NO851113L - ((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling - Google Patents
((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstillingInfo
- Publication number
- NO851113L NO851113L NO851113A NO851113A NO851113L NO 851113 L NO851113 L NO 851113L NO 851113 A NO851113 A NO 851113A NO 851113 A NO851113 A NO 851113A NO 851113 L NO851113 L NO 851113L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- pyrimidinyl
- ethyl
- methyl
- urea
- Prior art date
Links
- -1 (PYRIDINYL) -2-PYRIMIDINYL Chemical class 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 13
- 239000000496 cardiotonic agent Substances 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000012458 free base Substances 0.000 claims description 9
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 claims description 9
- RARQASBMHVVTIV-UHFFFAOYSA-N (5-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound C1=NC(NC(=O)N)=NC=C1C1=CC=NC=C1 RARQASBMHVVTIV-UHFFFAOYSA-N 0.000 claims description 7
- 230000000747 cardiac effect Effects 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 230000003177 cardiotonic effect Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- QTEPRBKZGLMNGH-UHFFFAOYSA-N 1-ethyl-3-(4-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound CCNC(=O)NC1=NC=CC(C=2C=CN=CC=2)=N1 QTEPRBKZGLMNGH-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- VODJCJGNEZWZJM-UHFFFAOYSA-N 1-butyl-3-(5-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound C1=NC(NC(=O)NCCCC)=NC=C1C1=CC=NC=C1 VODJCJGNEZWZJM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 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 21
- 239000000203 mixture Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 241000700199 Cavia porcellus Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 210000003540 papillary muscle Anatomy 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FOZPUAICCICVEX-UHFFFAOYSA-N (5-pyridin-4-ylpyrimidin-2-yl)cyanamide Chemical compound C1=NC(NC#N)=NC=C1C1=CC=NC=C1 FOZPUAICCICVEX-UHFFFAOYSA-N 0.000 description 5
- FUVYSMCPPZZZDT-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound C1=NC(NC(=O)NCC)=NC=C1C1=CC=NC=C1 FUVYSMCPPZZZDT-UHFFFAOYSA-N 0.000 description 5
- FMCZZTJYJOQZHC-UHFFFAOYSA-N 4-pyridin-4-ylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=CN=CC=2)=N1 FMCZZTJYJOQZHC-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 230000001746 atrial effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FSHIOHCNOLTWBC-UHFFFAOYSA-N 5-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=NC=C1 FSHIOHCNOLTWBC-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002357 guanidines Chemical class 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 3
- PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GQSARKAWVKBQNN-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)pyrimidin-2-amine Chemical compound C1=NC(C)=CC(C=2C=NC(N)=NC=2)=C1 GQSARKAWVKBQNN-UHFFFAOYSA-N 0.000 description 3
- PFUBNHHFFFSNDV-UHFFFAOYSA-N 5-pyridin-3-ylpyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=CN=C1 PFUBNHHFFFSNDV-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 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
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000036772 blood pressure Effects 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
- 238000001816 cooling Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WTYJBGQERCCGAD-UHFFFAOYSA-N 1-Methylguanidine sulfate (2:1) Chemical compound CN=C(N)N.CN=C(N)N.OS(O)(=O)=O WTYJBGQERCCGAD-UHFFFAOYSA-N 0.000 description 2
- GWBCZEQJRHMMJB-UHFFFAOYSA-N 3-(dimethylamino)-2-(2,6-dimethylpyridin-4-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC(C)=NC(C)=C1 GWBCZEQJRHMMJB-UHFFFAOYSA-N 0.000 description 2
- SUBBRFCUQHQJHO-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-methylpyridin-3-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=CN=C1C SUBBRFCUQHQJHO-UHFFFAOYSA-N 0.000 description 2
- RBZKQLKVNNSDRU-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-methylpyridin-4-yl)prop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC(C)=C1 RBZKQLKVNNSDRU-UHFFFAOYSA-N 0.000 description 2
- XIPGJDILNMOIBD-UHFFFAOYSA-N 3-butyl-1-methyl-1-(5-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound C1=NC(N(C)C(=O)NCCCC)=NC=C1C1=CC=NC=C1 XIPGJDILNMOIBD-UHFFFAOYSA-N 0.000 description 2
- UJXHZZXCWISPAL-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)pyrimidin-2-amine Chemical compound CC1=NC(C)=CC(C=2N=C(N)N=CC=2)=C1 UJXHZZXCWISPAL-UHFFFAOYSA-N 0.000 description 2
- BXGFXOUUPGGILH-UHFFFAOYSA-N 4-(2-methylpyridin-3-yl)pyrimidin-2-amine Chemical compound CC1=NC=CC=C1C1=CC=NC(N)=N1 BXGFXOUUPGGILH-UHFFFAOYSA-N 0.000 description 2
- QJXQYMFMRSJWLT-UHFFFAOYSA-N 4-(2-methylpyridin-4-yl)pyrimidin-2-amine Chemical compound C1=NC(C)=CC(C=2N=C(N)N=CC=2)=C1 QJXQYMFMRSJWLT-UHFFFAOYSA-N 0.000 description 2
- LQHQKYWYKPLKCH-UHFFFAOYSA-N 4-pyridin-3-ylpyrimidin-2-amine Chemical compound NC1=NC=CC(C=2C=NC=CC=2)=N1 LQHQKYWYKPLKCH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GFGKYCUOYUZGPZ-UHFFFAOYSA-N [5-(2,6-dimethylpyridin-4-yl)pyrimidin-2-yl]cyanamide Chemical compound CC1=NC(C)=CC(C=2C=NC(NC#N)=NC=2)=C1 GFGKYCUOYUZGPZ-UHFFFAOYSA-N 0.000 description 2
- UFXDDUQTHORSRA-UHFFFAOYSA-N [5-(2-methylpyridin-4-yl)pyrimidin-2-yl]cyanamide Chemical compound C1=NC(C)=CC(C=2C=NC(NC#N)=NC=2)=C1 UFXDDUQTHORSRA-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 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
- 210000002837 heart atrium Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 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
- GOERPUSQLHSQHQ-UHFFFAOYSA-N n-methyl-4-pyridin-4-ylpyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2C=CN=CC=2)=N1 GOERPUSQLHSQHQ-UHFFFAOYSA-N 0.000 description 2
- KUWUMFOHMSUHCV-UHFFFAOYSA-N n-methyl-5-pyridin-4-ylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=CC=NC=C1 KUWUMFOHMSUHCV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
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- LHSGWTUNOWYLPR-UHFFFAOYSA-N (4-pyridin-2-ylpyrimidin-2-yl)urea Chemical class NC(=O)NC1=NC=CC(C=2N=CC=CC=2)=N1 LHSGWTUNOWYLPR-UHFFFAOYSA-N 0.000 description 1
- OQSCZZBKDURHGZ-UHFFFAOYSA-N (4-pyridin-4-ylpyrimidin-2-yl)cyanamide Chemical compound N#CNC1=NC=CC(C=2C=CN=CC=2)=N1 OQSCZZBKDURHGZ-UHFFFAOYSA-N 0.000 description 1
- UDOPFIOGHAGDBA-UHFFFAOYSA-N (4-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC=CC(C=2C=CN=CC=2)=N1 UDOPFIOGHAGDBA-UHFFFAOYSA-N 0.000 description 1
- YAXKWNKIAKNMBR-UHFFFAOYSA-N (5-pyridin-3-ylpyrimidin-2-yl)cyanamide Chemical compound C1=NC(NC#N)=NC=C1C1=CC=CN=C1 YAXKWNKIAKNMBR-UHFFFAOYSA-N 0.000 description 1
- YHTJBBWTOXGQBN-UHFFFAOYSA-N (5-pyridin-3-ylpyrimidin-2-yl)urea Chemical compound C1=NC(NC(=O)N)=NC=C1C1=CC=CN=C1 YHTJBBWTOXGQBN-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- JXOZZNXONAPKPW-UHFFFAOYSA-N 1-[4-(2,6-dimethylpyridin-4-yl)pyrimidin-2-yl]-3-ethylurea Chemical compound CCNC(=O)NC1=NC=CC(C=2C=C(C)N=C(C)C=2)=N1 JXOZZNXONAPKPW-UHFFFAOYSA-N 0.000 description 1
- NWHNVZCVGRWNEM-UHFFFAOYSA-N 1-ethyl-3-(5-pyridin-3-ylpyrimidin-2-yl)urea Chemical compound C1=NC(NC(=O)NCC)=NC=C1C1=CC=CN=C1 NWHNVZCVGRWNEM-UHFFFAOYSA-N 0.000 description 1
- IUBNCNPCHFWNNI-UHFFFAOYSA-N 1-ethyl-3-[4-(2-methylpyridin-3-yl)pyrimidin-2-yl]urea Chemical compound CCNC(=O)NC1=NC=CC(C=2C(=NC=CC=2)C)=N1 IUBNCNPCHFWNNI-UHFFFAOYSA-N 0.000 description 1
- RFZMMURSYZGJGC-UHFFFAOYSA-N 1-methyl-3-(4-pyridin-4-ylpyrimidin-2-yl)urea Chemical compound CNC(=O)NC1=NC=CC(C=2C=CN=CC=2)=N1 RFZMMURSYZGJGC-UHFFFAOYSA-N 0.000 description 1
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- UTZJNWBGJMQMGW-UHFFFAOYSA-N 3-(dimethylamino)-1-(2-methylpyridin-4-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=NC(C)=C1 UTZJNWBGJMQMGW-UHFFFAOYSA-N 0.000 description 1
- MZLRFUCMBQWLNV-UHFFFAOYSA-N 3-(dimethylamino)-1-pyridin-3-ylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CN=C1 MZLRFUCMBQWLNV-UHFFFAOYSA-N 0.000 description 1
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- CUAAVFXFCLYBBV-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylbut-2-enal Chemical compound CN(C)C(C)=C(C=O)C1=CC=NC=C1 CUAAVFXFCLYBBV-UHFFFAOYSA-N 0.000 description 1
- OBWZJYGWTDFKRS-UHFFFAOYSA-N 5-(2,6-dimethylpyridin-4-yl)-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=CC(C)=NC(C)=C1 OBWZJYGWTDFKRS-UHFFFAOYSA-N 0.000 description 1
- SZPDVMOWLBYSJS-UHFFFAOYSA-N 5-(2,6-dimethylpyridin-4-yl)pyrimidin-2-amine Chemical compound CC1=NC(C)=CC(C=2C=NC(N)=NC=2)=C1 SZPDVMOWLBYSJS-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
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- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- JIOILEPXDZCENL-UHFFFAOYSA-N [5-(2,6-dimethylpyridin-4-yl)pyrimidin-2-yl]urea Chemical compound CC1=NC(C)=CC(C=2C=NC(NC(N)=O)=NC=2)=C1 JIOILEPXDZCENL-UHFFFAOYSA-N 0.000 description 1
- FCMNWGAGAMLVPG-UHFFFAOYSA-N [5-(2-methylpyridin-4-yl)pyrimidin-2-yl]urea Chemical compound C1=NC(C)=CC(C=2C=NC(NC(N)=O)=NC=2)=C1 FCMNWGAGAMLVPG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- RVAUVEOTZNLMQL-UHFFFAOYSA-N cyclohexanesulfinic acid Chemical compound OS(=O)C1CCCCC1 RVAUVEOTZNLMQL-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-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
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 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
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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
- MYTUAQVEXIXHCJ-UHFFFAOYSA-N n-methyl-4-pyridin-3-ylpyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2C=NC=CC=2)=N1 MYTUAQVEXIXHCJ-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 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
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/518,280 US4504482A (en) | 1983-07-28 | 1983-07-28 | [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO851113L true NO851113L (no) | 1985-03-20 |
