DE3310079C2 - - Google Patents
Info
- Publication number
- DE3310079C2 DE3310079C2 DE3310079A DE3310079A DE3310079C2 DE 3310079 C2 DE3310079 C2 DE 3310079C2 DE 3310079 A DE3310079 A DE 3310079A DE 3310079 A DE3310079 A DE 3310079A DE 3310079 C2 DE3310079 C2 DE 3310079C2
- Authority
- DE
- Germany
- Prior art keywords
- eye
- ophthalmic
- compounds
- cornea
- solution
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 231100000252 nontoxic Toxicity 0.000 claims description 12
- 230000003000 nontoxic effect Effects 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- GYRPAYDYHMZXQT-KZULUSFZSA-N N-[(1S,5R)-3-[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]-3-azabicyclo[3.1.0]hexan-1-yl]cyclopropanecarboxamide Chemical compound C1CC1C(=O)N[C@@]23C[C@@H]2CN(C3)C4=NC(=NC=C4F)NC5=CN(N=C5)CCO GYRPAYDYHMZXQT-KZULUSFZSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 210000001508 eye Anatomy 0.000 description 84
- 239000000243 solution Substances 0.000 description 35
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- 238000012360 testing method Methods 0.000 description 29
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- 229940079593 drug Drugs 0.000 description 22
- -1 methoxy, methylthio Chemical group 0.000 description 20
- 241000283973 Oryctolagus cuniculus Species 0.000 description 18
- 239000002674 ointment Substances 0.000 description 18
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- 210000000795 conjunctiva Anatomy 0.000 description 14
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- 238000000034 method Methods 0.000 description 14
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- 238000002360 preparation method Methods 0.000 description 13
- 206010046851 Uveitis Diseases 0.000 description 12
- 239000002997 ophthalmic solution Substances 0.000 description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 12
- 206010061218 Inflammation Diseases 0.000 description 11
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
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- 241001465754 Metazoa Species 0.000 description 9
- 210000004204 blood vessel Anatomy 0.000 description 9
- 239000003885 eye ointment Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
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- 229940054534 ophthalmic solution Drugs 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
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- 238000002474 experimental method Methods 0.000 description 6
- 208000030533 eye disease Diseases 0.000 description 6
- 230000007794 irritation Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 231100000344 non-irritating Toxicity 0.000 description 6
- 229910001961 silver nitrate Inorganic materials 0.000 description 6
- 230000008733 trauma Effects 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 210000001742 aqueous humor Anatomy 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 210000000695 crystalline len Anatomy 0.000 description 5
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- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 description 4
- 206010025421 Macule Diseases 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 239000012085 test solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010055665 Corneal neovascularisation Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010015946 Eye irritation Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 230000001886 ciliary effect Effects 0.000 description 3
- 201000000159 corneal neovascularization Diseases 0.000 description 3
- 229940012356 eye drops Drugs 0.000 description 3
- 231100000013 eye irritation Toxicity 0.000 description 3
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- 150000002500 ions Chemical class 0.000 description 3
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- 229960001017 tolmetin Drugs 0.000 description 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
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- 208000020564 Eye injury Diseases 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010038886 Retinal oedema Diseases 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229940031955 anhydrous lanolin Drugs 0.000 description 2
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Classifications
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- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
Landscapes
- Health & Medical Sciences (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)
