NO811041L - Imidazopyridiner og fremgangsmaate til deres fremstilling - Google Patents
Imidazopyridiner og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO811041L NO811041L NO811041A NO811041A NO811041L NO 811041 L NO811041 L NO 811041L NO 811041 A NO811041 A NO 811041A NO 811041 A NO811041 A NO 811041A NO 811041 L NO811041 L NO 811041L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- pyridine
- imidazo
- lower alkyl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title description 23
- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- 239000012458 free base Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 5
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical group COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000000496 cardiotonic agent Substances 0.000 abstract description 4
- 150000003222 pyridines Chemical class 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000747 cardiac effect Effects 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 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
- 230000003177 cardiotonic effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000001746 atrial effect Effects 0.000 description 5
- 210000003540 papillary muscle Anatomy 0.000 description 5
- MGBFXCHIJVPISN-UHFFFAOYSA-N 5-pyridin-4-ylpyridine-2,3-diamine Chemical compound N1=C(N)C(N)=CC(C=2C=CN=CC=2)=C1 MGBFXCHIJVPISN-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-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
- 239000003701 inert diluent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 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
- 230000002140 halogenating effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960003512 nicotinic acid Drugs 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QBIGMNMKAXJVBA-UHFFFAOYSA-N 2-[(3-amino-5-pyridin-4-ylpyridin-2-yl)amino]ethanol Chemical compound N1=C(NCCO)C(N)=CC(C=2C=CN=CC=2)=C1 QBIGMNMKAXJVBA-UHFFFAOYSA-N 0.000 description 2
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 2
- CJFDRYVHAYFUEU-UHFFFAOYSA-N 6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound C=1N=C2NC=NC2=CC=1C1=CC=NC=C1 CJFDRYVHAYFUEU-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
- 241000282326 Felis catus Species 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 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
- 230000036772 blood pressure Effects 0.000 description 2
- YYDZNOUMWKJXMG-UHFFFAOYSA-N chloro(phenyl)phosphane Chemical compound ClPC1=CC=CC=C1 YYDZNOUMWKJXMG-UHFFFAOYSA-N 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
- 239000000839 emulsion Substances 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-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
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000001968 nicotinic acid 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
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 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
- KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- HMTWZJMNNIVKNS-UHFFFAOYSA-N 1-butyl-6-pyridin-4-ylimidazo[4,5-b]pyridine Chemical compound C1=C2N(CCCC)C=NC2=NC=C1C1=CC=NC=C1 HMTWZJMNNIVKNS-UHFFFAOYSA-N 0.000 description 1
- JIGVOMYZBGSIBD-UHFFFAOYSA-N 1-ethyl-6-pyridin-4-ylimidazo[4,5-b]pyridine Chemical compound C1=C2N(CC)C=NC2=NC=C1C1=CC=NC=C1 JIGVOMYZBGSIBD-UHFFFAOYSA-N 0.000 description 1
- PYYJJJYYWJAPGQ-UHFFFAOYSA-N 1-propan-2-yl-6-pyridin-4-ylimidazo[4,5-b]pyridine Chemical compound C1=C2N(C(C)C)C=NC2=NC=C1C1=CC=NC=C1 PYYJJJYYWJAPGQ-UHFFFAOYSA-N 0.000 description 1
- NREQBBRSKFWUEZ-UHFFFAOYSA-N 1-propyl-6-pyridin-4-ylimidazo[4,5-b]pyridine Chemical compound C1=C2N(CCC)C=NC2=NC=C1C1=CC=NC=C1 NREQBBRSKFWUEZ-UHFFFAOYSA-N 0.000 description 1
- SCLZBENKYWECPB-UHFFFAOYSA-N 2-(2,5-dimethyl-6-pyridin-4-ylimidazo[4,5-b]pyridin-3-yl)ethanol Chemical compound CC=1N=C2N(CCO)C(C)=NC2=CC=1C1=CC=NC=C1 SCLZBENKYWECPB-UHFFFAOYSA-N 0.000 description 1
- IRXANNUDFAGBJS-UHFFFAOYSA-N 2-(2-methyl-6-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl)ethanol Chemical compound C1=C2N(CCO)C(C)=NC2=NC=C1C1=CC=NC=C1 IRXANNUDFAGBJS-UHFFFAOYSA-N 0.000 description 1
- MEHPWYANOYTBKB-UHFFFAOYSA-N 2-(5-methyl-6-pyridin-4-ylimidazo[4,5-b]pyridin-3-yl)ethanol Chemical compound CC1=NC=2N(CCO)C=NC=2C=C1C1=CC=NC=C1 MEHPWYANOYTBKB-UHFFFAOYSA-N 0.000 description 1
- AQSTTXVYQXTHBN-UHFFFAOYSA-N 2-(6-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl)ethanol Chemical compound C1=C2N(CCO)C=NC2=NC=C1C1=CC=NC=C1 AQSTTXVYQXTHBN-UHFFFAOYSA-N 0.000 description 1
- VSIXGVNTVWNLET-UHFFFAOYSA-N 2-[(2-amino-2-methyl-5-pyridin-4-yl-1h-pyridin-3-yl)amino]ethanol Chemical compound C1=C(NCCO)C(C)(N)NC=C1C1=CC=NC=C1 VSIXGVNTVWNLET-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
- 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
- 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 1
- NBPQDODRGWLFQS-UHFFFAOYSA-N 2-pyridin-3-yl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CN=CC(C=2NC3=CC=CN=C3N=2)=C1 NBPQDODRGWLFQS-UHFFFAOYSA-N 0.000 description 1
- RGMLYYSJGMFNCA-UHFFFAOYSA-N 2-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound N1C2=CC=CN=C2N=C1C1=CC=NC=C1 RGMLYYSJGMFNCA-UHFFFAOYSA-N 0.000 description 1
- YSLXQDIQJLXKDK-UHFFFAOYSA-N 3-(6-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl)propane-1,2-diol Chemical compound C1=C2N(CC(O)CO)C=NC2=NC=C1C1=CC=NC=C1 YSLXQDIQJLXKDK-UHFFFAOYSA-N 0.000 description 1
- FQGCQTWFASCKBR-UHFFFAOYSA-N 3-(6-pyridin-4-ylimidazo[4,5-b]pyridin-3-yl)propan-1-ol Chemical compound C=1N=C2N(CCCO)C=NC2=CC=1C1=CC=NC=C1 FQGCQTWFASCKBR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- WWRSYASATWQNKV-UHFFFAOYSA-N 3-nitro-5-pyridin-4-yl-1h-pyridin-2-one Chemical compound N1C(=O)C([N+](=O)[O-])=CC(C=2C=CN=CC=2)=C1 WWRSYASATWQNKV-UHFFFAOYSA-N 0.000 description 1
- FQMCZFYTTFQSDY-UHFFFAOYSA-N 3-propyl-6-pyridin-3-ylimidazo[4,5-b]pyridine Chemical compound C=1N=C2N(CCC)C=NC2=CC=1C1=CC=CN=C1 FQMCZFYTTFQSDY-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NIRCAUPPZAUKDX-UHFFFAOYSA-N 5-benzyl-2-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-6-methylpyridazin-3-one Chemical compound O=C1C=C(CC=2C=CC=CC=2)C(C)=NN1CN(CC1)CCN1C1=CC=CC(Cl)=C1 NIRCAUPPZAUKDX-UHFFFAOYSA-N 0.000 description 1
- SBPJAKWWSCDGJH-UHFFFAOYSA-N 5-butyl-6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound CCCCC1=NC=2NC=NC=2C=C1C1=CC=NC=C1 SBPJAKWWSCDGJH-UHFFFAOYSA-N 0.000 description 1
- HLSYKESXKOONOH-UHFFFAOYSA-N 5-pentyl-6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound CCCCCC1=NC=2NC=NC=2C=C1C1=CC=NC=C1 HLSYKESXKOONOH-UHFFFAOYSA-N 0.000 description 1
- CRDYSINJJAVORO-UHFFFAOYSA-N 5-propan-2-yl-6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound CC(C)C1=NC=2NC=NC=2C=C1C1=CC=NC=C1 CRDYSINJJAVORO-UHFFFAOYSA-N 0.000 description 1
- NEINDGNRXPXNKT-UHFFFAOYSA-N 5-propyl-6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine Chemical compound CCCC1=NC=2NC=NC=2C=C1C1=CC=NC=C1 NEINDGNRXPXNKT-UHFFFAOYSA-N 0.000 description 1
- JLEJXZDPNYUTIR-UHFFFAOYSA-N 5-pyridin-4-yl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=CN=CC=2)=C1 JLEJXZDPNYUTIR-UHFFFAOYSA-N 0.000 description 1
- DQBYZZRYBSPICX-UHFFFAOYSA-N 6-(5-methylpyridin-3-yl)-3-propan-2-ylimidazo[4,5-b]pyridine Chemical compound C=1N=C2N(C(C)C)C=NC2=CC=1C1=CN=CC(C)=C1 DQBYZZRYBSPICX-UHFFFAOYSA-N 0.000 description 1
- XVBRHUANLIHBOQ-UHFFFAOYSA-N 6-methyl-5-pyridin-4-ylpyridine-2,3-diamine Chemical compound CC1=NC(N)=C(N)C=C1C1=CC=NC=C1 XVBRHUANLIHBOQ-UHFFFAOYSA-N 0.000 description 1
- GESMUISTZFSANT-UHFFFAOYSA-N 6-pyridin-4-yl-1h-imidazo[4,5-b]pyridine;hydrate;hydrochloride Chemical compound O.Cl.C=1N=C2NC=NC2=CC=1C1=CC=NC=C1 GESMUISTZFSANT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
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- 210000002837 heart atrium Anatomy 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000002329 infrared spectrum Methods 0.000 description 1
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- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005342 ion exchange Methods 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
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- TZFZFUJIGCERBO-UHFFFAOYSA-N n,n-dimethyl-2-(6-pyridin-4-ylimidazo[4,5-b]pyridin-1-yl)ethanamine Chemical compound C1=C2N(CCN(C)C)C=NC2=NC=C1C1=CC=NC=C1 TZFZFUJIGCERBO-UHFFFAOYSA-N 0.000 description 1
- FPNUEKIMMIGRCU-UHFFFAOYSA-N n-(2-ethoxyethyl)-5-ethyl-6-(2-methylpyridin-4-yl)imidazo[4,5-b]pyridin-3-amine Chemical compound CCC=1N=C2N(NCCOCC)C=NC2=CC=1C1=CC=NC(C)=C1 FPNUEKIMMIGRCU-UHFFFAOYSA-N 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
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- 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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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
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- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 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
- C07D213/60—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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/135,211 US4276293A (en) | 1980-03-28 | 1980-03-28 | Compositions and their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
NO811041L true NO811041L (no) | 1981-09-28 |
Family
ID=22467044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO811041A NO811041L (no) | 1980-03-28 | 1981-03-26 | Imidazopyridiner og fremgangsmaate til deres fremstilling |
Country Status (22)
Country | Link |
---|---|
US (1) | US4276293A (fi) |
JP (1) | JPS56150090A (fi) |
KR (1) | KR830005217A (fi) |
AU (1) | AU6883781A (fi) |
BE (1) | BE888088A (fi) |
CA (1) | CA1159061A (fi) |
DE (1) | DE3112197A1 (fi) |
DK (1) | DK136881A (fi) |
ES (1) | ES8202343A1 (fi) |
FI (1) | FI810921L (fi) |
FR (1) | FR2479225A1 (fi) |
GB (1) | GB2072673B (fi) |
IL (1) | IL62403A0 (fi) |
IT (1) | IT1136972B (fi) |
LU (1) | LU83259A1 (fi) |
NL (1) | NL8101455A (fi) |
NO (1) | NO811041L (fi) |
NZ (1) | NZ196573A (fi) |
PH (1) | PH16999A (fi) |
PT (1) | PT72744B (fi) |
SE (1) | SE8101951L (fi) |
ZA (1) | ZA811776B (fi) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4363911A (en) * | 1981-09-03 | 1982-12-14 | Sterling Drug Inc. | 1,2-Dihydro-6-[2-(dimethylamino)ethenyl]-2-oxo-5-(pyridinyl) nicotinonitriles |
US4465686A (en) * | 1981-09-08 | 1984-08-14 | Sterling Drug Inc. | 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation |
US4347363A (en) * | 1981-09-17 | 1982-08-31 | Sterling Drug Inc. | Process for preparing 1,2-dihydro-6-methyl-2-oxo-5-(pyridinyl)nicotinonitriles |
US4599423A (en) * | 1982-04-26 | 1986-07-08 | Sterling Drug Inc. | Preparation of 5-(hydroxy- and/or aminophenyl-6-lower-alkyl)-2(1H)-pyridinones |
NZ204175A (en) * | 1982-05-24 | 1985-12-13 | Sterling Drug Inc | Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)-nicotinonitriles and nicotinamides;and pyridine intermediates therefor |
US4469871A (en) * | 1982-05-24 | 1984-09-04 | Sterling Drug Inc. | Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones |
US4417054A (en) * | 1982-05-24 | 1983-11-22 | Sterling Drug Inc. | 2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones |
US4413127A (en) * | 1982-05-24 | 1983-11-01 | Sterling Drug Inc. | Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles |
US4539327A (en) * | 1982-08-25 | 1985-09-03 | Sterling Drug Inc. | 5-(2-Substituted-4-thiazolyl)-6-alkyl-2(1H)-pyridinones and cardiotonic use thereof |
US4595762A (en) * | 1982-08-25 | 1986-06-17 | Sterling Drug Inc. | 5-α-bromoalkanoyl-2-oxo-3-pyridinecarbonitriles |
US4469699A (en) * | 1982-08-25 | 1984-09-04 | Sterling Drug Inc. | 5-(4-Thiazolyl)-6-alkyl-2(1H)-pyridinones and their cardiotonic use |
US4448780A (en) * | 1982-09-03 | 1984-05-15 | Sterling Drug Inc. | N-(Lower-alkyl)-N'-[5-(pyridinyl)-2-pyridinyl]ureas and cardiotonic use thereof |
US4517192A (en) * | 1983-01-31 | 1985-05-14 | Sterling Drug Inc. | 6-Alkyl-5-[4-(alkylsulfinyl or alkylsulfonyl)phenyl]-2(1H)-pyridinones and their use as cardiatonics |
AU3820989A (en) * | 1988-08-02 | 1990-02-08 | Ciba-Geigy Ag | 7-amino-3-beta-d-ribofuranosyl-3h-imidazo(4,5-b) pyridin-5-amine derivatives |
US4977144A (en) * | 1988-08-02 | 1990-12-11 | Ciba-Geigy Corporation | Imidazo[4,5-b]pyridine derivatives as cardiovascular agents |
US4963561A (en) * | 1990-02-28 | 1990-10-16 | Sterling Drug Inc. | Imidazopyridines, their preparation and use |
US5010086A (en) * | 1990-02-28 | 1991-04-23 | Sterling Drug Inc. | Imidazopyridines, compositions and use |
US6465484B1 (en) * | 1997-09-26 | 2002-10-15 | Merck & Co., Inc. | Angiogenesis inhibitors |
EP1362894B1 (en) | 2002-02-14 | 2007-12-19 | FUJIFILM Corporation | Method for optical measurement of multi-stranded nucleic acid using cyanine dyes |
-
1980
- 1980-03-28 NZ NZ196573A patent/NZ196573A/en unknown
- 1980-03-28 US US06/135,211 patent/US4276293A/en not_active Expired - Lifetime
-
1981
- 1981-03-17 IL IL62403A patent/IL62403A0/xx unknown
- 1981-03-18 ZA ZA00811776A patent/ZA811776B/xx unknown
- 1981-03-20 PH PH25393A patent/PH16999A/en unknown
- 1981-03-24 BE BE1/10186A patent/BE888088A/fr not_active IP Right Cessation
- 1981-03-24 GB GB8109259A patent/GB2072673B/en not_active Expired
- 1981-03-24 NL NL8101455A patent/NL8101455A/nl not_active Application Discontinuation
- 1981-03-25 FI FI810921A patent/FI810921L/fi not_active Application Discontinuation
- 1981-03-26 SE SE8101951A patent/SE8101951L/xx not_active Application Discontinuation
- 1981-03-26 PT PT72744A patent/PT72744B/pt unknown
- 1981-03-26 ES ES500727A patent/ES8202343A1/es not_active Expired
- 1981-03-26 NO NO811041A patent/NO811041L/no unknown
- 1981-03-26 DK DK136881A patent/DK136881A/da not_active IP Right Cessation
- 1981-03-26 FR FR8106072A patent/FR2479225A1/fr active Granted
- 1981-03-27 LU LU83259A patent/LU83259A1/fr unknown
- 1981-03-27 DE DE19813112197 patent/DE3112197A1/de not_active Withdrawn
- 1981-03-27 JP JP4533681A patent/JPS56150090A/ja active Pending
- 1981-03-27 KR KR1019810001015A patent/KR830005217A/ko unknown
- 1981-03-27 AU AU68837/81A patent/AU6883781A/en not_active Abandoned
- 1981-03-27 IT IT20784/81A patent/IT1136972B/it active
- 1981-03-27 CA CA000374059A patent/CA1159061A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ZA811776B (en) | 1982-04-28 |
IL62403A0 (en) | 1981-05-20 |
FI810921L (fi) | 1981-09-29 |
JPS56150090A (en) | 1981-11-20 |
GB2072673A (en) | 1981-10-07 |
IT1136972B (it) | 1986-09-03 |
DK136881A (da) | 1981-09-29 |
ES500727A0 (es) | 1982-01-16 |
FR2479225A1 (fr) | 1981-10-02 |
IT8120784A0 (it) | 1981-03-27 |
NL8101455A (nl) | 1981-10-16 |
PT72744A (en) | 1981-04-01 |
FR2479225B1 (fi) | 1984-05-18 |
GB2072673B (en) | 1983-11-02 |
PH16999A (en) | 1984-05-04 |
BE888088A (fr) | 1981-09-24 |
DE3112197A1 (de) | 1982-02-25 |
CA1159061A (en) | 1983-12-20 |
SE8101951L (sv) | 1981-09-29 |
NZ196573A (en) | 1984-03-16 |
LU83259A1 (fr) | 1981-10-29 |
PT72744B (en) | 1982-03-24 |
KR830005217A (ko) | 1983-08-03 |
ES8202343A1 (es) | 1982-01-16 |
AU6883781A (en) | 1981-10-08 |
US4276293A (en) | 1981-06-30 |
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