JP2008511586A5 - - Google Patents
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- Publication number
- JP2008511586A5 JP2008511586A5 JP2007528875A JP2007528875A JP2008511586A5 JP 2008511586 A5 JP2008511586 A5 JP 2008511586A5 JP 2007528875 A JP2007528875 A JP 2007528875A JP 2007528875 A JP2007528875 A JP 2007528875A JP 2008511586 A5 JP2008511586 A5 JP 2008511586A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- methoxy
- substituted
- morpholino
- 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.)
- Granted
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 23
- -1 amino, carboxyl Chemical group 0.000 claims 21
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000004076 pyridyl group Chemical group 0.000 claims 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 239000011737 fluorine Substances 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 6
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- 229920002554 vinyl polymer Chemical group 0.000 claims 3
- SGTXILTYXULEQD-UHFFFAOYSA-N 2H-triazolo[4,5-f]phthalazine Chemical group N1=NC=C2C3=NNN=C3C=CC2=C1 SGTXILTYXULEQD-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- DURLJUGBZLEILS-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NC(=O)C3CC3)C=CC=1)C1=CC=CC=C12 DURLJUGBZLEILS-UHFFFAOYSA-N 0.000 claims 1
- ZOZGQHDQFRUORE-UHFFFAOYSA-N n-[4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(NC(=O)C3CC3)=CC=1)C1=CC=CC=C12 ZOZGQHDQFRUORE-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04104221.9 | 2004-09-02 | ||
| EP04104221 | 2004-09-02 | ||
| PCT/EP2005/054266 WO2006024640A2 (en) | 2004-09-02 | 2005-08-31 | Triazolophthalazines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008511586A JP2008511586A (ja) | 2008-04-17 |
| JP2008511586A5 true JP2008511586A5 (enExample) | 2008-10-16 |
| JP5140427B2 JP5140427B2 (ja) | 2013-02-06 |
Family
ID=34929521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007528875A Expired - Fee Related JP5140427B2 (ja) | 2004-09-02 | 2005-08-31 | トリアゾロフタラジン |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7851472B2 (enExample) |
| EP (1) | EP1791543B1 (enExample) |
| JP (1) | JP5140427B2 (enExample) |
| KR (1) | KR101368093B1 (enExample) |
| CN (1) | CN101133057B (enExample) |
| AT (1) | ATE471324T1 (enExample) |
| AU (1) | AU2005279221C9 (enExample) |
| BR (1) | BRPI0514586A (enExample) |
| CA (1) | CA2578368C (enExample) |
| DE (1) | DE602005021894D1 (enExample) |
| EA (1) | EA014324B1 (enExample) |
| ES (1) | ES2347337T3 (enExample) |
| IL (1) | IL181271A (enExample) |
| NO (1) | NO20071127L (enExample) |
| NZ (1) | NZ553160A (enExample) |
| WO (1) | WO2006024640A2 (enExample) |
| ZA (1) | ZA200701137B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5240899B2 (ja) * | 2005-01-05 | 2013-07-17 | タケダ ゲゼルシャフト ミット ベシュレンクテル ハフツング | トリアゾロフタラジン |
| JP5130053B2 (ja) * | 2005-01-05 | 2013-01-30 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | トリアゾロフタラジン |
| PH12012501361A1 (en) | 2009-12-31 | 2012-10-22 | Centro Nac De Investigaciones Oncologicas Cnio | Tricyclic compounds for use as kinase inhibitors |
| US9540379B2 (en) | 2011-01-31 | 2017-01-10 | Boehringer Ingelheim International Gmbh | (1,2,4)triazolo[4,3-A]quinoxaline derivatives as inhibitors of phosphodiesterases |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| WO2015096651A1 (en) | 2013-12-23 | 2015-07-02 | Merck Sharp & Dohme Corp. | Pyrimidone carboxamide compounds as pde2 inhibitors |
| US9849132B2 (en) | 2014-01-08 | 2017-12-26 | Intra-Cellular Therapies, Inc. | Products and pharmaceutical compositions |
| RU2659070C9 (ru) | 2014-04-23 | 2018-08-24 | Дарт Нейросайенс (Кайман) Лтд. | ЗАМЕЩЕННЫЕ [1,2,4]ТРИАЗОЛО[1,5-a]ПИРИМИДИН-7-ИЛЬНЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ИНГИБИТОРОВ PDE2 |
| US10239882B2 (en) | 2014-11-05 | 2019-03-26 | Dart Neuroscience (Cayman) Ltd. | Substituted 5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine compounds as PDE2 inhibitors |
| KR102557603B1 (ko) | 2014-12-06 | 2023-07-19 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| CA2969597C (en) | 2014-12-06 | 2023-10-24 | Intra-Cellular Therapies, Inc. | 1h-pyrazolo[4,3-c][1,5]naphthyridin-4(5h)-one compounds and their use as pde2 inhibitors |
| WO2016145614A1 (en) | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| EP3285581B1 (en) | 2015-03-26 | 2021-08-11 | Merck Sharp & Dohme Corp. | Pyrazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016179059A1 (en) | 2015-05-05 | 2016-11-10 | Merck Sharp & Dohme Corp. | Heteroaryl-pyrimidinone compounds as pde2 inhibitors |
| WO2016183741A1 (en) | 2015-05-15 | 2016-11-24 | Merck Sharp & Dohme Corp. | Pyrimidinone amide compounds as pde2 inhibitors |
| WO2016191935A1 (en) | 2015-05-29 | 2016-12-08 | Merck Sharp & Dohme Corp. | 6-alkyl dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| WO2016192083A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| EP3313852B1 (en) | 2015-06-25 | 2021-01-20 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as pde2 inhibitors |
| WO2017000276A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds as pde2 inhibitors |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| PL3713572T3 (pl) | 2017-11-23 | 2025-09-22 | Oslo University Hospital Hf | Leczenie tachykardii |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI81350C (fi) | 1982-01-18 | 1990-10-10 | Lepetit Spa | Analogfoerfarande foer framstaellning av nya, farmakologiskt aktiva 6-substituerade s-triatsolo/3,4-a/ ftalazinderivat. |
| RU2128175C1 (ru) * | 1994-08-09 | 1999-03-27 | Эйсай Ко., Лтд. | Конденсированный пиридазин или его фармакологически приемлемая соль, средство, проявляющее ингибирующую активность в отношении циклической гмф- фосфодиэстеразы |
| WO1996008496A1 (en) * | 1994-09-16 | 1996-03-21 | Takeda Chemical Industries, Ltd. | Triazolopyridazines process and intermediates for their preparation and their use as medicaments |
| US5869486A (en) | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| JP4216905B2 (ja) * | 1996-07-25 | 2009-01-28 | メルク シヤープ エンド ドーム リミテツド | Ｇａｂａ受容体に対するリガンドとしての置換トリアゾローピリダジン誘導体 |
| CA2288789C (en) | 1997-05-08 | 2009-07-21 | Merck Sharp & Dohme Limited | Substituted 1,2,4-triazolo[3,4-a]phthalazine derivatives as gaba alpha 5 ligands |
| US6235741B1 (en) * | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| GB9715977D0 (en) * | 1997-07-29 | 1997-10-01 | Merck Sharp & Dohme | Therapeutic agents |
| GB9801208D0 (en) * | 1998-01-21 | 1998-03-18 | Merck Sharp & Dohme | Therapeutic agents |
| IT1303272B1 (it) * | 1998-10-29 | 2000-11-06 | Zambon Spa | Derivati triciclici inibitori della fosfodiesterasi 4 |
| GB0028583D0 (en) | 2000-11-23 | 2001-01-10 | Merck Sharp & Dohme | Therapeutic compounds |
| GB0108475D0 (en) * | 2001-04-04 | 2001-05-23 | Merck Sharp & Dohme | New compounds |
| US6958334B2 (en) * | 2001-04-10 | 2005-10-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| JP5130053B2 (ja) * | 2005-01-05 | 2013-01-30 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | トリアゾロフタラジン |
| JP5240899B2 (ja) * | 2005-01-05 | 2013-07-17 | タケダ ゲゼルシャフト ミット ベシュレンクテル ハフツング | トリアゾロフタラジン |
-
2005
- 2005-08-31 US US11/660,748 patent/US7851472B2/en not_active Expired - Fee Related
- 2005-08-31 EP EP05784647A patent/EP1791543B1/en not_active Expired - Lifetime
- 2005-08-31 AU AU2005279221A patent/AU2005279221C9/en not_active Ceased
- 2005-08-31 AT AT05784647T patent/ATE471324T1/de not_active IP Right Cessation
- 2005-08-31 JP JP2007528875A patent/JP5140427B2/ja not_active Expired - Fee Related
- 2005-08-31 KR KR1020077006869A patent/KR101368093B1/ko not_active Expired - Fee Related
- 2005-08-31 CN CN200580038057XA patent/CN101133057B/zh not_active Expired - Fee Related
- 2005-08-31 EA EA200700537A patent/EA014324B1/ru not_active IP Right Cessation
- 2005-08-31 DE DE602005021894T patent/DE602005021894D1/de not_active Expired - Lifetime
- 2005-08-31 CA CA2578368A patent/CA2578368C/en not_active Expired - Fee Related
- 2005-08-31 NZ NZ553160A patent/NZ553160A/en not_active IP Right Cessation
- 2005-08-31 ES ES05784647T patent/ES2347337T3/es not_active Expired - Lifetime
- 2005-08-31 WO PCT/EP2005/054266 patent/WO2006024640A2/en not_active Ceased
- 2005-08-31 BR BRPI0514586-4A patent/BRPI0514586A/pt not_active IP Right Cessation
-
2007
- 2007-02-08 ZA ZA200701137A patent/ZA200701137B/xx unknown
- 2007-02-11 IL IL181271A patent/IL181271A/en not_active IP Right Cessation
- 2007-02-28 NO NO20071127A patent/NO20071127L/no not_active Application Discontinuation
-
2010
- 2010-04-23 US US12/766,478 patent/US20100286140A1/en not_active Abandoned