KR102404650B1 - 포스포디에스테라아제 10a 억제제로서 융합된 트리아졸 유도체 - Google Patents
포스포디에스테라아제 10a 억제제로서 융합된 트리아졸 유도체 Download PDFInfo
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- KR102404650B1 KR102404650B1 KR1020167035389A KR20167035389A KR102404650B1 KR 102404650 B1 KR102404650 B1 KR 102404650B1 KR 1020167035389 A KR1020167035389 A KR 1020167035389A KR 20167035389 A KR20167035389 A KR 20167035389A KR 102404650 B1 KR102404650 B1 KR 102404650B1
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- Prior art keywords
- dimethyl
- triazolo
- pyrazine
- benzimidazol
- compound
- 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.)
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- 102100036377 cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Human genes 0.000 title abstract description 13
- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
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- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
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- 208000037765 diseases and disorders Diseases 0.000 claims abstract 3
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- 150000003839 salts Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- -1 6,8-dimethyl-2-(2-phenyl- 1H -imidazo[4,5- c ]pyridin-6-yl)[1,2,4]triazolo[1,5- a ]pyrazine 6,8-dimethyl-2-(2-phenyl- 1H -imidazo[4,5- b ]pyridin-6-yl)[1,2,4]triazolo[1,5- a ]pyrazine Chemical compound 0.000 claims description 9
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
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- JSEQTZXBMOTJCI-UHFFFAOYSA-N 2-[2-(5-chlorothiophen-2-yl)imidazo[1,2-a]pyrimidin-7-yl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound ClC1=CC=C(S1)C=1N=C2N(C=CC(=N2)C2=NN3C(C(=NC=C3C)C)=N2)C=1 JSEQTZXBMOTJCI-UHFFFAOYSA-N 0.000 claims description 4
- LAOQNTYYSNQKNC-UHFFFAOYSA-N 4-[6-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-1H-benzimidazol-2-yl]-1,3-oxazole Chemical compound CC1=CN=C(C)C2=NC(=NN12)C1=CC=C2NC(=NC2=C1)C1=COC=N1 LAOQNTYYSNQKNC-UHFFFAOYSA-N 0.000 claims description 4
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- DXZMHHDREXGTKJ-UHFFFAOYSA-N 5,8-dimethyl-2-(2-phenyl-1H-imidazo[4,5-b]pyridin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound CC1=CN=C(C=2N1N=C(N=2)C=1C=C2C(=NC=1)NC(=N2)C1=CC=CC=C1)C DXZMHHDREXGTKJ-UHFFFAOYSA-N 0.000 claims description 3
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- FMKYWWUBBPZFKX-UHFFFAOYSA-N 2-(6-bromo-2-phenylimidazo[1,2-a]pyrimidin-7-yl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound BrC=1C(=NC=2N(C=1)C=C(N=2)C1=CC=CC=C1)C1=NN2C(C(=NC=C2C)C)=N1 FMKYWWUBBPZFKX-UHFFFAOYSA-N 0.000 claims description 2
- FTYZGASAWVFMBU-UHFFFAOYSA-N 2-(6-fluoro-2-phenyl-1H-benzimidazol-5-yl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound CC1=CN=C(C)C2=NC(=NN12)C1=C(F)C=C2NC(=NC2=C1)C1=CC=CC=C1 FTYZGASAWVFMBU-UHFFFAOYSA-N 0.000 claims description 2
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- CYZRRJJJSPMKOX-UHFFFAOYSA-N 2-[2-(2-methoxyphenyl)-3H-benzimidazol-5-yl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine Chemical compound COC1=C(C=CC=C1)C1=NC2=CC(=CC=C2N1)C1=NN2C(=N1)C(C)=NC=C2C CYZRRJJJSPMKOX-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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| PCT/IB2015/053549 WO2015177688A1 (en) | 2014-05-19 | 2015-05-14 | Fused triazole derivatives as phosphodiesterase 10a inhibitors |
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| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| WO2017007301A1 (en) * | 2015-07-06 | 2017-01-12 | Universiti Sains Malaysia | Compound and method for inhibiting sirtuin activities |
| KR102587382B1 (ko) * | 2016-04-29 | 2023-10-12 | 솔루스첨단소재 주식회사 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
| CN111410657B (zh) * | 2019-01-08 | 2024-05-21 | 北京鼎材科技有限公司 | 一种发光材料及其应用 |
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| TWI501965B (zh) * | 2008-06-20 | 2015-10-01 | Lundbeck & Co As H | 作為pde10a酵素抑制劑之新穎苯基咪唑衍生物 |
| US8410117B2 (en) * | 2010-03-26 | 2013-04-02 | Hoffmann-La Roche Inc. | Imidazopyrimidine derivatives |
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Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF MEDICINAL CHEMISTRY, vol . 55, no. 17, 2012, pages 7299-7331 |
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| CN106459060B (zh) | 2019-04-05 |
| EA201692264A1 (ru) | 2017-04-28 |
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