TWI299041B - Bi-and tricyclic substituted phenyl methanones - Google Patents
Bi-and tricyclic substituted phenyl methanones Download PDFInfo
- Publication number
- TWI299041B TWI299041B TW094143890A TW94143890A TWI299041B TW I299041 B TWI299041 B TW I299041B TW 094143890 A TW094143890 A TW 094143890A TW 94143890 A TW94143890 A TW 94143890A TW I299041 B TWI299041 B TW I299041B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- alkyl
- formula
- group
- dihydro
- Prior art date
Links
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical class O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 31
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- -1 2-isopropoxy-5-methanesulfonyl-phenyl Chemical group 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- QGIGNHJWEORARI-UHFFFAOYSA-N 1-(2-methylpropoxy)-4-methylsulfonylbenzene Chemical compound CC(C)COC1=CC=C(S(C)(=O)=O)C=C1 QGIGNHJWEORARI-UHFFFAOYSA-N 0.000 description 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 239000012317 TBTU Substances 0.000 description 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000003860 topical agent Substances 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04106597 | 2004-12-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200634017A TW200634017A (en) | 2006-10-01 |
| TWI299041B true TWI299041B (en) | 2008-07-21 |
Family
ID=35841863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094143890A TWI299041B (en) | 2004-12-15 | 2005-12-12 | Bi-and tricyclic substituted phenyl methanones |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7375226B2 (https=) |
| EP (1) | EP1828200B1 (https=) |
| JP (1) | JP4709849B2 (https=) |
| KR (1) | KR100883003B1 (https=) |
| CN (1) | CN100586951C (https=) |
| AR (1) | AR052156A1 (https=) |
| AT (1) | ATE457989T1 (https=) |
| AU (1) | AU2005315914B2 (https=) |
| BR (1) | BRPI0519054A2 (https=) |
| CA (1) | CA2590316A1 (https=) |
| DE (1) | DE602005019465D1 (https=) |
| ES (1) | ES2338139T3 (https=) |
| IL (1) | IL183592A0 (https=) |
| MX (1) | MX2007006896A (https=) |
| NO (1) | NO20072833L (https=) |
| NZ (1) | NZ555476A (https=) |
| RU (1) | RU2007121768A (https=) |
| TW (1) | TWI299041B (https=) |
| WO (1) | WO2006063709A1 (https=) |
| ZA (1) | ZA200705044B (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7485637B2 (en) * | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| RU2338537C2 (ru) * | 2006-01-25 | 2008-11-20 | Сергей Олегович Бачурин | СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ ШИЗОФРЕНИИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b)ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| KR102065319B1 (ko) | 2007-03-12 | 2020-01-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| MX2010010773A (es) | 2008-04-01 | 2011-04-11 | Abbott Gmbh & Co Kg | Tetrahidroisoquinolinas, composiciones farmaceuticas que las contienen y su uso en terapia. |
| US8889767B2 (en) | 2009-02-06 | 2014-11-18 | Styrolution GmbH | Thermoplastic molding compounds based on styrene copolymers and polyamides having improved weathering resistance |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| TW201038569A (en) * | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP2611298A4 (en) * | 2010-08-31 | 2014-07-30 | Univ Vanderbilt | BICYCLIC OXAZOLE AND THIAZOL COMPOUNDS AND THEIR USE AS ALLOSTERIC MODULATORS OF MGLUR-5 RECEPTORS |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CA2844275A1 (en) | 2011-08-05 | 2013-02-14 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2014006004A (es) | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| AU2012357169B2 (en) * | 2011-12-22 | 2017-03-30 | Merck Patent Gmbh | Tetraaza-cyclopenta[a]indenyl and their use as positive allosteric modulators |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| SI2825541T1 (sl) * | 2012-03-16 | 2016-10-28 | Vitae Pharmaceuticals, Inc. | Modulatorji jetrnega receptorja X |
| ES2607113T3 (es) * | 2012-03-16 | 2017-03-29 | Vitae Pharmaceuticals, Inc. | Moduladores de los receptores X del hígado |
