JP2008526717A5 - - Google Patents
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- Publication number
- JP2008526717A5 JP2008526717A5 JP2007548843A JP2007548843A JP2008526717A5 JP 2008526717 A5 JP2008526717 A5 JP 2008526717A5 JP 2007548843 A JP2007548843 A JP 2007548843A JP 2007548843 A JP2007548843 A JP 2007548843A JP 2008526717 A5 JP2008526717 A5 JP 2008526717A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- alkyl
- methoxy
- triazolo
- phthalazin
- 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
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- -1 cyano, tetrazol-5-yl Chemical group 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 35
- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052757 nitrogen Inorganic materials 0.000 claims 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 20
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 4
- 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 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 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 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- BUYUFJZVMVFQLQ-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydroquinoxalin-2-yl)ethynyl]benzoic acid Chemical compound CC1(C=2N=CC(=NC=2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)C BUYUFJZVMVFQLQ-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 239000011737 fluorine Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- YDGXEJJOEYTQEP-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(3-pyrrolidin-1-ylsulfonylphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(=O)(=O)N1CCCC1)C1=CC=CC=C12 YDGXEJJOEYTQEP-UHFFFAOYSA-N 0.000 claims 1
- IZVSFCVCPDZGGF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[3-(2-methyltetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NN(C)N=N1)C1=CC=CC=C12 IZVSFCVCPDZGGF-UHFFFAOYSA-N 0.000 claims 1
- CQXHGLHIADVBQW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[3-(2h-tetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NNN=N1)C1=CC=CC=C12 CQXHGLHIADVBQW-UHFFFAOYSA-N 0.000 claims 1
- COMATYKLCBVMLD-UHFFFAOYSA-N 3-[[3-(2-bromophenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(NC=2C3=CC=CC=C3C3=NN=C(N3N=2)C=2C(=CC=CC=2)Br)=C1 COMATYKLCBVMLD-UHFFFAOYSA-N 0.000 claims 1
- KFJMSIIDLJNVOT-UHFFFAOYSA-N 3-[[3-(4-bromophenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(NC=2C3=CC=CC=C3C3=NN=C(N3N=2)C=2C=CC(Br)=CC=2)=C1 KFJMSIIDLJNVOT-UHFFFAOYSA-N 0.000 claims 1
- BERRTEMAKLHCEH-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(=O)(=O)N(C)C)C1=CC=CC=C12 BERRTEMAKLHCEH-UHFFFAOYSA-N 0.000 claims 1
- DMXZEAGYRDSWII-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C#N)C1=CC=CC=C12 DMXZEAGYRDSWII-UHFFFAOYSA-N 0.000 claims 1
- SCBFCULYXKHFII-UHFFFAOYSA-N 3-methoxy-n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=C(OC)C=CC=3)C=CC=1)C1=CC=CC=C12 SCBFCULYXKHFII-UHFFFAOYSA-N 0.000 claims 1
- NENVQQVAZMKJJY-UHFFFAOYSA-N 3-n-[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]benzene-1,3-diamine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(N)C=CC=1)C1=CC=CC=C12 NENVQQVAZMKJJY-UHFFFAOYSA-N 0.000 claims 1
- ZWLOLTMPNSGCHE-UHFFFAOYSA-N 4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)S(=O)(=O)N(C)C)C1=CC=CC=C12 ZWLOLTMPNSGCHE-UHFFFAOYSA-N 0.000 claims 1
- UXKSTFYIFOIWFA-UHFFFAOYSA-N 4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)C#N)C1=CC=CC=C12 UXKSTFYIFOIWFA-UHFFFAOYSA-N 0.000 claims 1
- PXAOPJAZZRRTMO-UHFFFAOYSA-N 4-acetyl-n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=CC(=CC=3)C(C)=O)C=CC=1)C1=CC=CC=C12 PXAOPJAZZRRTMO-UHFFFAOYSA-N 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- 208000028185 Angioedema Diseases 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
- 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
- 230000001154 acute effect Effects 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 230000002917 arthritic effect Effects 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- GLGNSAPAWZUDRT-UHFFFAOYSA-N morpholine-4-sulfonic acid Chemical compound OS(=O)(=O)N1CCOCC1 GLGNSAPAWZUDRT-UHFFFAOYSA-N 0.000 claims 1
- XKEMDWQSXAGUTA-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=CC(C)=CC=3)C=CC=1)C1=CC=CC=C12 XKEMDWQSXAGUTA-UHFFFAOYSA-N 0.000 claims 1
- LWNBXONNCSDUJI-UHFFFAOYSA-N n-[4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(NS(=O)(=O)CC=3C=CC=CC=3)=CC=1)C1=CC=CC=C12 LWNBXONNCSDUJI-UHFFFAOYSA-N 0.000 claims 1
- YJOFXVIATMLPER-UHFFFAOYSA-N n-[4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(NS(=O)(=O)C=3C=CC(C)=CC=3)=CC=1)C1=CC=CC=C12 YJOFXVIATMLPER-UHFFFAOYSA-N 0.000 claims 1
