DE2517277A1 - S-substituierte 2-thioadenosine - Google Patents
S-substituierte 2-thioadenosineInfo
- Publication number
- DE2517277A1 DE2517277A1 DE19752517277 DE2517277A DE2517277A1 DE 2517277 A1 DE2517277 A1 DE 2517277A1 DE 19752517277 DE19752517277 DE 19752517277 DE 2517277 A DE2517277 A DE 2517277A DE 2517277 A1 DE2517277 A1 DE 2517277A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- thioadenosine
- radical
- carbon atoms
- hydroxyl
- 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.)
- Ceased
Links
- -1 alkenyl radical Chemical class 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 32
- VLRCFULRQZKFRM-KQYNXXCUSA-N (2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S VLRCFULRQZKFRM-KQYNXXCUSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- REXMMGNMTMGANX-UBEDBUPSSA-N (2r,3r,4r,5r)-5-(6-amino-2-phenylpurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(C=3C=CC=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S REXMMGNMTMGANX-UBEDBUPSSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- DOKXIXJQSBQFJM-ZRFIDHNTSA-N (2R,3R,4R,5R)-5-[6-amino-2-(3-hydroxypropyl)purin-9-yl]-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(CCCO)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S DOKXIXJQSBQFJM-ZRFIDHNTSA-N 0.000 claims description 3
- XYALYMBFQYRZMV-CNEMSGBDSA-N (2r,3r,4r,5r)-5-[6-amino-2-(2-methylphenyl)purin-9-yl]-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound CC1=CC=CC=C1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)S)C2=N1 XYALYMBFQYRZMV-CNEMSGBDSA-N 0.000 claims description 3
- PJHZOKGRTWNTLY-UBEDBUPSSA-N (2r,3r,4r,5r)-5-[6-amino-2-(4-nitrophenyl)purin-9-yl]-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(C=3C=CC(=CC=3)[N+]([O-])=O)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S PJHZOKGRTWNTLY-UBEDBUPSSA-N 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- IORZBRDPDLWFKD-KHTYJDQRSA-N (2r,3r,4r,5r)-5-(6-amino-2-naphthalen-1-ylpurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(C=3C4=CC=CC=C4C=CC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S IORZBRDPDLWFKD-KHTYJDQRSA-N 0.000 claims 1
- MSKYOVKHZDVNFF-QEPJRFBGSA-N (2r,3r,4r,5r)-5-(6-amino-2-quinolin-3-ylpurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(C=3C=C4C=CC=CC4=NC=3)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S MSKYOVKHZDVNFF-QEPJRFBGSA-N 0.000 claims 1
- VNJHRKFKXVMFHQ-QEGZNWDBSA-N (2r,3r,4r,5r)-5-[6-amino-2-(2-hydroxycyclohexyl)purin-9-yl]-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C1=NC=2C(N)=NC(C3C(CCCC3)O)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S VNJHRKFKXVMFHQ-QEGZNWDBSA-N 0.000 claims 1
- MHKGCIMNHWGVLA-XWHPDVPISA-N 2-[6-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-sulfanyloxolan-2-yl]purin-2-yl]hexanoic acid Chemical compound C(=O)(O)C(CCCC)C=1N=C(C=2N=CN([C@H]3[C@H](S)[C@H](O)[C@@H](CO)O3)C=2N=1)N MHKGCIMNHWGVLA-XWHPDVPISA-N 0.000 claims 1
- PQCMUURSLPGBLP-IEJLNPMYSA-N 2-[6-amino-9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-sulfanyloxolan-2-yl]purin-2-yl]propanoic acid Chemical compound C(=O)(O)C(C)C=1N=C(C=2N=CN([C@H]3[C@H](S)[C@H](O)[C@@H](CO)O3)C=2N=1)N PQCMUURSLPGBLP-IEJLNPMYSA-N 0.000 claims 1
- IFVQYKIBIHMOQY-VXPJVLCTSA-N 2-[6-amino-9-[(2r,3r,4r,5r)-4-hydroxy-5-(hydroxymethyl)-3-sulfanyloxolan-2-yl]purin-2-yl]acetic acid Chemical compound C1=NC=2C(N)=NC(CC(O)=O)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S IFVQYKIBIHMOQY-VXPJVLCTSA-N 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 claims 1
