NO300591B1 - 4-£(2-benzotiazolyl)metylamino|-<alfa>-£(3,4-difluorfenoksy)metyl|-1-piperidinetanol - Google Patents
4-£(2-benzotiazolyl)metylamino|-<alfa>-£(3,4-difluorfenoksy)metyl|-1-piperidinetanol Download PDFInfo
- Publication number
- NO300591B1 NO300591B1 NO933010A NO933010A NO300591B1 NO 300591 B1 NO300591 B1 NO 300591B1 NO 933010 A NO933010 A NO 933010A NO 933010 A NO933010 A NO 933010A NO 300591 B1 NO300591 B1 NO 300591B1
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- Prior art keywords
- formula
- compound
- methyl
- acid
- compounds
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- -1 (2-benzothiazolyl) methylamino Chemical group 0.000 title claims description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000002253 acid Substances 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229920000858 Cyclodextrin Polymers 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 8
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000007853 buffer solution Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000006931 brain damage Effects 0.000 claims description 2
- 231100000874 brain damage Toxicity 0.000 claims description 2
- 208000029028 brain injury Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 12
- 230000000320 anti-stroke effect Effects 0.000 abstract description 8
- 239000000243 solution Substances 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 235000002639 sodium chloride Nutrition 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000002552 dosage form Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 206010061216 Infarction Diseases 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 238000007126 N-alkylation reaction Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 230000000141 anti-hypoxic effect Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- IGMKTIJBFUMVIN-UHFFFAOYSA-N Sabeluzole Chemical compound N=1C2=CC=CC=C2SC=1N(C)C(CC1)CCN1CC(O)COC1=CC=C(F)C=C1 IGMKTIJBFUMVIN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229960001701 chloroform Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
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- 230000007574 infarction Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000000272 proprioceptive effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 229950008900 sabeluzole Drugs 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KKOZKXBAPIYWAT-JTQLQIEISA-N (2s)-2-[(4-methylphenyl)sulfonylamino]pentanedioic acid Chemical compound CC1=CC=C(S(=O)(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 KKOZKXBAPIYWAT-JTQLQIEISA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- PVZOBVIINYAVEL-INIZCTEOSA-N (2s)-1-[4-(1,3-benzothiazol-2-ylmethylamino)piperidin-1-yl]-3-(3,4-difluorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC(CC1)NCC=1SC2=CC=CC=C2N=1)OC1=CC=C(F)C(F)=C1 PVZOBVIINYAVEL-INIZCTEOSA-N 0.000 description 1
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Paper (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65964591A | 1991-02-25 | 1991-02-25 | |
| PCT/EP1992/000356 WO1992014731A1 (en) | 1991-02-25 | 1992-02-14 | 4-[(2-BENZOTHIAZOLYL)METHYLAMINO]-α-[(3,4-DIFLUOROPHENOXY)METHYL]-1-PIPERIDINEETHANOL |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO933010D0 NO933010D0 (no) | 1993-08-24 |
| NO933010L NO933010L (no) | 1993-08-24 |
| NO300591B1 true NO300591B1 (no) | 1997-06-23 |
Family
ID=24646210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO933010A NO300591B1 (no) | 1991-02-25 | 1993-08-24 | 4-£(2-benzotiazolyl)metylamino|-<alfa>-£(3,4-difluorfenoksy)metyl|-1-piperidinetanol |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US5434168A (de) |
| EP (2) | EP0573473B1 (de) |
| JP (1) | JP2825652B2 (de) |
| KR (1) | KR0165901B1 (de) |
| CN (3) | CN1033454C (de) |
| AT (1) | ATE131478T1 (de) |
| AU (1) | AU649788B2 (de) |
| BG (1) | BG62332B1 (de) |
| CA (1) | CA2104000A1 (de) |
| CY (1) | CY1924A (de) |
| CZ (1) | CZ284705B6 (de) |
| DE (1) | DE69206787T2 (de) |
| DK (1) | DK0573473T3 (de) |
| DZ (1) | DZ1560A1 (de) |
| EE (1) | EE02983B1 (de) |
| ES (1) | ES2083737T3 (de) |
| FI (1) | FI933719A (de) |
| GR (1) | GR3018692T3 (de) |
| HK (1) | HK172296A (de) |
| HU (2) | HUT67695A (de) |
| IE (1) | IE69567B1 (de) |
| IL (3) | IL100952A (de) |
| LV (1) | LV11689B (de) |
| MA (1) | MA22447A1 (de) |
| MX (1) | MX9200777A (de) |
| NO (1) | NO300591B1 (de) |
| NZ (2) | NZ248437A (de) |
| PL (1) | PL168791B1 (de) |
| RO (1) | RO112959B1 (de) |
| RU (2) | RU2094434C1 (de) |
| SK (1) | SK278705B6 (de) |
| TN (1) | TNSN92017A1 (de) |
| TW (1) | TW218016B (de) |
| WO (1) | WO1992014731A1 (de) |
| ZA (1) | ZA921341B (de) |
| ZW (1) | ZW1992A1 (de) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZW1992A1 (en) * | 1991-02-25 | 1993-09-22 | Janssen Pharmaceutica Nv | 4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol |
| TW282469B (de) * | 1993-06-11 | 1996-08-01 | Janssen Pharmaceutica Nv | |
| NZ295132A (en) * | 1994-10-14 | 1998-06-26 | Janssen Pharmaceutica Nv | Sabeluzole aqueous suspension having ph from 8 to 10 |
| EP0794777A1 (de) * | 1994-11-24 | 1997-09-17 | Janssen Pharmaceutica N.V. | Lubeluzolhaltige intravenöse lösungen |
| JPH10501823A (ja) * | 1995-04-10 | 1998-02-17 | バクスター、インターナショナル、インコーポレイテッド | クモ膜下出血の治療における架橋ヘモグロビンの使用 |
| IL123083A0 (en) * | 1995-10-25 | 1998-09-24 | Janssen Pharmaceutica Nv | Lubeluzole n-oxides their preparation and pharmaceutical compositions containing them |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| US6756389B2 (en) | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| GB9815785D0 (en) * | 1998-07-20 | 1998-09-16 | Cerebrus Ltd | Chemical compounds |
| ATE296814T1 (de) * | 1999-05-12 | 2005-06-15 | Neurosearch As | Ionenkanal modulierende mittel |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963732A (en) * | 1973-05-30 | 1976-06-15 | Tiberio Bruzzese | Process for preparing dihydroxydiphenylmethane derivatives |
| US4310658A (en) * | 1980-06-18 | 1982-01-12 | Allied Corporation | Production of polyester thermally stabilized with an oxirane |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
| US4861785A (en) * | 1984-12-03 | 1989-08-29 | Janssen Pharmaceutica N.V. | Benzoxazol-and benzothiazolamine derivatives, useful as anti-anoxic agents |
| KR930005004B1 (ko) * | 1985-04-15 | 1993-06-11 | 쟈안센 파아마슈우티카 엔. 부이. | 치환된 n-[(4-피페리디닐)알킬]이환 축합 옥사졸아민 및 티아졸아민의 제조방법 |
| US4689330A (en) * | 1985-04-15 | 1987-08-25 | Janssen Pharmaceutica N.V. | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines |
| US4749702A (en) * | 1985-04-15 | 1988-06-07 | Janssen Pharmaceutica N. V. | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines |
| US4717760A (en) * | 1986-07-10 | 1988-01-05 | The Dow Chemical Company | Fluorinated tris-epoxides based on triphenyl methane |
| JPH0643426B2 (ja) * | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | イミダゾ〔４，５−ｂ〕ピリジン誘導体、その製造法及びそれを含有する抗潰瘍剤 |
| ZW1992A1 (en) * | 1991-02-25 | 1993-09-22 | Janssen Pharmaceutica Nv | 4-/(2-benzotiazolyl)methylamino/-b-/(3,4-difluorephenoxy)methyl/-1-piperidine ethanol |
-
1992
- 1992-02-10 ZW ZW19/92A patent/ZW1992A1/xx unknown
- 1992-02-11 NZ NZ24843792A patent/NZ248437A/xx unknown
- 1992-02-11 NZ NZ24159292A patent/NZ241592A/en unknown
- 1992-02-12 CN CN92101908A patent/CN1033454C/zh not_active Expired - Fee Related
- 1992-02-14 HU HU9302395A patent/HUT67695A/hu unknown
- 1992-02-14 RU RU9293053624A patent/RU2094434C1/ru active
- 1992-02-14 ES ES92905117T patent/ES2083737T3/es not_active Expired - Lifetime
- 1992-02-14 EP EP92905117A patent/EP0573473B1/de not_active Expired - Lifetime
- 1992-02-14 JP JP4504615A patent/JP2825652B2/ja not_active Expired - Fee Related
- 1992-02-14 DK DK92905117.5T patent/DK0573473T3/da active
- 1992-02-14 IL IL10095292A patent/IL100952A/en not_active IP Right Cessation
- 1992-02-14 AT AT92905117T patent/ATE131478T1/de not_active IP Right Cessation
- 1992-02-14 US US08/098,297 patent/US5434168A/en not_active Expired - Fee Related
- 1992-02-14 IL IL11383792A patent/IL113837A/en active IP Right Grant
- 1992-02-14 WO PCT/EP1992/000356 patent/WO1992014731A1/en active IP Right Grant
- 1992-02-14 DE DE69206787T patent/DE69206787T2/de not_active Expired - Fee Related
- 1992-02-14 AU AU12085/92A patent/AU649788B2/en not_active Ceased
- 1992-02-14 CA CA002104000A patent/CA2104000A1/en not_active Abandoned
- 1992-02-14 EP EP92200417A patent/EP0501552A1/de active Pending
- 1992-02-14 RU RU95112519/04A patent/RU2106348C1/ru not_active IP Right Cessation
- 1992-02-14 RO RO93-01147A patent/RO112959B1/ro unknown
- 1992-02-14 PL PL92300354A patent/PL168791B1/pl unknown
- 1992-02-20 TW TW081101226A patent/TW218016B/zh active
- 1992-02-21 SK SK512-92A patent/SK278705B6/sk unknown
- 1992-02-21 MA MA22735A patent/MA22447A1/fr unknown
- 1992-02-21 CZ CS92512A patent/CZ284705B6/cs not_active IP Right Cessation
- 1992-02-24 DZ DZ920018A patent/DZ1560A1/fr active
- 1992-02-24 IE IE920575A patent/IE69567B1/en not_active IP Right Cessation
- 1992-02-24 MX MX9200777A patent/MX9200777A/es not_active IP Right Cessation
- 1992-02-24 ZA ZA921341A patent/ZA921341B/xx unknown
- 1992-02-25 TN TNTNSN92017A patent/TNSN92017A1/fr unknown
-
1993
- 1993-08-23 KR KR1019930702525A patent/KR0165901B1/ko not_active IP Right Cessation
- 1993-08-24 FI FI933719A patent/FI933719A/fi unknown
- 1993-08-24 BG BG98068A patent/BG62332B1/bg unknown
- 1993-08-24 NO NO933010A patent/NO300591B1/no unknown
-
1994
- 1994-11-21 EE EE9400339A patent/EE02983B1/xx unknown
-
1995
- 1995-03-24 US US08/410,549 patent/US5675027A/en not_active Expired - Fee Related
- 1995-05-24 IL IL11383795A patent/IL113837A0/xx unknown
- 1995-05-30 CN CN95105632A patent/CN1043609C/zh not_active Expired - Fee Related
- 1995-05-30 CN CN95105633A patent/CN1117048A/zh active Pending
- 1995-06-21 HU HU95P/P00319P patent/HU211560A9/hu unknown
-
1996
- 1996-01-17 GR GR960400093T patent/GR3018692T3/el unknown
- 1996-08-13 LV LVP-96-334A patent/LV11689B/en unknown
- 1996-09-12 HK HK172296A patent/HK172296A/xx not_active IP Right Cessation
-
1997
- 1997-03-07 CY CY192497A patent/CY1924A/xx unknown
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