SE455306B - Lysinsalt av /(1-bensyl-1h-indazol-3-yl)oxi/-ettiksyra - Google Patents
Lysinsalt av /(1-bensyl-1h-indazol-3-yl)oxi/-ettiksyraInfo
- Publication number
- SE455306B SE455306B SE8200424A SE8200424A SE455306B SE 455306 B SE455306 B SE 455306B SE 8200424 A SE8200424 A SE 8200424A SE 8200424 A SE8200424 A SE 8200424A SE 455306 B SE455306 B SE 455306B
- Authority
- SE
- Sweden
- Prior art keywords
- bendazac
- salt
- placebo
- cortical
- benzyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 16
- -1 (1-BENZYL-1H-INDAZOL-3-YL) OXY Chemical class 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000004472 Lysine Substances 0.000 claims description 10
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 235000018977 lysine Nutrition 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 235000019766 L-Lysine Nutrition 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- BYFMCKSPFYVMOU-UHFFFAOYSA-N bendazac Chemical compound C12=CC=CC=C2C(OCC(=O)O)=NN1CC1=CC=CC=C1 BYFMCKSPFYVMOU-UHFFFAOYSA-N 0.000 description 31
- 229960005149 bendazac Drugs 0.000 description 27
- 230000001054 cortical effect Effects 0.000 description 20
- 239000000902 placebo Substances 0.000 description 20
- 229940068196 placebo Drugs 0.000 description 20
- 208000002177 Cataract Diseases 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- OCOCFNMFLNFNIA-ZSCHJXSPSA-N 2-(1-benzylindazol-3-yl)oxyacetic acid;(2s)-2,6-diaminohexanoic acid Chemical compound [NH3+]CCCC[C@H]([NH3+])C([O-])=O.C12=CC=CC=C2C(OCC(=O)[O-])=NN1CC1=CC=CC=C1 OCOCFNMFLNFNIA-ZSCHJXSPSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 2
- 229940033663 thimerosal Drugs 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 201000004569 Blindness Diseases 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 241000272168 Laridae Species 0.000 description 1
- 101710152384 Protein angel Proteins 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 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
- 210000001525 retina Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- JWFSRKUAFMGJSX-UHFFFAOYSA-M sodium;ethyl 4-hydroxybenzoate;benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1.CCOC(=O)C1=CC=C(O)C=C1 JWFSRKUAFMGJSX-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23768/80A IT1131779B (it) | 1980-07-29 | 1980-07-29 | Sale dell'acido (1-benzil-1h-indazol-3-il)-ossiacetico con la lisina e procedimento per la sua preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8200424L SE8200424L (sv) | 1983-07-28 |
| SE455306B true SE455306B (sv) | 1988-07-04 |
Family
ID=11209809
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8200424A SE455306B (sv) | 1980-07-29 | 1982-01-27 | Lysinsalt av /(1-bensyl-1h-indazol-3-yl)oxi/-ettiksyra |
| SE8302552A SE8302552L (sv) | 1980-07-29 | 1983-05-04 | ( (1-bensyl-1h-indazol-3-yl)oxi) ettiksyrasalt med lysin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8302552A SE8302552L (sv) | 1980-07-29 | 1983-05-04 | ( (1-bensyl-1h-indazol-3-yl)oxi) ettiksyrasalt med lysin |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4352813A (en, 2012) |
| JP (1) | JPS5753465A (en, 2012) |
| AR (1) | AR227677A1 (en, 2012) |
| AU (1) | AU536243B2 (en, 2012) |
| BE (1) | BE891914A (en, 2012) |
| BG (1) | BG60797B2 (en, 2012) |
| CA (1) | CA1166643A (en, 2012) |
| CH (1) | CH651556A5 (en, 2012) |
| DE (1) | DE3202561A1 (en, 2012) |
| ES (1) | ES503509A0 (en, 2012) |
| FR (1) | FR2489318B1 (en, 2012) |
| GB (1) | GB2081708B (en, 2012) |
| IT (1) | IT1131779B (en, 2012) |
| MX (1) | MX156471A (en, 2012) |
| NL (1) | NL8200222A (en, 2012) |
| PT (1) | PT73365B (en, 2012) |
| SE (2) | SE455306B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1189052B (it) * | 1981-11-27 | 1988-01-28 | Acraf | Trattamento della cataratta |
| IT1194564B (it) * | 1983-04-18 | 1988-09-22 | Acraf | Impiego del bendazac e dei suoi sali nel trattamento della retinite pigmentosa |
| IT1230441B (it) | 1989-02-07 | 1991-10-23 | Acraf | Eteri della serie dell'indazolo |