- 229960002963 ganciclovir Drugs 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000002769 thiazolinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- LTESOZAUMTUKQX-UUOKFMHZSA-N 6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-purine-2-thione Chemical compound C1=NC2=C(N)NC(=S)N=C2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O LTESOZAUMTUKQX-UUOKFMHZSA-N 0.000 description 20
- BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 4
- 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 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 229960005305 adenosine Drugs 0.000 description 4
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000002253 acid Substances 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229920001436 collagen Polymers 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- TXWHPSZYRUHEGT-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TXWHPSZYRUHEGT-UUOKFMHZSA-N 0.000 description 2
- WGJCBBASTRWVJL-UHFFFAOYSA-N 1,3-thiazolidine-2-thione Chemical compound SC1=NCCS1 WGJCBBASTRWVJL-UHFFFAOYSA-N 0.000 description 2
- RJPNVPITBYXBNB-UHFFFAOYSA-N 1-bromo-4-fluoro-2-methylbenzene Chemical compound CC1=CC(F)=CC=C1Br RJPNVPITBYXBNB-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- YHIWBVHIGCRVLE-UHFFFAOYSA-N 3-bromo-1h-indole Chemical compound C1=CC=C2C(Br)=CNC2=C1 YHIWBVHIGCRVLE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 230000001976 improved effect Effects 0.000 description 2
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- BJHARLJQBXHVKE-PHDIDXHHSA-N (1S,2R)-2-sulfanylcyclohexane-1-carboxylic acid Chemical compound S[C@H]1[C@@H](CCCC1)C(=O)O BJHARLJQBXHVKE-PHDIDXHHSA-N 0.000 description 1
- AAMCLCZHZXKWRV-PHDIDXHHSA-N (1r,2r)-2-bromocyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1Br AAMCLCZHZXKWRV-PHDIDXHHSA-N 0.000 description 1
- QXYOAWHKJRWNID-RRKCRQDMSA-N (1s,3r,4r)-3-bromobicyclo[2.2.1]heptane Chemical compound C1C[C@H]2[C@H](Br)C[C@@H]1C2 QXYOAWHKJRWNID-RRKCRQDMSA-N 0.000 description 1
- YZPPGXGPNZBNGY-ZRFIDHNTSA-N (2r,3r,4r,5r)-5-(6-amino-2-propylpurin-9-yl)-2-(hydroxymethyl)-4-sulfanyloxolan-3-ol Chemical compound C12=NC(CCC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1S YZPPGXGPNZBNGY-ZRFIDHNTSA-N 0.000 description 1
- HJXWZGVMHDPCRS-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(2,6-dichloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(Cl)=NC(Cl)=C2N=C1 HJXWZGVMHDPCRS-UUOKFMHZSA-N 0.000 description 1
- AJNDEAZTAFKOOO-KQYNXXCUSA-N (2r,3r,4s,5r)-2-(6-amino-2-methylsulfanylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(SC)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O AJNDEAZTAFKOOO-KQYNXXCUSA-N 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
- NOMHBBFEJSVGSC-UHFFFAOYSA-N 1-chloro-2-(2-chloroethylsulfinyl)ethane Chemical compound ClCCS(=O)CCCl NOMHBBFEJSVGSC-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- CRYCZDRIXVHNQB-UHFFFAOYSA-N 2-amino-8-bromo-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(Br)N2 CRYCZDRIXVHNQB-UHFFFAOYSA-N 0.000 description 1
- ANIJFZVZXZQFDH-UHFFFAOYSA-N 2-bromo-5-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=CN=C(Br)S1 ANIJFZVZXZQFDH-UHFFFAOYSA-N 0.000 description 1
- RCXJARRRXOPXBC-UHFFFAOYSA-N 2-bromoadamantane Chemical compound C1C(C2)CC3CC1C(Br)C2C3 RCXJARRRXOPXBC-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical compound IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
- LLVRMHAKYRGAGP-UHFFFAOYSA-N 3-bromoheptanoic acid Chemical compound CCCCC(Br)CC(O)=O LLVRMHAKYRGAGP-UHFFFAOYSA-N 0.000 description 1
- KKCPVSHZWAEYAS-UHFFFAOYSA-N 3-bromononanoic acid Chemical compound CCCCCCC(Br)CC(O)=O KKCPVSHZWAEYAS-UHFFFAOYSA-N 0.000 description 1
