CA2494146A1 - The 9, 11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma - Google Patents
The 9, 11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma Download PDFInfo
- Publication number
- CA2494146A1 CA2494146A1 CA002494146A CA2494146A CA2494146A1 CA 2494146 A1 CA2494146 A1 CA 2494146A1 CA 002494146 A CA002494146 A CA 002494146A CA 2494146 A CA2494146 A CA 2494146A CA 2494146 A1 CA2494146 A1 CA 2494146A1
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- Prior art keywords
- compound
- accordance
- alkyl
- heteroaromatic ring
- groups
- 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
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- 229940002612 prodrug Drugs 0.000 title claims abstract description 22
- 239000000651 prodrug Substances 0.000 title claims abstract description 22
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title abstract description 4
- 208000010412 Glaucoma Diseases 0.000 title description 5
- 206010030043 Ocular hypertension Diseases 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- -1 Latanaprost Chemical compound 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000004410 intraocular pressure Effects 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
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- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
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- GOUQZQORWGWEFM-WLOFLUCMSA-N prostaglandin H2 1-ethanolamide Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(=O)NCCO GOUQZQORWGWEFM-WLOFLUCMSA-N 0.000 abstract description 7
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
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- 150000003815 prostacyclins Chemical class 0.000 description 10
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- LGEQQWMQCRIYKG-DOFZRALJSA-N anandamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 description 9
- LGEQQWMQCRIYKG-UHFFFAOYSA-N arachidonic acid ethanolamide Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO LGEQQWMQCRIYKG-UHFFFAOYSA-N 0.000 description 9
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- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 229910000064 phosphane Inorganic materials 0.000 description 1
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- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
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- 235000011164 potassium chloride Nutrition 0.000 description 1
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- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/02—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2
- C07D317/06—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 2 condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/212,437 | 2002-08-05 | ||
| US10/212,437 US6864282B2 (en) | 2002-08-05 | 2002-08-05 | 9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma |
| PCT/US2003/024305 WO2004013119A1 (en) | 2002-08-05 | 2003-08-04 | The 9, 11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2494146A1 true CA2494146A1 (en) | 2004-02-12 |
Family
ID=31187772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002494146A Abandoned CA2494146A1 (en) | 2002-08-05 | 2003-08-04 | The 9, 11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6864282B2 (enExample) |
| EP (2) | EP1527063B1 (enExample) |
| JP (1) | JP2005539014A (enExample) |
| AT (1) | ATE334123T1 (enExample) |
| AU (1) | AU2003261352A1 (enExample) |
| CA (1) | CA2494146A1 (enExample) |
| DE (1) | DE60307106T2 (enExample) |
| ES (1) | ES2268433T3 (enExample) |
| WO (1) | WO2004013119A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7070768B2 (en) * | 2003-09-25 | 2006-07-04 | Allergan, Inc. | Method for imparting artificial tan to human skin |
| GB0501192D0 (en) * | 2005-01-20 | 2005-03-02 | Resolution Chemicals Ltd | Stable prostaglandin-containing compositions |
| WO2010102078A1 (en) | 2009-03-04 | 2010-09-10 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| US7851504B2 (en) | 2005-03-16 | 2010-12-14 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| US8030349B2 (en) | 2005-08-02 | 2011-10-04 | Santen Pharmaceutical Co., Ltd. | Method for prevention of degradation of thermally unstable medicament |
| WO2007111806A2 (en) * | 2006-03-23 | 2007-10-04 | Massachusetts Eye And Ear Infirmary | Cyclopentane heptanoic acid compounds for reducing body fat |
| US20110293549A1 (en) | 2009-02-03 | 2011-12-01 | Athena Cosmetics, Inc. | Composition, method and kit for enhancing hair |
| US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
| CA2824317C (en) | 2011-01-19 | 2014-12-16 | Terakine Therapeutics, Inc. | Uses of certain f-series prostaglandin analogs for treating diabetes and dyslipidemia |
| US8426471B1 (en) | 2011-12-19 | 2013-04-23 | Topokine Therapeutics, Inc. | Methods and compositions for reducing body fat and adipocytes |
| SG11201600237YA (en) | 2012-11-21 | 2016-02-26 | Topokine Therapeutics Inc | Methods and compositions for locally increasing body fat |
| NO2753788T3 (enExample) | 2013-05-10 | 2018-06-16 | ||
| US9820993B2 (en) | 2013-05-15 | 2017-11-21 | Topokine Therapeutics, Inc. | Methods and compositions for topical delivery of prostaglandins to subcutaneous fat |
| US9115109B2 (en) * | 2013-08-15 | 2015-08-25 | Chirogate International Inc. | Processes and intermediates for the preparations of isomer free prostaglandins |
| WO2015200425A1 (en) | 2014-06-27 | 2015-12-30 | Topokine Therapeutics, Inc. | Topical dosage regimen |
| US11571401B2 (en) | 2017-09-01 | 2023-02-07 | East Carolina University | Compounds, compositions, kits, and methods for activating immune cells and/or an immune system response |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599353A (en) * | 1982-05-03 | 1986-07-08 | The Trustees Of Columbia University In The City Of New York | Use of eicosanoids and their derivatives for treatment of ocular hypertension and glaucoma |
| US4867915A (en) * | 1986-05-21 | 1989-09-19 | Syntex (U.S.A.) Inc. | 16-Substituted polyunsaturated hexadecanoic fatty acids |
| DE68929435T2 (de) | 1988-09-06 | 2003-07-17 | Pharmacia Ab, Stockholm | Prostaglandinderivate zur Behandlung des grünen Stars oder einer okularen Hypertension |
| US5767154A (en) | 1991-02-07 | 1998-06-16 | Allergan | 5-trans-prostaglandins of the F series and their use as ocular hypotensives |
| US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5385945A (en) | 1992-10-21 | 1995-01-31 | Allergan, Inc. | 7-(5-substituted cyclopentyl) and (5-substituted cyclopentenyl) heptyl alcohols, heptylamines and heptanoic acid amides, and method of lowering intraocular pressure in the eye of a mammal by administration of these novel compounds |
| US5510383A (en) * | 1993-08-03 | 1996-04-23 | Alcon Laboratories, Inc. | Use of cloprostenol, fluprostenol and their salts and esters to treat glaucoma and ocular hypertension |
| CA2274708A1 (en) | 1997-10-13 | 1999-04-22 | R-Tech Ueno, Ltd. | Remedial composition for intraocular hypertension or glaucoma |
| US6066671A (en) | 1997-12-19 | 2000-05-23 | Alcon Laboratories, Inc. | Treatment of GLC1A glaucoma with 3-benzoyl-phenylacetic acids, esters, or amides |
| AU8474701A (en) | 2000-08-07 | 2002-02-18 | Univ Vanderbilt | Compositions and methods for detecting and quantifying cox-2 activity and 2-arachidonylglycerol metabolites |
-
2002
- 2002-08-05 US US10/212,437 patent/US6864282B2/en not_active Expired - Fee Related
-
2003
- 2003-08-04 ES ES03767129T patent/ES2268433T3/es not_active Expired - Lifetime
- 2003-08-04 EP EP03767129A patent/EP1527063B1/en not_active Expired - Lifetime
- 2003-08-04 EP EP06011653A patent/EP1731516A3/en not_active Withdrawn
- 2003-08-04 WO PCT/US2003/024305 patent/WO2004013119A1/en not_active Ceased
- 2003-08-04 AU AU2003261352A patent/AU2003261352A1/en not_active Abandoned
- 2003-08-04 DE DE60307106T patent/DE60307106T2/de not_active Expired - Fee Related
- 2003-08-04 CA CA002494146A patent/CA2494146A1/en not_active Abandoned
- 2003-08-04 AT AT03767129T patent/ATE334123T1/de not_active IP Right Cessation
- 2003-08-04 JP JP2004526380A patent/JP2005539014A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005539014A (ja) | 2005-12-22 |
| DE60307106D1 (de) | 2006-09-07 |
| EP1731516A3 (en) | 2007-01-03 |
| EP1731516A2 (en) | 2006-12-13 |
| ES2268433T3 (es) | 2007-03-16 |
| US20040023954A1 (en) | 2004-02-05 |
| EP1527063B1 (en) | 2006-07-26 |
| WO2004013119A1 (en) | 2004-02-12 |
| AU2003261352A1 (en) | 2004-02-23 |
| ATE334123T1 (de) | 2006-08-15 |
| DE60307106T2 (de) | 2007-02-22 |
| US6864282B2 (en) | 2005-03-08 |
| WO2004013119B1 (en) | 2004-05-06 |
| EP1527063A1 (en) | 2005-05-04 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |