MXPA01011834A - Derivados de purina, metodo de preparacion y composiciones farmaceuticas que los contienen. - Google Patents
Derivados de purina, metodo de preparacion y composiciones farmaceuticas que los contienen.Info
- Publication number
- MXPA01011834A MXPA01011834A MXPA01011834A MXPA01011834A MXPA01011834A MX PA01011834 A MXPA01011834 A MX PA01011834A MX PA01011834 A MXPA01011834 A MX PA01011834A MX PA01011834 A MXPA01011834 A MX PA01011834A MX PA01011834 A MXPA01011834 A MX PA01011834A
- Authority
- MX
- Mexico
- Prior art keywords
- radical
- formula
- amino
- cyclopentyl
- alkyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 9
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title claims description 7
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
- -1 -CH2- heterocyclic Chemical group 0.000 claims abstract description 364
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 67
- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 31
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 239000001301 oxygen Substances 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229940079593 drug Drugs 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 101100294106 Caenorhabditis elegans nhr-3 gene Chemical group 0.000 claims abstract description 4
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical group 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 241
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 162
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 151
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 148
- 150000003254 radicals Chemical class 0.000 claims description 128
- 125000004432 carbon atom Chemical group C* 0.000 claims description 121
- 238000000034 method Methods 0.000 claims description 88
- 229910021529 ammonia Inorganic materials 0.000 claims description 80
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 66
- 229920006395 saturated elastomer Polymers 0.000 claims description 50
- 125000000524 functional group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 30
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 150000007522 mineralic acids Chemical class 0.000 claims description 17
- 150000007524 organic acids Chemical class 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 150000007530 organic bases Chemical class 0.000 claims description 16
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 150000007529 inorganic bases Chemical class 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- 230000009466 transformation Effects 0.000 claims description 10
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 150000005840 aryl radicals Chemical class 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000003158 alcohol group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- 150000002148 esters Chemical group 0.000 claims description 6
- 150000003212 purines Chemical class 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 238000002512 chemotherapy Methods 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
- 208000030852 Parasitic disease Diseases 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000003080 antimitotic agent Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002576 ketones Chemical group 0.000 claims description 4
- 230000009223 neuronal apoptosis Effects 0.000 claims description 4
- 150000003462 sulfoxides Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000002555 anti-neurodegenerative effect Effects 0.000 claims description 3
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 150000002923 oximes Chemical group 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GQLASWZZHAIYKC-HEOZJBRKSA-N Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(N)cc2)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccc(N)cc2)c2ncn(C3CCCC3)c2n1 GQLASWZZHAIYKC-HEOZJBRKSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000006501 nitrophenyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract 6
- 239000005864 Sulphur Substances 0.000 abstract 2
- 239000000047 product Substances 0.000 description 576
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 450
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 399
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 315
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 309
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 255
- 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 190
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 181
- 239000000377 silicon dioxide Substances 0.000 description 126
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 111
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 106
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 96
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 88
- 239000013078 crystal Substances 0.000 description 87
- 239000002904 solvent Substances 0.000 description 78
- 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 71
- 238000004587 chromatography analysis Methods 0.000 description 71
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 65
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 60
- 238000000746 purification Methods 0.000 description 60
- 230000002829 reductive effect Effects 0.000 description 53
- 239000000243 solution Substances 0.000 description 51
- 238000003756 stirring Methods 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000003480 eluent Substances 0.000 description 32
- 239000011780 sodium chloride Substances 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 27
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 21
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 21
- 229910000024 caesium carbonate Inorganic materials 0.000 description 21
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 19
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000009471 action Effects 0.000 description 15
- 235000011114 ammonium hydroxide Nutrition 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 239000000908 ammonium hydroxide Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 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
- 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
- 238000010438 heat treatment Methods 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- GIZCKBSSWNIUMZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC=C(CN)C=C1 GIZCKBSSWNIUMZ-UHFFFAOYSA-N 0.000 description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 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
- 108091000080 Phosphotransferase Proteins 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 102000020233 phosphotransferase Human genes 0.000 description 5
- 238000005185 salting out Methods 0.000 description 5
- LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- XUJFOSLZQITUOI-UHFFFAOYSA-N 4-(trifluoromethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)F)C=C1 XUJFOSLZQITUOI-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 229910017974 NH40H Inorganic materials 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000022131 cell cycle Effects 0.000 description 4
- 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 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- FEWJPZIEWOKRBE-XIXRPRMCSA-L meso-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-XIXRPRMCSA-L 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- XDPCNPCKDGQBAN-UHFFFAOYSA-N 3-hydroxytetrahydrofuran Chemical compound OC1CCOC1 XDPCNPCKDGQBAN-UHFFFAOYSA-N 0.000 description 3
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 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
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000001174 sulfone 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
- 239000003826 tablet Substances 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
- DQARDWKWPIRJEH-UHFFFAOYSA-N tert-butyl n-(4-hydroxycyclohexyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(O)CC1 DQARDWKWPIRJEH-UHFFFAOYSA-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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- BJYXNFYVCZIXQC-UHFFFAOYSA-N thiolan-3-ol Chemical compound OC1CCSC1 BJYXNFYVCZIXQC-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
- 230000000699 topical effect Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (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)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| 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 |
| 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 |
|---|---|
| MXPA01011834A true MXPA01011834A (es) | 2002-04-17 |
Family
ID=9545846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA01011834A MXPA01011834A (es) | 1999-05-21 | 2000-05-18 | Derivados de purina, metodo de preparacion y composiciones farmaceuticas que los contienen. |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US7122669B1 (https=) |
| EP (1) | EP1183256B1 (https=) |
| JP (1) | JP2003500407A (https=) |
| KR (1) | KR100707895B1 (https=) |
| CN (1) | CN1298719C (https=) |
| AP (1) | AP1477A (https=) |
| AR (1) | AR035317A1 (https=) |
| AT (1) | ATE370951T1 (https=) |
| AU (1) | AU4764500A (https=) |
| BR (1) | BR0011282A (https=) |
| CA (1) | CA2374714A1 (https=) |
| CZ (1) | CZ20014163A3 (https=) |
| DE (1) | DE60036102T2 (https=) |
| DK (1) | DK1183256T3 (https=) |
| DZ (1) | DZ3166A1 (https=) |
| EA (1) | EA005072B1 (https=) |
| ES (1) | ES2290033T3 (https=) |
| FR (1) | FR2793794B1 (https=) |
| HU (1) | HUP0201649A3 (https=) |
| IL (1) | IL146441A0 (https=) |
| MA (1) | MA26791A1 (https=) |
| MX (1) | MXPA01011834A (https=) |
| NO (1) | NO20015659L (https=) |
| NZ (1) | NZ515556A (https=) |
| PL (1) | PL352293A1 (https=) |
| PT (1) | PT1183256E (https=) |
| SK (1) | SK16722001A3 (https=) |
| TR (1) | TR200103349T2 (https=) |
| TW (1) | TWI284130B (https=) |
| UA (1) | UA68441C2 (https=) |
| WO (1) | WO2000071543A1 (https=) |
| YU (1) | YU86601A (https=) |
| ZA (1) | ZA200109602B (https=) |
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 |
| AU3938802A (en) * | 2000-10-31 | 2002-06-03 | Aventis Pharma 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 |
| EP1578722A4 (en) * | 2001-10-12 | 2006-09-06 | Irm Llc | KINASEINHIBITOR SCAFFOLD AND METHOD FOR THE PRODUCTION THEREOF |
| WO2004035132A2 (en) * | 2002-10-15 | 2004-04-29 | 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 |
| US7951592B2 (en) * | 2003-11-10 | 2011-05-31 | The Scripps Research Institute | Compositions and methods for inducing cell dedifferentiation |
| CA2563123A1 (en) * | 2004-04-02 | 2005-10-20 | Adenosine Therapeutics, Llc | 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 |
| EP3134405B1 (en) | 2014-04-25 | 2019-08-28 | Pfizer Inc | Heteroaromatic compounds and their use as dopamine d1 ligands |
| CN114149432B (zh) * | 2016-09-30 | 2024-07-05 | 斯坦福国际研究院 | 用于癌症治疗的双重clk/cdk1抑制剂 |
| 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 |
| JP2026500305A (ja) | 2022-12-16 | 2026-01-06 | アストラゼネカ・アクチエボラーグ | ２，６，９三置換プリン |
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 |
| BR9611157A (pt) * | 1995-11-01 | 1999-03-30 | Novartis Ag | Derivados de purina e processos para sua preparação |
| 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 |
| US5866702A (en) * | 1996-08-02 | 1999-02-02 | Cv Therapeutics, Incorporation | Purine inhibitors of cyclin dependent kinase 2 |
| US6790958B2 (en) * | 1996-08-02 | 2004-09-14 | Robert T. Lum | Purine inhibitors of cyclin dependent kinase 2 & IKBA |
| AU4920397A (en) * | 1996-10-11 | 1998-05-11 | Chiron Corporation | Purine inhibitors of glycogen synthase kinase 3 (gsk3) |
| CA2297967A1 (en) * | 1997-08-07 | 1999-02-18 | The Regents Of The University Of California | Purine inhibitor of protein kinases, g proteins and polymerases |
| US6479487B1 (en) * | 1998-02-26 | 2002-11-12 | Aventis Pharmaceuticals Inc. | 6, 9-disubstituted 2-[trans-(4-aminocyclohexyl)amino] purines |
| US6413974B1 (en) * | 1998-02-26 | 2002-07-02 | 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 US US09/979,389 patent/US7122669B1/en not_active Expired - Fee Related
- 2000-05-18 EA EA200101224A patent/EA005072B1/ru not_active IP Right Cessation
- 2000-05-18 PT PT00929625T patent/PT1183256E/pt unknown
- 2000-05-18 DK DK00929625T patent/DK1183256T3/da active
- 2000-05-18 SK SK1672-2001A patent/SK16722001A3/sk unknown
- 2000-05-18 TR TR2001/03349T patent/TR200103349T2/xx unknown
- 2000-05-18 HU HU0201649A patent/HUP0201649A3/hu unknown
- 2000-05-18 JP JP2000619799A patent/JP2003500407A/ja not_active Abandoned
- 2000-05-18 PL PL00352293A patent/PL352293A1/xx not_active Application Discontinuation
- 2000-05-18 ES ES00929625T patent/ES2290033T3/es not_active Expired - Lifetime
- 2000-05-18 NZ NZ515556A patent/NZ515556A/en unknown
- 2000-05-18 CZ CZ20014163A patent/CZ20014163A3/cs unknown
- 2000-05-18 DZ DZ003166A patent/DZ3166A1/xx active
- 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 YU YU86601A patent/YU86601A/sh unknown
- 2000-05-18 CA CA002374714A patent/CA2374714A1/fr not_active Abandoned
- 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 AT AT00929625T patent/ATE370951T1/de not_active IP Right Cessation
- 2000-05-18 UA UA2001128864A patent/UA68441C2/uk unknown
- 2000-05-18 AP APAP/P/2001/002355A patent/AP1477A/en active
- 2000-05-18 KR KR1020017014800A patent/KR100707895B1/ko not_active Expired - Fee Related
- 2000-05-18 MX MXPA01011834A patent/MXPA01011834A/es active IP Right Grant
- 2000-05-18 BR BR0011282-8A patent/BR0011282A/pt not_active Application Discontinuation
- 2000-05-18 DE DE60036102T patent/DE60036102T2/de not_active Expired - Fee Related
- 2000-05-18 IL IL14644100A patent/IL146441A0/xx unknown
- 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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