LT3685B - Oxadiazolylalkylpurin derivatives, process for preparing them and pharmacological preparations - Google Patents
Oxadiazolylalkylpurin derivatives, process for preparing them and pharmacological preparations Download PDFInfo
- Publication number
- LT3685B LT3685B LTIP1455A LTIP1455A LT3685B LT 3685 B LT3685 B LT 3685B LT IP1455 A LTIP1455 A LT IP1455A LT IP1455 A LTIP1455 A LT IP1455A LT 3685 B LT3685 B LT 3685B
- Authority
- LT
- Lithuania
- Prior art keywords
- methyl
- dihydro
- dione
- purine
- oxadiazol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 oxyphenyl Chemical group 0.000 claims description 38
- GMSNIKWWOQHZGF-UHFFFAOYSA-N 3-methyl-9H-xanthine Chemical compound O=C1NC(=O)N(C)C2=C1N=CN2 GMSNIKWWOQHZGF-UHFFFAOYSA-N 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 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 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 150000004866 oxadiazoles Chemical class 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 1
- SNXCZWZKBPOLIM-UHFFFAOYSA-N 1-methylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N=C2N=CN=C21 SNXCZWZKBPOLIM-UHFFFAOYSA-N 0.000 claims 1
- ONJCDEAFNLJRMU-UHFFFAOYSA-N 3-methyl-7-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]purine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CC(N=1)=NOC=1C1=CC=CC=C1 ONJCDEAFNLJRMU-UHFFFAOYSA-N 0.000 claims 1
- ULZPUYUELWKFRH-UHFFFAOYSA-N 3-methyl-7-[2-[5-(2-piperidin-1-ylethyl)-1,2,4-oxadiazol-3-yl]ethyl]purine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CCC(N=1)=NOC=1CCN1CCCCC1 ULZPUYUELWKFRH-UHFFFAOYSA-N 0.000 claims 1
- CKAUVLFETOJMTP-UHFFFAOYSA-N 3-methyl-7-[2-[5-(piperidin-1-ylmethyl)-1,2,4-oxadiazol-3-yl]ethyl]purine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CCC(N=1)=NOC=1CN1CCCCC1 CKAUVLFETOJMTP-UHFFFAOYSA-N 0.000 claims 1
- NNOPXVXYXSEIEC-UHFFFAOYSA-N 4-[3-[(3-methyl-2,6-dioxopurin-7-yl)methyl]-1,2,4-oxadiazol-5-yl]butanoic acid Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CC1=NOC(CCCC(O)=O)=N1 NNOPXVXYXSEIEC-UHFFFAOYSA-N 0.000 claims 1
- FOZBRFZFJCRLQP-UHFFFAOYSA-N 5-(chloromethyl)-1,2,4-oxadiazole Chemical compound ClCC1=NC=NO1 FOZBRFZFJCRLQP-UHFFFAOYSA-N 0.000 claims 1
- ONVZNUCIHQOZSK-UHFFFAOYSA-N 7-[(5-butyl-1,2,4-oxadiazol-3-yl)methyl]-3-methylpurine-2,6-dione Chemical compound O1C(CCCC)=NC(CN2C=3C(=O)NC(=O)N(C)C=3N=C2)=N1 ONVZNUCIHQOZSK-UHFFFAOYSA-N 0.000 claims 1
- KSJHHVSNBGDFTR-UHFFFAOYSA-N 7-[[5-(2-hydroxyethyl)-1,2,4-oxadiazol-3-yl]methyl]-3-methylpurine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CC1=NOC(CCO)=N1 KSJHHVSNBGDFTR-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 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 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- 206010011224 Cough Diseases 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000003434 antitussive agent Substances 0.000 description 10
- 229940124584 antitussives Drugs 0.000 description 10
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical group C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 7
- RYQVRAILJXPCMZ-UHFFFAOYSA-N 3-methyl-7-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]purine-2,6-dione Chemical compound O1C(C)=NC(CN2C=3C(=O)NC(=O)N(C)C=3N=C2)=N1 RYQVRAILJXPCMZ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- CAZFYQLISAOCOV-UHFFFAOYSA-N n'-hydroxy-2-(3-methyl-2,6-dioxopurin-7-yl)ethanimidamide Chemical compound O=C1NC(=O)N(C)C2=C1N(CC(N)=NO)C=N2 CAZFYQLISAOCOV-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 229960004126 codeine Drugs 0.000 description 5
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960001985 dextromethorphan Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 3
- 235000020374 simple syrup Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
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- 229960000278 theophylline Drugs 0.000 description 3
- ROTWYIYTFZNLQP-UHFFFAOYSA-N 2-(3-methyl-2,6-dioxopurin-7-yl)acetonitrile Chemical compound O=C1NC(=O)N(C)C2=C1N(CC#N)C=N2 ROTWYIYTFZNLQP-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- FUIWJBVUUZLQSY-UHFFFAOYSA-N 7-[[5-(diethylaminomethyl)-1,2,4-oxadiazol-3-yl]methyl]-3-methylpurine-2,6-dione;hydrochloride Chemical compound Cl.O1C(CN(CC)CC)=NC(CN2C=3C(=O)NC(=O)N(C)C=3N=C2)=N1 FUIWJBVUUZLQSY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 241000700199 Cavia porcellus Species 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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- 230000004071 biological effect Effects 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 230000008025 crystallization Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- DIOYEFVIHLBWJX-UHFFFAOYSA-N 3-(diethylamino)propanoic acid Chemical compound CCN(CC)CCC(O)=O DIOYEFVIHLBWJX-UHFFFAOYSA-N 0.000 description 1
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- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 description 1
- FBHOTLWINLXBFB-UHFFFAOYSA-N 7-[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]-3-methylpurine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CC(N=1)=NOC=1CC1=CC=CC=C1 FBHOTLWINLXBFB-UHFFFAOYSA-N 0.000 description 1
- XNFBTIARAHKBPO-UHFFFAOYSA-N 7-[3-[5-[2-(diethylamino)ethyl]-1,2,4-oxadiazol-3-yl]propyl]-3-methylpurine-2,6-dione;hydrochloride Chemical compound Cl.O1C(CCN(CC)CC)=NC(CCCN2C=3C(=O)NC(=O)N(C)C=3N=C2)=N1 XNFBTIARAHKBPO-UHFFFAOYSA-N 0.000 description 1
- XISPUHUXJZHTFN-UHFFFAOYSA-N 7-[[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]methyl]-3-methylpurine-2,6-dione Chemical compound C1=2C(=O)NC(=O)N(C)C=2N=CN1CC1=NOC(CCl)=N1 XISPUHUXJZHTFN-UHFFFAOYSA-N 0.000 description 1
- SQSDOMCUQFVXOO-UHFFFAOYSA-N 7-[[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]methyl]-8-methyl-3h-purine-2,6-dione Chemical compound CC1=NC=2NC(=O)NC(=O)C=2N1CC1=NOC(CCl)=N1 SQSDOMCUQFVXOO-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- UPNLOPRVQAYLLY-UHFFFAOYSA-N CN1CNC=C2N(CN=C12)CCCC1=NOC(=N1)C Chemical compound CN1CNC=C2N(CN=C12)CCCC1=NOC(=N1)C UPNLOPRVQAYLLY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- IDCHQQSVJAAUQQ-UHFFFAOYSA-N N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine Chemical compound O1C(CCN(CC)CC)=NC(C=2C=CC=CC=2)=N1 IDCHQQSVJAAUQQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000001813 broncholytic effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000010216 calcium carbonate Nutrition 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
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003576 central nervous system agent Substances 0.000 description 1
- 229940125693 central nervous system agent Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 235000020438 lemon syrup Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229960003625 oxolamine Drugs 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- OQLJGQGTCQMUEG-UHFFFAOYSA-N purine-2,6-dione;hydrochloride Chemical compound Cl.O=C1NC(=O)C2=NC=NC2=N1 OQLJGQGTCQMUEG-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 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
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- 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
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- 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
- A61P11/14—Antitussive agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU864230A HU197574B (en) | 1986-10-09 | 1986-10-09 | Process for production of derivatives of 3,7-dihydro-3-methil-7-//1,2,4-oxadiasole/-3-il/alkylenil/-1h-purin-2,6-dion and medical compositions containing these substances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP1455A LTIP1455A (en) | 1995-05-25 |
| LT3685B true LT3685B (en) | 1996-01-25 |
Family
ID=10967389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP1455A LT3685B (en) | 1986-10-09 | 1993-11-10 | Oxadiazolylalkylpurin derivatives, process for preparing them and pharmacological preparations |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4840949A (en, 2012) |
| EP (1) | EP0264081B1 (en, 2012) |
| JP (1) | JPS63107980A (en, 2012) |
| KR (1) | KR960003612B1 (en, 2012) |
| CN (1) | CN1018644B (en, 2012) |
| AT (1) | ATE99685T1 (en, 2012) |
| AU (1) | AU595384B2 (en, 2012) |
| BG (1) | BG60403B2 (en, 2012) |
| CS (1) | CS276993B6 (en, 2012) |
| CY (1) | CY1843A (en, 2012) |
| DD (1) | DD262658A5 (en, 2012) |
| DE (1) | DE3788701D1 (en, 2012) |
| DK (1) | DK167806B1 (en, 2012) |
| ES (1) | ES2061465T3 (en, 2012) |
| FI (1) | FI87215C (en, 2012) |
| GE (3) | GEP19970842B (en, 2012) |
| HK (1) | HK78995A (en, 2012) |
| HU (1) | HU197574B (en, 2012) |
| IL (1) | IL84030A (en, 2012) |
| LT (1) | LT3685B (en, 2012) |
| LV (1) | LV10868B (en, 2012) |
| NO (1) | NO166323C (en, 2012) |
| PL (2) | PL268147A1 (en, 2012) |
| RU (1) | RU2007404C1 (en, 2012) |
| SU (2) | SU1602862A1 (en, 2012) |
| UA (2) | UA5572A1 (en, 2012) |
| YU (1) | YU47545B (en, 2012) |
| ZA (1) | ZA877333B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU197574B (en) * | 1986-10-09 | 1989-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for production of derivatives of 3,7-dihydro-3-methil-7-//1,2,4-oxadiasole/-3-il/alkylenil/-1h-purin-2,6-dion and medical compositions containing these substances |
| IT1199320B (it) * | 1986-12-16 | 1988-12-30 | Malesci Sas | 8-azaxantine alchilaminoalchil o eterociclilalchil sostituite sul nucleo triazolico,loro sali fisiologicamente accettabili,loro composizioni farmaceutiche ad attivita'antibroncospastica e relativo procedimento di preparazione |
| HU198933B (en) * | 1987-11-02 | 1989-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new xanthine derivatives and pharmaceutical compositions comprising same as active ingredient |
| HU206884B (en) * | 1990-11-22 | 1993-01-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing purin derivatives and pharmaceutical compositions containing them |
| HUP9700654A2 (hu) * | 1997-03-26 | 1999-09-28 | Dezső Korbonits | Teobromin tartalmú köhögéscsillapító készítmények |
| US7914828B2 (en) * | 2008-10-17 | 2011-03-29 | Levine Brian M | Combination herbal product to benefit respiratory tract |
| US8106234B2 (en) * | 2009-05-07 | 2012-01-31 | OptMed, Inc | Methylidene malonate process |
| US10414839B2 (en) | 2010-10-20 | 2019-09-17 | Sirrus, Inc. | Polymers including a methylene beta-ketoester and products formed therefrom |
| US8361519B2 (en) | 2010-11-18 | 2013-01-29 | Aadvantics Pharmaceuticals, Inc. | Combination herbal product to benefit respiratory tract in people exposed to smoke |
| CA2853073A1 (en) | 2011-10-19 | 2013-04-25 | Bioformix Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| JP6345644B2 (ja) | 2012-03-30 | 2018-06-20 | シラス・インコーポレイテッド | インク配合物およびコーティング配合物ならびにこれらを作製するための重合性の系 |
| US10913875B2 (en) | 2012-03-30 | 2021-02-09 | Sirrus, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
| WO2013181600A2 (en) | 2012-06-01 | 2013-12-05 | Bioformix Inc. | Optical material and articles formed therefrom |
| EP2920231B1 (en) | 2012-11-16 | 2020-05-06 | Sirrus, Inc. | Plastics bonding systems and methods |
| EP3712928A1 (en) | 2012-11-30 | 2020-09-23 | Sirrus, Inc. | Composite compositions for electronics applications |
| US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
| US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
| RU2754735C1 (ru) * | 2020-12-14 | 2021-09-06 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Ярославский государственный технический университет" ФГБОУВО "ЯГТУ" | Способ получения 3,5-дизамещенных 1,2,4-оксадиазолов, содержащих алкенильный фрагмент |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU190377B (en) * | 1982-03-12 | 1986-08-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing theophyllinyl-alkyl-oxadiazoles |
| HU197574B (en) * | 1986-10-09 | 1989-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for production of derivatives of 3,7-dihydro-3-methil-7-//1,2,4-oxadiasole/-3-il/alkylenil/-1h-purin-2,6-dion and medical compositions containing these substances |
-
1986
- 1986-10-09 HU HU864230A patent/HU197574B/hu not_active IP Right Cessation
-
1987
- 1987-09-29 ZA ZA877333A patent/ZA877333B/xx unknown
- 1987-09-29 IL IL84030A patent/IL84030A/xx not_active IP Right Cessation
- 1987-10-06 KR KR1019870011121A patent/KR960003612B1/ko not_active Expired - Fee Related
- 1987-10-08 YU YU185787A patent/YU47545B/sh unknown
- 1987-10-08 DK DK527087A patent/DK167806B1/da not_active IP Right Cessation
- 1987-10-08 AU AU79462/87A patent/AU595384B2/en not_active Ceased
- 1987-10-08 JP JP62254513A patent/JPS63107980A/ja active Granted
- 1987-10-08 NO NO874216A patent/NO166323C/no not_active IP Right Cessation
- 1987-10-09 UA UA4355201A patent/UA5572A1/uk unknown
- 1987-10-09 UA UA4203547A patent/UA26368A/uk unknown
- 1987-10-09 DD DD87307805A patent/DD262658A5/de not_active IP Right Cessation
- 1987-10-09 AT AT87114798T patent/ATE99685T1/de not_active IP Right Cessation
- 1987-10-09 EP EP87114798A patent/EP0264081B1/de not_active Expired - Lifetime
- 1987-10-09 US US07/107,693 patent/US4840949A/en not_active Expired - Fee Related
- 1987-10-09 FI FI874456A patent/FI87215C/fi not_active IP Right Cessation
- 1987-10-09 PL PL1987268147A patent/PL268147A1/xx unknown
- 1987-10-09 CN CN87107785A patent/CN1018644B/zh not_active Expired
- 1987-10-09 DE DE87114798T patent/DE3788701D1/de not_active Expired - Fee Related
- 1987-10-09 ES ES87114798T patent/ES2061465T3/es not_active Expired - Lifetime
- 1987-10-09 PL PL1987280763A patent/PL151206B1/pl unknown
- 1987-10-09 RU SU874203547A patent/RU2007404C1/ru active
- 1987-10-09 CS CS877327A patent/CS276993B6/cs not_active IP Right Cessation
-
1988
- 1988-02-19 SU SU884355201A patent/SU1602862A1/ru active
- 1988-09-19 SU SU884356424A patent/SU1635901A3/ru active
-
1993
- 1993-06-22 LV LVP-93-649A patent/LV10868B/lv unknown
- 1993-08-12 GE GEAP19931402A patent/GEP19970842B/en unknown
- 1993-08-12 GE GEAP19931394A patent/GEP19960657B/en unknown
- 1993-08-12 GE GEAP19931397A patent/GEP19970817B/en unknown
- 1993-11-10 LT LTIP1455A patent/LT3685B/lt not_active IP Right Cessation
- 1993-12-02 BG BG098265A patent/BG60403B2/bg unknown
-
1995
- 1995-05-18 HK HK78995A patent/HK78995A/xx not_active IP Right Cessation
-
1996
- 1996-03-08 CY CY184396A patent/CY1843A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19981110 |