SK281621B6 - Indolové deriváty, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie - Google Patents
Indolové deriváty, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie Download PDFInfo
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- SK281621B6 SK281621B6 SK1727-91A SK172791A SK281621B6 SK 281621 B6 SK281621 B6 SK 281621B6 SK 172791 A SK172791 A SK 172791A SK 281621 B6 SK281621 B6 SK 281621B6
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- 230000001225 therapeutic effect Effects 0.000 title description 5
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 172
- 239000000203 mixture Substances 0.000 claims abstract description 126
- 238000002360 preparation method Methods 0.000 claims abstract description 33
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- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 12
- 206010027599 migraine Diseases 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000011321 prophylaxis Methods 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 29
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 9
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002475 indoles Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 212
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
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- 239000002585 base Substances 0.000 description 17
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- 238000006243 chemical reaction Methods 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000012279 sodium borohydride Substances 0.000 description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 235000001508 sulfur Nutrition 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
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- 238000007792 addition Methods 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000006396 nitration reaction Methods 0.000 description 6
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- 239000007868 Raney catalyst Substances 0.000 description 5
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- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
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- 238000004452 microanalysis Methods 0.000 description 5
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- 238000007142 ring opening reaction Methods 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
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- ADZUEEUKBYCSEY-UHFFFAOYSA-N 1h-indole-5-carbaldehyde Chemical compound O=CC1=CC=C2NC=CC2=C1 ADZUEEUKBYCSEY-UHFFFAOYSA-N 0.000 description 2
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- OOOAMVGIUWTNRH-UHFFFAOYSA-N 4-[[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]methyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCC1C(C1=C2)=CNC1=CC=C2CC1NC(=O)OC1 OOOAMVGIUWTNRH-UHFFFAOYSA-N 0.000 description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QRMKTNANRJCRCY-UHFFFAOYSA-N ethylammonium acetate Chemical compound CC[NH3+].CC([O-])=O QRMKTNANRJCRCY-UHFFFAOYSA-N 0.000 description 1
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- 239000006210 lotion Substances 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 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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- BRHXZMRHUZCLAS-ZOWNYOTGSA-N n,n-dimethyl-2-[5-[[(4s)-oxathiazolidin-4-yl]methyl]-1h-indol-3-yl]ethanamine;hydrochloride Chemical compound Cl.C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COSN1 BRHXZMRHUZCLAS-ZOWNYOTGSA-N 0.000 description 1
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- NKOBWHOGNBPTDO-LLVKDONJSA-N norzolmitripan Chemical compound C1=C2C(CCN)=CNC2=CC=C1C[C@@H]1COC(=O)N1 NKOBWHOGNBPTDO-LLVKDONJSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
- 229960003418 phenoxybenzamine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
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- 235000010344 sodium nitrate Nutrition 0.000 description 1
- SNYDMZJXWYXCKT-UHFFFAOYSA-M sodium propane-1,2,3-triol benzoate Chemical compound [Na+].OCC(O)CO.[O-]C(=O)c1ccccc1 SNYDMZJXWYXCKT-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909012672A GB9012672D0 (en) | 1990-06-07 | 1990-06-07 | Therapeutic heterocyclic compounds |
| GB919102182A GB9102182D0 (en) | 1991-02-01 | 1991-02-01 | Therapeutic heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK281621B6 true SK281621B6 (sk) | 2001-05-10 |
Family
ID=26297174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1727-91A SK281621B6 (sk) | 1990-06-07 | 1991-06-06 | Indolové deriváty, spôsob ich prípravy, farmaceutické kompozície s ich obsahom a ich použitie |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US5399574A (pl) |
| EP (2) | EP0486666B1 (pl) |
| JP (1) | JP2738461B2 (pl) |
| KR (1) | KR100215627B1 (pl) |
| AT (2) | ATE204275T1 (pl) |
| AU (1) | AU646871B2 (pl) |
| CA (2) | CA2282890C (pl) |
| CZ (1) | CZ288351B6 (pl) |
| DE (3) | DE69127260T2 (pl) |
| DK (1) | DK0486666T3 (pl) |
| EG (1) | EG19650A (pl) |
| ES (1) | ES2104708T3 (pl) |
| FI (3) | FI105686B (pl) |
| GR (1) | GR3024828T3 (pl) |
| HK (1) | HK1000534A1 (pl) |
| HR (1) | HRP940524B1 (pl) |
| HU (2) | HU219974B (pl) |
| IE (1) | IE911931A1 (pl) |
| IL (3) | IL98392A (pl) |
| LT (1) | LT3264B (pl) |
| LU (1) | LU90205I2 (pl) |
| LV (1) | LV10274B (pl) |
| MC (1) | MC2210A1 (pl) |
| MX (1) | MX9203421A (pl) |
| MY (1) | MY110226A (pl) |
| NL (1) | NL980001I2 (pl) |
| NO (2) | NO300634B1 (pl) |
| NZ (1) | NZ238424A (pl) |
| PL (1) | PL166214B1 (pl) |
| PT (1) | PT97888B (pl) |
| RU (1) | RU2160736C2 (pl) |
| SA (1) | SA05260104B1 (pl) |
| SI (2) | SI9111010B (pl) |
| SK (1) | SK281621B6 (pl) |
| UA (1) | UA37178C2 (pl) |
| WO (1) | WO1991018897A1 (pl) |
| YU (1) | YU48855B (pl) |
Families Citing this family (123)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| TW263508B (pl) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| DE69230803T2 (de) * | 1991-11-25 | 2000-12-07 | Pfizer Inc., New York | 5-(hetero- oder carbocyclylamino)-indol derivate, deren herstellung und deren verwendung als 5-ht1 agonisten |
| GB9201038D0 (en) * | 1992-01-16 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
| TW288010B (pl) * | 1992-03-05 | 1996-10-11 | Pfizer | |
| WO1993018029A1 (en) * | 1992-03-13 | 1993-09-16 | Merck Sharp & Dohme Limited | Imidazole, triazole and tetrazole derivatives |
| GB9207396D0 (en) * | 1992-04-03 | 1992-05-13 | Merck Sharp & Dohme | Therapeutic agents |
| US6380233B1 (en) | 1992-04-07 | 2002-04-30 | Pfizer Inc | Indole derivatives as 5-HT1 agonists |
| BR9306201A (pt) * | 1992-04-07 | 1998-06-23 | Pfizer | Derivados de indol como agonistas 5-ht1 |
| ATE148465T1 (de) * | 1992-04-10 | 1997-02-15 | Pfizer | Acylaminoindolderivate als 5-ht1 agonisten |
| GB9207930D0 (en) * | 1992-04-10 | 1992-05-27 | Pfizer Ltd | Indoles |
| GB9208161D0 (en) * | 1992-04-14 | 1992-05-27 | Pfizer Ltd | Indoles |
| GB9208463D0 (en) * | 1992-04-16 | 1992-06-03 | Merck Sharp & Dohme | Therapeutic agents |
| GB9209882D0 (en) * | 1992-05-07 | 1992-06-24 | Glaxo Lab Sa | Compositions |
| GB9211277D0 (en) | 1992-05-28 | 1992-07-15 | Glaxo Group Inc | Pharmaceutical compositions |
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1991
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- 1991-06-06 WO PCT/GB1991/000908 patent/WO1991018897A1/en active IP Right Grant
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- 1991-06-06 RU RU95112537/04A patent/RU2160736C2/ru active
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1992
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1993
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1994
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1995
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1996
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1997
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1998
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20110606 |
|
| SPCE | Expiry of an spc |
Free format text: PRODUCT NAME: (S)-N,N-DIMETYL-2-¬5-(2-OXO-1,3-OXAZOLIDIN-4-YLMETYL)-1H- -INDOL-3-YL|ETYLAMIN (ZOLMITRIPTAN); NAT. REGISTRATION NO/DATE: 33/0013/00-S, 33/0014/00-S 20000127; FIRST REGISTRATION: GB PL 12619/0116-0117 19970307 Spc suppl protection certif: 17; 12-2002 Filing date: 20021223 Extension date: 20120307 |