)
- パルミトイルオレオイルホスファチジルコリン(POPC)のみで形成されてなるリポソームを含み、
前記リポソームがプロスタグランジンF2αを封入し、100〜300nmの直径を有し、
最大6月の間4℃で安定である、眼内送達のための安定したリポソーム製剤。 - 前記プロスタグランジンF2αがラタノプロスト、ビマトプロスト、トラボプロストまたはカルボプロストである、請求項1に記載のリポソーム製剤。
- 前記プロスタグランジンF2αがラタノプロストである、請求項2に記載のリポソーム製剤。
- ラタノプロストとPOPCとの比が0.01:1〜0.5:1のモル比を有する、請求項2または3に記載のリポソーム製剤。
- ラタノプロストとPOPCとの比が0.01:1〜0.175:1のモル比を有する、請求項4に記載のリポソーム製剤。
- 請求項1〜5のいずれか1項に記載のリポソーム製剤を含む、眼の障害の治療のための治療剤。
- 前記眼の障害が高眼圧症または緑内障である、請求項6に記載の治療剤。
- 結膜下注射により用いられる、請求項6または7に記載の治療剤。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/149,159 | 2014-01-07 | ||
US14/149,159 US9956195B2 (en) | 2014-01-07 | 2014-01-07 | Stable liposomal formulations for ocular drug delivery |
Publications (2)
Publication Number | Publication Date |
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JP2015129107A JP2015129107A (ja) | 2015-07-16 |
JP6463902B2 true JP6463902B2 (ja) | 2019-02-06 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2014094096A Active JP6463902B2 (ja) | 2014-01-07 | 2014-04-30 | 眼科薬送達のための安定したリポソーム製剤 |
Country Status (9)
Country | Link |
---|---|
US (1) | US9956195B2 (ja) |
EP (1) | EP2891484B1 (ja) |
JP (1) | JP6463902B2 (ja) |
KR (1) | KR102315264B1 (ja) |
CN (1) | CN104758249B (ja) |
ES (1) | ES2676213T3 (ja) |
HK (1) | HK1206254A1 (ja) |
TW (1) | TWI630925B (ja) |
WO (1) | WO2015105458A1 (ja) |
Families Citing this family (3)
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JP6408469B2 (ja) * | 2012-09-06 | 2018-10-17 | ナンヤン テクノロジカル ユニヴァーシティー | ヒアルロン酸をベースとする薬物送達システム |
WO2017184081A1 (en) * | 2016-04-19 | 2017-10-26 | Nanyang Technological University | Subconjuctival depot forming formulations for ocular drug delivery |
US11452703B2 (en) * | 2020-05-21 | 2022-09-27 | Peregrine Ophthalmic PTE LTD. | Methods and compositions for reducing adipocyte numbers |
Family Cites Families (67)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5925375A (en) | 1987-05-22 | 1999-07-20 | The Liposome Company, Inc. | Therapeutic use of multilamellar liposomal prostaglandin formulations |
WO1988009170A1 (en) | 1987-05-22 | 1988-12-01 | The Liposome Company, Inc. | Prostaglandin-lipid formulations |
US4938965A (en) | 1987-07-22 | 1990-07-03 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of National Defence Of Her Majesty's Canadian Government | Ocular delivery of prophylactic agents |
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