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
- 239000004033 plastic Substances 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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- 239000004317 sodium nitrate Substances 0.000 description 1
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Steroid Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (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 (es) |
EP (2) | EP0636623B1 (es) |
JP (1) | JP2738461B2 (es) |
KR (1) | KR100215627B1 (es) |
AT (2) | ATE156823T1 (es) |
AU (1) | AU646871B2 (es) |
CA (2) | CA2282890C (es) |
CZ (1) | CZ288351B6 (es) |
DE (3) | DE69127260T2 (es) |
DK (1) | DK0486666T3 (es) |
EG (1) | EG19650A (es) |
ES (1) | ES2104708T3 (es) |
FI (3) | FI105686B (es) |
GR (1) | GR3024828T3 (es) |
HK (1) | HK1000534A1 (es) |
HR (1) | HRP940524B1 (es) |
HU (2) | HU219974B (es) |
IE (1) | IE911931A1 (es) |
IL (3) | IL98392A (es) |
LT (1) | LT3264B (es) |
LU (1) | LU90205I2 (es) |
LV (1) | LV10274B (es) |
MC (1) | MC2210A1 (es) |
MX (1) | MX9203421A (es) |
MY (1) | MY110226A (es) |
NL (1) | NL980001I2 (es) |
NO (2) | NO300634B1 (es) |
NZ (1) | NZ238424A (es) |
PL (1) | PL166214B1 (es) |
PT (1) | PT97888B (es) |
RU (1) | RU2160736C2 (es) |
SA (1) | SA05260104B1 (es) |
SI (2) | SI21560B (es) |
SK (1) | SK281621B6 (es) |
UA (1) | UA37178C2 (es) |
WO (1) | WO1991018897A1 (es) |
YU (1) | YU48855B (es) |
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 (es) * | 1991-02-12 | 1995-11-21 | Pfizer | |
ES2143992T3 (es) * | 1991-11-25 | 2000-06-01 | Pfizer | Derivados de 5-(hetero- o carbociclilamino)-indol, su preparacion y uso como 5-ht1 agonistas. |
GB9201038D0 (en) * | 1992-01-16 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
TW288010B (es) * | 1992-03-05 | 1996-10-11 | Pfizer | |
JP3309982B2 (ja) * | 1992-03-13 | 2002-07-29 | メルク シヤープ エンド ドーム リミテツド | イミダゾール,トリアゾールおよびテトラゾール誘導体 |
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 |
UA27467C2 (uk) | 1992-04-07 | 2000-09-15 | Пфайзер Інк. | ПОХІДНІ ІНДОЛУ ЯК 5-НТ<sub>1</sub> АГОНІСТИ ТА ПРОМІЖНІ СПОЛУКИ |
AU670270B2 (en) * | 1992-04-10 | 1996-07-11 | Pfizer Inc. | Acylaminoindole derivatives as 5-HT1 agonists |
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 JP JP3510103A patent/JP2738461B2/ja not_active Expired - Lifetime
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- 1991-06-06 DK DK91911486.8T patent/DK0486666T3/da active
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- 1991-06-06 DE DE69127260T patent/DE69127260T2/de not_active Expired - Lifetime
- 1991-06-06 WO PCT/GB1991/000908 patent/WO1991018897A1/en active IP Right Grant
- 1991-06-06 CZ CS19911727A patent/CZ288351B6/cs not_active IP Right Cessation
- 1991-06-06 EP EP94115107A patent/EP0636623B1/en not_active Expired - Lifetime
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- 1991-06-06 SI SI9119001A patent/SI21560B/sl active Search and Examination
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- 1991-06-06 EG EG35491A patent/EG19650A/xx active
- 1991-06-06 EP EP91911486A patent/EP0486666B1/en not_active Expired - Lifetime
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- 1991-06-06 DE DE69132691T patent/DE69132691T2/de not_active Expired - Lifetime
- 1991-06-06 SI SI9111010A patent/SI9111010B/sl active Search and Examination
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- 1991-06-06 IE IE193191A patent/IE911931A1/en not_active IP Right Cessation
- 1991-06-06 AT AT91911486T patent/ATE156823T1/de active
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- 1991-06-06 UA UA93002089A patent/UA37178C2/uk unknown
- 1991-06-06 DE DE1991627260 patent/DE19775091I2/de active Active
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- 1991-06-06 NZ NZ238424A patent/NZ238424A/xx not_active IP Right Cessation
- 1991-06-06 AT AT94115107T patent/ATE204275T1/de active
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- 1991-06-06 HU HU9200384A patent/HU219974B/hu unknown
- 1991-06-06 PT PT97888A patent/PT97888B/pt not_active IP Right Cessation
- 1991-06-06 PL PL91293486A patent/PL166214B1/pl unknown
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1992
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1993
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1994
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- 1994-12-05 US US08/341,206 patent/US5466699A/en not_active Expired - Lifetime
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1995
- 1995-06-06 US US08/471,229 patent/US5863935A/en not_active Expired - Lifetime
- 1995-06-29 HU HU95P/P00532P patent/HU211479A9/hu unknown
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1996
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1997
- 1997-09-24 GR GR970402466T patent/GR3024828T3/el unknown
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1998
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2000
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Legal Events
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Expiry date: 20110606 |
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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 |