CA2454422A1 - Procede et composition pour le traitement de l'hypertension oculaire et des glaucomes - Google Patents
Procede et composition pour le traitement de l'hypertension oculaire et des glaucomes Download PDFInfo
- Publication number
- CA2454422A1 CA2454422A1 CA002454422A CA2454422A CA2454422A1 CA 2454422 A1 CA2454422 A1 CA 2454422A1 CA 002454422 A CA002454422 A CA 002454422A CA 2454422 A CA2454422 A CA 2454422A CA 2454422 A1 CA2454422 A1 CA 2454422A1
- Authority
- CA
- Canada
- Prior art keywords
- keto
- prostaglandin compound
- alkyl
- compound
- composition
- 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
- 208000010412 Glaucoma Diseases 0.000 title claims abstract description 15
- 206010030043 Ocular hypertension Diseases 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 16
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- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 32
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 239000003889 eye drop Substances 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
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- 125000001931 aliphatic group Chemical group 0.000 claims description 10
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- 125000004104 aryloxy group Chemical group 0.000 claims description 7
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
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- 238000012360 testing method Methods 0.000 description 5
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- 239000000243 solution Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
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- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
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- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- AIAKLPAJNLBVEA-UHFFFAOYSA-N n-[2-(2-benzamidophenoxy)phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1OC1=CC=CC=C1NC(=O)C1=CC=CC=C1 AIAKLPAJNLBVEA-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 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
- CBOMORHDRONZRN-QLOYDKTKSA-N prostaglandin E3 Chemical compound CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CBOMORHDRONZRN-QLOYDKTKSA-N 0.000 description 1
- 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
- 210000001747 pupil Anatomy 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- RYYVLZVUVIJVGH-UHFFFAOYSA-N trimethylxanthine Natural products CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cette invention se rapporte à un procédé servant à traiter l'hypertension oculaire et les glaucomes et qui consiste à administrer en mode topique dans les yeux d'un sujet mammifère nécessitant un tel traitement plus de 5 µg et moins de 50 µg par oeil par administration d'un composé de 15-céto-prostaglandine comportant une structure cyclique à l'extrémité de la chaîne .omega.. Le traitement faisant l'objet de cette invention ne produit pour ainsi dire pas d'effets secondaires irritants l'oeil ou en produit à un niveau réduit, même à une telle dose élevée.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30858901P | 2001-07-31 | 2001-07-31 | |
| US60/308,589 | 2001-07-31 | ||
| PCT/JP2002/007699 WO2003011299A2 (fr) | 2001-07-31 | 2002-07-30 | Procede et composition pour le traitement de l'hypertension oculaire et des glaucomes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2454422A1 true CA2454422A1 (fr) | 2003-02-13 |
Family
ID=23194562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002454422A Abandoned CA2454422A1 (fr) | 2001-07-31 | 2002-07-30 | Procede et composition pour le traitement de l'hypertension oculaire et des glaucomes |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1411950A2 (fr) |
| JP (1) | JP2004538306A (fr) |
| KR (1) | KR20040023707A (fr) |
| CN (1) | CN1646134A (fr) |
| BR (1) | BR0211545A (fr) |
| CA (1) | CA2454422A1 (fr) |
| MX (1) | MXPA04000980A (fr) |
| WO (2) | WO2003011299A2 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003215820A1 (en) * | 2002-03-28 | 2003-10-13 | Sucampo Ag | Method for treating ocular hypertension and glaucoma |
| US20040225014A1 (en) * | 2003-02-14 | 2004-11-11 | Sucampo Ag | Method for treating ocular hypertension and glaucoma |
| EP2069295B1 (fr) * | 2006-07-10 | 2013-12-18 | Allergan, Inc. | Derives de cyclopentane substitues comme agents therateutiques |
| ES2549863T3 (es) * | 2006-07-11 | 2015-11-02 | Allergan, Inc. | Derivados de ciclopentano como agentes antiglaucoma |
| US20080015219A1 (en) * | 2006-07-11 | 2008-01-17 | Allergan, Inc. | Therapeutic compounds |
| DK2170345T3 (da) * | 2007-07-03 | 2013-05-13 | Allergan Inc | Terapeutiske substituerede cyclopentaner til reduktion af intraokulært tryk |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0580268B1 (fr) * | 1988-10-01 | 1998-01-14 | R-Tech Ueno Ltd. | Agents oculaires hypotenseurs |
| CN100506232C (zh) * | 2000-03-16 | 2009-07-01 | 苏坎波公司 | 用于治疗眼压过高和青光眼的组合物 |
| US20020035148A1 (en) * | 2000-07-20 | 2002-03-21 | Ryuji Ueno | Treatment of ocular hypertension |
-
2002
- 2002-07-30 KR KR10-2004-7001587A patent/KR20040023707A/ko not_active Application Discontinuation
- 2002-07-30 MX MXPA04000980A patent/MXPA04000980A/es unknown
- 2002-07-30 CA CA002454422A patent/CA2454422A1/fr not_active Abandoned
- 2002-07-30 WO PCT/JP2002/007699 patent/WO2003011299A2/fr not_active Application Discontinuation
- 2002-07-30 EP EP02751774A patent/EP1411950A2/fr not_active Withdrawn
- 2002-07-30 BR BR0211545-0A patent/BR0211545A/pt not_active Application Discontinuation
- 2002-07-30 CN CNA028190947A patent/CN1646134A/zh active Pending
- 2002-07-30 JP JP2003516529A patent/JP2004538306A/ja not_active Withdrawn
- 2002-07-31 WO PCT/US2002/024072 patent/WO2003011178A2/fr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040023707A (ko) | 2004-03-18 |
| JP2004538306A (ja) | 2004-12-24 |
| CN1646134A (zh) | 2005-07-27 |
| MXPA04000980A (es) | 2004-04-20 |
| BR0211545A (pt) | 2004-07-13 |
| WO2003011299A3 (fr) | 2003-10-30 |
| WO2003011178A2 (fr) | 2003-02-13 |
| EP1411950A2 (fr) | 2004-04-28 |
| WO2003011299A2 (fr) | 2003-02-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |