CA2384690C - Rivastigmine for the treatment of ocular disorders - Google Patents
Rivastigmine for the treatment of ocular disorders Download PDFInfo
- Publication number
- CA2384690C CA2384690C CA2384690A CA2384690A CA2384690C CA 2384690 C CA2384690 C CA 2384690C CA 2384690 A CA2384690 A CA 2384690A CA 2384690 A CA2384690 A CA 2384690A CA 2384690 C CA2384690 C CA 2384690C
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- compound
- glaucoma
- rivastigmine
- methyl
- 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 - Fee Related
Links
- 208000022873 Ocular disease Diseases 0.000 title claims abstract description 9
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 title abstract description 25
- 229960004136 rivastigmine Drugs 0.000 title abstract description 25
- 206010067013 Normal tension glaucoma Diseases 0.000 claims abstract description 11
- 201000002978 low tension glaucoma Diseases 0.000 claims abstract description 11
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 10
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
- 210000001328 optic nerve Anatomy 0.000 claims abstract description 10
- 210000001525 retina Anatomy 0.000 claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 241000282414 Homo sapiens Species 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000000063 preceeding effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000005259 measurement Methods 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000004410 intraocular pressure Effects 0.000 description 5
- 210000001747 pupil Anatomy 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000003855 balanced salt solution Substances 0.000 description 3
- 210000004087 cornea Anatomy 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229940053973 novocaine Drugs 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 238000000585 Mann–Whitney U test Methods 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000002164 blood-aqueous barrier Anatomy 0.000 description 1
- 230000004420 blood-aqueous barrier Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 210000003560 epithelium corneal Anatomy 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- 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)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99120678 | 1999-10-19 | ||
| EP99120678.0 | 1999-10-19 | ||
| PCT/EP2000/010234 WO2001028553A1 (en) | 1999-10-19 | 2000-10-17 | Rivastigmine for the treatment of ocular disorders |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2384690A1 CA2384690A1 (en) | 2001-04-26 |
| CA2384690C true CA2384690C (en) | 2010-08-17 |
Family
ID=8239225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2384690A Expired - Fee Related CA2384690C (en) | 1999-10-19 | 2000-10-17 | Rivastigmine for the treatment of ocular disorders |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6534541B1 (enExample) |
| EP (1) | EP1225890B1 (enExample) |
| JP (1) | JP2003512324A (enExample) |
| AR (1) | AR026062A1 (enExample) |
| AT (1) | ATE285764T1 (enExample) |
| AU (1) | AU766001B2 (enExample) |
| CA (1) | CA2384690C (enExample) |
| DE (1) | DE60017174T2 (enExample) |
| DK (1) | DK1225890T3 (enExample) |
| ES (1) | ES2234708T3 (enExample) |
| NZ (1) | NZ518164A (enExample) |
| PT (1) | PT1225890E (enExample) |
| WO (1) | WO2001028553A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2237163T3 (es) | 1998-10-01 | 2005-07-16 | Novartis Ag | Nuevas formulaciones orales de revastigmina de liberacion controlada. |
| US9993558B2 (en) | 2004-10-01 | 2018-06-12 | Ramscor, Inc. | Sustained release eye drop formulations |
| US8541413B2 (en) * | 2004-10-01 | 2013-09-24 | Ramscor, Inc. | Sustained release eye drop formulations |
| WO2009022345A1 (en) * | 2007-08-14 | 2009-02-19 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Phenyl carbamates for the treatment of multiple sclerosis |
| US12478503B2 (en) | 2009-05-18 | 2025-11-25 | Glaukos Corporation | Implants with controlled drug delivery features and methods of using same |
| US10206813B2 (en) | 2009-05-18 | 2019-02-19 | Dose Medical Corporation | Implants with controlled drug delivery features and methods of using same |
| WO2011151359A1 (en) | 2010-06-02 | 2011-12-08 | Noscira, S.A. | Combined treatment with a cholinesterase inhibitor and a thiadiazolidinedione derivative |
| CN107417574B (zh) * | 2017-03-21 | 2019-12-03 | 浙江省医学科学院 | 2,4-双取代苯乙酮化合物及其旋光异构体、药学上可接受的盐及应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL74497A (en) | 1985-03-05 | 1990-02-09 | Proterra Ag | Pharmaceutical compositions containing phenyl carbamate derivatives and certain phenyl carbamate derivatives |
| HU201906B (en) * | 1987-03-04 | 1991-01-28 | Sandoz Ag | Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them |
| US4900748A (en) | 1988-03-04 | 1990-02-13 | The United States Of America As Represented By The Department Of Health And Human Services | Carbamates related to (-)-physostigmine as cholinergic agents |
| JP3708957B2 (ja) | 1991-09-26 | 2005-10-19 | アメリカ合衆国 | （−）−エゼロリン、（−）−ｎ１−ノルエゼロリンおよび（−）−ｎ１−ベンジルノルエゼロリンの置換フェンゼリンおよびフェニルカルバミン酸塩：特異的アセチルコリンエステラーゼ阻害薬としての使用 |
| ES2206449T3 (es) | 1991-09-26 | 2004-05-16 | The Government Of The Usa As Represented By The Secretary Of Department Of Health And Human Services | Inhibidores de colinesterasas, composiciones farmaceuticas y sus usos. |
| AU1138097A (en) * | 1995-12-22 | 1997-07-17 | Alcon Laboratories, Inc. | Combinations of prostaglandins and miotics for lowering intraocular pressure |
-
2000
- 2000-10-11 US US09/686,025 patent/US6534541B1/en not_active Expired - Fee Related
- 2000-10-17 ES ES00992430T patent/ES2234708T3/es not_active Expired - Lifetime
- 2000-10-17 PT PT00992430T patent/PT1225890E/pt unknown
- 2000-10-17 EP EP00992430A patent/EP1225890B1/en not_active Expired - Lifetime
- 2000-10-17 AU AU28349/01A patent/AU766001B2/en not_active Ceased
- 2000-10-17 JP JP2001531383A patent/JP2003512324A/ja active Pending
- 2000-10-17 DE DE60017174T patent/DE60017174T2/de not_active Expired - Lifetime
- 2000-10-17 AR ARP000105450A patent/AR026062A1/es unknown
- 2000-10-17 AT AT00992430T patent/ATE285764T1/de active
- 2000-10-17 WO PCT/EP2000/010234 patent/WO2001028553A1/en not_active Ceased
- 2000-10-17 NZ NZ518164A patent/NZ518164A/en not_active IP Right Cessation
- 2000-10-17 DK DK00992430T patent/DK1225890T3/da active
- 2000-10-17 CA CA2384690A patent/CA2384690C/en not_active Expired - Fee Related
-
2003
- 2003-01-23 US US10/349,718 patent/US6835748B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2234708T3 (es) | 2005-07-01 |
| US6835748B2 (en) | 2004-12-28 |
| PT1225890E (pt) | 2005-05-31 |
| JP2003512324A (ja) | 2003-04-02 |
| AR026062A1 (es) | 2002-12-26 |
| NZ518164A (en) | 2003-10-31 |
| EP1225890B1 (en) | 2004-12-29 |
| DK1225890T3 (da) | 2005-04-04 |
| WO2001028553A1 (en) | 2001-04-26 |
| DE60017174T2 (de) | 2005-12-22 |
| US20030119832A1 (en) | 2003-06-26 |
| US6534541B1 (en) | 2003-03-18 |
| AU2834901A (en) | 2001-04-30 |
| DE60017174D1 (de) | 2005-02-03 |
| ATE285764T1 (de) | 2005-01-15 |
| EP1225890A1 (en) | 2002-07-31 |
| AU766001B2 (en) | 2003-10-09 |
| CA2384690A1 (en) | 2001-04-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20131017 |