| IT1229674B (it) * | 1989-04-26 | 1991-09-06 | Acraf | Composizione farmaceutica per uso topico oftalmico contenente bendazac o 5-0h bendazac |
| US5217983A (en) * | 1992-03-27 | 1993-06-08 | Du Pont Merck Pharmaceutical Company | (N-benzyl) acetaldehyde bicyclic heterocycles useful as topical antiinflammatories |
| US5272169A (en) * | 1992-03-27 | 1993-12-21 | The Dupont Merck Pharmaceutical Company | (N-benzyl) acetaldehyde bicyclic heterocycles useful as topical antiinflammatories |
| IT1293794B1 (it) * | 1997-07-28 | 1999-03-10 | Acraf | Farmaco attivo nel ridurre la produzione di proteina mcp-1 |
| ITMI20062254A1 (it) * | 2006-11-24 | 2008-05-25 | Acraf | Uso di un acido metossi-alcanoico dell'indazolo per preparare una composizione farmaceutca |
| CN103641784B (zh) * | 2013-12-03 | 2018-06-19 | 杭州民生药业有限公司 | 一种苄达赖氨酸合成工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL28032A (en) * | 1966-08-29 | 1971-08-25 | Acraf | Indazol-3-yl-oxyalkanoic acids and process for the preparation thereof |
| FR1530097A (fr) | 1966-08-29 | 1968-06-21 | Acraf | Acides indazole-3-yl-oxyalcanoïques et procédé pour leur préparation |
| NL6717184A (en, 2012) * | 1967-12-16 | 1969-06-18 | Stamicarbon | |
| FR2217003A1 (en) * | 1973-02-14 | 1974-09-06 | Inst Investigaciones Terapeuti | Benzopyrilacetic acid deriv prepn - by reacting 1-(p-chlorobenzoyl-2-methyl)-5-methoxy-benzopyrilacetic acid with a base |
| DE2940373A1 (de) * | 1979-10-05 | 1981-04-23 | Troponwerke GmbH & Co KG, 5000 Köln | Lysin-(1-(p-chlorbenzoyl)-5-methoxy-2-methyl-3-indol) -acetoxy-acetate, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
-
1980
- 1980-07-29 IT IT23768/80A patent/IT1131779B/it active Protection Beyond IP Right Term
-
1981
- 1981-06-02 US US06/269,923 patent/US4352813A/en not_active Expired - Lifetime
- 1981-06-18 GB GB8118767A patent/GB2081708B/en not_active Expired
- 1981-06-23 MX MX187939A patent/MX156471A/es unknown
- 1981-06-29 ES ES503509A patent/ES503509A0/es active Granted
- 1981-07-14 PT PT73365A patent/PT73365B/pt unknown
- 1981-07-15 AR AR286096A patent/AR227677A1/es active
- 1981-07-27 FR FR8114549A patent/FR2489318B1/fr not_active Expired
- 1981-07-28 JP JP56119033A patent/JPS5753465A/ja active Granted
-
1982
- 1982-01-21 NL NL8200222A patent/NL8200222A/nl not_active Application Discontinuation
- 1982-01-26 CA CA000394976A patent/CA1166643A/en not_active Expired
- 1982-01-26 CH CH457/82A patent/CH651556A5/fr not_active IP Right Cessation
- 1982-01-27 AU AU79870/82A patent/AU536243B2/en not_active Ceased
- 1982-01-27 BE BE0/207152A patent/BE891914A/fr not_active IP Right Cessation
- 1982-01-27 DE DE19823202561 patent/DE3202561A1/de active Granted
- 1982-01-27 SE SE8200424A patent/SE455306B/sv not_active IP Right Cessation
-
1983
- 1983-05-04 SE SE8302552A patent/SE8302552L/xx not_active Application Discontinuation
-
1994
- 1994-02-24 BG BG098555A patent/BG60797B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE8302552L (sv) | 1983-07-28 |
| GB2081708B (en) | 1984-06-20 |
| AR227677A1 (es) | 1982-11-30 |
| CH651556A5 (en) | 1985-09-30 |
| BE891914A (fr) | 1982-05-17 |
| SE8302552D0 (sv) | 1983-05-04 |
| FR2489318B1 (fr) | 1986-01-03 |
| DE3202561A1 (de) | 1983-08-04 |
| BG60797B2 (bg) | 1996-03-29 |
| NL8200222A (nl) | 1983-08-16 |
| IT1131779B (it) | 1986-06-25 |
| FR2489318A1 (fr) | 1982-03-05 |
| GB2081708A (en) | 1982-02-24 |
| ES8203850A1 (es) | 1982-04-01 |
| JPS5753465A (en) | 1982-03-30 |
| PT73365A (en) | 1981-08-01 |
| ES503509A0 (es) | 1982-04-01 |
| CA1166643A (en) | 1984-05-01 |
| JPH0322384B2 (en, 2012) | 1991-03-26 |
| SE8200424L (sv) | 1983-07-28 |
| AU536243B2 (en) | 1984-05-03 |
| MX156471A (es) | 1988-08-26 |
| PT73365B (en) | 1982-09-23 |
| IT8023768A0 (it) | 1980-07-29 |
| AU7987082A (en) | 1983-08-04 |
| US4352813A (en) | 1982-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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