ES2370634T3 - Isómeros ópticos de un metabolito de iloperidona. - Google Patents
Isómeros ópticos de un metabolito de iloperidona. Download PDFInfo
- Publication number
- ES2370634T3 ES2370634T3 ES02767454T ES02767454T ES2370634T3 ES 2370634 T3 ES2370634 T3 ES 2370634T3 ES 02767454 T ES02767454 T ES 02767454T ES 02767454 T ES02767454 T ES 02767454T ES 2370634 T3 ES2370634 T3 ES 2370634T3
- Authority
- ES
- Spain
- Prior art keywords
- description
- formula
- compound
- iloperidone
- optical isomers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- XMXHEBAFVSFQEX-UHFFFAOYSA-N iloperidone Chemical class COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 XMXHEBAFVSFQEX-UHFFFAOYSA-N 0.000 title description 9
- 230000003287 optical effect Effects 0.000 title description 3
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 8
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000003937 drug carrier Substances 0.000 abstract description 2
- 239000008024 pharmaceutical diluent Substances 0.000 abstract description 2
- -1 6-fluoro-benzo [d] isoxazol-3-yl Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 229910000085 borane Inorganic materials 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000003556 assay Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229960003162 iloperidone Drugs 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
- SBKZGLWZGZQVHA-UHFFFAOYSA-N 1-[4-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanol Chemical compound COC1=CC(C(C)O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 SBKZGLWZGZQVHA-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940025084 amphetamine Drugs 0.000 description 3
- 230000035863 hyperlocomotion Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- SBKZGLWZGZQVHA-MRXNPFEDSA-N (1r)-1-[4-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanol Chemical compound COC1=CC([C@@H](C)O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 SBKZGLWZGZQVHA-MRXNPFEDSA-N 0.000 description 2
- SBKZGLWZGZQVHA-INIZCTEOSA-N (1s)-1-[4-[3-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanol Chemical compound COC1=CC([C@H](C)O)=CC=C1OCCCN1CCC(C=2C3=CC=C(F)C=C3ON=2)CC1 SBKZGLWZGZQVHA-INIZCTEOSA-N 0.000 description 2
- 208000020925 Bipolar disease Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000035873 hypermotility Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000002474 noradrenergic effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
- 229950010883 phencyclidine Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 108091005435 5-HT6 receptors Proteins 0.000 description 1
- 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 1
- 101150049660 DRD2 gene Proteins 0.000 description 1
- 101150104779 HTR2A gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 1
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 1
- 102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 description 1
- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229940127236 atypical antipsychotics Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- 238000003468 luciferase reporter gene assay Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000007962 solid dispersion Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31639001P | 2001-08-31 | 2001-08-31 | |
| US316390P | 2001-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2370634T3 true ES2370634T3 (es) | 2011-12-21 |
Family
ID=23228843
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10009915T Expired - Lifetime ES2398434T3 (es) | 2001-08-31 | 2002-08-30 | Isómeros ópticos de un metabolito de iloperidona |
| ES02767454T Expired - Lifetime ES2370634T3 (es) | 2001-08-31 | 2002-08-30 | Isómeros ópticos de un metabolito de iloperidona. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10009915T Expired - Lifetime ES2398434T3 (es) | 2001-08-31 | 2002-08-30 | Isómeros ópticos de un metabolito de iloperidona |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20050020632A1 (enExample) |
| EP (2) | EP1425272B1 (enExample) |
| JP (6) | JP2005504783A (enExample) |
| AT (1) | ATE518845T1 (enExample) |
| CY (2) | CY1112039T1 (enExample) |
| DK (2) | DK2305656T3 (enExample) |
| ES (2) | ES2398434T3 (enExample) |
| PT (2) | PT2305656E (enExample) |
| WO (1) | WO2003020707A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1441727B1 (en) | 2001-10-30 | 2010-12-29 | Novartis AG | Depot formulations of iloperidone and a star polymer |
| US7452888B2 (en) | 2002-03-27 | 2008-11-18 | Glaxo Group Limited | Quinoline derivatives and their use as 5-ht6 ligands |
| GB0216416D0 (en) | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
| EP1558582B1 (en) | 2003-07-22 | 2005-12-21 | Arena Pharmaceuticals, Inc. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
| GB0322994D0 (en) * | 2003-10-01 | 2003-11-05 | Novartis Ag | Organic compounds |
| US20100063093A1 (en) | 2007-03-28 | 2010-03-11 | Curt Wolfgang | Methods for the administration of iloperidone |
| CA2582022C (en) * | 2004-09-30 | 2021-05-18 | Vanda Pharmaceuticals, Inc. | Methods for the administration of iloperidone |
| US20070262395A1 (en) | 2006-05-11 | 2007-11-15 | Gibbons Jasper S | Memory cell access devices and methods of making the same |
| US8008144B2 (en) | 2006-05-11 | 2011-08-30 | Micron Technology, Inc. | Dual work function recessed access device and methods of forming |
| KR20090029200A (ko) * | 2006-05-22 | 2009-03-20 | 반다 파마슈티칼즈, 인코퍼레이티드. | 우울증 질환에 대한 치료 |
| JP5586094B2 (ja) | 2007-03-29 | 2014-09-10 | ヴァンダ ファーマシューティカルズ インコーポレイテッド | Ｑｔ延長に対する素因を予測する方法 |
| US20150259747A1 (en) | 2007-03-29 | 2015-09-17 | Vanda Pharmaceuticals Inc. | Method of predicting a predisposition to qt prolongation |
| US8198305B2 (en) | 2007-04-13 | 2012-06-12 | Concert Pharmaceuticals Inc. | 1,2-benzisoxazol-3-yl compounds |
| EP3075865B1 (en) | 2007-05-18 | 2018-05-09 | Vanda Pharmaceuticals Inc. | Genetic markers for efficacy of iloperidone in the treatment of psychotic symptoms |
| WO2009036100A2 (en) | 2007-09-10 | 2009-03-19 | Vanda Pharmaceuticals, Inc. | Prediction of qt prolongation based on snp genotype |
| US9084742B2 (en) | 2007-12-12 | 2015-07-21 | Axovant Sciences Ltd. | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-Quinoline |
| CA2709103C (en) | 2007-12-13 | 2017-01-17 | Vanda Pharmaceuticals Inc. | Method and composition for treating an alpha adrenoceptor-mediated condition |
| AU2008334933B2 (en) | 2007-12-13 | 2016-01-21 | Vanda Pharmaceuticals Inc. | Method and composition for treating a serotonin receptor-mediated condition |
| US20110061014A1 (en) | 2008-02-01 | 2011-03-10 | Energyhub | Interfacing to resource consumption management devices |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| US7824986B2 (en) | 2008-11-05 | 2010-11-02 | Micron Technology, Inc. | Methods of forming a plurality of transistor gates, and methods of forming a plurality of transistor gates having at least two different work functions |
| WO2010117943A1 (en) | 2009-04-06 | 2010-10-14 | Vanda Pharmaceuticals, Inc. | Method of predicting a predisposition to qt prolongation based on bai3 gene sequence or product thereof |
| WO2010117937A1 (en) | 2009-04-06 | 2010-10-14 | Vanda Pharmaceuticals, Inc. | Method of predicting a predisposition to qt prolongation |
| EP2417267B1 (en) | 2009-04-06 | 2016-08-17 | Vanda Pharmaceuticals Inc. | Method of treatment based on polymorphisms of the kcnq1 gene |
| EP2416778B1 (en) | 2009-04-06 | 2016-03-02 | Vanda Pharmaceuticals Inc. | Method of predicting a predisposition to qt prolongation based on abcc2 gene sequence or product thereof |
| MX2012007365A (es) | 2009-12-23 | 2012-08-15 | Lupin Ltd | Composiciones farmaceuticas de liberacion lenta de iloperidona. |
| WO2012032532A1 (en) * | 2010-09-07 | 2012-03-15 | Symed Labs Limited | "processes for the preparation of 4'-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidino]propoxy]-3'-methoxyacetophenone and intermediates thereof" |
| WO2012063269A2 (en) | 2010-11-12 | 2012-05-18 | Cadila Healthcare Limited | Process for preparing iloperidone |
| BR112014022687A8 (pt) * | 2012-03-14 | 2021-07-06 | Vanda Pharmaceuticals Inc | uso de uma quantidade eficaz de r-p88 ou um sal farmaceuticamente aceitável do mesmo, ou um éster do mesmo ou um sal farmaceuticamente aceitável de um éster do mesmo, composição farmacêutica, r-p88 ou um sal farmaceuticamente aceitável do mesmo, ou um éster do mesmo ou um sal farmaceuticamente aceitável de um éster do mesmo |
| EP3258935B1 (en) | 2015-02-17 | 2021-04-07 | Vanda Pharmaceuticals Inc. | Iloperidone for the treatment of schizophrenia |
| CN109562085A (zh) | 2015-06-12 | 2019-04-02 | 阿速万科学有限责任公司 | 用于预防和治疗rem睡眠行为障碍的二芳基和芳基杂芳基脲衍生物 |
| KR20180064373A (ko) | 2015-07-15 | 2018-06-14 | 엑소반트 사이언시즈 게엠베하 | 신경퇴행성 질환과 관련된 환각의 예방 및 치료에 유용한 5-ht2a 세로토닌 수용체의 조절자로서의 다이아릴 및 아릴헤테로아릴 우레아 유도체 |
| US11773118B2 (en) | 2019-02-21 | 2023-10-03 | Obi Pharma, Inc. | Methods of making high enantioselective secondary alcohols |
| US11607408B2 (en) | 2019-10-15 | 2023-03-21 | Vanda Pharmaceuticals Inc. | Method of treatment of schizophrenia |
| EP4507698A1 (en) | 2022-04-13 | 2025-02-19 | Vanda Pharmaceuticals Inc. | Treatment of parkinson's disease and parkinson's disease psychosis |
| IL321015A (en) | 2022-12-19 | 2025-07-01 | Vanda Pharmaceuticals Inc | ILOPERIDONE dosing regimen for the treatment of bipolar I disorder and schizophrenia |
| CN121218989A (zh) | 2023-06-02 | 2025-12-26 | 万达制药公司 | 使用伊潘立酮的治疗方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804663A (en) * | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| US5158952A (en) * | 1988-11-07 | 1992-10-27 | Janssen Pharmaceutica N.V. | 3-[2-[4-(6-fluoro-1,2-benzisoxozol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9 tetrahydro-9-hydroxy-2-methyl-4H-pyrido [1,2-a]pyrimidin-4-one, compositions and method of use |
| US5364866A (en) * | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| US5776963A (en) | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| EP0402644B1 (en) * | 1989-05-19 | 1995-08-16 | Hoechst-Roussel Pharmaceuticals Incorporated | N-(aryloxyalkyl)heteroarylpiperidines and -heteroarylpiperazines,a process for their preparation and their use as medicaments |
| JPH05286868A (ja) | 1992-04-03 | 1993-11-02 | Kiyoshi Okawa | 制がん剤複合体およびそのスクリーニング法 |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| AU735249B2 (en) * | 1997-07-03 | 2001-07-05 | Asahi Kasei Kabushiki Kaisha | Novel tricyclic compounds having saturated rings and medicinal compositions containing the same |
| MXPA05000294A (es) | 2002-07-30 | 2005-08-19 | Peter Migaly | Terapia combinada para la depresion, prevencion de suicidios y varias condiciones medicas y psiquiatricas. |
-
2002
- 2002-08-30 ES ES10009915T patent/ES2398434T3/es not_active Expired - Lifetime
- 2002-08-30 AT AT02767454T patent/ATE518845T1/de active
- 2002-08-30 WO PCT/EP2002/009700 patent/WO2003020707A1/en not_active Ceased
- 2002-08-30 EP EP02767454A patent/EP1425272B1/en not_active Expired - Lifetime
- 2002-08-30 JP JP2003524978A patent/JP2005504783A/ja not_active Withdrawn
- 2002-08-30 DK DK10009915.9T patent/DK2305656T3/da active
- 2002-08-30 US US10/488,128 patent/US20050020632A1/en not_active Abandoned
- 2002-08-30 DK DK02767454.8T patent/DK1425272T3/da active
- 2002-08-30 PT PT100099159T patent/PT2305656E/pt unknown
- 2002-08-30 ES ES02767454T patent/ES2370634T3/es not_active Expired - Lifetime
- 2002-08-30 EP EP10009915A patent/EP2305656B1/en not_active Expired - Lifetime
- 2002-08-30 PT PT02767454T patent/PT1425272E/pt unknown
-
2009
- 2009-03-13 US US12/403,755 patent/US7977356B2/en not_active Expired - Lifetime
- 2009-12-11 JP JP2009281094A patent/JP2010100633A/ja not_active Withdrawn
-
2011
- 2011-04-28 US US13/096,015 patent/US8314129B2/en not_active Expired - Lifetime
- 2011-11-02 CY CY20111101053T patent/CY1112039T1/el unknown
-
2012
- 2012-10-26 US US13/661,609 patent/US20130296366A1/en not_active Abandoned
-
2013
- 2013-01-23 CY CY20131100058T patent/CY1113550T1/el unknown
- 2013-01-31 JP JP2013017050A patent/JP2013116905A/ja not_active Withdrawn
- 2013-07-08 JP JP2013142873A patent/JP2013227335A/ja active Pending
-
2015
- 2015-08-06 JP JP2015156358A patent/JP2015227368A/ja active Pending
- 2015-08-06 JP JP2015156359A patent/JP2015214577A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2305656B1 (en) | 2012-10-24 |
| EP2305656A1 (en) | 2011-04-06 |
| US20050020632A1 (en) | 2005-01-27 |
| DK2305656T3 (da) | 2013-02-11 |
| US20130296366A1 (en) | 2013-11-07 |
| HK1156309A1 (en) | 2012-09-07 |
| US7977356B2 (en) | 2011-07-12 |
| CY1112039T1 (el) | 2015-11-04 |
| ES2398434T3 (es) | 2013-03-19 |
| PT1425272E (pt) | 2011-10-19 |
| EP1425272B1 (en) | 2011-08-03 |
| WO2003020707A1 (en) | 2003-03-13 |
| JP2013227335A (ja) | 2013-11-07 |
| US8314129B2 (en) | 2012-11-20 |
| JP2010100633A (ja) | 2010-05-06 |
| JP2005504783A (ja) | 2005-02-17 |
| US20110201646A1 (en) | 2011-08-18 |
| US20090176739A1 (en) | 2009-07-09 |
| EP1425272A1 (en) | 2004-06-09 |
| DK1425272T3 (da) | 2011-11-21 |
| JP2015227368A (ja) | 2015-12-17 |
| ES2398434T8 (es) | 2017-10-09 |
| PT2305656E (pt) | 2013-01-10 |
| HK1066536A1 (en) | 2005-03-24 |
| JP2015214577A (ja) | 2015-12-03 |
| ATE518845T1 (de) | 2011-08-15 |
| JP2013116905A (ja) | 2013-06-13 |
| CY1113550T1 (el) | 2016-06-22 |
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