CA2882743C - Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes - Google Patents
Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes Download PDFInfo
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- CA2882743C CA2882743C CA2882743A CA2882743A CA2882743C CA 2882743 C CA2882743 C CA 2882743C CA 2882743 A CA2882743 A CA 2882743A CA 2882743 A CA2882743 A CA 2882743A CA 2882743 C CA2882743 C CA 2882743C
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- unsubstituted
- substituted
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- alkyl
- hydroxyl
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- 206010071164 Corneal thickening Diseases 0.000 title claims abstract description 7
- 150000002148 esters Chemical class 0.000 title abstract description 17
- 239000000651 prodrug Substances 0.000 title abstract description 15
- 229940002612 prodrug Drugs 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 164
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 18
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- 238000011200 topical administration Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 36
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- 206010028980 Neoplasm Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 230000003247 decreasing effect Effects 0.000 description 3
- 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 3
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- 125000005730 thiophenylene group Chemical group 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
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- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
- BSCXGQXKCWFKPX-NCXUSEDFSA-N 5-[3-[(1r,2r,3r,5r)-5-chloro-2-[2-(3,5-dichlorophenyl)ethyl]-3-hydroxycyclopentyl]propyl]thiophene-2-carboxylic acid Chemical compound C([C@H]1[C@H](Cl)C[C@H]([C@@H]1CCC=1C=C(Cl)C=C(Cl)C=1)O)CCC1=CC=C(C(O)=O)S1 BSCXGQXKCWFKPX-NCXUSEDFSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US201261693437P | 2012-08-27 | 2012-08-27 | |
| US61/693,437 | 2012-08-27 | ||
| PCT/US2013/056418 WO2014035827A1 (en) | 2012-08-27 | 2013-08-23 | Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes |
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| CA2882743A1 CA2882743A1 (en) | 2014-03-06 |
| CA2882743C true CA2882743C (en) | 2021-11-30 |
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| KR102304111B1 (ko) | 2012-08-27 | 2021-09-23 | 알레간 인코포레이티드 | 베타-클로로시클로펜탄의 친수성 에스테르 전구약물의 이용에 의한 감소된 중심 각막 비후 |
| TR201902864T4 (tr) * | 2014-02-20 | 2019-03-21 | Allergan Inc | Beta-klorosiklopentanların hidrofilik ester ön ilaçlarının kullanımı ile azaltılmış merkezi korneal kalınlaşma. |
| US9981938B2 (en) | 2014-05-12 | 2018-05-29 | Allergan, Inc. | Quaternary ammonium alkyl esters as stable prodrugs |
| US9573926B2 (en) | 2014-05-22 | 2017-02-21 | Allergan, Inc. | Amidoalkylenyl and amidoaryl esters, compositions thereof, and methods for their use |
| EP3201192B1 (en) * | 2014-10-02 | 2019-08-21 | Allergan, Inc. | Ester prodrugs of gamma-lactams and their use |
| TWI707849B (zh) | 2018-02-13 | 2020-10-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| CA3093130C (en) | 2018-04-19 | 2023-10-17 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| TWI809427B (zh) | 2018-07-13 | 2023-07-21 | 美商基利科學股份有限公司 | Pd‐1/pd‐l1抑制劑 |
| EP3870566A1 (en) | 2018-10-24 | 2021-09-01 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