| WO2013155504A1 (en) | 2012-04-14 | 2013-10-17 | Intra-Cellular Therapies, Inc. | Novel methods |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| HUE053159T2 (hu) | 2013-03-15 | 2021-06-28 | Intra Cellular Therapies Inc | Szerves vegyületek |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| CA2924689A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| IL305990B2 (en) | 2013-12-03 | 2025-12-01 | Intra Cellular Therapies Inc | Long-acting injectable composition comprising polymeric microspheres of heterocycle fused gamma-carboline compounds or a pharmaceutical composition for sustained or delayed release comprising the compounds and their use in the treatment of bipolar disorder i and/or bipolar ii disorder |
| MX365969B (es) | 2014-04-04 | 2019-06-21 | Intra Cellular Therapies Inc | Gamma-carbolinas fusionadas con heterociclos sustituidas con deuterio. |
| RU2016143091A (ru) | 2014-04-04 | 2018-05-08 | Интра-Селлулар Терапиз, Инк. | Органические соединения |
| CN108883111B (zh) | 2016-01-26 | 2021-10-08 | 细胞内治疗公司 | 有机化合物 |
| PL3407889T3 (pl) | 2016-03-25 | 2021-11-22 | Intra-Cellular Therapies, Inc. | Związki organiczne i ich zastosowanie w leczeniu lub zapobieganiu zaburzeniom ośrodkowego układu nerwowego |
| JP2019513143A (ja) | 2016-03-28 | 2019-05-23 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規塩類および結晶 |
| US11014925B2 (en) | 2016-03-28 | 2021-05-25 | Intra-Cellular Therapies, Inc. | Co-crystals of 1-(4-fluoro-phenyl)-4-((6bR,1OaS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,51_pyrrolo [1,2,3-delqcuinoxalin-8-yl)-butan-1-one with nicotinamide or isonicotinamide |
| EP3436083A4 (en) | 2016-03-28 | 2019-11-27 | Intra-Cellular Therapies, Inc. | NOVEL COMPOSITIONS AND METHOD |
| US11331316B2 (en) | 2016-10-12 | 2022-05-17 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
| US10961245B2 (en) | 2016-12-29 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for treatment of central nervous system disorders |
| US10906906B2 (en) | 2016-12-29 | 2021-02-02 | Intra-Cellular Therapies, Inc. | Organic compounds |
| IL268970B2 (en) | 2017-03-24 | 2023-12-01 | Intra Cellular Therapies Inc | Oral transmucosal formulations of substituted heterocycle fused gamma carbolines |
| JP7223742B2 (ja) | 2017-07-26 | 2023-02-16 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| JP7224333B2 (ja) | 2017-07-26 | 2023-02-17 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| AU2019240226B2 (en) | 2018-03-23 | 2024-11-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| IL321985A (en) | 2018-06-06 | 2025-09-01 | Intra Cellular Therapies Inc | New salts and crystals |
| WO2019237037A1 (en) | 2018-06-08 | 2019-12-12 | Intra-Cellular Therapies, Inc. | Novel methods |
| CA3106447A1 (en) | 2018-06-11 | 2019-12-19 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
| EP3843729A4 (en) | 2018-08-29 | 2022-06-01 | Intra-Cellular Therapies, Inc. | NOVEL COMPOSITIONS AND PROCESSES |
| CA3108558A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| CN112584837A (zh) | 2018-08-31 | 2021-03-30 | 细胞内治疗公司 | 新方法 |
| EP3898580A4 (en) | 2018-12-17 | 2022-08-10 | Intra-Cellular Therapies, Inc. | SYNTHESIS OF CONDENSED GAMMA-CARBOLINES WITH SUBSTITUTED HETEROCYCLE |
| IL283963B2 (en) | 2018-12-17 | 2025-01-01 | Intra Cellular Therapies Inc | Synthesis of condensed gamma-carbolines and converted heterocycles |
| JP7673040B2 (ja) | 2019-07-07 | 2025-05-08 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
| EP4072554A4 (en) | 2019-12-11 | 2023-12-20 | Intra-Cellular Therapies, Inc. | ORGANIC CONNECTION |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
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| DE2423847A1 (de) | 1973-05-28 | 1975-01-02 | Ciba Geigy Ag | Neue sulfamoylbenzoesaeureamide |
| DE2611705A1 (de) | 1976-03-18 | 1977-09-22 | Josef Dipl Chem Dr Rer N Klosa | N-5-(nitrofurfuryliden-)-1-amino- hydantoin enthaltende kristalloesungsmittel |
| IT1176613B (it) | 1984-08-14 | 1987-08-18 | Ravizza Spa | Derivati piperazinici farmacologicamente attivi e processo per la loro preparazione |
| RU2124511C1 (ru) | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
| JPH08325234A (ja) * | 1995-05-30 | 1996-12-10 | Yamanouchi Pharmaceut Co Ltd | 安息香酸誘導体又はその塩 |
| US6001854A (en) * | 1996-05-31 | 1999-12-14 | Allelix Neuroscience Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
| EP1058684A1 (en) * | 1998-03-06 | 2000-12-13 | Janssen Pharmaceutica N.V. | Glycine transport inhibitors |
| IL138228A0 (en) * | 1998-03-06 | 2001-10-31 | Janssen Pharmaceutica Nv | Glycine transport inhibitors |
| AU2001254546A1 (en) * | 2000-04-20 | 2001-11-07 | Nps Allelix Corp. | Aminopiperidines |
| GB0021419D0 (en) | 2000-08-31 | 2000-10-18 | Oxford Glycosciences Uk Ltd | Compounds |
| EP1421071B1 (en) | 2001-07-02 | 2009-11-18 | High Point Pharmaceuticals, LLC | Substituted piperazine and diazepane derivaives as histamine h3 receptor modulators |
| WO2003035602A1 (en) | 2001-10-25 | 2003-05-01 | Sankyo Company, Limited | Lipid modulators |
| TWI329111B (en) * | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US20060052597A1 (en) | 2002-10-22 | 2006-03-09 | Best Desmond J | Aryloxyalkylamine derivatives as h3 receptor ligands |
| RS53252B (sr) | 2003-08-11 | 2014-08-29 | F.Hoffmann-La Roche Ag. | Piperazin sa or-supstituisanom fenil grupom i njihova upotreba kao inhibitora glyt1 |
| PT1663232E (pt) | 2003-09-09 | 2007-12-12 | Hoffmann La Roche | Derivados de 1- (2-amino-benzol) -piperazina como inibidores de absorção de glicina para o tratamento de psicoses |
| DK1703909T3 (da) * | 2003-09-09 | 2009-06-22 | Hoffmann La Roche | 1-benzoyl-piperazinderivater som glycinoptagelsesinhibitorer til behandling af psykoser |
-
2005
- 2005-12-05 WO PCT/EP2005/012994 patent/WO2006063709A1/en not_active Ceased
- 2005-12-05 BR BRPI0519054-1A patent/BRPI0519054A2/pt not_active IP Right Cessation
- 2005-12-05 AT AT05823127T patent/ATE457989T1/de active
- 2005-12-05 JP JP2007545891A patent/JP4709849B2/ja not_active Expired - Fee Related
- 2005-12-05 ES ES05823127T patent/ES2338139T3/es not_active Expired - Lifetime
- 2005-12-05 RU RU2007121768/04A patent/RU2007121768A/ru not_active Application Discontinuation
- 2005-12-05 DE DE602005019465T patent/DE602005019465D1/de not_active Expired - Lifetime
- 2005-12-05 CA CA002590316A patent/CA2590316A1/en not_active Abandoned
- 2005-12-05 MX MX2007006896A patent/MX2007006896A/es active IP Right Grant
- 2005-12-05 CN CN200580042730A patent/CN100586951C/zh not_active Expired - Fee Related
- 2005-12-05 KR KR1020077013440A patent/KR100883003B1/ko not_active Expired - Fee Related
- 2005-12-05 AU AU2005315914A patent/AU2005315914B2/en not_active Ceased
- 2005-12-05 EP EP05823127A patent/EP1828200B1/en not_active Expired - Lifetime
- 2005-12-05 NZ NZ555476A patent/NZ555476A/en not_active IP Right Cessation
- 2005-12-08 US US11/297,597 patent/US7375226B2/en not_active Expired - Fee Related
- 2005-12-12 TW TW094143890A patent/TWI299041B/zh not_active IP Right Cessation
- 2005-12-13 AR ARP050105207A patent/AR052156A1/es not_active Application Discontinuation
-
2007
- 2007-05-31 IL IL183592A patent/IL183592A0/en unknown
- 2007-06-04 NO NO20072833A patent/NO20072833L/no not_active Application Discontinuation
- 2007-06-07 ZA ZA200705044A patent/ZA200705044B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP4709849B2 (ja) | 2011-06-29 |
| ES2338139T3 (es) | 2010-05-04 |
| AU2005315914B2 (en) | 2011-03-03 |
| ZA200705044B (en) | 2008-09-25 |
| BRPI0519054A2 (pt) | 2008-12-23 |
| DE602005019465D1 (de) | 2010-04-01 |
| EP1828200B1 (en) | 2010-02-17 |
| CN100586951C (zh) | 2010-02-03 |
| NZ555476A (en) | 2009-09-25 |
| MX2007006896A (es) | 2007-06-26 |
| JP2008523126A (ja) | 2008-07-03 |
| TW200634017A (en) | 2006-10-01 |
| EP1828200A1 (en) | 2007-09-05 |
| WO2006063709A1 (en) | 2006-06-22 |
| CA2590316A1 (en) | 2006-06-22 |
| US20060128713A1 (en) | 2006-06-15 |
| KR20070086196A (ko) | 2007-08-27 |
| IL183592A0 (en) | 2007-09-20 |
| US7375226B2 (en) | 2008-05-20 |
| AU2005315914A1 (en) | 2006-06-22 |
| ATE457989T1 (de) | 2010-03-15 |
| NO20072833L (no) | 2007-07-17 |
| CN101076532A (zh) | 2007-11-21 |
| KR100883003B1 (ko) | 2009-02-12 |
| RU2007121768A (ru) | 2009-01-27 |
| AR052156A1 (es) | 2007-03-07 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |