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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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 |
|---|---|---|---|
| ES02767454T Expired - Lifetime ES2370634T3 (es) | 2001-08-31 | 2002-08-30 | Isómeros ópticos de un metabolito de iloperidona. |
| ES10009915T Expired - Lifetime ES2398434T3 (es) | 2001-08-31 | 2002-08-30 | Isómeros ópticos de un metabolito de iloperidona |
Family Applications After (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) | ES2370634T3 (enExample) |
| PT (2) | PT1425272E (enExample) |
| WO (1) | WO2003020707A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2358416T3 (es) | 2001-10-30 | 2011-05-10 | Novartis Ag | Formulaciones de liberación prolongada de iloperidona y polímero en forma de estrella. |
| PT1497266E (pt) | 2002-03-27 | 2008-09-10 | Glaxo Group Ltd | Derivados de quinolina e sua utilização como ligandos 5-ht6 |
| GB0216416D0 (en) | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
| DE602004000260T2 (de) | 2003-07-22 | 2006-08-24 | Arena Pharmaceuticals, Inc., San Diego | Diaryl- und arylheteroarylharnstoffderivate als modulatoren des 5-ht2a-serotoninrezeptors, die sich zur prophylaxe und behandlung von damit im zusammenhang stehenden erkrankungen eignen |
| 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 |
| ES2825949T3 (es) * | 2004-09-30 | 2021-05-17 | Vanda Pharmaceuticals Inc | Métodos para administrar iloperidona |
| US8008144B2 (en) | 2006-05-11 | 2011-08-30 | Micron Technology, Inc. | Dual work function recessed access device and methods of forming |
| US20070262395A1 (en) | 2006-05-11 | 2007-11-15 | Gibbons Jasper S | Memory cell access devices and methods of making the same |
| EP2029136A4 (en) * | 2006-05-22 | 2010-01-06 | Vanda Pharmaceuticals Inc | TREATMENT FOR DEPRESSION DISEASES |
| US20150259747A1 (en) | 2007-03-29 | 2015-09-17 | Vanda Pharmaceuticals Inc. | Method of predicting a predisposition to qt prolongation |
| EP2134873B1 (en) | 2007-03-29 | 2015-05-06 | 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 |
| EP2198048A2 (en) | 2007-09-10 | 2010-06-23 | Vanda Pharmaceuticals Inc. | Prediction of qt prolongation based on snp genotype |
| EP2254564A1 (en) | 2007-12-12 | 2010-12-01 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| NZ585923A (en) | 2007-12-13 | 2012-09-28 | Vanda Pharmaceuticals Inc | Use of 4-[3-[4-(6-fluoro-1,2,-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxy-benzoic acid for treating a condition that is mediated by a 5-HT2A receptor |
| CA2709103C (en) * | 2007-12-13 | 2017-01-17 | Vanda Pharmaceuticals Inc. | Method and composition for treating an alpha adrenoceptor-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 |
| JP5692872B2 (ja) | 2009-04-06 | 2015-04-01 | 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 | Ｂａｉ遺伝子の配列又はその産物に基づいてｑｔ延長に対する素因を予測する方法 |
| JP5881598B2 (ja) | 2009-04-06 | 2016-03-09 | 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 | Ａｂｃｃ２遺伝子の配列又はその産物に基づいてｑｔ延長に対する素因を予測する方法 |
| WO2010117931A1 (en) | 2009-04-06 | 2010-10-14 | Vanda Pharmaceuticals, Inc. | Method of treatment based on polymorphisms of the kcnq1 gene |
| WO2010117937A1 (en) | 2009-04-06 | 2010-10-14 | Vanda Pharmaceuticals, Inc. | Method of predicting a predisposition to qt prolongation |
| EP2515863A2 (en) | 2009-12-23 | 2012-10-31 | Lupin Limited | Slow release pharmaceutical compositions of iloperidone |
| 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 |
| IN2014DN08495A (enExample) * | 2012-03-14 | 2015-05-08 | Vanda Pharmaceuticals Inc | |
| BR112017017608A2 (en) | 2015-02-17 | 2018-05-08 | Vanda Pharmaceuticals Inc. | methods for treating schizophrenia or a symptom of schizophrenia, to prevent a schizophrenic relapse and to maintain the effect of iloperidone for schizophrenia. |
| RU2017145976A (ru) | 2015-06-12 | 2019-07-15 | Аксовант Сайенсиз Гмбх | Производные диарил- и арилгетероарилмочевины, применимые для профилактики и лечения нарушения поведения во время REM-фазы сна |
| TW201720439A (zh) | 2015-07-15 | 2017-06-16 | Axovant Sciences Gmbh | 用於預防及治療與神經退化性疾病相關的幻覺之作為５－ｈｔ２ａ血清素受體的二芳基及芳基雜芳基脲衍生物 |
| KR20210132092A (ko) | 2019-02-21 | 2021-11-03 | 아센타위츠 파마슈티컬즈 리미티드 | 고 거울상 선택성 2차 알코올의 제조 방법 |
| 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 |
| AU2024278999A1 (en) | 2023-06-02 | 2025-11-13 | Vanda Pharmaceuticals Inc. | Method of treatment with iloperidone |
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 |
| DE69021645T2 (de) | 1989-05-19 | 1996-02-22 | Hoechst-Roussel Pharmaceuticals Inc., Somerville, N.J. | N-(aryloxyalkyl)heteroarylpiperidine und -heteroarylpiperazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente. |
| 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 |
| 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 |
| DE997458T1 (de) * | 1997-07-03 | 2001-03-01 | Asahi Kasei Kogyo K.K., Osaka | Tricyclische verbindungen mit gesättigten ringen und diese enthaltende medizinische zubereitungen |
| WO2004010932A2 (en) | 2002-07-30 | 2004-02-05 | Peter Migaly | Combination therapy for depression, prevention of suicide, and varous medical and psychiatric conditions |
-
2002
- 2002-08-30 JP JP2003524978A patent/JP2005504783A/ja not_active Withdrawn
- 2002-08-30 EP EP02767454A patent/EP1425272B1/en not_active Expired - Lifetime
- 2002-08-30 DK DK10009915.9T patent/DK2305656T3/da active
- 2002-08-30 DK DK02767454.8T patent/DK1425272T3/da active
- 2002-08-30 WO PCT/EP2002/009700 patent/WO2003020707A1/en not_active Ceased
- 2002-08-30 AT AT02767454T patent/ATE518845T1/de active
- 2002-08-30 ES ES02767454T patent/ES2370634T3/es not_active Expired - Lifetime
- 2002-08-30 PT PT02767454T patent/PT1425272E/pt unknown
- 2002-08-30 US US10/488,128 patent/US20050020632A1/en not_active Abandoned
- 2002-08-30 PT PT100099159T patent/PT2305656E/pt unknown
- 2002-08-30 ES ES10009915T patent/ES2398434T3/es not_active Expired - Lifetime
- 2002-08-30 EP EP10009915A patent/EP2305656B1/en not_active Expired - Lifetime
-
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 |
|---|---|
| JP2015214577A (ja) | 2015-12-03 |
| JP2013116905A (ja) | 2013-06-13 |
| JP2013227335A (ja) | 2013-11-07 |
| EP2305656A1 (en) | 2011-04-06 |
| ATE518845T1 (de) | 2011-08-15 |
| JP2015227368A (ja) | 2015-12-17 |
| PT2305656E (pt) | 2013-01-10 |
| ES2398434T3 (es) | 2013-03-19 |
| US20130296366A1 (en) | 2013-11-07 |
| HK1156309A1 (en) | 2012-09-07 |
| EP2305656B1 (en) | 2012-10-24 |
| US7977356B2 (en) | 2011-07-12 |
| DK1425272T3 (da) | 2011-11-21 |
| CY1113550T1 (el) | 2016-06-22 |
| WO2003020707A1 (en) | 2003-03-13 |
| US20110201646A1 (en) | 2011-08-18 |
| EP1425272A1 (en) | 2004-06-09 |
| EP1425272B1 (en) | 2011-08-03 |
| CY1112039T1 (el) | 2015-11-04 |
| ES2398434T8 (es) | 2017-10-09 |
| US20090176739A1 (en) | 2009-07-09 |
| DK2305656T3 (da) | 2013-02-11 |
| JP2010100633A (ja) | 2010-05-06 |
| US20050020632A1 (en) | 2005-01-27 |
| HK1066536A1 (en) | 2005-03-24 |
| JP2005504783A (ja) | 2005-02-17 |
| US8314129B2 (en) | 2012-11-20 |
| PT1425272E (pt) | 2011-10-19 |
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