CA1266469A - Guanine derivatives - Google Patents
Guanine derivativesInfo
- Publication number
- CA1266469A CA1266469A CA000475232A CA475232A CA1266469A CA 1266469 A CA1266469 A CA 1266469A CA 000475232 A CA000475232 A CA 000475232A CA 475232 A CA475232 A CA 475232A CA 1266469 A CA1266469 A CA 1266469A
- Authority
- CA
- Canada
- Prior art keywords
- guanine
- methyl
- pharmaceutically acceptable
- compound
- general formula
- 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.)
- Expired - Fee Related
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 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 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- VDNKYOQGCLFAQH-UHFFFAOYSA-N 2-amino-8-bromo-9-[(4-methoxyphenyl)methyl]-3h-purin-6-one Chemical compound C1=CC(OC)=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1Br VDNKYOQGCLFAQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- IXVSPCWAUAOFQA-UHFFFAOYSA-N 2,8-diamino-9-[(2-methoxyphenyl)methyl]-3h-purin-6-one Chemical compound COC1=CC=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1N IXVSPCWAUAOFQA-UHFFFAOYSA-N 0.000 claims 1
- VLRNWDWLYQPKER-UHFFFAOYSA-N 2,8-diamino-9-[(3-methoxyphenyl)methyl]-3h-purin-6-one Chemical compound COC1=CC=CC(CN2C3=C(C(NC(N)=N3)=O)N=C2N)=C1 VLRNWDWLYQPKER-UHFFFAOYSA-N 0.000 claims 1
- FUMNOBYTYRYDCK-UHFFFAOYSA-N 2,8-diamino-9-[(4-chlorophenyl)methyl]-3h-purin-6-one Chemical compound NC1=NC(C(NC(N)=N2)=O)=C2N1CC1=CC=C(Cl)C=C1 FUMNOBYTYRYDCK-UHFFFAOYSA-N 0.000 claims 1
- REODRRYRLFQGDE-UHFFFAOYSA-N 2,8-diamino-9-[(4-fluorophenyl)methyl]-3h-purin-6-one Chemical compound NC1=NC(C(NC(N)=N2)=O)=C2N1CC1=CC=C(F)C=C1 REODRRYRLFQGDE-UHFFFAOYSA-N 0.000 claims 1
- YGWXNYYDIYDXRK-UHFFFAOYSA-N 2,8-diamino-9-[(4-methoxyphenyl)methyl]-3h-purin-6-one Chemical compound C1=CC(OC)=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1N YGWXNYYDIYDXRK-UHFFFAOYSA-N 0.000 claims 1
- GLDXYBAHPFUJBR-UHFFFAOYSA-N 2,8-diamino-9-[(4-methylphenyl)methyl]-3h-purin-6-one Chemical compound C1=CC(C)=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1N GLDXYBAHPFUJBR-UHFFFAOYSA-N 0.000 claims 1
- QQNCNKCZYOKDDJ-UHFFFAOYSA-N 2,8-diamino-9-[[2-(dimethylamino)phenyl]methyl]-3h-purin-6-one Chemical compound CN(C)C1=CC=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1N QQNCNKCZYOKDDJ-UHFFFAOYSA-N 0.000 claims 1
- PEERHUDPSLIVCB-UHFFFAOYSA-N 2,8-diamino-9-[[4-(dimethylamino)phenyl]methyl]-3h-purin-6-one Chemical compound C1=CC(N(C)C)=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1N PEERHUDPSLIVCB-UHFFFAOYSA-N 0.000 claims 1
- GUXUEGCCFPFNRR-UHFFFAOYSA-N 2-amino-8-bromo-9-[(2-methoxyphenyl)methyl]-3h-purin-6-one Chemical compound COC1=CC=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1Br GUXUEGCCFPFNRR-UHFFFAOYSA-N 0.000 claims 1
- BUWJLWZZOMQVTD-UHFFFAOYSA-N 2-amino-8-bromo-9-[(3,4-dichlorophenyl)methyl]-3h-purin-6-one Chemical compound BrC1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=C(Cl)C(Cl)=C1 BUWJLWZZOMQVTD-UHFFFAOYSA-N 0.000 claims 1
- BZKAMORAXJKSCO-UHFFFAOYSA-N 2-amino-8-bromo-9-[(4-chlorophenyl)methyl]-3h-purin-6-one Chemical compound BrC1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=C(Cl)C=C1 BZKAMORAXJKSCO-UHFFFAOYSA-N 0.000 claims 1
- APJLYGNABKPBCT-UHFFFAOYSA-N 2-amino-8-bromo-9-[(4-fluorophenyl)methyl]-3h-purin-6-one Chemical compound BrC1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=C(F)C=C1 APJLYGNABKPBCT-UHFFFAOYSA-N 0.000 claims 1
- GMPNMQXKZUKIDZ-UHFFFAOYSA-N 2-amino-8-bromo-9-[(4-methylphenyl)methyl]-3h-purin-6-one Chemical compound C1=CC(C)=CC=C1CN1C(N=C(N)NC2=O)=C2N=C1Br GMPNMQXKZUKIDZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011260 aqueous acid Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 9
- -1 particularly Chemical class 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 description 2
- YKBGVTZYEHREMT-UHFFFAOYSA-N 2'-deoxyguanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1CC(O)C(CO)O1 YKBGVTZYEHREMT-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- VGONTNSXDCQUGY-UHFFFAOYSA-N desoxyinosine Natural products C1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 VGONTNSXDCQUGY-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- UTTPUMOOQSNOHH-UHFFFAOYSA-N 2-amino-6-chloro-5-nitro-1h-pyrimidin-4-one Chemical compound NC1=NC(=O)C([N+]([O-])=O)=C(Cl)N1 UTTPUMOOQSNOHH-UHFFFAOYSA-N 0.000 description 1
- FBHSUDNNMWXKFW-UHFFFAOYSA-N 2-amino-9-[(4-fluorophenyl)methyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1CC1=CC=C(F)C=C1 FBHSUDNNMWXKFW-UHFFFAOYSA-N 0.000 description 1
- SMHBTBYHDWNJEG-UHFFFAOYSA-N 2-amino-9-benzyl-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1CC1=CC=CC=C1 SMHBTBYHDWNJEG-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 1
- YJLDARBFSHRLAI-UHFFFAOYSA-N 8-amino-2-[(2-methoxyphenyl)methylamino]-3,7-dihydropurin-6-one Chemical compound COC1=CC=CC=C1CNC(N1)=NC(=O)C2=C1N=C(N)N2 YJLDARBFSHRLAI-UHFFFAOYSA-N 0.000 description 1
- 150000005021 8-aminopurines Chemical class 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101001090860 Homo sapiens Myeloblastin Proteins 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
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- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 102100034681 Myeloblastin Human genes 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 102000009097 Phosphorylases Human genes 0.000 description 1
- 108010073135 Phosphorylases Proteins 0.000 description 1
- 208000035208 Ring chromosome 20 syndrome Diseases 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000287433 Turdus Species 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- BUXYRJPVMAZQSY-UHFFFAOYSA-N benzene;methanamine Chemical class NC.C1=CC=CC=C1 BUXYRJPVMAZQSY-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000013882 gravy Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000007365 immunoregulation Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229960003786 inosine Drugs 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical class COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 101150067766 mpl2 gene Proteins 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59306384A | 1984-03-26 | 1984-03-26 | |
| US698,805 | 1985-02-11 | ||
| US06/698,805 US4748177A (en) | 1984-03-26 | 1985-02-11 | Guanine derivatives |
| US593,063 | 1990-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1266469A true CA1266469A (en) | 1990-03-06 |
Family
ID=27081607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000475232A Expired - Fee Related CA1266469A (en) | 1984-03-26 | 1985-02-27 | Guanine derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4748177A (en, 2012) |
| EP (1) | EP0156559B1 (en, 2012) |
| AU (1) | AU580039B2 (en, 2012) |
| CA (1) | CA1266469A (en, 2012) |
| DE (1) | DE3571985D1 (en, 2012) |
| DK (1) | DK125485A (en, 2012) |
| ES (1) | ES8702911A1 (en, 2012) |
| GR (1) | GR850728B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4923872A (en) * | 1986-08-26 | 1990-05-08 | Warner-Lambert Co. | Analogues of pyrrolo[3,2d]pyrimidin-4-ones |
| CA1294960C (en) * | 1986-10-24 | 1992-01-28 | Thomas C. Malone | 7-deazaguanines as immunomodulators |
| US4921858A (en) * | 1986-10-24 | 1990-05-01 | Warner-Lambert Company | 7-deazaguanines as immunomodulators |
| EP0363320A3 (de) * | 1988-10-06 | 1991-11-21 | Ciba-Geigy Ag | Substituierte 9H-Purine |
| CA2150609C (en) * | 1994-06-01 | 1998-12-08 | Mikiro Yanaka | Pyrimidine derivatives and pharmaceutical composition |
| AU695032B2 (en) * | 1994-10-05 | 1998-08-06 | Darwin Discovery Limited | Purine and guanine compounds as inhibitors of PNP |
| GB9520364D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compouundds |
| GB9520363D0 (en) * | 1995-10-05 | 1995-12-06 | Chiroscience Ltd | Compounds |
| GB0014861D0 (en) * | 2000-06-16 | 2000-08-09 | Pharmacia & Upjohn Spa | Novel telomerase inhibitors |
| US20070129334A1 (en) * | 2001-10-30 | 2007-06-07 | Conforma Therapeutics Corporation | Orally Active Purine-Based Inhibitors of Heat Shock Protein 90 |
| EP1440072A4 (en) * | 2001-10-30 | 2005-02-02 | Conforma Therapeutic Corp | PURINE ANALOGS HAVING HSP90 INHIBITORY ACTIVITY |
| CA2539548A1 (en) | 2003-09-18 | 2005-03-31 | Conforma Therapeutics Corporation | Novel heterocyclic compounds as hsp90-inhibitors |
| GB0401645D0 (en) * | 2004-01-26 | 2004-02-25 | Cytec Tech Corp | Stabilizable preform precursors and stabilized preforms for composite materials and processes for stabilizing and debulking preforms |
| CA2602257A1 (en) * | 2005-03-30 | 2006-10-05 | Conforma Therapeutics Corporation | Alkynyl pyrrolopyrimidines and related analogs as hsp90-inhibitors |
| US20070105874A1 (en) * | 2005-09-23 | 2007-05-10 | Conforma Therapeutics Corporation | Anti-Tumor Methods Using Multi Drug Resistance Independent Synthetic HSP90 Inhibitors |
| WO2013066729A1 (en) | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Aminopyrimidinones as interleukin receptor-associated kinase inhibitors |
| US11512084B2 (en) | 2017-07-10 | 2022-11-29 | Tohoku University | Degradation agent using autophagic mechanism of damaged mitochondria |
| AU2023403422A1 (en) * | 2022-11-30 | 2025-07-17 | Regeneron Pharmaceuticals, Inc. | Tlr7 agonists and antibody-drug-conjugates thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900474A (en) * | 1973-05-14 | 1975-08-19 | Kendall & Co | Trifluoroalkyl, fluorobenzyl, pentafluorobenzyl, fluorobenzenesulfonyl, and pentafluorobenzenesulfonyl theophyllines |
| US3930005A (en) * | 1973-06-15 | 1975-12-30 | Squibb & Sons Inc | Antiinflammatory agents and their use |
-
1985
- 1985-02-11 US US06/698,805 patent/US4748177A/en not_active Expired - Fee Related
- 1985-02-27 CA CA000475232A patent/CA1266469A/en not_active Expired - Fee Related
- 1985-03-07 DE DE8585301561T patent/DE3571985D1/de not_active Expired
- 1985-03-07 EP EP85301561A patent/EP0156559B1/en not_active Expired
- 1985-03-20 DK DK125485A patent/DK125485A/da not_active Application Discontinuation
- 1985-03-21 AU AU40219/85A patent/AU580039B2/en not_active Ceased
- 1985-03-21 GR GR850728A patent/GR850728B/el unknown
- 1985-03-25 ES ES541552A patent/ES8702911A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4748177A (en) | 1988-05-31 |
| EP0156559B1 (en) | 1989-08-02 |
| DE3571985D1 (en) | 1989-09-07 |
| AU580039B2 (en) | 1988-12-22 |
| DK125485A (da) | 1985-09-27 |
| GR850728B (en, 2012) | 1985-07-19 |
| AU4021985A (en) | 1985-10-03 |
| ES8702911A1 (es) | 1987-01-16 |
| DK125485D0 (da) | 1985-03-20 |
| EP0156559A3 (en) | 1986-10-08 |
| EP0156559A2 (en) | 1985-10-02 |
| ES541552A0 (es) | 1987-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |