RU2080322C1 - Производные полициклического гуанина - Google Patents
Производные полициклического гуанина Download PDFInfo
- Publication number
- RU2080322C1 RU2080322C1 RU9192016466A RU92016466A RU2080322C1 RU 2080322 C1 RU2080322 C1 RU 2080322C1 RU 9192016466 A RU9192016466 A RU 9192016466A RU 92016466 A RU92016466 A RU 92016466A RU 2080322 C1 RU2080322 C1 RU 2080322C1
- Authority
- RU
- Russia
- Prior art keywords
- phenylmethyl
- purin
- methyl
- imidazo
- dimethyl
- Prior art date
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- -1 Polycyclic guanine derivatives Chemical class 0.000 title claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 229910052717 sulfur Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 239000011593 sulfur Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 22
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 7
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 3
- 125000003367 polycyclic group Chemical group 0.000 abstract description 3
- 230000004648 relaxation of smooth muscle Effects 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 abstract 1
- 206010021118 Hypotonia Diseases 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000036640 muscle relaxation Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 193
- 239000007787 solid Substances 0.000 description 125
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000460 chlorine Substances 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 53
- 238000010265 fast atom bombardment Methods 0.000 description 48
- 239000000203 mixture Substances 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000006260 foam Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000003480 eluent Substances 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 14
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 150000001414 amino alcohols Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 0 CC(c1c(C(C2*I)=*)[n](*)c(*)c1)C2=C Chemical compound CC(c1c(C(C2*I)=*)[n](*)c(*)c1)C2=C 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 9
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- OSXKHFTZRHDUJN-UHFFFAOYSA-N N(2),3-ethenoguanine Chemical compound O=C1NC2=NC=CN2C2=C1NC=N2 OSXKHFTZRHDUJN-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 230000036772 blood pressure Effects 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 150000003230 pyrimidines Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- JFFOUICIRBXFRC-RFZPGFLSSA-N (1r,2r)-2-aminocyclopentan-1-ol Chemical compound N[C@@H]1CCC[C@H]1O JFFOUICIRBXFRC-RFZPGFLSSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- OCXGTPDKNBIOTF-UHFFFAOYSA-N dibromo(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Br)(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 OCXGTPDKNBIOTF-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- 241000283690 Bos taurus Species 0.000 description 4
- 206010006482 Bronchospasm Diseases 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000007885 bronchoconstriction Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 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 4
- ZGLYVAGJXIRECZ-UHFFFAOYSA-N 1,7-dibenzyl-2-chloropurin-6-one Chemical compound C1=2C(=O)N(CC=3C=CC=CC=3)C(Cl)=NC=2N=CN1CC1=CC=CC=C1 ZGLYVAGJXIRECZ-UHFFFAOYSA-N 0.000 description 3
- IAUXHRVJAVWRKD-HUUCEWRRSA-N 7-benzyl-2-[[(1r,2r)-2-hydroxycyclopentyl]amino]-1,8-dimethylpurin-6-one Chemical compound CN1C(=O)C=2N(CC=3C=CC=CC=3)C(C)=NC=2N=C1N[C@@H]1CCC[C@H]1O IAUXHRVJAVWRKD-HUUCEWRRSA-N 0.000 description 3
- UAXKLFOSJJRTTP-UHFFFAOYSA-N 7-benzyl-2-chloro-1,8-dimethylpurin-6-one Chemical compound CC1=NC=2N=C(Cl)N(C)C(=O)C=2N1CC1=CC=CC=C1 UAXKLFOSJJRTTP-UHFFFAOYSA-N 0.000 description 3
- FHJHVHCVYRREAY-UHFFFAOYSA-N 7-benzyl-2-chloro-1-methylpurin-6-one Chemical compound C1=2C(=O)N(C)C(Cl)=NC=2N=CN1CC1=CC=CC=C1 FHJHVHCVYRREAY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000001506 calcium phosphate Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010849 ion bombardment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 150000003212 purines Chemical class 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MDJOUBKGOCDAAP-NHCUHLMSSA-N 1,7-dibenzyl-2-[[(1r,2r)-2-hydroxycyclohexyl]amino]purin-6-one Chemical compound O[C@@H]1CCCC[C@H]1NC(N(C1=O)CC=2C=CC=CC=2)=NC2=C1N(CC=1C=CC=CC=1)C=N2 MDJOUBKGOCDAAP-NHCUHLMSSA-N 0.000 description 2
- UYYWPCLRSSPZHM-UHFFFAOYSA-N 1,7-dibenzyl-3h-purine-2,6-dione Chemical compound C1=2C(=O)N(CC=3C=CC=CC=3)C(=O)NC=2N=CN1CC1=CC=CC=C1 UYYWPCLRSSPZHM-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical class ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- MCOUPKWEDYTSHY-UHFFFAOYSA-N 2-bromo-7-cyclopentyl-1-methylpurin-6-one Chemical compound C1=2C(=O)N(C)C(Br)=NC=2N=CN1C1CCCC1 MCOUPKWEDYTSHY-UHFFFAOYSA-N 0.000 description 2
- UVXZZIOIPMBVCG-UHFFFAOYSA-N 2-bromo-7-cyclopentyl-3h-purin-6-one Chemical compound C1=2C(=O)NC(Br)=NC=2N=CN1C1CCCC1 UVXZZIOIPMBVCG-UHFFFAOYSA-N 0.000 description 2
- XWLDBUWSUISBKX-UHFFFAOYSA-N 2-bromo-9-cyclopentyl-1-methylpurin-6-one Chemical compound C1=NC=2C(=O)N(C)C(Br)=NC=2N1C1CCCC1 XWLDBUWSUISBKX-UHFFFAOYSA-N 0.000 description 2
- XKVATRYEPITAPH-UHFFFAOYSA-N 2-chloro-6-phenylmethoxy-7h-purine Chemical compound C=12NC=NC2=NC(Cl)=NC=1OCC1=CC=CC=C1 XKVATRYEPITAPH-UHFFFAOYSA-N 0.000 description 2
- YGLUIFSARZOYNS-UHFFFAOYSA-N 2-chloro-7-cyclopentyl-1-methylpurin-6-one Chemical compound C1=2C(=O)N(C)C(Cl)=NC=2N=CN1C1CCCC1 YGLUIFSARZOYNS-UHFFFAOYSA-N 0.000 description 2
- GNUQTXZOZWTAAE-UHFFFAOYSA-N 2-chloro-7-cyclopentyl-3h-purin-6-one Chemical compound C1=2C(=O)NC(Cl)=NC=2N=CN1C1CCCC1 GNUQTXZOZWTAAE-UHFFFAOYSA-N 0.000 description 2
- FBDVCEJREATIMN-UHFFFAOYSA-N 2-chloro-7-cyclopentyl-6-phenylmethoxypurine Chemical compound C=12N(C3CCCC3)C=NC2=NC(Cl)=NC=1OCC1=CC=CC=C1 FBDVCEJREATIMN-UHFFFAOYSA-N 0.000 description 2
- JBMBVWROWJGFMG-UHFFFAOYSA-N 2-chloro-7h-purine Chemical compound ClC1=NC=C2NC=NC2=N1 JBMBVWROWJGFMG-UHFFFAOYSA-N 0.000 description 2
- POXQKFWAIFQDFD-UHFFFAOYSA-N 2-chloro-9-cyclopentyl-1-methylpurin-6-one Chemical compound C1=NC=2C(=O)N(C)C(Cl)=NC=2N1C1CCCC1 POXQKFWAIFQDFD-UHFFFAOYSA-N 0.000 description 2
- YZOGBMRPJDMCHI-UHFFFAOYSA-N 2-chloro-9-cyclopentyl-6-phenylmethoxypurine Chemical compound C=12N=CN(C3CCCC3)C2=NC(Cl)=NC=1OCC1=CC=CC=C1 YZOGBMRPJDMCHI-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- JCGJSBVUVFPNHB-UHFFFAOYSA-N 6-amino-3-benzyl-1h-pyrimidine-2,4-dione Chemical compound O=C1NC(N)=CC(=O)N1CC1=CC=CC=C1 JCGJSBVUVFPNHB-UHFFFAOYSA-N 0.000 description 2
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- XOVSRHHCHKUFKM-UHFFFAOYSA-N s-methylthiohydroxylamine Chemical compound CSN XOVSRHHCHKUFKM-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Filtering Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54156890A | 1990-06-21 | 1990-06-21 | |
| US541.568 | 1990-06-21 | ||
| US541568 | 1990-06-21 | ||
| PCT/US1991/004154 WO1991019717A1 (en) | 1990-06-21 | 1991-06-20 | Polycyclic guanine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU92016466A RU92016466A (ru) | 1995-05-20 |