- ZGIKWINFUGEQEO-UHFFFAOYSA-N 3-bromoquinoline Chemical compound C1=CC=CC2=CC(Br)=CN=C21 ZGIKWINFUGEQEO-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- MARYDOMJDFATPK-UHFFFAOYSA-N 3-hydroxy-1h-pyridine-2-thione Chemical compound OC1=CC=CN=C1S MARYDOMJDFATPK-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- JLAMDELLBBZOOX-UHFFFAOYSA-N 3h-1,3,4-thiadiazole-2-thione Chemical compound SC1=NN=CS1 JLAMDELLBBZOOX-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GNXBFFHXJDZGEK-UHFFFAOYSA-N 4-tert-butylbenzenethiol Chemical compound CC(C)(C)C1=CC=C(S)C=C1 GNXBFFHXJDZGEK-UHFFFAOYSA-N 0.000 description 1
- YVTQHZDUDUCGRD-UHFFFAOYSA-N 5-bromofuran-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)O1 YVTQHZDUDUCGRD-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- MLEASHATKJSLCC-IZLXSQMJSA-N OC(=O)[C@H]1CC[C@H](Br)CC1 Chemical compound OC(=O)[C@H]1CC[C@H](Br)CC1 MLEASHATKJSLCC-IZLXSQMJSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- KJEIVNIICCEMEV-IOSLPCCCSA-N [(2r,3r,4r,5r)-5-(6-amino-2-methylpurin-9-yl)-3-hydroxy-4-sulfanyloxolan-2-yl]methyl dihydrogen phosphate Chemical compound C12=NC(C)=NC(N)=C2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1S KJEIVNIICCEMEV-IOSLPCCCSA-N 0.000 description 1
- NGQCHEXEOUXSFF-UHFFFAOYSA-N adamantane-2-thiol Chemical compound C1C(C2)CC3CC1C(S)C2C3 NGQCHEXEOUXSFF-UHFFFAOYSA-N 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4271874A JPS5347117B2 (enExample) | 1974-04-18 | 1974-04-18 | |
| JP4343074A JPS55400B2 (enExample) | 1974-04-19 | 1974-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2517277A1 true DE2517277A1 (de) | 1975-11-06 |
Family
ID=26382448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752517277 Ceased DE2517277A1 (de) | 1974-04-18 | 1975-04-18 | S-substituierte 2-thioadenosine |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3968102A (enExample) |
| DE (1) | DE2517277A1 (enExample) |
| FR (1) | FR2267789B1 (enExample) |
| GB (1) | GB1493684A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5277091A (en) * | 1975-12-24 | 1977-06-29 | Kohjin Co Ltd | Preparation of 2-substituted adenosines |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4269839A (en) | 1979-09-13 | 1981-05-26 | Bristol-Myers Company | Alkylthio-adenines used as bronchodilators |
| US4683223A (en) * | 1985-09-09 | 1987-07-28 | Warner-Lambert Company | N6 -Benzopyrano-and benzothiopyrano adenosines and methods of use |
| US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
| US5063233A (en) * | 1986-11-14 | 1991-11-05 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives useful as adenosine receptor agonists |
| US4968697A (en) * | 1987-02-04 | 1990-11-06 | Ciba-Geigy Corporation | 2-substituted adenosine 5'-carboxamides as antihypertensive agents |
| US20010051612A1 (en) * | 2000-02-23 | 2001-12-13 | Gloria Cristalli | 2-Thioether A2A receptor agonists |
| GB2372741A (en) | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,8-Disubstituted adenosine derivatives and their different uses |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752805A (en) * | 1969-06-05 | 1973-08-14 | Univ Sydney | 2-loweralkylthioadenosines |
| JPS4826038B1 (enExample) * | 1970-09-25 | 1973-08-03 |
-
1975
- 1975-04-16 US US05/568,491 patent/US3968102A/en not_active Expired - Lifetime
- 1975-04-17 GB GB15800/75A patent/GB1493684A/en not_active Expired
- 1975-04-18 DE DE19752517277 patent/DE2517277A1/de not_active Ceased
- 1975-04-18 FR FR7512224A patent/FR2267789B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5277091A (en) * | 1975-12-24 | 1977-06-29 | Kohjin Co Ltd | Preparation of 2-substituted adenosines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2267789A1 (enExample) | 1975-11-14 |
| GB1493684A (en) | 1977-11-30 |
| FR2267789B1 (enExample) | 1978-07-28 |
| US3968102A (en) | 1976-07-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |