CA2076023A1 - Utilisation de la 5-trans-prostaglandine f2a en tant qu'agent hypotenseur oculaire - Google Patents
Utilisation de la 5-trans-prostaglandine f2a en tant qu'agent hypotenseur oculaireInfo
- Publication number
- CA2076023A1 CA2076023A1 CA002076023A CA2076023A CA2076023A1 CA 2076023 A1 CA2076023 A1 CA 2076023A1 CA 002076023 A CA002076023 A CA 002076023A CA 2076023 A CA2076023 A CA 2076023A CA 2076023 A1 CA2076023 A1 CA 2076023A1
- Authority
- CA
- Canada
- Prior art keywords
- trans
- pgf2
- ocular
- alpha
- prostaglandin
- 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
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 title description 4
- 239000002220 antihypertensive agent Substances 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000004410 intraocular pressure Effects 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- PXGPLTODNUVGFL-UAAPODJFSA-N 5-trans-PGF2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O PXGPLTODNUVGFL-UAAPODJFSA-N 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 12
- 206010030043 Ocular hypertension Diseases 0.000 claims description 6
- 229940054534 ophthalmic solution Drugs 0.000 claims description 5
- 239000002997 ophthalmic solution Substances 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims 3
- 230000003000 nontoxic effect Effects 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 abstract description 2
- 208000010412 Glaucoma Diseases 0.000 description 13
- 229960001342 dinoprost Drugs 0.000 description 13
- PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 description 13
- 150000003180 prostaglandins Chemical class 0.000 description 13
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 8
- 230000001077 hypotensive effect Effects 0.000 description 7
- -1 l-isopropyl ester Chemical class 0.000 description 7
- 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 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 208000001953 Hypotension Diseases 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000036439 ocular surface hyperemia Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 2
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- 206010020565 Hyperaemia Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010030348 Open-Angle Glaucoma Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229960000711 alprostadil Drugs 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 229960002986 dinoprostone Drugs 0.000 description 2
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 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 2
- 230000035807 sensation Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 201000004569 Blindness Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 208000031969 Eye Hemorrhage Diseases 0.000 description 1
- 206010018307 Glaucoma and ocular hypertension Diseases 0.000 description 1
- 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
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100286668 Mus musculus Irak1bp1 gene Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 206010068960 Narrow anterior chamber angle Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000007950 Ocular Hypotension Diseases 0.000 description 1
- 208000022873 Ocular disease Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 108010087367 P-glycoprotein 2 Proteins 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 244000292604 Salvia columbariae Species 0.000 description 1
- 235000012377 Salvia columbariae var. columbariae Nutrition 0.000 description 1
- 235000001498 Salvia hispanica Nutrition 0.000 description 1
- 101150094640 Siae gene Proteins 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 241000289690 Xenarthra Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 201000001326 acute closed-angle glaucoma Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 201000005667 central retinal vein occlusion Diseases 0.000 description 1
- 235000014167 chia Nutrition 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002066 eicosanoids Chemical class 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 229960004716 idoxuridine Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 208000018769 loss of vision Diseases 0.000 description 1
- 231100000864 loss of vision Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- PDTFCHSETJBPTR-UHFFFAOYSA-N phenylmercuric nitrate Chemical compound [O-][N+](=O)O[Hg]C1=CC=CC=C1 PDTFCHSETJBPTR-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 230000001179 pupillary effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000004644 retinal vein occlusion Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49687990A | 1990-03-19 | 1990-03-19 | |
| US496,879 | 1990-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2076023A1 true CA2076023A1 (fr) | 1991-09-20 |
Family
ID=23974569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002076023A Abandoned CA2076023A1 (fr) | 1990-03-19 | 1991-02-12 | Utilisation de la 5-trans-prostaglandine f2a en tant qu'agent hypotenseur oculaire |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0521009A4 (fr) |
| JP (1) | JPH05505605A (fr) |
| CA (1) | CA2076023A1 (fr) |
| FI (1) | FI924205A7 (fr) |
| HU (1) | HUT61666A (fr) |
| IE (1) | IE910865A1 (fr) |
| WO (1) | WO1991014428A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5468778A (en) * | 1992-09-24 | 1995-11-21 | Allergan, Inc. | Method of lowering intraocular pressure by administering a pharmaceutical composition containing 7-(5-substituted cyclopentyl) and 7-(5-substituted-cyclopentenyl) 5-heptenoic acids and derivatives |
| DE69311361T2 (de) * | 1992-10-13 | 1998-01-08 | Alcon Lab Inc | Zusammensetzungen zur behandlung von glaukoma die prostaglandine und clonidinderivate enthalten |
| US6294563B1 (en) | 1994-10-27 | 2001-09-25 | Allergan Sales, Inc. | Combinations of prostaglandins and brimonidine or derivatives thereof |
| US6414021B1 (en) * | 2000-08-25 | 2002-07-02 | Sucampo Ag | Control of intraocular pressure during surgery |
| DE60315846T2 (de) | 2002-10-04 | 2008-05-21 | Tyco Healthcare Group Lp, Norwalk | Zusammenbau von chirurgischem klammerwerkzeug |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA715163B (en) * | 1970-09-15 | 1972-04-26 | Upjohn Co | Prostanoic acid derivatives |
| 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 |
| SE8703854D0 (sv) * | 1987-10-07 | 1987-10-07 | Pharmacia Ab | Prostaglandinderivat for behandling av glaukom eller okuler hypertension |
-
1991
- 1991-02-12 HU HU922572A patent/HUT61666A/hu unknown
- 1991-02-12 JP JP91505356A patent/JPH05505605A/ja active Pending
- 1991-02-12 FI FI924205A patent/FI924205A7/fi not_active Application Discontinuation
- 1991-02-12 WO PCT/US1991/000986 patent/WO1991014428A1/fr not_active Ceased
- 1991-02-12 EP EP19910905501 patent/EP0521009A4/en not_active Withdrawn
- 1991-02-12 CA CA002076023A patent/CA2076023A1/fr not_active Abandoned
- 1991-03-15 IE IE086591A patent/IE910865A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0521009A1 (fr) | 1993-01-07 |
| WO1991014428A1 (fr) | 1991-10-03 |
| JPH05505605A (ja) | 1993-08-19 |
| IE910865A1 (en) | 1991-09-25 |
| HUT61666A (en) | 1993-03-01 |
| FI924205L (fi) | 1992-09-18 |
| FI924205A0 (fi) | 1992-09-18 |
| HU9202572D0 (en) | 1992-12-28 |
| EP0521009A4 (en) | 1993-02-24 |
| FI924205A7 (fi) | 1992-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |