NO811783L - Kardiotonisk virksomme aminofenylpyridin-derivater og fremgangsmaate til deres fremstilling - Google Patents
Kardiotonisk virksomme aminofenylpyridin-derivater og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO811783L NO811783L NO811783A NO811783A NO811783L NO 811783 L NO811783 L NO 811783L NO 811783 A NO811783 A NO 811783A NO 811783 A NO811783 A NO 811783A NO 811783 L NO811783 L NO 811783L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- phenyl
- benzenamine
- acid
- hours
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 6
- XTHJCITVHCRQRD-UHFFFAOYSA-N 2-phenylpyridin-3-amine Chemical class NC1=CC=CN=C1C1=CC=CC=C1 XTHJCITVHCRQRD-UHFFFAOYSA-N 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims description 26
- -1 acetoxyacetyl Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- GKVYVZSNXXTOMQ-UHFFFAOYSA-N 4-pyridin-4-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=NC=C1 GKVYVZSNXXTOMQ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000908 ammonium hydroxide Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 210000003540 papillary muscle Anatomy 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 230000001746 atrial effect Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ADHASKYQWAONSZ-UHFFFAOYSA-N 3-(2,6-dimethylpyridin-4-yl)aniline Chemical compound CC1=NC(C)=CC(C=2C=C(N)C=CC=2)=C1 ADHASKYQWAONSZ-UHFFFAOYSA-N 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- HPHSKFSQHJEHHL-UHFFFAOYSA-N 3-(2-ethylpyridin-4-yl)aniline Chemical compound C1=NC(CC)=CC(C=2C=C(N)C=CC=2)=C1 HPHSKFSQHJEHHL-UHFFFAOYSA-N 0.000 description 3
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 125000003047 N-acetyl group Chemical group 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000000496 cardiotonic agent Substances 0.000 description 3
- 230000003177 cardiotonic effect 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
- 235000019253 formic acid Nutrition 0.000 description 3
- 210000002837 heart atrium Anatomy 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000010998 test method 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
- 239000008096 xylene Substances 0.000 description 3
- FAVFPMQOVRVRAY-UHFFFAOYSA-N (4-pyridin-4-ylphenyl)urea Chemical compound C1=CC(NC(=O)N)=CC=C1C1=CC=NC=C1 FAVFPMQOVRVRAY-UHFFFAOYSA-N 0.000 description 2
- AJEBAQYCSUIEAL-UHFFFAOYSA-N 2,2-dimethyl-n-(4-pyridin-4-ylphenyl)propanamide Chemical compound C1=CC(NC(=O)C(C)(C)C)=CC=C1C1=CC=NC=C1 AJEBAQYCSUIEAL-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- HRJAPLOSNVCRBN-UHFFFAOYSA-N 2-hydroxy-n-(4-pyridin-4-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)CO)=CC=C1C1=CC=NC=C1 HRJAPLOSNVCRBN-UHFFFAOYSA-N 0.000 description 2
- ZLYDUJLJCMXNQG-UHFFFAOYSA-N 2-hydroxy-n-(4-pyridin-4-ylphenyl)propanamide Chemical compound C1=CC(NC(=O)C(O)C)=CC=C1C1=CC=NC=C1 ZLYDUJLJCMXNQG-UHFFFAOYSA-N 0.000 description 2
- PTIFIIAWJRZAHT-UHFFFAOYSA-N 2-methoxy-n-(4-pyridin-4-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)COC)=CC=C1C1=CC=NC=C1 PTIFIIAWJRZAHT-UHFFFAOYSA-N 0.000 description 2