Family
ID=24063294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO851113A NO851113L (no) | 1983-07-28 | 1985-03-20 | ((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4504482A (fr) |
| EP (1) | EP0150205A4 (fr) |
| JP (1) | JPS60502003A (fr) |
| KR (1) | KR850001193A (fr) |
| AU (1) | AU3154184A (fr) |
| DK (1) | DK132285D0 (fr) |
| FI (1) | FI73989C (fr) |
| IL (1) | IL72411A (fr) |
| IT (1) | IT1213193B (fr) |
| NO (1) | NO851113L (fr) |
| NZ (1) | NZ208817A (fr) |
| PH (1) | PH19913A (fr) |
| WO (1) | WO1985000603A1 (fr) |
| ZA (1) | ZA845424B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE135699T1 (de) * | 1986-01-13 | 1996-04-15 | American Cyanamid Co | 4,5,6-substituierte 2-pyrimidinamine |
| US6025355A (en) * | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| EP0925300A1 (fr) * | 1996-02-15 | 1999-06-30 | Cambridge Neuroscience, Inc. | Composes pharmaceutiquement actifs et leurs methodes d'utilisation |
| JP2000506532A (ja) | 1996-03-13 | 2000-05-30 | スミスクライン・ビーチャム・コーポレイション | サイトカイン介在疾患の治療にて有用な新規ピリミジン化合物 |
| US5958934A (en) * | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| US5952331A (en) * | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| DE60113104D1 (de) * | 2000-06-13 | 2005-10-06 | Basf Ag | 5 phenyl substituierte 2-(cyanoamino)-pyrimidine als fungizide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008235A (en) * | 1975-03-07 | 1977-02-15 | Sterling Drug Inc. | N-[2-(pyridinyl)-4-pyrimidinyl]ureas |
-
1983
- 1983-07-28 US US06/518,280 patent/US4504482A/en not_active Expired - Fee Related
-
1984
- 1984-06-29 JP JP59502842A patent/JPS60502003A/ja active Pending
- 1984-06-29 WO PCT/US1984/001049 patent/WO1985000603A1/fr not_active Application Discontinuation
- 1984-06-29 EP EP19840902864 patent/EP0150205A4/fr not_active Withdrawn
- 1984-06-29 AU AU31541/84A patent/AU3154184A/en not_active Abandoned
- 1984-07-06 NZ NZ208817A patent/NZ208817A/en unknown
- 1984-07-13 IL IL72411A patent/IL72411A/xx unknown
- 1984-07-13 ZA ZA845424A patent/ZA845424B/xx unknown
- 1984-07-20 IT IT8421976A patent/IT1213193B/it active
- 1984-07-20 PH PH31006A patent/PH19913A/en unknown
- 1984-07-23 KR KR1019840004428A patent/KR850001193A/ko not_active Application Discontinuation
-
1985
- 1985-03-20 NO NO851113A patent/NO851113L/no unknown
- 1985-03-22 DK DK132285A patent/DK132285D0/da not_active Application Discontinuation
- 1985-03-22 FI FI851167A patent/FI73989C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI851167L (fi) | 1985-03-22 |
| AU3154184A (en) | 1985-03-04 |
| ZA845424B (en) | 1985-02-27 |
| IL72411A0 (en) | 1984-11-30 |
| FI73989C (fi) | 1987-12-10 |
| FI851167A0 (fi) | 1985-03-22 |
| EP0150205A1 (fr) | 1985-08-07 |
| IL72411A (en) | 1988-04-29 |
| IT1213193B (it) | 1989-12-14 |
| KR850001193A (ko) | 1985-03-16 |
| WO1985000603A1 (fr) | 1985-02-14 |
| DK132285A (da) | 1985-03-22 |
| PH19913A (en) | 1986-08-14 |
| FI73989B (fi) | 1987-08-31 |
| IT8421976A0 (it) | 1984-07-20 |
| US4504482A (en) | 1985-03-12 |
| JPS60502003A (ja) | 1985-11-21 |
| EP0150205A4 (fr) | 1986-02-20 |
| DK132285D0 (da) | 1985-03-22 |
| NZ208817A (en) | 1988-02-12 |
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