| RU2080322C1 true RU2080322C1 (ru) | 1997-05-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU9192016466A RU2080322C1 (ru) | 1990-06-21 | 1991-06-20 | Производные полициклического гуанина |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5393755A (enExample) |
| EP (1) | EP0538332B1 (enExample) |
| JP (1) | JPH0747589B2 (enExample) |
| KR (1) | KR960004532B1 (enExample) |
| AT (1) | ATE155786T1 (enExample) |
| AU (1) | AU651607B2 (enExample) |
| CA (1) | CA2085733C (enExample) |
| CZ (1) | CZ281920B6 (enExample) |
| DE (1) | DE69126980T2 (enExample) |
| FI (1) | FI925731A0 (enExample) |
| HU (1) | HUT65623A (enExample) |
| IE (1) | IE912126A1 (enExample) |
| IL (1) | IL98559A0 (enExample) |
| NO (1) | NO924940L (enExample) |
| NZ (1) | NZ238609A (enExample) |
| OA (1) | OA09723A (enExample) |
| PL (1) | PL169481B1 (enExample) |
| RU (1) | RU2080322C1 (enExample) |
| TW (1) | TW197441B (enExample) |
| WO (1) | WO1991019717A1 (enExample) |
| ZA (1) | ZA914727B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2258705C2 (ru) * | 1999-07-27 | 2005-08-20 | Алмираль Продесфарма С.А. | ПРОИЗВОДНЫЕ 8-ФЕНИЛ-6,9-ДИГИДРО[1,2,4]-ТРИАЗОЛО[3,4-i]ПУРИН-5-ОНА, СПОСОБЫ ИХ ПОЛУЧЕНИЯ, ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ЛЕЧЕНИЯ |
| RU2436777C2 (ru) * | 2005-11-09 | 2011-12-20 | Тосох корпорейшн | Нуклеиновое основание, имеющее перфторалкильную группу и способ его получения |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI953981A7 (fi) * | 1993-02-26 | 1995-08-24 | Schering Corp | 2-Bentsyyli-polysykliset guaniinijohdannaiset ja menetelmä niiden valmistamiseksi |
| US5929046A (en) * | 1994-06-08 | 1999-07-27 | Cancer Research Campaign Technology Limited | Pyrimidine and purine derivatives and their use in treating tumour cells |
| US5661153A (en) * | 1994-07-19 | 1997-08-26 | Japan Energy Corporation | 1-arylpyrimidine derivatives and pharmaceutical use thereof |
| ZA969888B (en) * | 1995-11-28 | 1997-05-26 | Schering Corp | 2'-[[4'-halo-[1,1-biphenyl]-4-yl]methyl]-5'-methyl-spiro[cyclopentane-1,7'(8'H)-[3H]imidazo[2,1-b]purin]-4'(5'H)-ones |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2258705C2 (ru) * | 1999-07-27 | 2005-08-20 | Алмираль Продесфарма С.А. | ПРОИЗВОДНЫЕ 8-ФЕНИЛ-6,9-ДИГИДРО[1,2,4]-ТРИАЗОЛО[3,4-i]ПУРИН-5-ОНА, СПОСОБЫ ИХ ПОЛУЧЕНИЯ, ПРОМЕЖУТОЧНЫЕ СОЕДИНЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ЛЕЧЕНИЯ |
| RU2436777C2 (ru) * | 2005-11-09 | 2011-12-20 | Тосох корпорейшн | Нуклеиновое основание, имеющее перфторалкильную группу и способ его получения |
Also Published As
| Publication number | Publication date |
|---|---|
| NO924940D0 (no) | 1992-12-18 |
| ZA914727B (en) | 1992-03-25 |
| EP0538332B1 (en) | 1997-07-23 |
| JPH05508647A (ja) | 1993-12-02 |
| IL98559A0 (en) | 1992-07-15 |
| FI925731A7 (fi) | 1992-12-17 |
| AU651607B2 (en) | 1994-07-28 |
| NZ238609A (en) | 1993-12-23 |
| HUT65623A (en) | 1994-07-28 |
| AU8199291A (en) | 1992-01-07 |
| DE69126980T2 (de) | 1998-01-08 |
| CA2085733C (en) | 1996-03-05 |
| HU9204032D0 (en) | 1993-03-29 |
| ATE155786T1 (de) | 1997-08-15 |
| IE912126A1 (en) | 1992-01-01 |
| PL169481B1 (pl) | 1996-07-31 |
| TW197441B (enExample) | 1993-01-01 |
| CA2085733A1 (en) | 1991-12-22 |
| JPH0747589B2 (ja) | 1995-05-24 |
| CZ281920B6 (cs) | 1997-04-16 |
| PL297299A1 (enExample) | 1992-07-13 |
| OA09723A (en) | 1993-08-30 |
| US5393755A (en) | 1995-02-28 |
| DE69126980D1 (de) | 1997-09-04 |
| NO924940L (no) | 1992-12-18 |
| WO1991019717A1 (en) | 1991-12-26 |
| CZ374992A3 (en) | 1993-10-13 |
| KR960004532B1 (ko) | 1996-04-06 |
| EP0538332A1 (en) | 1993-04-28 |
| FI925731A0 (fi) | 1992-12-17 |
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