NO823026L - 2(1h)-pyridinoner og fremgangsmaate for deres fremstilling - Google Patents
2(1h)-pyridinoner og fremgangsmaate for deres fremstillingInfo
- Publication number
- NO823026L NO823026L NO823026A NO823026A NO823026L NO 823026 L NO823026 L NO 823026L NO 823026 A NO823026 A NO 823026A NO 823026 A NO823026 A NO 823026A NO 823026 L NO823026 L NO 823026L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- hydroxy
- methyl
- amino
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title claims description 22
- 150000005300 2(1H)-pyridinones Chemical class 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 49
- -1 hydroxy, methoxy Chemical group 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 5
- ADFOIRNDERJSNZ-UHFFFAOYSA-N 5-(4-hydroxy-3-nitrophenyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=C(C(O)=CC=2)[N+]([O-])=O)=C1C ADFOIRNDERJSNZ-UHFFFAOYSA-N 0.000 claims description 5
- QFPSCSGNKGYEGV-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=CC(O)=CC=2)=C1C QFPSCSGNKGYEGV-UHFFFAOYSA-N 0.000 claims description 5
- RHIYBCQHCZZWDU-UHFFFAOYSA-N 5-(4-methoxyphenyl)-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C)NC(=O)C(C#N)=C1 RHIYBCQHCZZWDU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- HLHMGCZBOVLBBU-UHFFFAOYSA-N 5-(3-methoxyphenyl)-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound COC1=CC=CC(C2=C(NC(=O)C(C#N)=C2)C)=C1 HLHMGCZBOVLBBU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- GADQSVJNSDNLTA-UHFFFAOYSA-N 5-(3,4-dihydroxyphenyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=C(O)C(O)=CC=2)=C1C GADQSVJNSDNLTA-UHFFFAOYSA-N 0.000 claims description 2
- DXUSMVNCSXZTKZ-UHFFFAOYSA-N 5-(3-amino-4-hydroxyphenyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=C(N)C(O)=CC=2)=C1C DXUSMVNCSXZTKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 230000000875 corresponding effect Effects 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- 239000000496 cardiotonic agent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 210000003540 papillary muscle Anatomy 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 230000001746 atrial effect Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- RMIMMZMFWOWQGJ-UHFFFAOYSA-N 5-(4-hydroxyphenyl)-1h-pyridin-2-one Chemical compound C1=CC(O)=CC=C1C1=CNC(=O)C=C1 RMIMMZMFWOWQGJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- LMEAOACSJKVJMH-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-6-methyl-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(C=2C=C(O)C=CC=2)=C1C LMEAOACSJKVJMH-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000003177 cardiotonic effect Effects 0.000 description 3
- 239000003795 chemical substances by application 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
- 230000008602 contraction Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003756 stirring Methods 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
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- LUNRXENHXLPCRC-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-1h-pyridin-2-one Chemical compound OC1=CC=CC(C2=CNC(=O)C=C2)=C1 LUNRXENHXLPCRC-UHFFFAOYSA-N 0.000 description 2
- KNYJDLYSXYMKTA-UHFFFAOYSA-N 5-phenylpiperidin-2-one Chemical compound C1NC(=O)CCC1C1=CC=CC=C1 KNYJDLYSXYMKTA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-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
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700198 Cavia Species 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229960002105 amrinone Drugs 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 125000005805 dimethoxy phenyl group Chemical group 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
- 210000002837 heart atrium Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 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
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000035485 pulse pressure Effects 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid 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
- 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
- MKWLJQPRBDFJAV-UHFFFAOYSA-N 1-(2,3-dimethoxyphenoxy)-2,3-dimethoxybenzene Chemical class COC1=CC=CC(OC=2C(=C(OC)C=CC=2)OC)=C1OC MKWLJQPRBDFJAV-UHFFFAOYSA-N 0.000 description 1
- GBOQOXOOCJDVOJ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-(4-hydroxyphenyl)-6-methyl-2-oxopyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)N(CCO)C(C)=C1C1=CC=C(O)C=C1 GBOQOXOOCJDVOJ-UHFFFAOYSA-N 0.000 description 1