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| US4911920A (en) | 1986-07-30 | 1990-03-27 | Alcon Laboratories, Inc. | Sustained release, comfort formulation for glaucoma therapy |
| FR2588189B1 (fr) | 1985-10-03 | 1988-12-02 | Merck Sharp & Dohme | Composition pharmaceutique de type a transition de phase liquide-gel |
| DE69212850T2 (de) | 1991-01-15 | 1997-03-06 | Alcon Lab Inc | Verwendung von Karrageenan in topischen ophthalmologischen Zusammensetzungen |
| US5212162A (en) | 1991-03-27 | 1993-05-18 | Alcon Laboratories, Inc. | Use of combinations gelling polysaccharides and finely divided drug carrier substrates in topical ophthalmic compositions |
| US6309853B1 (en) | 1994-08-17 | 2001-10-30 | The Rockfeller University | Modulators of body weight, corresponding nucleic acids and proteins, and diagnostic and therapeutic uses thereof |
| US6353000B1 (en) | 1996-11-12 | 2002-03-05 | Alcon Laboratories, Inc. | 11-halo prostaglandins for the treatment of glaucoma or ocular hypertension |
| DE10322843A1 (de) | 2003-05-19 | 2004-12-16 | Clariant Gmbh | Verfahren zur Herstellung von Anilinboronsäuren und ihren Derivaten |
| JP2008517941A (ja) * | 2004-10-21 | 2008-05-29 | デューク・ユニバーシティー | 眼科用薬剤 |
| US7091231B2 (en) * | 2004-12-10 | 2006-08-15 | Allergan, Inc. | 12-Aryl prostaglandin analogs |
| US20070254920A1 (en) | 2006-04-26 | 2007-11-01 | Aerie Pharmaceuticals, Inc. | Prodrug derivatives of acids using alcohols with homotopic hydroxy groups and methods for their preparation and use |
| EP2043993B1 (en) * | 2006-07-11 | 2015-07-01 | Allergan, Inc. | Cyclopentane derivatives as antiglaucoma agents |
| US7947732B2 (en) * | 2007-07-13 | 2011-05-24 | Allergan, Inc. | Therapeutic substituted chlorocyclopentanols |
| US7732443B2 (en) | 2008-03-18 | 2010-06-08 | Yariv Donde | Therapeutic substituted cyclopentanes |
| US7737140B2 (en) * | 2008-04-24 | 2010-06-15 | Allergan, Inc. | Therapeutic compounds |
| WO2009140205A2 (en) * | 2008-05-15 | 2009-11-19 | Allergan, Inc. | Therapeutic substituted cyclopentanes |
| US20120322882A1 (en) | 2009-11-09 | 2012-12-20 | Allergan, Inc. | Compositions And Methods For Stimulating Hair Growth |
| US20110136872A1 (en) | 2009-12-09 | 2011-06-09 | Burk Robert M | Stable aqueous compositions of prostglandin agonist prodrugs and methods for use thereof |
| KR102304111B1 (ko) | 2012-08-27 | 2021-09-23 | 알레간 인코포레이티드 | 베타-클로로시클로펜탄의 친수성 에스테르 전구약물의 이용에 의한 감소된 중심 각막 비후 |
| US9090595B2 (en) | 2012-08-27 | 2015-07-28 | Allergan, Inc. | Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes |
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| KR20150046269A (ko) | 2015-04-29 |
| AU2013309124A1 (en) | 2015-03-12 |
| JP2015528463A (ja) | 2015-09-28 |
| AU2013309124B2 (en) | 2018-03-01 |
| KR20200110820A (ko) | 2020-09-25 |
| CA2882743A1 (en) | 2014-03-06 |
| EP2888239A1 (en) | 2015-07-01 |
| KR102304111B1 (ko) | 2021-09-23 |
| US20140057975A1 (en) | 2014-02-27 |
| HK1211031A1 (en) | 2016-05-13 |
| JP6270848B2 (ja) | 2018-01-31 |
| EP2888239B1 (en) | 2018-11-28 |
| ES2711425T3 (es) | 2019-05-03 |
| US20150322036A1 (en) | 2015-11-12 |
| DK2888239T3 (en) | 2019-03-04 |
| WO2014035827A1 (en) | 2014-03-06 |
| US9024042B2 (en) | 2015-05-05 |
| US9427401B2 (en) | 2016-08-30 |
| TR201900863T4 (tr) | 2019-02-21 |
| CN104684904A (zh) | 2015-06-03 |
| CN104684904B (zh) | 2017-10-13 |
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