CA2374714A1 - Derives de la purine, leur procede de preparation, et compositions pharmaceutiques les contenant - Google Patents
Derives de la purine, leur procede de preparation, et compositions pharmaceutiques les contenant Download PDFInfo
- Publication number
- CA2374714A1 CA2374714A1 CA002374714A CA2374714A CA2374714A1 CA 2374714 A1 CA2374714 A1 CA 2374714A1 CA 002374714 A CA002374714 A CA 002374714A CA 2374714 A CA2374714 A CA 2374714A CA 2374714 A1 CA2374714 A1 CA 2374714A1
- Authority
- CA
- Canada
- Prior art keywords
- radical
- formula
- amino
- radicals
- cyclopentyl
- 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
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
- -1 -CH¿2?- heterocyclic Chemical group 0.000 claims abstract description 359
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 42
- 125000003118 aryl group Chemical group 0.000 claims abstract description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229940079593 drug Drugs 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 275
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 162
- 150000003254 radicals Chemical class 0.000 claims description 134
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 229910021529 ammonia Inorganic materials 0.000 claims description 80
- 239000002253 acid Substances 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 33
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 33
- 239000011707 mineral Substances 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 29
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 150000007513 acids Chemical class 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 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 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 230000009466 transformation Effects 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 7
- 150000002148 esters Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 230000006907 apoptotic process Effects 0.000 claims description 6
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 230000002927 anti-mitotic effect Effects 0.000 claims description 5
- 238000002512 chemotherapy Methods 0.000 claims description 5
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 150000002576 ketones Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003080 antimitotic agent Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 230000002555 anti-neurodegenerative effect Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 150000002923 oximes Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- NULKIJGSLWQSBK-UHFFFAOYSA-N 9-cyclopentyl-6-N-(4-nitrophenyl)purine-2,6-diamine Chemical compound C1(CCCC1)N1C2=NC(=NC(=C2N=C1)NC1=CC=C(C=C1)[N+](=O)[O-])N NULKIJGSLWQSBK-UHFFFAOYSA-N 0.000 claims 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 230000001405 anti-neuronal effect Effects 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000009223 neuronal apoptosis Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 150000002431 hydrogen Chemical class 0.000 abstract 6
- 239000005864 Sulphur Substances 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 582
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 390
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 315
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 289
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 258
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 229
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 180
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 150
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 135
- 239000000377 silicon dioxide Substances 0.000 description 129
- 239000003480 eluent Substances 0.000 description 125
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 108
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 99
- 229910001868 water Inorganic materials 0.000 description 99
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
- 239000013078 crystal Substances 0.000 description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 83
- 235000019441 ethanol Nutrition 0.000 description 83
- 239000002904 solvent Substances 0.000 description 77
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 74
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 66
- 238000004587 chromatography analysis Methods 0.000 description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 62
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 62
- 238000000746 purification Methods 0.000 description 57
- 239000000243 solution Substances 0.000 description 55
- 238000003756 stirring Methods 0.000 description 50
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 29
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 29
- 239000011780 sodium chloride Substances 0.000 description 26
- 239000007864 aqueous solution Substances 0.000 description 23
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 235000010755 mineral Nutrition 0.000 description 21
- 229910017974 NH40H Inorganic materials 0.000 description 19
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 18
- 229910000024 caesium carbonate Inorganic materials 0.000 description 18
- 230000009471 action Effects 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 14
- 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 12
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 11
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 239000002027 dichloromethane extract Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 229940095102 methyl benzoate Drugs 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 239000006196 drop Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000004540 pour-on Substances 0.000 description 4
- 150000003212 purines Chemical class 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 3
- XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- FTHGKDLUXAQKFS-UHFFFAOYSA-N oxolane-2-thiol Chemical compound SC1CCCO1 FTHGKDLUXAQKFS-UHFFFAOYSA-N 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical compound OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- YJGRCQPSXYULTO-UHFFFAOYSA-N thiolan-2-ol Chemical compound OC1CCCS1 YJGRCQPSXYULTO-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/24—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one nitrogen and one sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Communicable Diseases (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9906456A FR2793794B1 (fr) | 1999-05-21 | 1999-05-21 | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
| FR99/06456 | 1999-05-21 | ||
| PCT/FR2000/001335 WO2000071543A1 (fr) | 1999-05-21 | 2000-05-18 | Derives de la purine, leur procede de preparation, et compositions pharmaceutiques les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2374714A1 true CA2374714A1 (fr) | 2000-11-30 |
Family
ID=9545846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002374714A Abandoned CA2374714A1 (fr) | 1999-05-21 | 2000-05-18 | Derives de la purine, leur procede de preparation, et compositions pharmaceutiques les contenant |
Country Status (33)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6413974B1 (en) * | 1998-02-26 | 2002-07-02 | Aventis Pharmaceuticals Inc. | 6,9,-disubstituted 2-[trans-(4-aminocyclohexyl) amino] purines |
| US6479487B1 (en) * | 1998-02-26 | 2002-11-12 | Aventis Pharmaceuticals Inc. | 6, 9-disubstituted 2-[trans-(4-aminocyclohexyl)amino] purines |
| US6969720B2 (en) | 1999-03-17 | 2005-11-29 | Amr Technology, Inc. | Biaryl substituted purine derivatives as potent antiproliferative agents |
| EP1377579B1 (en) * | 2000-10-31 | 2009-03-25 | Aventis Pharmaceuticals Inc. | Acyl and sulfonyl derivatives of 6,9-disubstituted 2-(trans-1,4-diaminocyclohexyl)-purines and their use as antiproliferative agents |
| US6861524B2 (en) * | 2000-10-31 | 2005-03-01 | Aventis Pharmaceuticals Inc. | Acyl and sulfonyl derivatives of 6,9-disubstituted 2-(trans-1,4-diaminocyclohexyl)-purines and their use as antiproliferative agents |
| FR2818642B1 (fr) * | 2000-12-26 | 2005-07-15 | Hoechst Marion Roussel Inc | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilistion |
| US6812232B2 (en) | 2001-09-11 | 2004-11-02 | Amr Technology, Inc. | Heterocycle substituted purine derivatives as potent antiproliferative agents |
| US6667311B2 (en) * | 2001-09-11 | 2003-12-23 | Albany Molecular Research, Inc. | Nitrogen substituted biaryl purine derivatives as potent antiproliferative agents |
| CA2463563A1 (en) * | 2001-10-12 | 2003-04-17 | Irm Llc | Kinase inhibitor scaffolds and methods for their preparation |
| AU2003301407B2 (en) * | 2002-10-15 | 2010-04-22 | Irm Llc | Compositions and methods for inducing osteogenesis |
| FR2851248B1 (fr) * | 2003-02-18 | 2005-04-08 | Aventis Pharma Sa | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
| WO2005047524A2 (en) | 2003-11-10 | 2005-05-26 | The Scripps Research Institute | Compositions and methods for inducing cell dedifferentiation |
| AU2005231440B9 (en) * | 2004-04-02 | 2012-02-23 | Dogwood Pharmaceuticals, Inc. | Selective antagonists of A2A adenosine receptors |
| CZ302122B6 (cs) * | 2009-01-28 | 2010-10-20 | Univerzita Palackého v Olomouci | Substituované deriváty 6-(2-aminobenzylamino)purinu, jejich použití jako léciva a prípravky tyto slouceniny obsahující |
| WO2012142029A2 (en) | 2011-04-10 | 2012-10-18 | Florida A&M University | Serms for the treatment of estrogen receptor-mediated disorders |
| WO2015162518A1 (en) | 2014-04-25 | 2015-10-29 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
| EP4086257A1 (en) * | 2016-09-30 | 2022-11-09 | SRI International | Dual clk/cdk1 inhibitors for cancer treatment |
| CZ308029B6 (cs) | 2017-03-20 | 2019-11-06 | Univerzita PalackĂ©ho v Olomouci | 2,6-Disubstituované-9-cyklopentyl-9H-puriny, jejich použití jako léčiva a farmaceutické přípravky |
| AR131380A1 (es) | 2022-12-16 | 2025-03-12 | Astrazeneca Ab | Purinas 2,6,9-trisustituidas |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4008858A1 (de) * | 1990-03-20 | 1991-09-26 | Hoechst Ag | Substituierte purine, verfahren zu ihrer hertellung sowie ihre verwendung als antivirale mittel |
| EP0841810B1 (en) * | 1991-12-05 | 2000-06-21 | Texas Instruments Incorporated | Method to improve a video signal |
| CA2084222C (en) * | 1991-12-06 | 2004-04-06 | David R. Borcherding | Novel trans cyclopentanyl purine analogs useful as immunosuppressants |
| CN1066147C (zh) * | 1995-11-01 | 2001-05-23 | 诺瓦提斯公司 | 嘌呤衍生物及其制备方法 |
| FR2741881B1 (fr) * | 1995-12-01 | 1999-07-30 | Centre Nat Rech Scient | Nouveaux derives de purine possedant notamment des prorietes anti-proliferatives et leurs applications biologiques |
| US6790958B2 (en) * | 1996-08-02 | 2004-09-14 | Robert T. Lum | Purine inhibitors of cyclin dependent kinase 2 & IKBA |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| WO1998016528A1 (en) * | 1996-10-11 | 1998-04-23 | Chiron Corporation | Purine inhibitors of glycogen synthase kinase 3 (gsk3) |
| WO1999007705A1 (en) * | 1997-08-07 | 1999-02-18 | The Regents Of The University Of California | Purine inhibitor of protein kinases, g proteins and polymerases |
| US6413974B1 (en) * | 1998-02-26 | 2002-07-02 | Aventis Pharmaceuticals Inc. | 6,9,-disubstituted 2-[trans-(4-aminocyclohexyl) amino] purines |
| US6479487B1 (en) * | 1998-02-26 | 2002-11-12 | Aventis Pharmaceuticals Inc. | 6, 9-disubstituted 2-[trans-(4-aminocyclohexyl)amino] purines |
| GB9903762D0 (en) * | 1999-02-18 | 1999-04-14 | Novartis Ag | Organic compounds |
| FR2818642B1 (fr) * | 2000-12-26 | 2005-07-15 | Hoechst Marion Roussel Inc | Nouveaux derives de la purine, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilistion |
-
1999
- 1999-05-21 FR FR9906456A patent/FR2793794B1/fr not_active Expired - Fee Related
-
2000
- 2000-05-09 TW TW089108817A patent/TWI284130B/zh not_active IP Right Cessation
- 2000-05-18 PL PL00352293A patent/PL352293A1/xx not_active Application Discontinuation
- 2000-05-18 DZ DZ003166A patent/DZ3166A1/xx active
- 2000-05-18 JP JP2000619799A patent/JP2003500407A/ja not_active Abandoned
- 2000-05-18 AT AT00929625T patent/ATE370951T1/de not_active IP Right Cessation
- 2000-05-18 NZ NZ515556A patent/NZ515556A/en unknown
- 2000-05-18 US US09/979,389 patent/US7122669B1/en not_active Expired - Fee Related
- 2000-05-18 DE DE60036102T patent/DE60036102T2/de not_active Expired - Fee Related
- 2000-05-18 TR TR2001/03349T patent/TR200103349T2/xx unknown
- 2000-05-18 PT PT00929625T patent/PT1183256E/pt unknown
- 2000-05-18 UA UA2001128864A patent/UA68441C2/uk unknown
- 2000-05-18 IL IL14644100A patent/IL146441A0/xx unknown
- 2000-05-18 HU HU0201649A patent/HUP0201649A3/hu unknown
- 2000-05-18 ES ES00929625T patent/ES2290033T3/es not_active Expired - Lifetime
- 2000-05-18 SK SK1672-2001A patent/SK16722001A3/sk unknown
- 2000-05-18 CA CA002374714A patent/CA2374714A1/fr not_active Abandoned
- 2000-05-18 BR BR0011282-8A patent/BR0011282A/pt not_active Application Discontinuation
- 2000-05-18 CN CNB008106509A patent/CN1298719C/zh not_active Expired - Fee Related
- 2000-05-18 AU AU47645/00A patent/AU4764500A/en not_active Abandoned
- 2000-05-18 CZ CZ20014163A patent/CZ20014163A3/cs unknown
- 2000-05-18 EA EA200101224A patent/EA005072B1/ru not_active IP Right Cessation
- 2000-05-18 AP APAP/P/2001/002355A patent/AP1477A/en active
- 2000-05-18 YU YU86601A patent/YU86601A/sh unknown
- 2000-05-18 MX MXPA01011834A patent/MXPA01011834A/es active IP Right Grant
- 2000-05-18 DK DK00929625T patent/DK1183256T3/da active
- 2000-05-18 WO PCT/FR2000/001335 patent/WO2000071543A1/fr not_active Ceased
- 2000-05-18 EP EP00929625A patent/EP1183256B1/fr not_active Expired - Lifetime
- 2000-05-18 KR KR1020017014800A patent/KR100707895B1/ko not_active Expired - Fee Related
- 2000-05-19 AR ARP000102428A patent/AR035317A1/es not_active Application Discontinuation
-
2001
- 2001-11-15 MA MA26410A patent/MA26791A1/fr unknown
- 2001-11-20 NO NO20015659A patent/NO20015659L/no not_active Application Discontinuation
- 2001-11-21 ZA ZA200109602A patent/ZA200109602B/xx unknown
-
2004
- 2004-12-07 US US11/006,013 patent/US7208598B2/en not_active Expired - Fee Related
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