CA2015767A1 - Treatment of glaucoma - Google Patents
Treatment of glaucomaInfo
- Publication number
- CA2015767A1 CA2015767A1 CA002015767A CA2015767A CA2015767A1 CA 2015767 A1 CA2015767 A1 CA 2015767A1 CA 002015767 A CA002015767 A CA 002015767A CA 2015767 A CA2015767 A CA 2015767A CA 2015767 A1 CA2015767 A1 CA 2015767A1
- Authority
- CA
- Canada
- Prior art keywords
- inhibitor
- pharmaceutically acceptable
- formulation
- methyl
- acceptable salt
- 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
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- 238000000034 method Methods 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 241000124008 Mammalia Species 0.000 claims abstract 4
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims abstract 3
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 37
- 229940124530 sulfonamide Drugs 0.000 claims description 31
- 238000009472 formulation Methods 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 23
- -1 2-(L-phenylalanylimino)-3-ethyl-1,3,4-thiadiazoline-5-sulphonamide Chemical group 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 230000009885 systemic effect Effects 0.000 claims description 4
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- ZRQMYQZOHYAIDS-UHFFFAOYSA-N 2-amino-n-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide Chemical compound CN1N=C(S(N)(=O)=O)SC1=NC(=O)CN ZRQMYQZOHYAIDS-UHFFFAOYSA-N 0.000 claims 3
- AVXYPXXCXMDFSI-BYPYZUCNSA-N (2s)-2-amino-n-(3-ethyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)propanamide Chemical compound CCN1N=C(S(N)(=O)=O)SC1=NC(=O)[C@H](C)N AVXYPXXCXMDFSI-BYPYZUCNSA-N 0.000 claims 2
- PQVQPCJGUCPWSY-VIFPVBQESA-N (2s)-2-amino-n-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)-3-phenylpropanamide Chemical compound CN1N=C(S(N)(=O)=O)SC1=NC(=O)[C@@H](N)CC1=CC=CC=C1 PQVQPCJGUCPWSY-VIFPVBQESA-N 0.000 claims 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 2
- MHLXJWFBIVIZMJ-YFKPBYRVSA-N (2s)-2-amino-3-methyl-n-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)butanamide Chemical group CC(C)[C@H](N)C(=O)N=C1SC(S(N)(=O)=O)=NN1C MHLXJWFBIVIZMJ-YFKPBYRVSA-N 0.000 claims 1
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- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
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- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
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- BLFWHYXWBKKRHI-JYBILGDPSA-N plap Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(O)=O)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@@H](N)CCC(O)=O BLFWHYXWBKKRHI-JYBILGDPSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/346,493 US4975446A (en) | 1989-05-02 | 1989-05-02 | Treatment of glaucoma |
| US346,493 | 1989-05-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2015767A1 true CA2015767A1 (en) | 1990-11-02 |
Family
ID=23359648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002015767A Abandoned CA2015767A1 (en) | 1989-05-02 | 1990-04-30 | Treatment of glaucoma |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4975446A (OSRAM) |
| CA (1) | CA2015767A1 (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5242937A (en) * | 1990-03-19 | 1993-09-07 | Research Corporation Technologies, Inc. | Topically active ocular thiadiazole sulfonamide carbonic anhydrase inhibitors |
| US5824645A (en) * | 1991-12-30 | 1998-10-20 | Neurex Corporation | Method of treating inflammation |
-
1989
- 1989-05-02 US US07/346,493 patent/US4975446A/en not_active Expired - Fee Related
-
1990
- 1990-04-30 CA CA002015767A patent/CA2015767A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US4975446B1 (OSRAM) | 1993-06-08 |
| US4975446A (en) | 1990-12-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |