CA2783707A1 - Stable aqueous compositions of prostglandin agonist prodrugs and methods for use thereof - Google Patents
Stable aqueous compositions of prostglandin agonist prodrugs and methods for use thereof Download PDFInfo
- Publication number
- CA2783707A1 CA2783707A1 CA2783707A CA2783707A CA2783707A1 CA 2783707 A1 CA2783707 A1 CA 2783707A1 CA 2783707 A CA2783707 A CA 2783707A CA 2783707 A CA2783707 A CA 2783707A CA 2783707 A1 CA2783707 A1 CA 2783707A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- carboxylic acid
- alkyl
- prostanoid
- acute
- 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 89
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000000556 agonist Substances 0.000 title claims abstract description 20
- 229940002612 prodrug Drugs 0.000 title claims abstract description 15
- 239000000651 prodrug Substances 0.000 title claims abstract description 15
- 229940127293 prostanoid Drugs 0.000 claims abstract description 35
- 150000003814 prostanoids Chemical class 0.000 claims abstract description 34
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 28
- 208000022873 Ocular disease Diseases 0.000 claims abstract description 6
- 238000009472 formulation Methods 0.000 claims description 29
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 208000010412 Glaucoma Diseases 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 13
- 208000029977 White Dot Syndromes Diseases 0.000 claims description 11
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 11
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 11
- 235000019800 disodium phosphate Nutrition 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 208000002780 macular degeneration Diseases 0.000 claims description 9
- -1 oxyalkenyl Chemical group 0.000 claims description 9
- 230000001154 acute effect Effects 0.000 claims description 8
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 206010046851 Uveitis Diseases 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 5
- 229920001992 poloxamer 407 Polymers 0.000 claims description 5
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 5
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 5
- 229920000053 polysorbate 80 Polymers 0.000 claims description 5
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- 125000000732 arylene group Chemical group 0.000 claims description 4
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
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- 230000004406 elevated intraocular pressure Effects 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- 206010012688 Diabetic retinal oedema Diseases 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000000699 topical effect Effects 0.000 abstract description 4
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- 150000001875 compounds Chemical class 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 238000011084 recovery Methods 0.000 description 8
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 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 description 3
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- 125000005907 alkyl ester group Chemical group 0.000 description 3
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- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229960004543 anhydrous citric acid Drugs 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 150000002066 eicosanoids Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 235000011008 sodium phosphates Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- SGUARWQDISKGTC-UHFFFAOYSA-N 2-hydroxyimino-2-nitroacetonitrile Chemical compound ON=C(C#N)[N+]([O-])=O SGUARWQDISKGTC-UHFFFAOYSA-N 0.000 description 1
- 229940082496 Adrenoreceptor antagonist Drugs 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010018325 Congenital glaucomas Diseases 0.000 description 1
- 206010012565 Developmental glaucoma Diseases 0.000 description 1
- 208000031969 Eye Hemorrhage Diseases 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 206010070245 Foreign body Diseases 0.000 description 1
- 241000223783 Glaucoma Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 206010067684 Iris bombe Diseases 0.000 description 1
- 206010068960 Narrow anterior chamber angle Diseases 0.000 description 1
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- 208000023564 acute macular neuroretinopathy Diseases 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- 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
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
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- A61K47/02—Inorganic compounds
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- 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
- A61K47/26—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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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
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- A61P27/02—Ophthalmic agents
- A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26789709P | 2009-12-09 | 2009-12-09 | |
| US61/267,897 | 2009-12-09 | ||
| PCT/US2010/055590 WO2011071620A1 (en) | 2009-12-09 | 2010-11-05 | Stable aqueous compositions of prostglandin agonist prodrugs and methods for use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2783707A1 true CA2783707A1 (en) | 2011-06-16 |
Family
ID=43503864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2783707A Abandoned CA2783707A1 (en) | 2009-12-09 | 2010-11-05 | Stable aqueous compositions of prostglandin agonist prodrugs and methods for use thereof |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20110136872A1 (enExample) |
| EP (1) | EP2509582A1 (enExample) |
| JP (2) | JP5955774B2 (enExample) |
| KR (1) | KR20120106788A (enExample) |
| CN (1) | CN102762195B (enExample) |
| AR (1) | AR078929A1 (enExample) |
| AU (1) | AU2010328555B2 (enExample) |
| CA (1) | CA2783707A1 (enExample) |
| CL (1) | CL2012001545A1 (enExample) |
| IL (1) | IL220240A0 (enExample) |
| MX (1) | MX2012006622A (enExample) |
| NZ (1) | NZ600577A (enExample) |
| RU (1) | RU2012127869A (enExample) |
| SG (1) | SG181600A1 (enExample) |
| TW (1) | TW201138766A (enExample) |
| WO (1) | WO2011071620A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6270848B2 (ja) | 2012-08-27 | 2018-01-31 | アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ | ベータ−クロロシクロペンタンの親水性エステルプロドラッグの使用による角膜中央部肥厚の低下 |
| KR101535825B1 (ko) | 2012-09-25 | 2015-07-10 | 엘지디스플레이 주식회사 | 표시장치 및 이의 라인결함 검출방법 |
| WO2015175075A1 (en) * | 2014-02-20 | 2015-11-19 | Allergan, Inc. | Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes |
| ES2757798T3 (es) | 2014-10-02 | 2020-04-30 | Allergan Inc | Profármacos de éster de gamma-lactamas y su uso |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994274A (en) * | 1989-07-27 | 1991-02-19 | Allergan, Inc. | Intraocular pressure reducing 11,15-diacyl prostaglandins and method of using |
| US5034413A (en) | 1989-07-27 | 1991-07-23 | Allergan, Inc. | Intraocular pressure reducing 9,11-diacyl prostaglandins |
| CA2021316C (en) * | 1989-07-27 | 2000-10-24 | Ming Fai Chan | Intraocular pressure reducing 11-acyl prostaglandins |
| US5028624A (en) * | 1989-07-27 | 1991-07-02 | Allergan, Inc. | Intraocular pressure reducing 9,15-diacyl prostaglandins |
| WO2000004898A1 (en) * | 1998-07-21 | 2000-02-03 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| PT1321144E (pt) * | 2000-09-13 | 2011-03-10 | Santen Pharmaceutical Co Ltd | Colírio |
| EP1532981B1 (en) * | 2002-08-23 | 2007-09-26 | Santen Pharmaceutical Co., Ltd. | Stable eye drops containing latanoprost as the active ingredient |
| ES2320770T3 (es) * | 2004-05-26 | 2009-05-28 | Arturo Jimenez Bayardo | Metodo de preparacion de una solucion oftalmica de latanoprost y la solucion asi producida. |
| US20050276867A1 (en) * | 2004-06-09 | 2005-12-15 | Allergan, Inc. | Stabilized compositions comprising a therapeutically active agent and an oxidizing preservative |
| EP1856042B1 (en) * | 2005-03-10 | 2012-06-27 | Allergan, Inc. | Substituted gamma lactams as therapeutic agents |
| EP2123278B1 (en) * | 2007-02-07 | 2013-01-09 | Teika Pharmaceutical Co., Ltd. | Eye drop preparation comprising latanoprost |
| US7820661B2 (en) * | 2008-04-24 | 2010-10-26 | Allergan, Inc. | Substituted gamma lactams as therapeutics agents |
| EP2127638A1 (en) * | 2008-05-30 | 2009-12-02 | Santen Pharmaceutical Co., Ltd | Method and composition for treating ocular hypertension and glaucoma |
-
2010
- 2010-11-04 US US12/939,861 patent/US20110136872A1/en not_active Abandoned
- 2010-11-05 JP JP2012543111A patent/JP5955774B2/ja not_active Expired - Fee Related
- 2010-11-05 EP EP10782082A patent/EP2509582A1/en not_active Withdrawn
- 2010-11-05 WO PCT/US2010/055590 patent/WO2011071620A1/en not_active Ceased
- 2010-11-05 TW TW099138227A patent/TW201138766A/zh unknown
- 2010-11-05 CN CN201080063225.1A patent/CN102762195B/zh not_active Expired - Fee Related
- 2010-11-05 KR KR1020127017676A patent/KR20120106788A/ko not_active Ceased
- 2010-11-05 CA CA2783707A patent/CA2783707A1/en not_active Abandoned
- 2010-11-05 NZ NZ600577A patent/NZ600577A/en not_active IP Right Cessation
- 2010-11-05 AU AU2010328555A patent/AU2010328555B2/en not_active Ceased
- 2010-11-05 SG SG2012042461A patent/SG181600A1/en unknown
- 2010-11-05 MX MX2012006622A patent/MX2012006622A/es not_active Application Discontinuation
- 2010-11-05 RU RU2012127869/15A patent/RU2012127869A/ru not_active Application Discontinuation
- 2010-11-05 AR ARP100104122A patent/AR078929A1/es unknown
-
2012
- 2012-06-07 IL IL220240A patent/IL220240A0/en unknown
- 2012-06-08 CL CL2012001545A patent/CL2012001545A1/es unknown
-
2015
- 2015-08-26 US US14/836,785 patent/US20160220677A1/en not_active Abandoned
-
2016
- 2016-01-14 JP JP2016005576A patent/JP2016056207A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP5955774B2 (ja) | 2016-07-20 |
| AR078929A1 (es) | 2011-12-14 |
| CL2012001545A1 (es) | 2012-08-31 |
| IL220240A0 (en) | 2012-07-31 |
| KR20120106788A (ko) | 2012-09-26 |
| WO2011071620A1 (en) | 2011-06-16 |
| CN102762195B (zh) | 2016-05-18 |
| US20110136872A1 (en) | 2011-06-09 |
| MX2012006622A (es) | 2012-08-15 |
| NZ600577A (en) | 2014-10-31 |
| JP2013513606A (ja) | 2013-04-22 |
| SG181600A1 (en) | 2012-07-30 |
| TW201138766A (en) | 2011-11-16 |
| AU2010328555A1 (en) | 2012-07-05 |
| JP2016056207A (ja) | 2016-04-21 |
| RU2012127869A (ru) | 2014-01-20 |
| CN102762195A (zh) | 2012-10-31 |
| EP2509582A1 (en) | 2012-10-17 |
| AU2010328555B2 (en) | 2016-05-26 |
| US20160220677A1 (en) | 2016-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20151026 |
|
| FZDE | Discontinued |
Effective date: 20180403 |