- YZFXPFCBJYEBPC-UHFFFAOYSA-N n-[4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]morpholine-4-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(NS(=O)(=O)N3CCOCC3)=CC=1)C1=CC=CC=C12 YZFXPFCBJYEBPC-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 230000007170 pathology Effects 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
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05100044.6 | 2005-01-05 | ||
| EP05100045 | 2005-01-05 | ||
| EP05100045.3 | 2005-01-05 | ||
| EP05100044 | 2005-01-05 | ||
| PCT/EP2006/050041 WO2006072615A2 (en) | 2005-01-05 | 2006-01-04 | Triazolophthalazines as pde2-inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526717A JP2008526717A (ja) | 2008-07-24 |
| JP2008526717A5 true JP2008526717A5 (https=) | 2009-02-19 |
| JP5240899B2 JP5240899B2 (ja) | 2013-07-17 |
Family
ID=36604687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548843A Expired - Fee Related JP5240899B2 (ja) | 2005-01-05 | 2006-01-04 | トリアゾロフタラジン |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8106047B2 (https=) |
| EP (1) | EP1836207B1 (https=) |
| JP (1) | JP5240899B2 (https=) |
| KR (1) | KR20070095986A (https=) |
| CN (1) | CN101103033B (https=) |
| AU (1) | AU2006204454B2 (https=) |
| BR (1) | BRPI0606379A2 (https=) |
| CA (1) | CA2592007C (https=) |
| EA (1) | EA012505B1 (https=) |
| ES (1) | ES2397080T3 (https=) |
| IL (1) | IL183919A (https=) |
| MX (1) | MX2007008137A (https=) |
| NO (1) | NO20073921L (https=) |
| NZ (1) | NZ555661A (https=) |
| WO (1) | WO2006072615A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11851449B2 (en) | 2013-07-03 | 2023-12-26 | Takeda Pharmaceutical Company Limited | Heterocyclic amide compounds having an RORvt inhibitory action |
Families Citing this family (29)
| 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 |
| CA2591991C (en) * | 2005-01-05 | 2013-11-19 | Altana Pharma Ag | Triazolophthalazines |
| 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 |
| CA2836851C (en) * | 2011-06-07 | 2016-06-21 | Christopher J. Helal | Pyrazolo[3,4-d]pyrimidine compounds and their use as pde2 inhibitors and/or cyp3a4 inhibitors |
| NZ631258A (en) | 2012-04-25 | 2016-11-25 | Takeda Pharmaceuticals Co | Nitrogenated heterocyclic compound |
| WO2013166276A1 (en) * | 2012-05-02 | 2013-11-07 | Southern Research Institute | Triazolopyridazine compounds, use as inhibitors of the kinase lrrk2, and methods for preparation thereof |
| 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 |
| 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 |
| CN103694244B (zh) * | 2014-01-09 | 2016-03-30 | 郑州大学 | 3,6位取代-1,2,4-三氮唑并[3,4-a]酞嗪类化合物及其制备和用途 |
| 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 |
| CA2969594A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Pde2 inhibiting organic compounds |
| HK1244427A1 (zh) | 2014-12-06 | 2018-08-10 | Intra-Cellular Therapies, Inc. | 有机化合物 |
| WO2016145614A1 (en) * | 2015-03-17 | 2016-09-22 | Merck Sharp & Dohme Corp. | Triazolyl pyrimidinone compounds as pde2 inhibitors |
| WO2016154081A1 (en) | 2015-03-26 | 2016-09-29 | 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 |
| US10647727B2 (en) | 2015-06-25 | 2020-05-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors |
| WO2017000277A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Substituted triazolo bicycliccompounds as pde2 inhibitors |
| WO2017000276A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds 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 |
| AU2018371216B2 (en) | 2017-11-23 | 2024-09-19 | Oslo University Hospital Hf | Treatment of tachycardia |
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| 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 |
| CA2591991C (en) * | 2005-01-05 | 2013-11-19 | Altana Pharma Ag | Triazolophthalazines |
| 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 |
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2006
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- 2006-01-04 EP EP06700240A patent/EP1836207B1/en not_active Expired - Lifetime
- 2006-01-04 MX MX2007008137A patent/MX2007008137A/es active IP Right Grant
- 2006-01-04 WO PCT/EP2006/050041 patent/WO2006072615A2/en not_active Ceased
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- 2006-01-04 ES ES06700240T patent/ES2397080T3/es not_active Expired - Lifetime
- 2006-01-04 KR KR1020077017407A patent/KR20070095986A/ko not_active Ceased
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11851449B2 (en) | 2013-07-03 | 2023-12-26 | Takeda Pharmaceutical Company Limited | Heterocyclic amide compounds having an RORvt inhibitory action |
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