CA2702082A1 - Aqueous ophthalmic formulations - Google Patents
Aqueous ophthalmic formulations Download PDFInfo
- Publication number
- CA2702082A1 CA2702082A1 CA2702082A CA2702082A CA2702082A1 CA 2702082 A1 CA2702082 A1 CA 2702082A1 CA 2702082 A CA2702082 A CA 2702082A CA 2702082 A CA2702082 A CA 2702082A CA 2702082 A1 CA2702082 A1 CA 2702082A1
- Authority
- CA
- Canada
- Prior art keywords
- ophthalmic formulation
- cyclosporine
- acetate
- alpha
- formulation
- 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 116
- 238000009472 formulation Methods 0.000 title claims abstract description 95
- 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 abstract description 108
- 108010036949 Cyclosporine Proteins 0.000 claims abstract description 103
- 229930182912 cyclosporin Natural products 0.000 claims abstract description 95
- 229960001265 ciclosporin Drugs 0.000 claims abstract description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000035475 disorder Diseases 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 19
- 239000013011 aqueous formulation Substances 0.000 claims description 52
- 239000003246 corticosteroid Substances 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 229930105110 Cyclosporin A Natural products 0.000 claims description 18
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 claims description 17
- LRJOMUJRLNCICJ-JZYPGELDSA-N Prednisolone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O LRJOMUJRLNCICJ-JZYPGELDSA-N 0.000 claims description 17
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 17
- 229920000053 polysorbate 80 Polymers 0.000 claims description 17
- 229960002800 prednisolone acetate Drugs 0.000 claims description 17
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- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 15
- 229940068968 polysorbate 80 Drugs 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 239000008213 purified water Substances 0.000 claims description 14
- 239000012929 tonicity agent Substances 0.000 claims description 14
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- 239000003755 preservative agent Substances 0.000 claims description 13
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 8
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- 208000021921 corneal disease Diseases 0.000 claims description 6
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- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 230000002335 preservative effect Effects 0.000 claims description 6
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- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 4
- HYRKAAMZBDSJFJ-LFDBJOOHSA-N Paramethasone acetate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]2(C)C[C@@H]1O HYRKAAMZBDSJFJ-LFDBJOOHSA-N 0.000 claims description 4
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 4
- 208000025865 Ulcer Diseases 0.000 claims description 4
- 208000027418 Wounds and injury Diseases 0.000 claims description 4
- RACDDTQBAFEERP-PLTZVPCUSA-N [2-[(6s,8s,9s,10r,13s,14s,17r)-6-chloro-17-hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1([C@@H](Cl)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@](C(=O)COC(=O)C)(O)[C@@]2(C)CC1=O RACDDTQBAFEERP-PLTZVPCUSA-N 0.000 claims description 4
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 230000007815 allergy Effects 0.000 claims description 4
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 4
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 4
- 229960001357 clocortolone pivalate Drugs 0.000 claims description 4
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- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 claims description 4
- RYJIRNNXCHOUTQ-OJJGEMKLSA-L cortisol sodium phosphate Chemical compound [Na+].[Na+].O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)COP([O-])([O-])=O)[C@@H]4[C@@H]3CCC2=C1 RYJIRNNXCHOUTQ-OJJGEMKLSA-L 0.000 claims description 4
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- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 4
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- 230000004410 intraocular pressure Effects 0.000 claims description 4
- DMKSVUSAATWOCU-HROMYWEYSA-N loteprednol etabonate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)OCCl)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O DMKSVUSAATWOCU-HROMYWEYSA-N 0.000 claims description 4
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| EP07360047.0 | 2007-10-08 | ||
| EP07360047 | 2007-10-08 | ||
| PCT/EP2008/008482 WO2009046967A1 (en) | 2007-10-08 | 2008-10-08 | Aqueous ophthalmic formulations |
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| CA2702082A1 true CA2702082A1 (en) | 2009-04-16 |
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| EP (1) | EP2195033A1 (enExample) |
| JP (1) | JP5640207B2 (enExample) |
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| WO (1) | WO2009046967A1 (enExample) |
| ZA (1) | ZA201003195B (enExample) |
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| US10307372B2 (en) | 2010-09-10 | 2019-06-04 | The Johns Hopkins University | Rapid diffusion of large polymeric nanoparticles in the mammalian brain |
| BR112013034051A2 (pt) * | 2011-06-29 | 2019-09-24 | Allergan Inc | formulações de macrogol 15 hidroxiestearato |
| US20130029919A1 (en) * | 2011-07-26 | 2013-01-31 | Allergan, Inc. | Two part formulation system for opthalmic delivery |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| 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 |
| CN104363924B (zh) | 2012-03-16 | 2018-04-17 | 约翰霍普金斯大学 | 用于递送hif‑1抑制剂的控制释放调配物 |
| JP6138904B2 (ja) | 2012-03-16 | 2017-05-31 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 活性剤の送達のための非線状マルチブロックコポリマー薬物コンジュゲート |
| FR2988297B1 (fr) * | 2012-03-22 | 2014-03-28 | Thea Lab | Solution ophtalmique aqueuse a base de ciclosporine a sans conservateur |
| KR101211902B1 (ko) * | 2012-04-30 | 2012-12-13 | 주식회사 휴온스 | 사이클로스포린 함유 무자극성 나노에멀젼 안약 조성물 |
| US9827191B2 (en) | 2012-05-03 | 2017-11-28 | The Johns Hopkins University | Compositions and methods for ophthalmic and/or other applications |
| US11596599B2 (en) | 2012-05-03 | 2023-03-07 | The Johns Hopkins University | Compositions and methods for ophthalmic and/or other applications |
| US9056057B2 (en) | 2012-05-03 | 2015-06-16 | Kala Pharmaceuticals, Inc. | Nanocrystals, compositions, and methods that aid particle transport in mucus |
| EP2844227B1 (en) | 2012-05-03 | 2020-11-18 | Kala Pharmaceuticals, Inc. | Pharmaceutical nanoparticles showing improved mucosal transport |
| JP6392209B2 (ja) | 2012-05-04 | 2018-09-19 | ザ・ジョンズ・ホプキンス・ユニバーシティー | 粘液内層を通過する迅速な透過のための脂質ベース薬物キャリア |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| 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 |
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| NZ704247A (en) | 2012-07-27 | 2018-04-27 | Glia Llc | Compositions and treatment for eye diseases and disorders |
| KR101363776B1 (ko) * | 2012-12-21 | 2014-02-17 | 이상필 | 사이클로스포린을 포함하는 투명 점안액 조성물 |
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- 2008-10-08 WO PCT/EP2008/008482 patent/WO2009046967A1/en not_active Ceased
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- 2008-10-08 CA CA2702082A patent/CA2702082A1/en not_active Abandoned
- 2008-10-08 CN CN2008801107475A patent/CN101820917B/zh not_active Expired - Fee Related
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| MX2010003774A (es) | 2010-04-27 |
| EA019867B1 (ru) | 2014-06-30 |
| HK1147937A1 (en) | 2011-08-26 |
| BRPI0819081A2 (pt) | 2015-04-22 |
| WO2009046967A1 (en) | 2009-04-16 |
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| AU2008309923A1 (en) | 2009-04-16 |
| EP2195033A1 (en) | 2010-06-16 |
| AU2008309923B2 (en) | 2014-04-03 |
| JP2010540671A (ja) | 2010-12-24 |
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