NO810833L - Fremgangsmaate til fremstilling av pyrazolpyridinoner og pyridinylnikotinater - Google Patents
Fremgangsmaate til fremstilling av pyrazolpyridinoner og pyridinylnikotinaterInfo
- Publication number
- NO810833L NO810833L NO810833A NO810833A NO810833L NO 810833 L NO810833 L NO 810833L NO 810833 A NO810833 A NO 810833A NO 810833 A NO810833 A NO 810833A NO 810833 L NO810833 L NO 810833L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- dihydro
- methyl
- pyrazolo
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 11
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000011664 nicotinic acid Substances 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 10
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229960003512 nicotinic acid Drugs 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- TUPZMLLDXCWVKH-UHFFFAOYSA-N pyrazolo[4,3-b]pyridin-3-one Chemical class C1=CN=C2C(=O)N=NC2=C1 TUPZMLLDXCWVKH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- POKRAHUBNKIFGZ-UHFFFAOYSA-N pyridin-2-yl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC1=CC=CC=N1 POKRAHUBNKIFGZ-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 15
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 210000003540 papillary muscle Anatomy 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VXJYFSSVLUDBPQ-UHFFFAOYSA-N methyl 2-chloro-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC(C=2C=CN=CC=2)=C1 VXJYFSSVLUDBPQ-UHFFFAOYSA-N 0.000 description 9
- 230000001746 atrial effect Effects 0.000 description 8
- 230000003177 cardiotonic effect Effects 0.000 description 8
- 235000001968 nicotinic acid Nutrition 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000000496 cardiotonic agent Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- SRXIDMKVAKYNMQ-UHFFFAOYSA-N 1-methyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(C)NC(=O)C2=CC=1C1=CC=NC=C1 SRXIDMKVAKYNMQ-UHFFFAOYSA-N 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 210000002837 heart atrium Anatomy 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 210000005245 right atrium Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WKDNSRJXCYJQBV-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC(C=2C=CN=CC=2)=C1 WKDNSRJXCYJQBV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KGSXRRPUGHXSIK-UHFFFAOYSA-N 1-(2-hydroxyethyl)-6-methyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CC1=NC=2N(CCO)NC(=O)C=2C=C1C1=CC=NC=C1 KGSXRRPUGHXSIK-UHFFFAOYSA-N 0.000 description 2
- XTXBQMYTNUKYAY-UHFFFAOYSA-N 5-pyridin-2-yl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one Chemical class C1=C2C(=O)NNC2=NC=C1C1=CC=CC=N1 XTXBQMYTNUKYAY-UHFFFAOYSA-N 0.000 description 2
- OEWMZQADKLAIMV-UHFFFAOYSA-N 5-pyridin-4-yl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one Chemical compound C1=C2C(=O)NNC2=NC=C1C1=CC=NC=C1 OEWMZQADKLAIMV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N Sec-butyl alcohol Natural products CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- GYBZRRVXHWVXCS-UHFFFAOYSA-N 1,6-diethyl-5-(2-methylpyridin-4-yl)-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CCC1=NC=2N(CC)NC(=O)C=2C=C1C1=CC=NC(C)=C1 GYBZRRVXHWVXCS-UHFFFAOYSA-N 0.000 description 1
- SSVAFINFVMVKBX-UHFFFAOYSA-N 1,6-dimethyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CC1=NC=2N(C)NC(=O)C=2C=C1C1=CC=NC=C1 SSVAFINFVMVKBX-UHFFFAOYSA-N 0.000 description 1
- GUNMLHGFZBENDG-UHFFFAOYSA-N 1-(2-ethoxyethyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCOCC)NC(=O)C2=CC=1C1=CC=NC=C1 GUNMLHGFZBENDG-UHFFFAOYSA-N 0.000 description 1
- CSGOZWUVYRAZLE-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-(2-methylpyridin-3-yl)-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CC1=NC=CC=C1C1=CN=C(N(CCO)NC2=O)C2=C1 CSGOZWUVYRAZLE-UHFFFAOYSA-N 0.000 description 1
- RRDIHMVEHMYUDI-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-(2-methylpyridin-4-yl)-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C1=NC(C)=CC(C=2C=C3C(=O)NN(CCO)C3=NC=2)=C1 RRDIHMVEHMYUDI-UHFFFAOYSA-N 0.000 description 1
- QRVKOEQJKHTWCF-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCO)NC(=O)C2=CC=1C1=CC=NC=C1 QRVKOEQJKHTWCF-UHFFFAOYSA-N 0.000 description 1
- ALCKRMQIZFZHEW-UHFFFAOYSA-N 1-(2-hydroxyethyl)-6-(2-methylpropyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CC(C)CC1=NC=2N(CCO)NC(=O)C=2C=C1C1=CC=NC=C1 ALCKRMQIZFZHEW-UHFFFAOYSA-N 0.000 description 1
- CMOFMQLRXOVYBT-UHFFFAOYSA-N 1-(2-methoxyethyl)-5-(2-methylpyridin-4-yl)-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCOC)NC(=O)C2=CC=1C1=CC=NC(C)=C1 CMOFMQLRXOVYBT-UHFFFAOYSA-N 0.000 description 1
- SIDNRRVMRQXHTP-UHFFFAOYSA-N 1-(2-methoxyethyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCOC)NC(=O)C2=CC=1C1=CC=NC=C1 SIDNRRVMRQXHTP-UHFFFAOYSA-N 0.000 description 1
- FZNKJZHAXRLINM-UHFFFAOYSA-N 1-(2-methoxypropyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CC(C)OC)NC(=O)C2=CC=1C1=CC=NC=C1 FZNKJZHAXRLINM-UHFFFAOYSA-N 0.000 description 1
- QHNHAUFUJOTBQC-UHFFFAOYSA-N 1-(2-methylpropyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CC(C)C)NC(=O)C2=CC=1C1=CC=NC=C1 QHNHAUFUJOTBQC-UHFFFAOYSA-N 0.000 description 1
- PQSYLWMUEOLJJT-UHFFFAOYSA-N 1-(3-methoxypropyl)-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCCOC)NC(=O)C2=CC=1C1=CC=NC=C1 PQSYLWMUEOLJJT-UHFFFAOYSA-N 0.000 description 1
- GATLWDACMZVFQA-UHFFFAOYSA-N 1-butan-2-yl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(C(C)CC)NC(=O)C2=CC=1C1=CC=NC=C1 GATLWDACMZVFQA-UHFFFAOYSA-N 0.000 description 1
- IJJUSEAKPBBSOT-UHFFFAOYSA-N 1-butyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCCC)NC(=O)C2=CC=1C1=CC=NC=C1 IJJUSEAKPBBSOT-UHFFFAOYSA-N 0.000 description 1
- XTFVUKCQWUQYCP-UHFFFAOYSA-N 1-ethyl-5-(5-methylpyridin-3-yl)-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CC)NC(=O)C2=CC=1C1=CN=CC(C)=C1 XTFVUKCQWUQYCP-UHFFFAOYSA-N 0.000 description 1
- KIAKLHFXPJPTEV-UHFFFAOYSA-N 1-ethyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CC)NC(=O)C2=CC=1C1=CC=NC=C1 KIAKLHFXPJPTEV-UHFFFAOYSA-N 0.000 description 1
- HKNNPBHWNXUOIG-UHFFFAOYSA-N 1-ethyl-6-methyl-5-pyridin-3-yl-2H-pyrazolo[3,4-b]pyridin-3-one Chemical compound CC=1N=C2N(CC)NC(=O)C2=CC=1C1=CC=CN=C1 HKNNPBHWNXUOIG-UHFFFAOYSA-N 0.000 description 1
- VRJGDDLNGUTPSM-UHFFFAOYSA-N 1-hexyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCCCCC)NC(=O)C2=CC=1C1=CC=NC=C1 VRJGDDLNGUTPSM-UHFFFAOYSA-N 0.000 description 1
- IGOYRLZKOODERF-UHFFFAOYSA-N 1-methyl-5-pyridin-3-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(C)NC(=O)C2=CC=1C1=CC=CN=C1 IGOYRLZKOODERF-UHFFFAOYSA-N 0.000 description 1
- QPLYRKOCZUIFLY-UHFFFAOYSA-N 1-methyl-6-pentyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CCCCCC1=NC=2N(C)NC(=O)C=2C=C1C1=CC=NC=C1 QPLYRKOCZUIFLY-UHFFFAOYSA-N 0.000 description 1
- WYGKPFYMYXMZKP-UHFFFAOYSA-N 1-methyl-6-propyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound CCCC1=NC=2N(C)NC(=O)C=2C=C1C1=CC=NC=C1 WYGKPFYMYXMZKP-UHFFFAOYSA-N 0.000 description 1
- QKFUMGBPPOFYTF-UHFFFAOYSA-N 1-propan-2-yl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(C(C)C)NC(=O)C2=CC=1C1=CC=NC=C1 QKFUMGBPPOFYTF-UHFFFAOYSA-N 0.000 description 1
- FFZOSZPVUYZPSQ-UHFFFAOYSA-N 1-propyl-5-pyridin-4-yl-2h-pyrazolo[3,4-b]pyridin-3-one Chemical compound C=1N=C2N(CCC)NC(=O)C2=CC=1C1=CC=NC=C1 FFZOSZPVUYZPSQ-UHFFFAOYSA-N 0.000 description 1
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical group C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 1
- PDDJLINWLJPTAT-UHFFFAOYSA-N 2-(2h-pyridin-1-yl)ethanol Chemical compound OCCN1CC=CC=C1 PDDJLINWLJPTAT-UHFFFAOYSA-N 0.000 description 1
- YYWUUBRRAZTHJK-UHFFFAOYSA-N 2-chloro-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(Cl)=NC=C1C1=CC=NC=C1 YYWUUBRRAZTHJK-UHFFFAOYSA-N 0.000 description 1
- WIXMPDLXXXOPCB-UHFFFAOYSA-N 2-ethoxyethylhydrazine Chemical compound CCOCCNN WIXMPDLXXXOPCB-UHFFFAOYSA-N 0.000 description 1
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- IBELBRDFPCFICX-UHFFFAOYSA-N 2-methoxyethylhydrazine Chemical compound COCCNN IBELBRDFPCFICX-UHFFFAOYSA-N 0.000 description 1
- NGSOWKPBNFOQCR-UHFFFAOYSA-N 2-methylpropylhydrazine Chemical compound CC(C)CNN NGSOWKPBNFOQCR-UHFFFAOYSA-N 0.000 description 1
- SEQOYYYZFNJQSV-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=NC=C1 SEQOYYYZFNJQSV-UHFFFAOYSA-N 0.000 description 1
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical class O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- UXYCBKADHOUWRS-UHFFFAOYSA-N ethyl 2-chloro-5-pyridin-3-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CC(C=2C=NC=CC=2)=C1 UXYCBKADHOUWRS-UHFFFAOYSA-N 0.000 description 1
- WNVRIHUUTKQSDE-UHFFFAOYSA-N ethyl 2-chloro-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CC(C=2C=CN=CC=2)=C1 WNVRIHUUTKQSDE-UHFFFAOYSA-N 0.000 description 1
- CXYIFFJBEDIGIC-UHFFFAOYSA-N ethyl 2-chloro-6-propan-2-yl-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCC)=CC(C=2C=CN=CC=2)=C1C(C)C CXYIFFJBEDIGIC-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- UNOAPBGSMKKGDT-UHFFFAOYSA-N methyl 2-chloro-5-(2,6-dimethylpyridin-4-yl)pyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC(C=2C=C(C)N=C(C)C=2)=C1 UNOAPBGSMKKGDT-UHFFFAOYSA-N 0.000 description 1
- RJOXPDYZZNGAFF-UHFFFAOYSA-N methyl 2-chloro-6-(2-methylpropyl)-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC(C=2C=CN=CC=2)=C1CC(C)C RJOXPDYZZNGAFF-UHFFFAOYSA-N 0.000 description 1
- CVDIGODNCHPJJJ-UHFFFAOYSA-N methyl 2-chloro-6-methyl-5-pyridin-3-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC(C=2C=NC=CC=2)=C1C CVDIGODNCHPJJJ-UHFFFAOYSA-N 0.000 description 1
- HCOYNMKTTORNAT-UHFFFAOYSA-N methyl 2-chloro-6-methyl-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC)=CC(C=2C=CN=CC=2)=C1C HCOYNMKTTORNAT-UHFFFAOYSA-N 0.000 description 1
- JJKNOQXYBJJLEO-UHFFFAOYSA-N methyl 2-chloro-6-pentyl-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound CCCCCC1=NC(Cl)=C(C(=O)OC)C=C1C1=CC=NC=C1 JJKNOQXYBJJLEO-UHFFFAOYSA-N 0.000 description 1
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- WHTSEWDEUNIVMR-UHFFFAOYSA-N methyl 6-butyl-2-chloro-5-pyridin-4-ylpyridine-3-carboxylate Chemical compound CCCCC1=NC(Cl)=C(C(=O)OC)C=C1C1=CC=NC=C1 WHTSEWDEUNIVMR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
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- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- SWBUGSDBGJYRNA-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(5-methylpyridin-3-yl)pyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C=C(C)C=NC=2)=C1 SWBUGSDBGJYRNA-UHFFFAOYSA-N 0.000 description 1
- JZCZCSJUPKBVEK-UHFFFAOYSA-N propan-2-yl 2-chloro-6-ethyl-5-pyridin-3-ylpyridine-3-carboxylate Chemical compound CCC1=NC(Cl)=C(C(=O)OC(C)C)C=C1C1=CC=CN=C1 JZCZCSJUPKBVEK-UHFFFAOYSA-N 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- FXQRYNKCPUQWBQ-UHFFFAOYSA-N propyl 2-chloro-5-(2-methylpyridin-3-yl)pyridine-3-carboxylate Chemical compound N1=C(Cl)C(C(=O)OCCC)=CC(C=2C(=NC=CC=2)C)=C1 FXQRYNKCPUQWBQ-UHFFFAOYSA-N 0.000 description 1
- UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
