WO1995026729A1 - Nouveaux derives de prostaglandine servant a traiter le glaucome ou l'hypertension oculaire - Google Patents
Nouveaux derives de prostaglandine servant a traiter le glaucome ou l'hypertension oculaire Download PDFInfo
- Publication number
- WO1995026729A1 WO1995026729A1 PCT/SE1995/000347 SE9500347W WO9526729A1 WO 1995026729 A1 WO1995026729 A1 WO 1995026729A1 SE 9500347 W SE9500347 W SE 9500347W WO 9526729 A1 WO9526729 A1 WO 9526729A1
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- WIPO (PCT)
- Prior art keywords
- groups
- deoxy
- phenyl
- derivative
- ring
- Prior art date
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- 208000010412 Glaucoma Diseases 0.000 title claims abstract description 14
- 206010030043 Ocular hypertension Diseases 0.000 title claims abstract description 8
- 150000003180 prostaglandins Chemical class 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 150000003169 prostaglandin F2α derivatives Chemical class 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 230000004410 intraocular pressure Effects 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
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- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 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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- 229960002986 dinoprostone Drugs 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- BORBLDJNKYHVJP-FXBDTBDDSA-N dolichodial Chemical compound C[C@H]1CC[C@H](C(=C)C=O)[C@@H]1C=O BORBLDJNKYHVJP-FXBDTBDDSA-N 0.000 description 1
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- 238000000338 in vitro Methods 0.000 description 1
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
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- 231100000864 loss of vision Toxicity 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000008289 pathophysiological mechanism Effects 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- AFWJMEQIMAXCBI-QNOMZHJSSA-N propan-2-yl (z)-7-[(1r,2r,3r,5s)-3,5-dihydroxy-2-[(e)-oct-1-enyl]cyclopentyl]hept-5-enoate Chemical compound CCCCCC\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)OC(C)C AFWJMEQIMAXCBI-QNOMZHJSSA-N 0.000 description 1
- MYNMJEGQTXQGKQ-RXMNKVFOSA-N propan-2-yl (z)-7-[(1r,2s)-2-[(e,3s)-3-hydroxyoct-1-enyl]-5-oxocyclopent-3-en-1-yl]hept-5-enoate Chemical compound CCCCC[C@H](O)\C=C\[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(=O)OC(C)C MYNMJEGQTXQGKQ-RXMNKVFOSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- ZNVGYHOBTCWGTO-UHFFFAOYSA-N solutin Natural products Cc1cc(O)cc2OC(C)(O)C(=O)c12 ZNVGYHOBTCWGTO-UHFFFAOYSA-N 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- 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
Abstract
Dérivés thérapeutiquement efficaces et physiologiquement acceptables de 11-désoxy prostaglandine F2α contenant une chaîne oméga à noyau substitué, et leur utilisation dans la préparation de compositions servant à traiter le glaucome ou l'hypertension oculaire.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU21559/95A AU2155995A (en) | 1994-03-31 | 1995-03-31 | New prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9401087A SE9401087D0 (sv) | 1994-03-31 | 1994-03-31 | New prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
| SE9401087-3 | 1994-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995026729A1 true WO1995026729A1 (fr) | 1995-10-12 |
Family
ID=20393491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/SE1995/000347 WO1995026729A1 (fr) | 1994-03-31 | 1995-03-31 | Nouveaux derives de prostaglandine servant a traiter le glaucome ou l'hypertension oculaire |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2155995A (fr) |
| SE (1) | SE9401087D0 (fr) |
| WO (1) | WO1995026729A1 (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997023223A1 (fr) * | 1995-12-22 | 1997-07-03 | Alcon Laboratories, Inc. | Analogues tetrahidrofuranniques substitues de prostaglandines utilises comme hypotenseurs oculaires |
| WO1998020880A2 (fr) * | 1996-11-12 | 1998-05-22 | Alcon Laboratories, Inc. | 11-halo prostaglandines destinees au traitement du glaucome ou de l'hypertension oculaire |
| US5814660A (en) * | 1995-12-22 | 1998-09-29 | Alcon Laboratories, Inc. | 9-oxa prostaglandin analogs as ocular hypotensives |
| WO1998057930A1 (fr) * | 1997-06-18 | 1998-12-23 | Alcon Laboratories, Inc. | Analogues tetrahydrofuraniques ceto-substitues de prostaglandines utilises comme hypotenseurs oculaires |
| WO2000050040A1 (fr) * | 1999-02-25 | 2000-08-31 | Synphora Ab | Methode et composition de prevention de la formation de cicatrices dans une bulle de filtration de glaucome et une fistule de drainage |
| WO2006020510A1 (fr) * | 2004-08-10 | 2006-02-23 | Allergan Inc. | Acide cyclopentane heptan(èn)oique, dérivés de 2-hétéroarylalcényle et leur utilisation comme modulateurs de reception de la prostaglandine |
| WO2008073752A2 (fr) * | 2006-12-11 | 2008-06-19 | Allergan, Inc. | Composés thérapeutiques |
| US8389566B2 (en) | 2005-11-03 | 2013-03-05 | Allergan, Inc. | Prostaglandins and analogues as agents for lowering intraocular pressure |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1485352A (en) * | 1975-01-20 | 1977-09-08 | Upjohn Co | Prostaglandins |
| US4131737A (en) * | 1976-07-19 | 1978-12-26 | American Cyanamid Company | 15-Deoxy-16-hydroxy-16-substituted-3-thia-prostanoic acids |
| GB1595998A (en) * | 1977-03-30 | 1981-08-19 | American Cyanamid Co | Prostenoic acids and esters |
| WO1990002553A1 (fr) * | 1988-09-06 | 1990-03-22 | Pharmacia Ab | Derives de prostaglandine servant au traitement des glaucomes ou de l'hypertension oculaire |
| EP0471856A1 (fr) * | 1990-03-08 | 1992-02-26 | Shionogi & Co., Ltd. | Derive de 15-desoxyprostaglandine |
-
1994
- 1994-03-31 SE SE9401087A patent/SE9401087D0/xx unknown
-
1995
- 1995-03-31 AU AU21559/95A patent/AU2155995A/en not_active Abandoned
- 1995-03-31 WO PCT/SE1995/000347 patent/WO1995026729A1/fr active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1485352A (en) * | 1975-01-20 | 1977-09-08 | Upjohn Co | Prostaglandins |
| US4131737A (en) * | 1976-07-19 | 1978-12-26 | American Cyanamid Company | 15-Deoxy-16-hydroxy-16-substituted-3-thia-prostanoic acids |
| GB1595998A (en) * | 1977-03-30 | 1981-08-19 | American Cyanamid Co | Prostenoic acids and esters |
| WO1990002553A1 (fr) * | 1988-09-06 | 1990-03-22 | Pharmacia Ab | Derives de prostaglandine servant au traitement des glaucomes ou de l'hypertension oculaire |
| EP0471856A1 (fr) * | 1990-03-08 | 1992-02-26 | Shionogi & Co., Ltd. | Derive de 15-desoxyprostaglandine |
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF LIPID MEDIATORS, Volume 6, 1993, DAVID F. WOODWARD et al., "Intracular Pressure Effects of Selective Prostanoid Receptor Agonists Involve Different Receptor Subtypes According to Radioligand Binding Studies", pages 545-553. * |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6369102B2 (en) | 1995-12-22 | 2002-04-09 | Alcon Manufacturing, Ltd. | Substituted tetrahydrofuran analogs of prostaglandins as ocular hypotensives |
| US5814660A (en) * | 1995-12-22 | 1998-09-29 | Alcon Laboratories, Inc. | 9-oxa prostaglandin analogs as ocular hypotensives |
| US5866602A (en) * | 1995-12-22 | 1999-02-02 | Alcon Laboratories, Inc. | Keto-substituted tetrahydrofuran analogs of prostaglandins as ocular hypotensives |
| US5994397A (en) * | 1995-12-22 | 1999-11-30 | Alcon Laboratories, Inc. | Substituted tetrahydrofuran analogs of prostaglandins as ocular hypotensives |
| WO1997023223A1 (fr) * | 1995-12-22 | 1997-07-03 | Alcon Laboratories, Inc. | Analogues tetrahidrofuranniques substitues de prostaglandines utilises comme hypotenseurs oculaires |
| US6197812B1 (en) | 1995-12-22 | 2001-03-06 | Alcon Laboratories, Inc. | Substituted tetrahydrofuran analogs of prostaglandins as ocular hypotensives |
| US6025392A (en) * | 1995-12-22 | 2000-02-15 | Alcon Laboratories, Inc. | substituted tetrahydrofuran analogs of prostaglandins as ocular hypotensives |
| WO1998020880A2 (fr) * | 1996-11-12 | 1998-05-22 | Alcon Laboratories, Inc. | 11-halo prostaglandines destinees au traitement du glaucome ou de l'hypertension oculaire |
| WO1998020880A3 (fr) * | 1996-11-12 | 1998-08-20 | Alcon Lab Inc | 11-halo prostaglandines destinees au traitement du glaucome ou de l'hypertension oculaire |
| WO1998057930A1 (fr) * | 1997-06-18 | 1998-12-23 | Alcon Laboratories, Inc. | Analogues tetrahydrofuraniques ceto-substitues de prostaglandines utilises comme hypotenseurs oculaires |
| WO2000050040A1 (fr) * | 1999-02-25 | 2000-08-31 | Synphora Ab | Methode et composition de prevention de la formation de cicatrices dans une bulle de filtration de glaucome et une fistule de drainage |
| US6495563B1 (en) | 1999-02-25 | 2002-12-17 | Synphora Ab | Method and composition for prevention of scar formation in glaucoma filtration bleb and drainage fistula |
| US7183310B2 (en) | 2004-08-10 | 2007-02-27 | Allergan, Inc. | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| WO2006020510A1 (fr) * | 2004-08-10 | 2006-02-23 | Allergan Inc. | Acide cyclopentane heptan(èn)oique, dérivés de 2-hétéroarylalcényle et leur utilisation comme modulateurs de reception de la prostaglandine |
| US7863319B2 (en) | 2004-08-10 | 2011-01-04 | Allergan, Inc. | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US8557860B2 (en) | 2004-08-10 | 2013-10-15 | Allergan, Inc. | Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US8389566B2 (en) | 2005-11-03 | 2013-03-05 | Allergan, Inc. | Prostaglandins and analogues as agents for lowering intraocular pressure |
| WO2008073752A2 (fr) * | 2006-12-11 | 2008-06-19 | Allergan, Inc. | Composés thérapeutiques |
| WO2008073752A3 (fr) * | 2006-12-11 | 2008-10-02 | Allergan Inc | Composés thérapeutiques |
| US8193373B2 (en) | 2006-12-11 | 2012-06-05 | Allergan, Inc. | Therapeutic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2155995A (en) | 1995-10-23 |
| SE9401087D0 (sv) | 1994-03-31 |
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