- OBHXBEFIMRVLEB-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-(4-hydroxyphenyl)-6-methylpyridin-2-one Chemical compound C1=CC(=O)N(CCO)C(C)=C1C1=CC=C(O)C=C1 OBHXBEFIMRVLEB-UHFFFAOYSA-N 0.000 description 1
- CMEJERKZJIUJPN-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-(4-methoxyphenyl)-6-methyl-2-oxopyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=C(C)N(CCO)C(=O)C(C#N)=C1 CMEJERKZJIUJPN-UHFFFAOYSA-N 0.000 description 1
- HYWNLNKGSCTKMU-UHFFFAOYSA-N 1-hydroxy-1-phenylbut-3-en-2-one Chemical compound C=CC(=O)C(O)C1=CC=CC=C1 HYWNLNKGSCTKMU-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- GPTCNPDHDYHZER-UHFFFAOYSA-N 2-chloro-5-phenylpyridine Chemical compound C1=NC(Cl)=CC=C1C1=CC=CC=C1 GPTCNPDHDYHZER-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- NTHQYHTZRJMPFI-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carbonitrile Chemical class C1=C(C#N)C(=O)NC=C1C1=CC=CC=N1 NTHQYHTZRJMPFI-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 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
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- SLRDDAMHLUPGGV-UHFFFAOYSA-N 5-(3,4-diaminophenyl)-1h-pyridin-2-one Chemical compound C1=C(N)C(N)=CC=C1C1=CNC(=O)C=C1 SLRDDAMHLUPGGV-UHFFFAOYSA-N 0.000 description 1
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- FGSVFIMJFPAZGP-UHFFFAOYSA-N 5-(3,4-dihydroxyphenyl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=C(O)C(O)=CC=C1C1=CNC(=O)C(C#N)=C1 FGSVFIMJFPAZGP-UHFFFAOYSA-N 0.000 description 1
- OATCSTWNNHKUSP-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=CNC(=O)C(C#N)=C1 OATCSTWNNHKUSP-UHFFFAOYSA-N 0.000 description 1
- ILRJQTVMTTXEQF-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C)NC(=O)C(C#N)=C1 ILRJQTVMTTXEQF-UHFFFAOYSA-N 0.000 description 1
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- NDTOGYXXBVSCRL-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1=CNC(=O)C(C#N)=C1 NDTOGYXXBVSCRL-UHFFFAOYSA-N 0.000 description 1
- RWFAQYWIBBVEBY-UHFFFAOYSA-N 5-phenyl-1h-pyridin-2-one Chemical class N1C(=O)C=CC(C=2C=CC=CC=2)=C1 RWFAQYWIBBVEBY-UHFFFAOYSA-N 0.000 description 1
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
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- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- GENAHGKEFJLNJB-QMTHXVAHSA-N lysergamide Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-QMTHXVAHSA-N 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
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-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
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- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
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- 239000002304 perfume Substances 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 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
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- 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
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 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
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance 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
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- 235000020357 syrup Nutrition 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30029481A | 1981-09-08 | 1981-09-08 | |
| US06/372,174 US4465686A (en) | 1981-09-08 | 1982-04-26 | 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones, their cardiotonic use and preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823026L true NO823026L (no) | 1983-03-09 |
Family
ID=26971699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823026A NO823026L (no) | 1981-09-08 | 1982-09-07 | 2(1h)-pyridinoner og fremgangsmaate for deres fremstilling |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4465686A (de) |
| EP (1) | EP0074091A3 (de) |
| AU (1) | AU8794382A (de) |
| DK (1) | DK399482A (de) |
| ES (1) | ES8400407A1 (de) |
| FI (1) | FI823085L (de) |
| GR (1) | GR77646B (de) |
| NO (1) | NO823026L (de) |
| PT (1) | PT75506B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4515797A (en) * | 1981-09-08 | 1985-05-07 | Sterling Drug Inc. | 3-Amino-5-(hydroxy- and/or aminophenyl)-6-(lower-alkyl)-2(1H)-pyridinones and cardiotonic use thereof |
| FR2527206B1 (fr) * | 1982-05-18 | 1986-12-05 | Sandoz Sa | Nouveaux derives de la 2(1h)-pyridinone, leur preparation et leur utilisation comme medicaments |
| IL70169A0 (en) * | 1982-11-18 | 1984-02-29 | Sterling Drug Inc | 2(1h)-pyridinones,their preparation and pharmaceutical compositions containing them |
| EP0200024B1 (de) | 1985-04-30 | 1992-07-01 | ARZNEIMITTELWERK DRESDEN GmbH | 3-Cyan-pyridine, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| US5714493A (en) * | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US6645969B1 (en) * | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| USRE37650E1 (en) | 1991-05-10 | 2002-04-09 | Aventis Pharmacetical Products, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
| US5710158A (en) * | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5480883A (en) * | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5409930A (en) * | 1991-05-10 | 1995-04-25 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US6436972B1 (en) | 2000-04-10 | 2002-08-20 | Dalhousie University | Pyridones and their use as modulators of serine hydrolase enzymes |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| DK3442972T3 (da) | 2016-04-15 | 2020-04-27 | Abbvie Inc | Bromdomænehæmmere |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA865757A (en) * | 1971-03-09 | F. Czaja Robert | Production of 3-phenyl-2(1h)-pyridone | |
| US3655679A (en) * | 1969-06-25 | 1972-04-11 | Merck & Co Inc | Certain aryl pyridine carboxylic acid derivatives |
| US3703582A (en) * | 1970-04-20 | 1972-11-21 | Merck & Co Inc | Aryl pyridine carboxylic acids in the treatment of inflammation |
| US3718743A (en) * | 1970-11-19 | 1973-02-27 | Merck & Co Inc | 5-phenyl-2-piperidones and 5-phenyl-2-thiopiperidones in compositions and methods for treating pain, fever and inflammation |
| US3853896A (en) * | 1971-06-25 | 1974-12-10 | Merck & Co Inc | Certain dilioweralkylamino-methylene(or ethylene)-2(ih)pyridones |
| US4065290A (en) * | 1975-07-03 | 1977-12-27 | Eli Lilly And Company | Herbicidal β-phenyl-4-piperidinones |
| US4072746A (en) * | 1975-10-14 | 1978-02-07 | Sterling Drug Inc. | 3-Amino-5-(pyridinyl)-2(1H)-pyridinones |
| US4004012A (en) * | 1975-10-14 | 1977-01-18 | Sterling Drug Inc. | 3-Cyano-5-(pyridinyl)-2(1H)-pyridinones |
| US4297362A (en) * | 1979-05-18 | 1981-10-27 | Sterling Drug Inc. | 4-(3,4-Diaminophenyl)pyridine or salts, and use thereof as cardiotonic |
| US4297360A (en) * | 1980-03-28 | 1981-10-27 | Sterling Drug Inc. | 5-(Pyridinyl)pyridine-2,3-diamines, preparation thereof and their cardiotonic use |
| NZ195564A (en) * | 1979-11-26 | 1983-09-30 | Sterling Drug Inc | 5-pyridinyl-2(1h)-pyridinones pharmaceutical compositions intermediate pyridine compounds |
| US4313951A (en) * | 1979-11-26 | 1982-02-02 | Sterling Drug Inc. | 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their cardiotonic use and intermediates therefor |
| US4302462A (en) * | 1979-12-20 | 1981-11-24 | Sterling Drug Inc. | 4(or 3)-(3,4-Dihydroxyphenyl)pyridines, their cardiotonic use and cardiotonic use of their methyl ethers |
| DE3106460A1 (de) * | 1980-03-03 | 1982-01-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 2(1h)-pyridinon-derivate, ihre herstellung und sie enthaltende pharmazeutische zubereitungen |
| NZ196573A (en) * | 1980-03-28 | 1984-03-16 | Sterling Drug Inc | 6-pyrid-(3 or 4)-yl-(1h or 3h)-imidazo (4,5-b)pyridines |
| 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 |
| US4431651A (en) * | 1982-11-18 | 1984-02-14 | Sterling Drug Inc. | 2-Pyridinones and their use as cardiotonic agents |
-
1982
- 1982-04-26 US US06/372,174 patent/US4465686A/en not_active Expired - Fee Related
- 1982-09-02 EP EP82108104A patent/EP0074091A3/de not_active Withdrawn
- 1982-09-02 AU AU87943/82A patent/AU8794382A/en not_active Abandoned
- 1982-09-03 PT PT75506A patent/PT75506B/pt unknown
- 1982-09-07 ES ES515530A patent/ES8400407A1/es not_active Expired
- 1982-09-07 NO NO823026A patent/NO823026L/no unknown
- 1982-09-07 FI FI823085A patent/FI823085L/fi not_active Application Discontinuation
- 1982-09-07 DK DK399482A patent/DK399482A/da not_active Application Discontinuation
- 1982-09-08 GR GR69223A patent/GR77646B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK399482A (da) | 1983-03-09 |
| FI823085L (fi) | 1983-03-09 |
| ES515530A0 (es) | 1983-10-16 |
| EP0074091A3 (de) | 1983-09-14 |
| AU8794382A (en) | 1983-03-17 |
| US4465686A (en) | 1984-08-14 |
| EP0074091A2 (de) | 1983-03-16 |
| GR77646B (de) | 1984-09-25 |
| PT75506B (en) | 1984-12-04 |
| ES8400407A1 (es) | 1983-10-16 |
| FI823085A0 (fi) | 1982-09-07 |
| PT75506A (en) | 1982-10-01 |
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