- 230000010349 pulsation Effects 0.000 description 1
- YAYRMUVEORJPCX-UHFFFAOYSA-N pyrazolo[3,4-b]pyridin-3-one Chemical class C1=CC=C2C(=O)N=NC2=N1 YAYRMUVEORJPCX-UHFFFAOYSA-N 0.000 description 1
- 150000005229 pyrazolopyridines Chemical class 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/130,628 US4264612A (en) | 1980-03-17 | 1980-03-17 | Lower-alkyl 2-halo-5-(pyridinyl)nicotinates, their preparation and use as cardiotonics |
| US06/130,623 US4265895A (en) | 1980-03-17 | 1980-03-17 | 1,2-Dihydro-5-pyridinyl-3H-pyrazolo[3,4-b]pyridin-3-ones and their use as cardiotonics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810833L true NO810833L (no) | 1981-09-18 |
Family
ID=26828659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810833A NO810833L (no) | 1980-03-17 | 1981-03-11 | Fremgangsmaate til fremstilling av pyrazolpyridinoner og pyridinylnikotinater |
Country Status (16)
| Country | Link |
|---|---|
| AU (1) | AU6813881A (da) |
| DE (1) | DE3110313A1 (da) |
| DK (1) | DK117081A (da) |
| ES (1) | ES8205410A1 (da) |
| FI (1) | FI810779L (da) |
| FR (1) | FR2478098A1 (da) |
| GB (1) | GB2073179A (da) |
| IL (1) | IL62306A0 (da) |
| IT (1) | IT1141999B (da) |
| LU (1) | LU83221A1 (da) |
| NL (1) | NL8101269A (da) |
| NO (1) | NO810833L (da) |
| NZ (1) | NZ196453A (da) |
| PH (1) | PH15978A (da) |
| PT (1) | PT72674B (da) |
| SE (1) | SE8101592L (da) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953571A (en) * | 1957-12-13 | 1960-09-20 | Gen Aniline & Film Corp | Pyrazolopyridines |
| AU454992B2 (en) * | 1970-06-03 | 1974-10-28 | Euclid Inc | Exhaust diverting valve for dumpable vehicles having heated dump bodies |
| DE2232038A1 (de) * | 1972-06-30 | 1974-01-10 | Hoechst Ag | 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung |
| US4081451A (en) * | 1975-03-20 | 1978-03-28 | Schering Corporation | Process for preparing 2-halogeno nicotinic acids |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
-
1981
- 1981-03-05 IL IL62306A patent/IL62306A0/xx unknown
- 1981-03-06 AU AU68138/81A patent/AU6813881A/en not_active Abandoned
- 1981-03-09 NZ NZ196453A patent/NZ196453A/xx unknown
- 1981-03-10 IT IT20272/81A patent/IT1141999B/it active
- 1981-03-10 PH PH25338A patent/PH15978A/en unknown
- 1981-03-11 GB GB8107632A patent/GB2073179A/en not_active Withdrawn
- 1981-03-11 NO NO810833A patent/NO810833L/no unknown
- 1981-03-12 SE SE8101592A patent/SE8101592L/xx not_active Application Discontinuation
- 1981-03-13 FI FI810779A patent/FI810779L/fi not_active Application Discontinuation
- 1981-03-16 DK DK117081A patent/DK117081A/da not_active Application Discontinuation
- 1981-03-16 LU LU83221A patent/LU83221A1/fr unknown
- 1981-03-16 NL NL8101269A patent/NL8101269A/nl not_active Application Discontinuation
- 1981-03-16 FR FR8105222A patent/FR2478098A1/fr not_active Withdrawn
- 1981-03-16 ES ES500395A patent/ES8205410A1/es not_active Expired
- 1981-03-17 PT PT72674A patent/PT72674B/pt unknown
- 1981-03-17 DE DE19813110313 patent/DE3110313A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478098A1 (fr) | 1981-09-18 |
| IT1141999B (it) | 1986-10-08 |
| NZ196453A (en) | 1983-12-16 |
| PT72674A (en) | 1981-04-01 |
| PT72674B (en) | 1982-03-22 |
| ES500395A0 (es) | 1982-06-01 |
| AU6813881A (en) | 1981-09-24 |
| FI810779L (fi) | 1981-09-18 |
| LU83221A1 (fr) | 1981-10-30 |
| SE8101592L (sv) | 1981-09-18 |
| PH15978A (en) | 1983-05-16 |
| IL62306A0 (en) | 1981-05-20 |
| DE3110313A1 (de) | 1981-12-24 |
| NL8101269A (nl) | 1981-10-16 |
| ES8205410A1 (es) | 1982-06-01 |
| GB2073179A (en) | 1981-10-14 |
| DK117081A (da) | 1981-09-18 |
| IT8120272A0 (it) | 1981-03-10 |
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