JP2008526716A5 - - Google Patents
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- Publication number
- JP2008526716A5 JP2008526716A5 JP2007548842A JP2007548842A JP2008526716A5 JP 2008526716 A5 JP2008526716 A5 JP 2008526716A5 JP 2007548842 A JP2007548842 A JP 2007548842A JP 2007548842 A JP2007548842 A JP 2007548842A JP 2008526716 A5 JP2008526716 A5 JP 2008526716A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- triazolo
- phthalazin
- amine
- methoxyphenyl
- 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
- -1 nitro, phenyl Chemical group 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims 4
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000003511 endothelial effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- GBQQNNJZFFAQDX-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(4-phenylmethoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(OCC=3C=CC=CC=3)=CC=1)C1=CC=CC=C12 GBQQNNJZFFAQDX-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000028185 Angioedema Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OFTYEOLBXXMQSO-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=NN=C2N1N=C(C1=CC=CC=C21)NC2=CC(=CC=C2)OC2=CC=CC=C2.COC2=CC=C(C=C2)C2=NN=C1N2N=C(C2=CC=CC=C12)NC1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound COC1=CC=C(C=C1)C1=NN=C2N1N=C(C1=CC=CC=C21)NC2=CC(=CC=C2)OC2=CC=CC=C2.COC2=CC=C(C=C2)C2=NN=C1N2N=C(C2=CC=CC=C12)NC1=CC=C(C=C1)OC1=CC=CC=C1 OFTYEOLBXXMQSO-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 101100135859 Dictyostelium discoideum regA gene Proteins 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 101100082606 Plasmodium falciparum (isolate 3D7) PDEbeta gene Proteins 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 101100135860 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PDE2 gene Proteins 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 230000002917 arthritic effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- LMCYASVGPDDNFA-UHFFFAOYSA-N ethoxy-methoxy-phenylmethoxy-lambda3-chlorane Chemical group COCl(OCC1=CC=CC=C1)OCC LMCYASVGPDDNFA-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- AQCVUDLYFUQNLF-UHFFFAOYSA-N n,3-bis(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1NC(C1=CC=CC=C11)=NN2C1=NN=C2C1=CC=C(OC)C=C1 AQCVUDLYFUQNLF-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 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 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 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
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05100043 | 2005-01-05 | ||
| EP05100043.8 | 2005-01-05 | ||
| PCT/EP2006/050032 WO2006072612A2 (en) | 2005-01-05 | 2006-01-04 | Triazolophthalazines as pde2- inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526716A JP2008526716A (ja) | 2008-07-24 |
| JP2008526716A5 true JP2008526716A5 (https=) | 2009-02-19 |
| JP5130053B2 JP5130053B2 (ja) | 2013-01-30 |
Family
ID=34938484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548842A Expired - Fee Related JP5130053B2 (ja) | 2005-01-05 | 2006-01-04 | トリアゾロフタラジン |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7671050B2 (https=) |
| EP (1) | EP1874775B1 (https=) |
| JP (1) | JP5130053B2 (https=) |
| AU (1) | AU2006204451C1 (https=) |
| CA (1) | CA2591991C (https=) |
| ES (1) | ES2397082T3 (https=) |
| WO (1) | WO2006072612A2 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101368093B1 (ko) * | 2004-09-02 | 2014-03-14 | 다케다 게엠베하 | 트리아졸로프탈라진 |
| CN101103033B (zh) * | 2005-01-05 | 2010-08-04 | 尼科梅德有限责任公司 | 作为pde2抑制剂的三唑并酞嗪 |
| 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 |
| KR101548443B1 (ko) * | 2011-02-23 | 2015-08-28 | 화이자 인코포레이티드 | 신경 장애의 치료를 위한 이미다조[5,1-f][1,2,4]트라이아진 |
| NZ631258A (en) | 2012-04-25 | 2016-11-25 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| WO2014010732A1 (ja) * | 2012-07-13 | 2014-01-16 | 武田薬品工業株式会社 | 複素環化合物 |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| EP2975031A4 (en) | 2013-03-14 | 2017-04-19 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| EP3018123B1 (en) | 2013-07-03 | 2023-05-10 | Takeda Pharmaceutical Company Limited | Amide compound |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| JP6696904B2 (ja) | 2014-01-08 | 2020-05-20 | 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． | 製剤および医薬組成物 |
| HUE057317T2 (hu) | 2014-04-23 | 2022-04-28 | Dart Neuroscience Llc | Helyettesített [1,2,4]triazolo[1,5-A]pirimidin-7-IL vegyületeket tartalmazó készítmények mint PDE2 inhibítorok |
| TWI568737B (zh) | 2014-11-05 | 2017-02-01 | 達特神經科學（開曼）有限責任公司 | 作為ｐｄｅ２抑制劑之經取代的５－甲基－［１，２，４］三唑并［１，５－ａ］嘧啶－２－胺化合物 |
| HK1244427A1 (zh) | 2014-12-06 | 2018-08-10 | Intra-Cellular Therapies, Inc. | 有机化合物 |
| CA2969594A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Pde2 inhibiting organic compounds |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| AU2018371216B2 (en) | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH21834A (en) * | 1982-01-18 | 1988-03-17 | Lepetit Spa | New 6-substituted-s-triazolo(3,4-a)phthalazine derivatives |
| IT1194310B (it) * | 1983-07-12 | 1988-09-14 | Lepetit Spa | Derivati triazolo (3,4-a) ftalazinici 3,6-disostituiti |
| US5869486A (en) | 1995-02-24 | 1999-02-09 | Ono Pharmaceutical Co., Ltd. | Fused pyrimidines and pyriazines as pharmaceutical compounds |
| KR20000029548A (ko) | 1996-07-25 | 2000-05-25 | 더블유. 지. 콜 | 가바수용체에대한리간드로서의치환된트리아졸로-피리다진유도체 |
| 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 |
| IT1303272B1 (it) * | 1998-10-29 | 2000-11-06 | Zambon Spa | Derivati triciclici inibitori della fosfodiesterasi 4 |
| WO2001047929A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Aktiengesellschaft | Triazolotriazinone und ihre verwendung |
| GB0028583D0 (en) * | 2000-11-23 | 2001-01-10 | Merck Sharp & Dohme | Therapeutic compounds |
| US6958334B2 (en) | 2001-04-10 | 2005-10-25 | Merck & Co., Inc. | Inhibitors of Akt activity |
| CA2497539A1 (en) | 2002-09-04 | 2004-03-18 | Schering Corporation | Novel pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US20070179161A1 (en) | 2003-03-31 | 2007-08-02 | Vernalis (Cambridge) Limited. | Pyrazolopyrimidine compounds and their use in medicine |
| KR101368093B1 (ko) * | 2004-09-02 | 2014-03-14 | 다케다 게엠베하 | 트리아졸로프탈라진 |
| CN101103033B (zh) * | 2005-01-05 | 2010-08-04 | 尼科梅德有限责任公司 | 作为pde2抑制剂的三唑并酞嗪 |
-
2006
- 2006-01-04 CA CA2591991A patent/CA2591991C/en not_active Expired - Fee Related
- 2006-01-04 AU AU2006204451A patent/AU2006204451C1/en not_active Ceased
- 2006-01-04 ES ES06700346T patent/ES2397082T3/es not_active Expired - Lifetime
- 2006-01-04 JP JP2007548842A patent/JP5130053B2/ja not_active Expired - Fee Related
- 2006-01-04 EP EP06700346A patent/EP1874775B1/en not_active Expired - Lifetime
- 2006-01-04 US US11/794,129 patent/US7671050B2/en not_active Expired - Fee Related
- 2006-01-04 WO PCT/EP2006/050032 patent/WO2006072612A2/en not_active Ceased
-
2009
- 2009-11-05 US US12/591,038 patent/US20110136803A1/en not_active Abandoned
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