JP2011509994A5 - - Google Patents
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- Publication number
- JP2011509994A5 JP2011509994A5 JP2010542727A JP2010542727A JP2011509994A5 JP 2011509994 A5 JP2011509994 A5 JP 2011509994A5 JP 2010542727 A JP2010542727 A JP 2010542727A JP 2010542727 A JP2010542727 A JP 2010542727A JP 2011509994 A5 JP2011509994 A5 JP 2011509994A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopenta
- tetrahydro
- acridin
- hydroxy
- group
- 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
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- HWZUIEJQHZQNFL-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-cyclopenta[c]acridine Chemical class C1C=C2C=C3C=CC=CC3=NC2=C2C1CCC2 HWZUIEJQHZQNFL-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229920000570 polyether Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 7
- 239000003112 inhibitor Substances 0.000 claims 5
- -1 C 4 alkyl compound Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- ORRCVHQTDZHEKH-UHFFFAOYSA-N 1-tert-butyl-5-hydroxy-8-methoxy-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1C(O)C2=CC3=CC(OC)=CC=C3N=C2C2=C(C(C)(C)C)C(=O)CC21 ORRCVHQTDZHEKH-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- LTOZXSOKJCGRQP-UHFFFAOYSA-N 5-hydroxy-3-methyl-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1=CC=C2N=C(C=3C(C(C(C=3[Si](C)(C)C)=O)C)CC3O)C3=CC2=C1 LTOZXSOKJCGRQP-UHFFFAOYSA-N 0.000 claims 2
- JAXIMGVTBDOXDU-UHFFFAOYSA-N 5-hydroxy-8,9-dimethoxy-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound OC1CC2CC(=O)C([Si](C)(C)C)=C2C2=C1C=C1C=C(OC)C(OC)=CC1=N2 JAXIMGVTBDOXDU-UHFFFAOYSA-N 0.000 claims 2
- GPLFVGIGKBFDJY-UHFFFAOYSA-N 5-hydroxy-8-methoxy-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1C(O)C2=CC3=CC(OC)=CC=C3N=C2C2=C([Si](C)(C)C)C(=O)CC21 GPLFVGIGKBFDJY-UHFFFAOYSA-N 0.000 claims 2
- LLFGZHHEIQWCBU-UHFFFAOYSA-N 5-hydroxy-9-methoxy-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound OC1CC2CC(=O)C([Si](C)(C)C)=C2C2=NC3=CC(OC)=CC=C3C=C21 LLFGZHHEIQWCBU-UHFFFAOYSA-N 0.000 claims 2
- WQINECCWRIHLAF-UHFFFAOYSA-N 5-hydroxy-9-methoxy-3-methyl-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound OC1CC2C(C)C(=O)C([Si](C)(C)C)=C2C2=NC3=CC(OC)=CC=C3C=C21 WQINECCWRIHLAF-UHFFFAOYSA-N 0.000 claims 2
- 239000002775 capsule Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical class N1N=NC(=C1)* 0.000 claims 1
- MSFMVNKGLJRQAG-UHFFFAOYSA-N 1,3,3a,4-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1C(CC2CC=C3C=C4C=CC=CC4=NC3=C21)=O MSFMVNKGLJRQAG-UHFFFAOYSA-N 0.000 claims 1
- CFFHONNHMXLQEC-UHFFFAOYSA-N 1-[2-(2-trimethylsilylethynyl)quinolin-3-yl]but-3-en-1-ol Chemical compound C1=CC=C2C=C(C(O)CC=C)C(C#C[Si](C)(C)C)=NC2=C1 CFFHONNHMXLQEC-UHFFFAOYSA-N 0.000 claims 1
- CBLHIEOQXDYNOW-UHFFFAOYSA-N 1-[6,7-dimethoxy-2-(2-trimethylsilylethynyl)quinolin-3-yl]but-3-en-1-ol Chemical compound C=CCC(O)C1=C(C#C[Si](C)(C)C)N=C2C=C(OC)C(OC)=CC2=C1 CBLHIEOQXDYNOW-UHFFFAOYSA-N 0.000 claims 1
- YMPYWNJSHPOFLZ-UHFFFAOYSA-N 1-[6-methoxy-2-(2-trimethylsilylethynyl)quinolin-3-yl]but-3-en-1-ol Chemical compound N1=C(C#C[Si](C)(C)C)C(C(O)CC=C)=CC2=CC(OC)=CC=C21 YMPYWNJSHPOFLZ-UHFFFAOYSA-N 0.000 claims 1
- LWHXWZMKRQOEIH-UHFFFAOYSA-N 1-butyl-5-hydroxy-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1=CC=C2N=C3C4=C(CCCC)C(=O)CC4CC(O)C3=CC2=C1 LWHXWZMKRQOEIH-UHFFFAOYSA-N 0.000 claims 1
- YIFLAIPOBKQQPO-UHFFFAOYSA-N 1-trimethylsilyl-3a,4-dihydro-3h-cyclopenta[c]acridine-2,5-dione Chemical compound C1=CC=C2N=C3C4=C([Si](C)(C)C)C(=O)CC4CC(=O)C3=CC2=C1 YIFLAIPOBKQQPO-UHFFFAOYSA-N 0.000 claims 1
- WTMPXTNEZVKUCY-UHFFFAOYSA-N 1h-acridin-2-one Chemical compound C1=CC=C2N=C(C=CC(=O)C3)C3=CC2=C1 WTMPXTNEZVKUCY-UHFFFAOYSA-N 0.000 claims 1