- Veterinary Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Epidemiology (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/360,754 US4454151A (en) | 1982-03-22 | 1982-03-22 | Use of pyrrolo pyrroles in treatment of ophthalmic diseases |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3310079A1 DE3310079A1 (de) | 1983-09-22 |
| DE3310079C2 true DE3310079C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-10-18 |
Family
ID=23419287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833310079 Granted DE3310079A1 (de) | 1982-03-22 | 1983-03-21 | Topische ophthalmische arzneimittel |
Country Status (6)
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| PT2044111E (pt) | 2006-06-21 | 2014-11-12 | Univ Colorado Regents | Abordagem seletiva do fator h do complemento para o tratamento de doenças |
| WO2008034244A1 (en) * | 2006-09-21 | 2008-03-27 | Waratah Pharmaceuticals Inc. | The combination of a cyclohexanehexol and a nsaid for the treatment of neurodegenerative diseases |
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| US20090018057A1 (en) * | 2007-07-09 | 2009-01-15 | Gregory Lambert | OIL IN WATER EMULSION COMPRISING NSAIDs AND QUATERNARY AMMONIUM HALIDES |
| US8602959B1 (en) * | 2010-05-21 | 2013-12-10 | Robert Park | Methods and devices for delivery of radiation to the posterior portion of the eye |
| RU2359658C1 (ru) * | 2008-02-22 | 2009-06-27 | Ирина Александровна Глущенко | Средство для профилактики и лечения офтальмологических заболеваний |
| US9192571B2 (en) * | 2008-03-03 | 2015-11-24 | Allergan, Inc. | Ketorolac tromethamine compositions for treating or preventing ocular pain |
| US7842714B2 (en) * | 2008-03-03 | 2010-11-30 | Allergan, Inc. | Ketorolac tromethamine compositions for treating ocular pain |
| CA2740124A1 (en) * | 2008-10-09 | 2010-04-15 | Waratah Pharmaceuticals Inc. | Use of scyllo-inositols for the treatment of macular degeneration-related disorders |
| US8778999B2 (en) | 2009-03-05 | 2014-07-15 | Insite Vision Incorporated | Non-steroidal anti-inflammatory ophthalmic compositions |
| SG186397A1 (en) | 2010-06-22 | 2013-01-30 | Univ Colorado Regents | Antibodies to the c3d fragment of complement component 3 |
| PT2968461T (pt) | 2013-03-13 | 2022-12-26 | Genzyme Corp | Proteínas de fusão que compreendem porções de ligação ao pdgf e ao vegf e seus métodos de utilização |
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| WO2025015317A2 (en) | 2023-07-13 | 2025-01-16 | Kriya Therapeutics, Inc. | Complement pathway inhibitor fusions and methods of using the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087539A (en) * | 1976-07-14 | 1978-05-02 | Syntex (U.S.A.) Inc. | 5-(2-Furoyl)-, 5-(2-thenoyl)-, 5-(3-furoyl)- and 5-(3-thenoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| US4089969A (en) * | 1976-07-14 | 1978-05-16 | Syntex (U.S.A.) Inc. | 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| US4097579A (en) * | 1977-03-31 | 1978-06-27 | Syntex (U.S.A.) Inc. | 5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof |
| US4140698A (en) * | 1977-07-25 | 1979-02-20 | Syntex (Usa) Inc. | 1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles |
| US4232038A (en) * | 1979-08-31 | 1980-11-04 | Syntex (U.S.A.) Inc. | 5-Alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl-1,2-dihydro-3H-pyrrolo[1,]pyrrole-1-carboxylic acids |
| US4344943A (en) * | 1980-06-09 | 1982-08-17 | Syntex (U.S.A.) Inc. | 6-Chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof |
-
1982
- 1982-03-22 US US06/360,754 patent/US4454151A/en not_active Expired - Lifetime
-
1983
- 1983-03-18 JP JP58044525A patent/JPS58172314A/ja active Granted
- 1983-03-21 AU AU12651/83A patent/AU568072B2/en not_active Expired
- 1983-03-21 DE DE19833310079 patent/DE3310079A1/de active Granted
- 1983-03-21 NZ NZ203639A patent/NZ203639A/en unknown
- 1983-03-21 IT IT67315/83A patent/IT1162842B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1162842B (it) | 1987-04-01 |
| IT8367315A0 (it) | 1983-03-21 |
| US4454151A (en) | 1984-06-12 |
| NZ203639A (en) | 1988-05-30 |
| JPH047324B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-02-10 |
| JPS58172314A (ja) | 1983-10-11 |
| DE3310079A1 (de) | 1983-09-22 |
| AU568072B2 (en) | 1987-12-17 |
| AU1265183A (en) | 1983-09-29 |
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Free format text: BARZ, P., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 80803 MUENCHEN |