NO823775L - 3-(1-substituert-4-piperidyl)-1,2-benzisoksazoler, fremgangsmaate til deres fremstilling, farmasoeytisk blanding inneholdende disse og deres bruk som legemidler - Google Patents
3-(1-substituert-4-piperidyl)-1,2-benzisoksazoler, fremgangsmaate til deres fremstilling, farmasoeytisk blanding inneholdende disse og deres bruk som legemidlerInfo
- Publication number
- NO823775L NO823775L NO823775A NO823775A NO823775L NO 823775 L NO823775 L NO 823775L NO 823775 A NO823775 A NO 823775A NO 823775 A NO823775 A NO 823775A NO 823775 L NO823775 L NO 823775L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- benzisoxazole
- group
- piperidyl
- fluoro
- Prior art date
Links
- -1 1-SUBSTITUTED-4-PIPERIDYL Chemical class 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title claims 2
- 239000000203 mixture Substances 0.000 title abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 235000013312 flour Nutrition 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 102
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 41
- 239000003921 oil Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 39
- 239000007787 solid Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 238000004458 analytical method Methods 0.000 description 33
- 235000011181 potassium carbonates Nutrition 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
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- 238000001953 recrystallisation Methods 0.000 description 16
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
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- 239000000741 silica gel Substances 0.000 description 14
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000012258 stirred mixture Substances 0.000 description 10
- UXXLTPGCINZEFM-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCl)C1=CC=C(F)C=C1 UXXLTPGCINZEFM-UHFFFAOYSA-N 0.000 description 9
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- XONBKLFCLPGIPC-UHFFFAOYSA-N 3-(3-chloropropyl)-6-fluoro-1,2-benzoxazole Chemical compound FC1=CC=C2C(CCCCl)=NOC2=C1 XONBKLFCLPGIPC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 229960004046 apomorphine Drugs 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- GUMPYDGUYXOYML-UHFFFAOYSA-N 3-(3-chloropropyl)-1h-benzimidazol-2-one Chemical compound C1=CC=C2NC(=O)N(CCCCl)C2=C1 GUMPYDGUYXOYML-UHFFFAOYSA-N 0.000 description 5
- RYCGIMLNIZWGDI-UHFFFAOYSA-N 3-[3-(benzenesulfonyl)propyl]-2-methyl-1h-indole Chemical compound CC=1NC2=CC=CC=C2C=1CCCS(=O)(=O)C1=CC=CC=C1 RYCGIMLNIZWGDI-UHFFFAOYSA-N 0.000 description 5
- KEIQPPQTKPFHLZ-UHFFFAOYSA-N 3-piperidin-4-yl-1,2-benzoxazole Chemical class C1CNCCC1C1=NOC2=CC=CC=C12 KEIQPPQTKPFHLZ-UHFFFAOYSA-N 0.000 description 5
- MWBRMKAAQVRANL-UHFFFAOYSA-N 6-chloro-3-piperidin-4-yl-1,2-benzoxazole Chemical compound N=1OC2=CC(Cl)=CC=C2C=1C1CCNCC1 MWBRMKAAQVRANL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 description 5
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 5
- 230000009194 climbing Effects 0.000 description 5
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
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- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229940001593 sodium carbonate Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- 238000006073 displacement reaction Methods 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 125000005936 piperidyl group Chemical group 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
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- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/319,872 US4352811A (en) | 1981-11-12 | 1981-11-12 | 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823775L true NO823775L (no) | 1983-05-13 |
Family
ID=23243961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823775A NO823775L (no) | 1981-11-12 | 1982-11-11 | 3-(1-substituert-4-piperidyl)-1,2-benzisoksazoler, fremgangsmaate til deres fremstilling, farmasoeytisk blanding inneholdende disse og deres bruk som legemidler |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4352811A (el) |
| EP (1) | EP0079564B1 (el) |
| JP (1) | JPS5890583A (el) |
| AT (1) | ATE18669T1 (el) |
| AU (1) | AU556307B2 (el) |
| CA (1) | CA1196334A (el) |
| DE (1) | DE3270015D1 (el) |
| DK (1) | DK503082A (el) |
| ES (5) | ES517249A0 (el) |
| FI (1) | FI823860L (el) |
| GR (1) | GR78402B (el) |
| HU (1) | HU191366B (el) |
| IL (1) | IL67235A (el) |
| NO (1) | NO823775L (el) |
| NZ (1) | NZ202457A (el) |
| PT (1) | PT75848A (el) |
| ZA (1) | ZA828278B (el) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4355037A (en) * | 1981-11-12 | 1982-10-19 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidyl)-1,2-benzisoxales |
| US4352811A (en) * | 1981-11-12 | 1982-10-05 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles |
| US4469868A (en) * | 1982-05-24 | 1984-09-04 | Warner-Lambert Company | Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines |
| US4469869A (en) * | 1982-08-11 | 1984-09-04 | Hoechst-Roussel Pharmaceuticals, Inc. | 3-(4-Piperidinium)-1,2-benzisoxazoles |
| US4524074A (en) * | 1983-05-31 | 1985-06-18 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
| US4458076A (en) * | 1983-05-31 | 1984-07-03 | Hoechst-Roussel Pharmaceuticals | 3-(4-Piperidinyl)-1,2-benzisothiazoles |
| US4528292A (en) * | 1984-04-23 | 1985-07-09 | Hoechst-Roussel Pharmaceuticals Inc. | Antihypertensive 1,2-benzisothiazole piperidines |
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
| CA1335289C (en) * | 1987-10-26 | 1995-04-18 | Fujio Antoku | Piperidinyl benzisoxazole derivatives, their production and pharmaceutical use |
| FR2654104B1 (fr) * | 1989-11-07 | 1992-01-03 | Adir | Nouveaux derives du 1,2-benzisoxazole, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2671350A1 (fr) * | 1991-01-08 | 1992-07-10 | Adir | Nouveaux derives de benzisoxazole et de benzisothiazole, leur procede de preparation, et les compositions pharmaceutiques les renfermant. |
| US5147881A (en) * | 1990-11-14 | 1992-09-15 | Pfizer Inc | 4-(1,2-benzisoxazolyl)piperidine antipsychotic agents |
| US5532240A (en) * | 1991-12-26 | 1996-07-02 | Yoshitomi Pharmaceutical Industries, Ltd. | Condensed thiophene compound and pharmaceutical use thereof |
| SK282231B6 (sk) | 1993-11-19 | 2001-12-03 | Janssen Pharmaceutica N. V. | Farmaceutický prostriedok na liečenie psychotických porúch |
| ES2074966B1 (es) * | 1994-02-11 | 1996-06-16 | Vita Invest Sa | Procedimiento para la obtencion de 3-(2-(4-(6-fluoro-benzo(d)isoxazol-3-il)piperidin-1-il)-etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido-(1,2-a)pirimidin-4-ona. |
| FR2749304B1 (fr) * | 1996-06-04 | 1998-06-26 | Adir | Nouveaux derives du 3-(piperid-4-yl)1,2-benzisoxazole et du 3-(piperazin-4-yl)1,2-benzisoxazole, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| AU3327399A (en) * | 1998-02-09 | 1999-08-23 | Duphar International Research B.V. | Benzisoxazole derivatives having d4-antagonistic activity |
| US20050232995A1 (en) | 2002-07-29 | 2005-10-20 | Yam Nyomi V | Methods and dosage forms for controlled delivery of paliperidone and risperidone |
| JP4836797B2 (ja) | 2003-10-23 | 2011-12-14 | 大塚製薬株式会社 | 放出制御性無菌注射アリピプラゾール製剤および方法 |
| ES2523459T3 (es) * | 2005-02-25 | 2014-11-26 | Raqualia Pharma Inc | Derivados de benzisoxazol |
| DK2170279T3 (en) * | 2007-07-31 | 2018-03-12 | Otsuka Pharma Co Ltd | PROCEDURES FOR PREPARING AN ARIPIPRAZOL SUSPENSION AND A FREEZER DRIED FORMULATION |
| WO2009025859A1 (en) * | 2007-08-21 | 2009-02-26 | Teva Pharmaceutical Industries Ltd. | Paliperidone sustained release formulation |
| CN101759693B (zh) * | 2008-12-23 | 2011-09-14 | 江苏恩华药业股份有限公司 | 苯骈异恶唑哌啶衍生物及在制备镇痛、镇静药物中的应用 |
| WO2016071723A1 (en) * | 2014-11-03 | 2016-05-12 | Sifavitor S.R.L. | Process for the preparation of a fluspirilene intermediate |
| CN104829591B (zh) * | 2015-04-27 | 2017-05-03 | 梯尔希（南京）药物研发有限公司 | 氘代匹莫齐特的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE633495A (el) * | 1962-06-13 | |||
| US3678062A (en) * | 1970-09-08 | 1972-07-18 | American Cyanamid Co | Certain 4-/(indazol-3-yl)-pyridinium/compounds |
| JPS5545545B2 (el) * | 1972-03-17 | 1980-11-18 | ||
| US4217349A (en) * | 1974-07-01 | 1980-08-12 | Sumitomo Chemical Company, Limited | Benzisoxazole derivatives |
| JPS51136666A (en) * | 1975-05-19 | 1976-11-26 | Dainippon Pharmaceut Co Ltd | Process for preparing 3-aminoalkyl-1,2-benzisoxazole derivatives. |
| FR2421899A1 (fr) * | 1978-01-16 | 1979-11-02 | Roussel Uclaf | Nouveaux derives du tetrahydropyridinyl-indole et leurs sels, le procede de preparation et l'application a titre de medicaments de ces nouveaux produits |
| US4352811A (en) * | 1981-11-12 | 1982-10-05 | Hoechst-Roussel Pharmaceuticals Inc. | 3-(1-Substituted-4-piperidyl)-1,2-benzisoxazoles |
-
1981
- 1981-11-12 US US06/319,872 patent/US4352811A/en not_active Expired - Lifetime
-
1982
- 1982-11-09 AT AT82110311T patent/ATE18669T1/de not_active IP Right Cessation
- 1982-11-09 EP EP82110311A patent/EP0079564B1/en not_active Expired
- 1982-11-09 DE DE8282110311T patent/DE3270015D1/de not_active Expired
- 1982-11-10 CA CA000415362A patent/CA1196334A/en not_active Expired
- 1982-11-10 GR GR69770A patent/GR78402B/el unknown
- 1982-11-10 ES ES517249A patent/ES517249A0/es active Granted
- 1982-11-10 NZ NZ202457A patent/NZ202457A/en unknown
- 1982-11-10 FI FI823860A patent/FI823860L/fi not_active Application Discontinuation
- 1982-11-11 AU AU90391/82A patent/AU556307B2/en not_active Ceased
- 1982-11-11 IL IL67235A patent/IL67235A/xx unknown
- 1982-11-11 NO NO823775A patent/NO823775L/no unknown
- 1982-11-11 JP JP57196886A patent/JPS5890583A/ja active Pending
- 1982-11-11 ZA ZA828278A patent/ZA828278B/xx unknown
- 1982-11-11 DK DK503082A patent/DK503082A/da not_active Application Discontinuation
- 1982-11-11 HU HU823630A patent/HU191366B/hu unknown
- 1982-11-12 PT PT75848A patent/PT75848A/pt unknown
-
1984
- 1984-01-31 ES ES529312A patent/ES529312A0/es active Granted
- 1984-01-31 ES ES529313A patent/ES529313A0/es active Granted
- 1984-01-31 ES ES529314A patent/ES529314A0/es active Granted
- 1984-01-31 ES ES529315A patent/ES529315A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI823860L (fi) | 1983-05-13 |
| ES8506705A1 (es) | 1985-08-01 |
| FI823860A0 (fi) | 1982-11-10 |
| IL67235A (en) | 1987-03-31 |
| EP0079564A1 (en) | 1983-05-25 |
| NZ202457A (en) | 1986-05-09 |
| PT75848A (en) | 1982-12-01 |
| ES8506293A1 (es) | 1985-07-01 |
| EP0079564B1 (en) | 1986-03-19 |
| AU556307B2 (en) | 1986-10-30 |
| ES8506657A1 (es) | 1985-07-16 |
| ATE18669T1 (de) | 1986-04-15 |
| ES529312A0 (es) | 1985-07-01 |
| ES529314A0 (es) | 1985-08-01 |
| GR78402B (el) | 1984-09-27 |
| CA1196334A (en) | 1985-11-05 |
| HU191366B (en) | 1987-02-27 |
| ES8405396A1 (es) | 1984-06-01 |
| DE3270015D1 (en) | 1986-04-24 |
| ES8506658A1 (es) | 1985-08-01 |
| IL67235A0 (en) | 1983-03-31 |
| DK503082A (da) | 1983-05-13 |
| ES529315A0 (es) | 1985-08-01 |
| AU9039182A (en) | 1983-05-19 |
| ZA828278B (en) | 1983-09-28 |
| ES517249A0 (es) | 1984-06-01 |
| ES529313A0 (es) | 1985-07-16 |
| US4352811A (en) | 1982-10-05 |
| JPS5890583A (ja) | 1983-05-30 |
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