SE436033B - 2-alkoxi-9-(cyklohexyl eller cyklohexenyl)-9h-adenin och farmaceutisk komposition for behandling av bronkokonstriktion - Google Patents
2-alkoxi-9-(cyklohexyl eller cyklohexenyl)-9h-adenin och farmaceutisk komposition for behandling av bronkokonstriktionInfo
- Publication number
- SE436033B SE436033B SE7903976A SE7903976A SE436033B SE 436033 B SE436033 B SE 436033B SE 7903976 A SE7903976 A SE 7903976A SE 7903976 A SE7903976 A SE 7903976A SE 436033 B SE436033 B SE 436033B
- Authority
- SE
- Sweden
- Prior art keywords
- adenine
- formula
- cyclohexyl
- cyclohexenyl
- compounds
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- -1 CYCLOHEXYL Chemical class 0.000 title description 27
- 238000010276 construction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 229940124630 bronchodilator Drugs 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 229960000643 adenine Drugs 0.000 claims description 8
- FCODSIQKLKDEBK-UHFFFAOYSA-N 2-butoxy-9-cyclohexylpurin-6-amine Chemical compound C12=NC(OCCCC)=NC(N)=C2N=CN1C1CCCCC1 FCODSIQKLKDEBK-UHFFFAOYSA-N 0.000 claims description 6
- AYVHHXZXJWFOBE-UHFFFAOYSA-N 2-chloro-9-cyclohex-2-en-1-ylpurin-6-amine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1C1CCCC=C1 AYVHHXZXJWFOBE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- 150000003212 purines Chemical class 0.000 claims description 4
- 230000007885 bronchoconstriction Effects 0.000 claims description 3
- 239000000168 bronchodilator agent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 2
- 230000001129 nonadrenergic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 238000010898 silica gel chromatography Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 26
- 230000000694 effects Effects 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 16
- 239000012442 inert solvent Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 6
- 229960003556 aminophylline Drugs 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 230000001077 hypotensive effect Effects 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229910052720 vanadium Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 210000000748 cardiovascular system Anatomy 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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
- 241000124008 Mammalia Species 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005059 halophenyl group Chemical group 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011591 potassium Chemical group 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- PVASNXZESHWYPC-UHFFFAOYSA-N 2-chloro-9-cyclohexylpurin-6-amine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1C1CCCCC1 PVASNXZESHWYPC-UHFFFAOYSA-N 0.000 description 3
- AJKDUJRRWLQXHM-UHFFFAOYSA-N 3-bromocyclohexene Chemical compound BrC1CCCC=C1 AJKDUJRRWLQXHM-UHFFFAOYSA-N 0.000 description 3
- BCPNLBRDCZWAOW-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-ethoxypurin-6-amine Chemical compound C12=NC(OCC)=NC(N)=C2N=CN1C1CCCC=C1 BCPNLBRDCZWAOW-UHFFFAOYSA-N 0.000 description 3
- VKWRMDLYSDSZBQ-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-propoxypurin-6-amine Chemical compound C12=NC(OCCC)=NC(N)=C2N=CN1C1CCCC=C1 VKWRMDLYSDSZBQ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 238000007796 conventional method Methods 0.000 description 3
- 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 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
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- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical class Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 2
- LTESOZAUMTUKQX-UUOKFMHZSA-N 6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-purine-2-thione Chemical class 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 2
- UZFGEUYUBSBADQ-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-(2-methylpropoxy)purin-6-amine Chemical compound C12=NC(OCC(C)C)=NC(N)=C2N=CN1C1CCCC=C1 UZFGEUYUBSBADQ-UHFFFAOYSA-N 0.000 description 2
- DONZXFYPODDITG-UHFFFAOYSA-N 9-cyclohex-2-en-1-yl-2-hexoxypurin-6-amine Chemical compound C12=NC(OCCCCCC)=NC(N)=C2N=CN1C1CCCC=C1 DONZXFYPODDITG-UHFFFAOYSA-N 0.000 description 2
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- 229920001615 Tragacanth Polymers 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 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
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- 239000011230 binding agent Substances 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
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- 239000002026 chloroform extract Substances 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
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- 239000008120 corn starch Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- DZFYOYRNBGNPJW-UHFFFAOYSA-N ethoxythallium Chemical compound [Tl+].CC[O-] DZFYOYRNBGNPJW-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
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- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
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- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
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- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/904,146 US4172829A (en) | 1978-05-09 | 1978-05-09 | 2,9-Disubstituted adenine derivatives and their use as non-adrenergic bronchodilators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7903976L SE7903976L (sv) | 1979-11-10 |
| SE436033B true SE436033B (sv) | 1984-11-05 |
Family
ID=25418652
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7903976A SE436033B (sv) | 1978-05-09 | 1979-05-07 | 2-alkoxi-9-(cyklohexyl eller cyklohexenyl)-9h-adenin och farmaceutisk komposition for behandling av bronkokonstriktion |
| SE8401493A SE449864B (sv) | 1978-05-09 | 1984-03-16 | 2-kloradeninderivat med farmakologisk aktivitet och even anvendbara som mellanprodukter |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8401493A SE449864B (sv) | 1978-05-09 | 1984-03-16 | 2-kloradeninderivat med farmakologisk aktivitet och even anvendbara som mellanprodukter |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4172829A (en, 2012) |
| JP (2) | JPS55373A (en, 2012) |
| AU (1) | AU532056B2 (en, 2012) |
| BE (1) | BE876122A (en, 2012) |
| CA (1) | CA1109871A (en, 2012) |
| CH (1) | CH640534A5 (en, 2012) |
| DE (1) | DE2918261A1 (en, 2012) |
| DK (1) | DK145698C (en, 2012) |
| FI (1) | FI66615C (en, 2012) |
| FR (2) | FR2432519A1 (en, 2012) |
| GB (2) | GB2020655B (en, 2012) |
| GR (1) | GR73535B (en, 2012) |
| IE (1) | IE48216B1 (en, 2012) |
| IT (1) | IT1116833B (en, 2012) |
| LU (1) | LU81238A1 (en, 2012) |
| NL (1) | NL7903650A (en, 2012) |
| SE (2) | SE436033B (en, 2012) |
| YU (1) | YU41632B (en, 2012) |
| ZA (1) | ZA792186B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI802401A7 (fi) * | 1979-08-06 | 1981-01-01 | Bristol Myers Co | Keuhkoputkia laajentava puriini. |
| US4232155A (en) * | 1979-09-13 | 1980-11-04 | Bristol-Myers Company | Purine compounds |
| US4269839A (en) * | 1979-09-13 | 1981-05-26 | Bristol-Myers Company | Alkylthio-adenines used as bronchodilators |
| US4278675A (en) * | 1979-09-13 | 1981-07-14 | Bristol-Myers Company | Bronchodilating process |
| US4286093A (en) * | 1980-02-25 | 1981-08-25 | Mead Johnson & Company | 9-Cyclohexyl-2-alkoxy-9H-adenine process |
| JPS6237165Y2 (en, 2012) * | 1980-05-29 | 1987-09-22 | ||
| US4419358A (en) * | 1981-11-12 | 1983-12-06 | Mead Johnson & Company | Isethionic acid salt of 9-cyclohexyl-2-propoxy-9H-purine-6-amine and compositions containing an effective bronchodilating concentration of it |
| US5015739A (en) * | 1988-04-22 | 1991-05-14 | Schering Corporation | Processes for preparation of cyclopentyl purine derivatives |
| JPH027537A (ja) * | 1988-06-27 | 1990-01-11 | Dainippon Printing Co Ltd | 移動装置及び形状測定装置 |
| US4999428A (en) * | 1989-04-14 | 1991-03-12 | Schering Corporation | Process for preparing cyclopentyl purine derivatives |
| JPH0379236U (en, 2012) * | 1990-08-24 | 1991-08-13 | ||
| JPH0379235U (en, 2012) * | 1990-08-24 | 1991-08-13 | ||
| DK199801455A (da) | 1998-11-10 | 2000-05-11 | Fls Miljoe A S | Fremgangsmåde til imprægnering eller ekstrahering af et harpiksholdigt træsubstrat |
| AU4589800A (en) * | 1999-05-05 | 2000-11-21 | Darwin Discovery Limited | 9-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,9-dihydropurin-6-one derivatives as pde7inhibitors |
| AU7653300A (en) * | 1999-09-10 | 2001-04-10 | Stichting Rega Vzw | Carbocyclic nucleosides and process for obtaining such |
| CN1501928A (zh) * | 2000-11-02 | 2004-06-02 | 斯隆-凯特林癌症研究所 | 结合hsp90的小分子组合物 |
| EP3020829B1 (en) * | 2013-07-12 | 2021-11-17 | Kyoto University | Pharmaceutical composition capable of inhibiting abnormal splicing causative of onset or progress of a genetic disease |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3930005A (en) * | 1973-06-15 | 1975-12-30 | Squibb & Sons Inc | Antiinflammatory agents and their use |
| US3917837A (en) * | 1974-10-21 | 1975-11-04 | American Cyanamid Co | Method of using trans-2-(6-amino-9H-purin-9-yl)-cyclopentanol |
| JPS5271492A (en) * | 1975-12-10 | 1977-06-14 | Kohjin Co Ltd | Synthesis of 9-substituted-2-substituted thioadenines |
| DE2610985A1 (de) | 1976-03-16 | 1977-09-29 | Byk Gulden Lomberg Chem Fab | Arzneimittel enthaltend beta-d-1 (6-amino-9h-purin-9-yl)-1-deoxyribofuranuronsaeurederivate |
| US4076711A (en) * | 1976-04-05 | 1978-02-28 | Schering Corporation | Triazolo [4,5-d]-pyrimidines |
-
1978
- 1978-05-09 US US05/904,146 patent/US4172829A/en not_active Expired - Lifetime
-
1979
- 1979-05-03 GR GR58997A patent/GR73535B/el unknown
- 1979-05-03 GB GB7915401A patent/GB2020655B/en not_active Expired
- 1979-05-03 GB GB8122732A patent/GB2097785B/en not_active Expired
- 1979-05-07 DE DE19792918261 patent/DE2918261A1/de active Granted
- 1979-05-07 ZA ZA792186A patent/ZA792186B/xx unknown
- 1979-05-07 DK DK188279A patent/DK145698C/da active
- 1979-05-07 SE SE7903976A patent/SE436033B/sv not_active IP Right Cessation
- 1979-05-07 FI FI791456A patent/FI66615C/fi not_active IP Right Cessation
- 1979-05-08 CH CH431779A patent/CH640534A5/de not_active IP Right Cessation
- 1979-05-08 FR FR7911604A patent/FR2432519A1/fr active Granted
- 1979-05-08 CA CA327,184A patent/CA1109871A/en not_active Expired
- 1979-05-08 BE BE0/195057A patent/BE876122A/xx not_active IP Right Cessation
- 1979-05-08 JP JP5532279A patent/JPS55373A/ja active Granted
- 1979-05-09 NL NL7903650A patent/NL7903650A/xx not_active Application Discontinuation
- 1979-05-09 AU AU46896/79A patent/AU532056B2/en not_active Ceased
- 1979-05-09 YU YU1085/79A patent/YU41632B/xx unknown
- 1979-05-09 IT IT48986/79A patent/IT1116833B/it active
- 1979-05-09 LU LU81238A patent/LU81238A1/xx unknown
- 1979-08-08 IE IE878/79A patent/IE48216B1/en unknown
- 1979-08-23 FR FR7921304A patent/FR2429793A1/fr active Granted
-
1984
- 1984-03-16 SE SE8401493A patent/SE449864B/sv not_active IP Right Cessation
-
1986
- 1986-09-12 JP JP61214083A patent/JPS62116583A/ja active Granted
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
| SE436033B (sv) | 2-alkoxi-9-(cyklohexyl eller cyklohexenyl)-9h-adenin och farmaceutisk komposition for behandling av bronkokonstriktion | |
| US4201860A (en) | Purine derivatives | |
| SU858569A3 (ru) | Способ получени производных пурина или их кислотно-аддитивных солей | |
| AU602909B2 (en) | Pyrimidine derivatives | |
| EP0212535A1 (de) | N6-Disubstituierte Purinderivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
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