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 fremstilling

Info

Publication number: NO851113L
Authority: NO; Norway
Prior art keywords: pyridinyl; pyrimidinyl; ethyl; methyl; urea
Prior art date: 1983-07-28

Application number

NO851113A

Other languages

English (en)

Norwegian (no)

Inventor

George Yohe Lesher

Baldev Singh

Original Assignee

Sterling Drug Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-07-28

Filing date

1985-03-20

Publication date

1985-03-20

1985-03-20 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1985-03-20 Publication of NO851113L publication Critical patent/NO851113L/no

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
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
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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239000000126 substance Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
238000009736 wetting Methods 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
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
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
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
DCIOJVQYSNUSBG-UHFFFAOYSA-N 3-(dimethylamino)-1-(2,6-dimethylpyridin-4-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC(C)=NC(C)=C1 DCIOJVQYSNUSBG-UHFFFAOYSA-N 0.000 description 1
VAUHZSNUJPFABP-UHFFFAOYSA-N 3-(dimethylamino)-1-(2-methylpyridin-3-yl)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CN=C1C VAUHZSNUJPFABP-UHFFFAOYSA-N 0.000 description 1
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
JZGHSXBVKSMAKH-UHFFFAOYSA-N 3-(dimethylamino)-1-pyridin-4-ylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=NC=C1 JZGHSXBVKSMAKH-UHFFFAOYSA-N 0.000 description 1
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
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LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
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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)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO851113A 1983-07-28 1985-03-20 ((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling NO851113L (no)

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 (it)
EP (1)	EP0150205A4 (it)
JP (1)	JPS60502003A (it)
KR (1)	KR850001193A (it)
AU (1)	AU3154184A (it)
DK (1)	DK132285D0 (it)
FI (1)	FI73989C (it)
IL (1)	IL72411A (it)
IT (1)	IT1213193B (it)
NO (1)	NO851113L (it)
NZ (1)	NZ208817A (it)
PH (1)	PH19913A (it)
WO (1)	WO1985000603A1 (it)
ZA (1)	ZA845424B (it)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2087056T3 (es) *	1986-01-13	1996-07-16	American Cyanamid Co	2-pirimidinaminas sustituidas en las posiciones 4, 5 y 6.
US6025355A (en) *	1997-05-19	2000-02-15	Cambridge Neuroscience, Inc.	Pharmaceutically active compounds and methods of use
JP2000504730A (ja) *	1996-02-15	2000-04-18	ケンブリッジ・ニューロサイエンス・インコーポレーテッド	製薬学的活性物質及び使用方法
US6096748A (en) *	1996-03-13	2000-08-01	Smithkline Beecham Corporation	Pyrimidine compounds useful in treating cytokine mediated diseases
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
JP2004503542A (ja)	2000-06-13	2004-02-05	ビーエーエスエフ　アクチェンゲゼルシャフト	殺真菌性５−フェニル置換２−（シアノアミノ）ピリミジン誘導体

Family Cites Families (1)

* Cited by examiner, † Cited by third party
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 AU AU31541/84A patent/AU3154184A/en not_active Abandoned
- 1984-06-29 WO PCT/US1984/001049 patent/WO1985000603A1/en not_active Ceased
- 1984-06-29 EP EP19840902864 patent/EP0150205A4/en not_active Withdrawn
- 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 Ceased
1985
- 1985-03-20 NO NO851113A patent/NO851113L/no unknown
- 1985-03-22 FI FI851167A patent/FI73989C/fi not_active IP Right Cessation
- 1985-03-22 DK DK132285A patent/DK132285D0/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
NZ208817A (en)	1988-02-12
IT8421976A0 (it)	1984-07-20
EP0150205A1 (en)	1985-08-07
EP0150205A4 (en)	1986-02-20
KR850001193A (ko)	1985-03-16
FI73989B (fi)	1987-08-31
IL72411A (en)	1988-04-29
US4504482A (en)	1985-03-12
DK132285A (da)	1985-03-22
IL72411A0 (en)	1984-11-30
FI73989C (fi)	1987-12-10
JPS60502003A (ja)	1985-11-21
ZA845424B (en)	1985-02-27
IT1213193B (it)	1989-12-14
PH19913A (en)	1986-08-14
AU3154184A (en)	1985-03-04
FI851167L (fi)	1985-03-22
DK132285D0 (da)	1985-03-22
WO1985000603A1 (en)	1985-02-14
FI851167A0 (fi)	1985-03-22

