CA2711931A1 - Derives de tetrahydrocyclopenta[c]acridines inhibiteurs de kinases et leurs applications biologiques - Google Patents
Derives de tetrahydrocyclopenta[c]acridines inhibiteurs de kinases et leurs applications biologiques Download PDFInfo
- Publication number
- CA2711931A1 CA2711931A1 CA2711931A CA2711931A CA2711931A1 CA 2711931 A1 CA2711931 A1 CA 2711931A1 CA 2711931 A CA2711931 A CA 2711931A CA 2711931 A CA2711931 A CA 2711931A CA 2711931 A1 CA2711931 A1 CA 2711931A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrahydro
- cyclopenta
- acridin
- hydroxy
- trimethylsilanyl
- 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.)
- Abandoned
Links
- 229940043355 kinase inhibitor Drugs 0.000 title claims abstract description 7
- 239000003757 phosphotransferase inhibitor Substances 0.000 title claims abstract description 7
- 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 title claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 3
- 239000011630 iodine Substances 0.000 claims abstract description 3
- 229920000570 polyether Polymers 0.000 claims abstract description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- -1 C1-C12 alkyl radical Chemical class 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 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 description 7
- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims description 6
- 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 108091007914 CDKs Proteins 0.000 claims description 5
- 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 claims description 5
- 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 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 description 4
- 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 description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
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- 230000004770 neurodegeneration Effects 0.000 claims description 3
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- 108060006633 protein kinase Proteins 0.000 claims description 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
- CFFHONNHMXLQEC-UHFFFAOYSA-N 1-[2-(2-trimethylsilylethynyl)quinolin-3-yl]but-3-en-1-ol Chemical group C1=CC=C2C=C(C(O)CC=C)C(C#C[Si](C)(C)C)=NC2=C1 CFFHONNHMXLQEC-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 238000003747 Grignard reaction Methods 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- MXEMOFBQQGBPST-UHFFFAOYSA-N OC1CC2C(C=3N=C4C=CC=CC4=CC13)=C(C(C2)=O)CCCC.O=C2CC1C(C=3N=C4C=CC=CC4=CC23)=CC(C1)=O Chemical compound OC1CC2C(C=3N=C4C=CC=CC4=CC13)=C(C(C2)=O)CCCC.O=C2CC1C(C=3N=C4C=CC=CC4=CC23)=CC(C1)=O MXEMOFBQQGBPST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000008298 dragée Substances 0.000 claims description 2
- 239000006196 drop Substances 0.000 claims description 2
- 150000004795 grignard reagents Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 150000002576 ketones Chemical group 0.000 claims description 2
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
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- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 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
- 229940124639 Selective inhibitor Drugs 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 238000005649 metathesis reaction Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 101150015860 MC1R gene Proteins 0.000 description 12
- 102100034216 Melanocyte-stimulating hormone receptor Human genes 0.000 description 12
- 108091000080 Phosphotransferase Proteins 0.000 description 11
- 102000020233 phosphotransferase Human genes 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 4
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- KZHSNAUODDELLD-UHFFFAOYSA-N cyclopenta[c]acridin-2-one Chemical compound C1=CC=C2N=C(C=3C(=CC(C=3)=O)C=C3)C3=CC2=C1 KZHSNAUODDELLD-UHFFFAOYSA-N 0.000 description 4
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- 102000004190 Enzymes Human genes 0.000 description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 3
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- 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 description 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 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 102000006538 Nitric Oxide Synthase Type I Human genes 0.000 description 2
- 108010008858 Nitric Oxide Synthase Type I Proteins 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
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- 150000000177 1,2,3-triazoles Chemical class 0.000 description 1
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- BGYVXOMYRDVVBG-UHFFFAOYSA-N 2-ethynylquinoline-3-carbaldehyde Chemical class C1=CC=C2N=C(C#C)C(C=O)=CC2=C1 BGYVXOMYRDVVBG-UHFFFAOYSA-N 0.000 description 1
- QAUIPRDXELRYPS-UHFFFAOYSA-N 3,3a,4,5-tetrahydrocyclopenta[c]acridin-2-one Chemical compound C1=CC=C2N=C(C=3C(CC(C=3)=O)CC3)C3=CC2=C1 QAUIPRDXELRYPS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DTBVVEICJUMPBB-UHFFFAOYSA-N 6,7-dimethoxy-2-(2-trimethylsilylethynyl)quinoline-3-carbaldehyde Chemical compound O=CC1=C(C#C[Si](C)(C)C)N=C2C=C(OC)C(OC)=CC2=C1 DTBVVEICJUMPBB-UHFFFAOYSA-N 0.000 description 1
- MMIQBIRTJPWMJP-UHFFFAOYSA-N 6-methoxy-2-(2-trimethylsilylethynyl)quinoline-3-carbaldehyde Chemical compound N1=C(C#C[Si](C)(C)C)C(C=O)=CC2=CC(OC)=CC=C21 MMIQBIRTJPWMJP-UHFFFAOYSA-N 0.000 description 1
- 229920000936 Agarose Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 102000003989 Aurora kinases Human genes 0.000 description 1
- 108090000433 Aurora kinases Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000002554 Cyclin A Human genes 0.000 description 1
- 108010068192 Cyclin A Proteins 0.000 description 1
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- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
- XQGSVNHIIVBMPX-UHFFFAOYSA-N Improsulfan tosylate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CS(=O)(=O)OCCC[NH2+]CCCOS(C)(=O)=O XQGSVNHIIVBMPX-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- UFWZSGRXZKLWHU-UHFFFAOYSA-N OC1CC2C(C=3N=C4C=CC=CC4=CC13)=C(C(C2)=O)[Si](C)(C)C.ClC2CC1C(C=3N=C4C=CC=CC4=CC23)=C(C(C1)=O)[Si](C)(C)C Chemical compound OC1CC2C(C=3N=C4C=CC=CC4=CC13)=C(C(C2)=O)[Si](C)(C)C.ClC2CC1C(C=3N=C4C=CC=CC4=CC23)=C(C(C1)=O)[Si](C)(C)C UFWZSGRXZKLWHU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 230000002018 overexpression Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical class C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA2711931A1 true CA2711931A1 (fr) | 2009-07-23 |
Family
ID=39477561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2711931A Abandoned CA2711931A1 (fr) | 2008-01-18 | 2009-01-19 | Derives de tetrahydrocyclopenta[c]acridines inhibiteurs de kinases et leurs applications biologiques |
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
Also Published As
| Publication number | Publication date |
|---|---|
| JP5879036B2 (ja) | 2016-03-08 |
| US20100285124A1 (en) | 2010-11-11 |
| FR2926550A1 (fr) | 2009-07-24 |
| FR2926550B1 (fr) | 2010-09-10 |
| WO2009090623A1 (fr) | 2009-07-23 |
| EP2244707A1 (fr) | 2010-11-03 |
| JP2011509994A (ja) | 2011-03-31 |
| US8999955B2 (en) | 2015-04-07 |
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