IL97892A - 3-] 4-) 6-Fluoro-1,2-benziazoxazole-3-yl (piperidine-1-ilalkyl [-H4- pyrido] A-1,2 [pyrimidine-4-lobes 9-metamorphoses, their preparation and crude preparations - Google Patents
3-] 4-) 6-Fluoro-1,2-benziazoxazole-3-yl (piperidine-1-ilalkyl [-H4- pyrido] A-1,2 [pyrimidine-4-lobes 9-metamorphoses, their preparation and crude preparationsInfo
- Publication number
- IL97892A IL97892A IL9789291A IL9789291A IL97892A IL 97892 A IL97892 A IL 97892A IL 9789291 A IL9789291 A IL 9789291A IL 9789291 A IL9789291 A IL 9789291A IL 97892 A IL97892 A IL 97892A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- compounds
- methyl
- alk
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- -1 5-methyl-2-furanyl Chemical group 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 239000012442 inert solvent Substances 0.000 claims description 12
- 150000002923 oximes Chemical class 0.000 claims description 11
- 230000000561 anti-psychotic effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 36
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 abstract description 10
- 208000028017 Psychotic disease Diseases 0.000 abstract description 6
- 230000001154 acute effect Effects 0.000 abstract description 5
- 229960003638 dopamine Drugs 0.000 abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 239000005557 antagonist Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- 239000000543 intermediate Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 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 13
- 229960004046 apomorphine Drugs 0.000 description 13
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000008485 antagonism Effects 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 238000013019 agitation Methods 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
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- 241000282472 Canis lupus familiaris Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 229940025084 amphetamine Drugs 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000010 aprotic solvent Substances 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-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
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003210 dopamine receptor blocking agent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
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- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 239000002202 Polyethylene glycol Substances 0.000 description 4
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
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- 238000011200 topical administration Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909008850A GB9008850D0 (en) | 1990-04-19 | 1990-04-19 | Novel 2,9-disubstituted-4h-pyridol(1,2-a)pyrimidin-4-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97892A0 IL97892A0 (en) | 1992-06-21 |
| IL97892A true IL97892A (en) | 1995-03-30 |
Family
ID=10674694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9789291A IL97892A (en) | 1990-04-19 | 1991-04-17 | 3-] 4-) 6-Fluoro-1,2-benziazoxazole-3-yl (piperidine-1-ilalkyl [-H4- pyrido] A-1,2 [pyrimidine-4-lobes 9-metamorphoses, their preparation and crude preparations |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5482943A (ja) |
| EP (1) | EP0453042B1 (ja) |
| JP (1) | JP3216889B2 (ja) |
| KR (1) | KR100190297B1 (ja) |
| CN (1) | CN1027506C (ja) |
| AT (1) | ATE186301T1 (ja) |
| AU (1) | AU636969B2 (ja) |
| BG (2) | BG60394B1 (ja) |
| CA (1) | CA2040086C (ja) |
| CZ (1) | CZ281135B6 (ja) |
| DE (1) | DE69131759T2 (ja) |
| DK (1) | DK0453042T3 (ja) |
| ES (1) | ES2140381T3 (ja) |
| FI (1) | FI96206C (ja) |
| GB (1) | GB9008850D0 (ja) |
| GR (1) | GR3032122T3 (ja) |
| HU (1) | HUT57763A (ja) |
| IE (1) | IE911301A1 (ja) |
| IL (1) | IL97892A (ja) |
| NO (1) | NO176840C (ja) |
| NZ (1) | NZ237713A (ja) |
| PL (2) | PL169744B1 (ja) |
| PT (1) | PT97395B (ja) |
| RU (1) | RU2037495C1 (ja) |
| SK (1) | SK279005B6 (ja) |
| ZA (1) | ZA912913B (ja) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2050069B1 (es) * | 1992-07-10 | 1994-12-16 | Vita Invest Sa | Procedimiento para la obtencion de 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-il)piperidino)etil)-2-metil-6,7,8,9-tetrahidro-4h-pirido(1,2-a) pirimidin-4-ona. |
| ES2159526T3 (es) | 1992-07-13 | 2001-10-16 | Janssen Pharmaceutica Nv | Nuevos derivados de 4-(3-benzofuranil)piperidinilo y 4-(3-benzotienil)piperidinilo y composiciones farmaceuticas que los contienen. |
| JP3553951B2 (ja) * | 1993-11-23 | 2004-08-11 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 新規な９−ヒドロキシ−ピリド［１，２−ａ］ピリミジン−４−オンエーテル誘導体 |
| ES2085234B1 (es) * | 1994-02-24 | 1997-01-16 | Vita Invest Sa | Agente activo sobre el sistema nervioso central, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| JP3274579B2 (ja) * | 1995-01-12 | 2002-04-15 | 住友製薬株式会社 | 脳血管障害に伴う精神症候治療剤 |
| ES2141671B1 (es) * | 1997-12-26 | 2001-01-01 | Vita Invest Sa | Compuesto pirimidinico activo sobre el sistema nervioso central, procedimiento para su preparacion y composiciones farmaceuticas que lo contienen. |
| HU227118B1 (en) * | 2001-11-13 | 2010-07-28 | Egis Gyogyszergyar Nyilvanosan | Process for the preparation of 3-{2-[4-(6-fluoro-1,2-benzizoxazol-3-yl)-1-piperidinyl]-ethyl}-6,7,8,9-tetrahydro-2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one |
| ES2197801B1 (es) * | 2002-03-05 | 2005-03-16 | Ferrer Internacional,S.A | Procedimiento de obtencion de la 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. |
| WO2004009591A1 (en) * | 2002-07-22 | 2004-01-29 | Aurobindo Pharma Ltd. | A process for the preparation of antipsychotic risperidone |
| AU2003256006A1 (en) * | 2002-08-30 | 2004-03-19 | Sunil Sadanand Nadkarni | Improved process for preparation of risperidone |
| KR20040025224A (ko) * | 2002-09-18 | 2004-03-24 | 주식회사 대웅 | 2-(2-메틸-4-옥소-6,7,8,9-테트라하이드로-4Ｈ-피리도[1,2-ａ]피리미딘-3-일)아세트알데히드 및 그 제조방법 |
| EP1560814A1 (en) | 2002-11-13 | 2005-08-10 | Synthon B.V. | Process for making risperidone and intermediates therefor |
| EP1615924A1 (en) * | 2003-04-22 | 2006-01-18 | Synthon B.V. | Water soluble salts of risperidone |
| HUP0401379A3 (en) * | 2004-07-08 | 2006-04-28 | Richter Gedeon Vegyeszet | Process for the preparation of risperidon |
| HUP0402163A2 (en) * | 2004-10-25 | 2006-05-29 | Richter Gedeon Vegyeszet | Process for the preparation of risperidone |
| EP1690540A1 (en) * | 2005-02-15 | 2006-08-16 | Neuro3D | Composition comprising ocaperidone |
| EP1695973A1 (en) * | 2005-02-24 | 2006-08-30 | Neuro3D | Ocaperidone salt and pharmaceutical compositions containing the same |
| JO2769B1 (en) * | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| WO2009077551A1 (en) * | 2007-12-18 | 2009-06-25 | Janssen Pharmaceutica Nv | Process for preparing risperidone |
| IL313904A (en) | 2022-01-11 | 2024-08-01 | Suven Life Sciences Ltd | Heterocyclic derivatives and their use in the treatment of central nervous system disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485107A (en) * | 1982-11-01 | 1984-11-27 | Janssen Pharmaceutica N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones |
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| NZ223654A (en) * | 1987-03-09 | 1990-03-27 | Janssen Pharmaceutica Nv | 1-alkyl-substituted-benzimidazole-4-piperidinamines and pharmaceutical compositions |
| US4777252A (en) * | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| CA2000786C (en) * | 1988-11-07 | 1999-01-26 | Cornelus G. M. Janssen | 3-piperidinyl-1,2-benzisoxazoles |
| GB8900382D0 (en) * | 1989-01-09 | 1989-03-08 | Janssen Pharmaceutica Nv | 2-aminopyrimidinone derivatives |
-
1990
- 1990-04-19 GB GB909008850A patent/GB9008850D0/en active Pending
-
1991
- 1991-03-28 US US07/676,681 patent/US5482943A/en not_active Expired - Lifetime
- 1991-04-05 NZ NZ237713A patent/NZ237713A/en unknown
- 1991-04-09 CA CA002040086A patent/CA2040086C/en not_active Expired - Lifetime
- 1991-04-11 AU AU74366/91A patent/AU636969B2/en not_active Expired
- 1991-04-16 AT AT91200897T patent/ATE186301T1/de not_active IP Right Cessation
- 1991-04-16 JP JP10968691A patent/JP3216889B2/ja not_active Expired - Lifetime
- 1991-04-16 ES ES91200897T patent/ES2140381T3/es not_active Expired - Lifetime
- 1991-04-16 DE DE69131759T patent/DE69131759T2/de not_active Expired - Lifetime
- 1991-04-16 DK DK91200897T patent/DK0453042T3/da active
- 1991-04-16 EP EP91200897A patent/EP0453042B1/en not_active Expired - Lifetime
- 1991-04-17 IL IL9789291A patent/IL97892A/en not_active IP Right Cessation
- 1991-04-17 KR KR1019910006108A patent/KR100190297B1/ko not_active IP Right Cessation
- 1991-04-18 ZA ZA912913A patent/ZA912913B/xx unknown
- 1991-04-18 FI FI911885A patent/FI96206C/fi active
- 1991-04-18 SK SK1099-91A patent/SK279005B6/sk not_active IP Right Cessation
- 1991-04-18 PT PT97395A patent/PT97395B/pt not_active IP Right Cessation
- 1991-04-18 PL PL91312561A patent/PL169744B1/pl unknown
- 1991-04-18 IE IE130191A patent/IE911301A1/en not_active IP Right Cessation
- 1991-04-18 NO NO911525A patent/NO176840C/no not_active IP Right Cessation
- 1991-04-18 PL PL91289935A patent/PL169740B1/pl unknown
- 1991-04-18 RU SU914895183A patent/RU2037495C1/ru active
- 1991-04-18 CZ CS911099A patent/CZ281135B6/cs not_active IP Right Cessation
- 1991-04-18 BG BG94282A patent/BG60394B1/bg unknown
- 1991-04-19 HU HU911301A patent/HUT57763A/hu unknown
- 1991-04-19 CN CN91102516A patent/CN1027506C/zh not_active Expired - Lifetime
- 1991-09-30 BG BG095241A patent/BG95241A/bg unknown
-
1999
- 1999-12-14 GR GR990403201T patent/GR3032122T3/el unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| EXP | Patent expired |