- SDKQWXCBSNMYBN-UHFFFAOYSA-N 2-chloroquinoline-3-carbaldehyde Chemical class C1=CC=C2C=C(C=O)C(Cl)=NC2=C1 SDKQWXCBSNMYBN-UHFFFAOYSA-N 0.000 claims 1
- OIIOPIIGGQSDJQ-UHFFFAOYSA-N 5-hydroxy-1-trimethylsilyl-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1=CC=C2N=C3C4=C([Si](C)(C)C)C(=O)CC4CC(O)C3=CC2=C1 OIIOPIIGGQSDJQ-UHFFFAOYSA-N 0.000 claims 1
- GZJRXZGQPOVZMD-UHFFFAOYSA-N 5-hydroxy-3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C12=NC3=CC=CC=C3C=C2C(O)CC2C1=CC(=O)C2 GZJRXZGQPOVZMD-UHFFFAOYSA-N 0.000 claims 1
- 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 claims 1
- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims 1
- 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 claims 1
- 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 claims 1
- 238000003747 Grignard reaction Methods 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 229940124639 Selective inhibitor Drugs 0.000 claims 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- GRERYAZQWYKFMG-UHFFFAOYSA-N but-3-en-1-ol Chemical compound [CH2]C=CCO GRERYAZQWYKFMG-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000005686 cross metathesis reaction Methods 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 239000006196 drop Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004795 grignard reagents Chemical group 0.000 claims 1
- 230000036512 infertility Effects 0.000 claims 1
- 239000007972 injectable composition Substances 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 239000008174 sterile solution Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UNPLRYRWJLTVAE-UHFFFAOYSA-N Cloperastine hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 UNPLRYRWJLTVAE-UHFFFAOYSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000008482 dysregulation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0800275A FR2926550B1 (fr) | 2008-01-18 | 2008-01-18 | Derives de tetrahydrocyclopenta°c!acridines inhibiteurs de kinases et leurs applications biologiques |
| FR08/00275 | 2008-01-18 | ||
| PCT/IB2009/050179 WO2009090623A1 (fr) | 2008-01-18 | 2009-01-19 | Dérivés de tétrahydrocyclopenta[c]acridines inhibiteurs de kinases et leurs applications biologiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509994A JP2011509994A (ja) | 2011-03-31 |
| JP2011509994A5 true JP2011509994A5 (enExample) | 2012-03-01 |
| JP5879036B2 JP5879036B2 (ja) | 2016-03-08 |
Family
ID=39477561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542727A Expired - Fee Related JP5879036B2 (ja) | 2008-01-18 | 2009-01-19 | キナーゼ阻害剤としてのテトラヒドロシクロペンタ［ｃ］アクリジン誘導体およびその生物学的適用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8999955B2 (enExample) |
| EP (1) | EP2244707A1 (enExample) |
| JP (1) | JP5879036B2 (enExample) |
| CA (1) | CA2711931A1 (enExample) |
| FR (1) | FR2926550B1 (enExample) |
| WO (1) | WO2009090623A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018135268A (ja) * | 2015-06-05 | 2018-08-30 | 大日本住友製薬株式会社 | 新規ヘテロアリールアミノ−３−ピラゾール誘導体およびその薬理学上許容される塩 |
| CN105820119B (zh) * | 2015-07-06 | 2019-04-02 | 盐城工学院 | 一种5，6-二氢苯并菲啶衍生物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK569087A (da) * | 1986-10-31 | 1988-05-01 | Sumitomo Pharma | Quinolin-derivater, deres fremstilling og anvendelse |
-
2008
- 2008-01-18 FR FR0800275A patent/FR2926550B1/fr not_active Expired - Fee Related
-
2009
- 2009-01-19 JP JP2010542727A patent/JP5879036B2/ja not_active Expired - Fee Related
- 2009-01-19 EP EP09702789A patent/EP2244707A1/fr not_active Withdrawn
- 2009-01-19 CA CA2711931A patent/CA2711931A1/fr not_active Abandoned
- 2009-01-19 WO PCT/IB2009/050179 patent/WO2009090623A1/fr not_active Ceased
- 2009-01-19 US US12/735,463 patent/US8999955B2/en not_active Expired - Fee Related