Publication	Publication Date	Title
DE69304243T2 (de)	1997-03-06	Chinolin-Verbindungen als Angiotensin-II-Antagoniste
CA1155848A (en)	1983-10-25	6-(pyridinyl)-3(2h)-pyridazinones, their preparation and use as cardiotonics
CH631981A5 (en)	1982-09-15	Process for preparing novel derivatives of pyrimid-4-one and pyrimid-4-thione, and their salts with acids
NO851113L (no)	1985-03-20	((pyridinyl)-2-pyrimidinyl)ureaforbindelser egnet som kardiotoniske midler og fremgangsmaate for deres fremstilling
NO851066L (no)	1985-03-18	Pyridinyl-2-pyrimidinaminer egnet som kardiotoniske midler samt fremstilling derav
NO820036L (no)	1982-07-12	Pyridinyl-substituerte benzimidazolderivater og fremgangsmaate for deres fremstilling
NO803911L (no)	1981-06-29	3-acylamino-5-(pyridinyl)-2(1h)-pyridinoner og fremgangsmaate til fremstilling derav
CA1161440A (en)	1984-01-31	4-[4(or 3)-acylaminophenyl]pyridines, their preparation and cardiotonic use
CA1166253A (en)	1984-04-24	4-amino-6-(pyridinyl)-3(2h)-pyridazinones, preparation and cardiotonic use
US4337253A (en)	1982-06-29	4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a cardiotonic
US4304775A (en)	1981-12-08	3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof
US4391811A (en)	1983-07-05	2-Amino-6-(pyridinyl)-3H-imidazo[4,5-b]pyridines and their cardiotonic use
US4473571A (en)	1984-09-25	8-Substituted-2-(4-pyridinyl)-9H-purin-6-amines and their cardiotonic use
US4346221A (en)	1982-08-24	Preparation of 4-amino-6-(pyridinyl)-3(2H)-pyridazinones from 6-(pyridinyl)-3(2H)-pyridazinones
US4590194A (en)	1986-05-20	3-[methyl or dimethyl)amino]-6-(pyridinyl)pyridazines and their cardiotonic use
EP0074229A1 (en)	1983-03-16	Triazole gastric anti-secretory agents
US4376775A (en)	1983-03-15	N-[4-(4-Pyridinyl)phenyl]ureas and their cardiotonic use
US4304776A (en)	1981-12-08	4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as intermediates and cardiotonics
US4362734A (en)	1982-12-07	2-(Substituted-amino)-5-(pyridinyl-nicotinonitriles, and their cardiotonic use
US4377585A (en)	1983-03-22	Use of 4-[4(or 3)-aminophenyl]pyridines as cardiotonic agents
US4354026A (en)	1982-10-12	3-Chloro-6-(pyridinyl)-pyridazines
US4503228A (en)	1985-03-05	2-(Pyridinyl)-4,5,6-pyrimidinetriamines
US4362735A (en)	1982-12-07	3-[(3-Oxo-1-butenyl)amino]-5-(pyridinyl)-2(1H)-pyridinones and their cardiotonic use
US4366319A (en)	1982-12-28	Process for preparing 5-(pyridinyl)benzoxazol-2(3H)-ones
NZ196844A (en)	1984-04-27	4-substituted-6-pyrid-(3 or 4)-ylpyridazin-3(2h)-ones