- XDGVYNJOBCLHQU-UHFFFAOYSA-N 3-(2,5-dimethylpyridin-4-yl)aniline Chemical compound C1=NC(C)=CC(C=2C=C(N)C=CC=2)=C1C XDGVYNJOBCLHQU-UHFFFAOYSA-N 0.000 description 2
- ONKMSGUSWLVUSQ-UHFFFAOYSA-N 3-methyl-n-(4-pyridin-4-ylphenyl)butanamide Chemical compound C1=CC(NC(=O)CC(C)C)=CC=C1C1=CC=NC=C1 ONKMSGUSWLVUSQ-UHFFFAOYSA-N 0.000 description 2
- YTJQJGKMRLQBJP-UHFFFAOYSA-N 3-pyridin-3-ylaniline Chemical compound NC1=CC=CC(C=2C=NC=CC=2)=C1 YTJQJGKMRLQBJP-UHFFFAOYSA-N 0.000 description 2
- BDSBSHZVSVKIHM-UHFFFAOYSA-N 3-pyridin-4-ylaniline Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1 BDSBSHZVSVKIHM-UHFFFAOYSA-N 0.000 description 2
- BTUAJLKZYOKCLL-UHFFFAOYSA-N 4-oxo-4-(4-pyridin-4-ylanilino)butanoic acid Chemical compound C1=CC(NC(=O)CCC(=O)O)=CC=C1C1=CC=NC=C1 BTUAJLKZYOKCLL-UHFFFAOYSA-N 0.000 description 2
- DKFDPLVNPGJNDE-UHFFFAOYSA-N 4-pyridin-3-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=CN=C1 DKFDPLVNPGJNDE-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- SRYKRRKNAURXTP-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1C1=CC=NC=C1 SRYKRRKNAURXTP-UHFFFAOYSA-N 0.000 description 2
- OVHHAJRAXHVSMR-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)formamide Chemical compound C1=CC(NC=O)=CC=C1C1=CC=NC=C1 OVHHAJRAXHVSMR-UHFFFAOYSA-N 0.000 description 2
- CYCLQVBFWPFMRS-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C1=CC=NC=C1 CYCLQVBFWPFMRS-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ALHZEIINTQJLOT-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) acetate Chemical compound ClC(=O)C(C)OC(C)=O ALHZEIINTQJLOT-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- ORZMSMCZBZARKY-UHFFFAOYSA-N 1,3,2$l^{6}-benzodioxathiole 2,2-dioxide Chemical compound C1=CC=C2OS(=O)(=O)OC2=C1 ORZMSMCZBZARKY-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 1
- UQUUIVHHGJOMGW-UHFFFAOYSA-N 2-hydroxy-n-(4-pyridin-4-ylphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)CO)=CC=C1C1=CC=NC=C1 UQUUIVHHGJOMGW-UHFFFAOYSA-N 0.000 description 1
- VPZCNNNHCMBJCM-UHFFFAOYSA-N 2-pyridin-2-ylaniline Chemical compound NC1=CC=CC=C1C1=CC=CC=N1 VPZCNNNHCMBJCM-UHFFFAOYSA-N 0.000 description 1
- DHBUBMKZHXHCPG-UHFFFAOYSA-N 3-(2,3-dimethylpyridin-4-yl)aniline Chemical compound CC1=NC=CC(C=2C=C(N)C=CC=2)=C1C DHBUBMKZHXHCPG-UHFFFAOYSA-N 0.000 description 1
- OUHPMRGTIAPXAA-UHFFFAOYSA-N 3-(2,6-diethylpyridin-4-yl)aniline Chemical compound CCC1=NC(CC)=CC(C=2C=C(N)C=CC=2)=C1 OUHPMRGTIAPXAA-UHFFFAOYSA-N 0.000 description 1
- RBQLZXGSNYUPSO-UHFFFAOYSA-N 3-(3-methylpyridin-4-yl)aniline Chemical compound CC1=CN=CC=C1C1=CC=CC(N)=C1 RBQLZXGSNYUPSO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FHEXYCPVNOMQOH-UHFFFAOYSA-N 3-methyl-n-(4-pyridin-4-ylphenyl)butanamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)CC(C)C)=CC=C1C1=CC=NC=C1 FHEXYCPVNOMQOH-UHFFFAOYSA-N 0.000 description 1
- YLNMGMIEOWFPRX-UHFFFAOYSA-N 3-pyridin-2-ylaniline Chemical class NC1=CC=CC(C=2N=CC=CC=2)=C1 YLNMGMIEOWFPRX-UHFFFAOYSA-N 0.000 description 1
- QORUYQWFGMIEHN-UHFFFAOYSA-N 4-(3-aminophenyl)-6-methyl-1h-pyridin-2-one Chemical compound OC1=NC(C)=CC(C=2C=C(N)C=CC=2)=C1 QORUYQWFGMIEHN-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 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
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- 125000001589 carboacyl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- GPNIWPLWJCGDQI-UHFFFAOYSA-N methanesulfonic acid;n-(4-pyridin-4-ylphenyl)but-2-enamide Chemical compound CS(O)(=O)=O.C1=CC(NC(=O)C=CC)=CC=C1C1=CC=NC=C1 GPNIWPLWJCGDQI-UHFFFAOYSA-N 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 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
- OPIBZZLCZBMFGN-UHFFFAOYSA-N n-(3-pyridin-4-ylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CN=CC=2)=C1 OPIBZZLCZBMFGN-UHFFFAOYSA-N 0.000 description 1
- TVDNEGMISVKBKZ-UHFFFAOYSA-N n-(3-pyridin-4-ylphenyl)formamide Chemical compound O=CNC1=CC=CC(C=2C=CN=CC=2)=C1 TVDNEGMISVKBKZ-UHFFFAOYSA-N 0.000 description 1
- MQQYGJCXMBUSHR-UHFFFAOYSA-N n-(3-pyridin-4-ylphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(C=2C=CN=CC=2)=C1 MQQYGJCXMBUSHR-UHFFFAOYSA-N 0.000 description 1
- OEUISWQRWMXWPS-UHFFFAOYSA-N n-(4-pyridin-3-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=CN=C1 OEUISWQRWMXWPS-UHFFFAOYSA-N 0.000 description 1
- FQMAHGGXAGIEQX-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=NC=C1 FQMAHGGXAGIEQX-UHFFFAOYSA-N 0.000 description 1
- VHNWUXIVFUAFAK-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)butanamide;hydrochloride Chemical compound Cl.C1=CC(NC(=O)CCC)=CC=C1C1=CC=NC=C1 VHNWUXIVFUAFAK-UHFFFAOYSA-N 0.000 description 1
- WOCKOOBTGCEPGM-UHFFFAOYSA-N n-(4-pyridin-4-ylphenyl)formamide;hydrochloride Chemical compound Cl.C1=CC(NC=O)=CC=C1C1=CC=NC=C1 WOCKOOBTGCEPGM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 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
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 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
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 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
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/152,991 US4317827A (en) | 1980-05-27 | 1980-05-27 | 4-[4(or 3)-Acylaminophenyl]pyridines and their use as cardiotonics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811783L true NO811783L (no) | 1981-11-30 |
Family
ID=22545324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811783A NO811783L (no) | 1980-05-27 | 1981-05-26 | Kardiotonisk virksomme aminofenylpyridin-derivater og fremgangsmaate til deres fremstilling |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4317827A (ja) |
| JP (1) | JPS5711965A (ja) |
| AR (1) | AR228155A1 (ja) |
| AT (1) | ATA238481A (ja) |
| AU (1) | AU7090181A (ja) |
| BE (1) | BE888963A (ja) |
| CA (1) | CA1161440A (ja) |
| DE (1) | DE3120954A1 (ja) |
| DK (1) | DK229881A (ja) |
| ES (1) | ES502493A0 (ja) |
| FI (1) | FI811576L (ja) |
| FR (2) | FR2483233A1 (ja) |
| GB (1) | GB2076815B (ja) |
| IL (1) | IL62929A0 (ja) |
| IT (1) | IT1137232B (ja) |
| LU (1) | LU83396A1 (ja) |
| NL (1) | NL8102582A (ja) |
| NO (1) | NO811783L (ja) |
| NZ (1) | NZ197155A (ja) |
| PT (1) | PT73083B (ja) |
| SE (1) | SE8103325L (ja) |
| ZA (1) | ZA813474B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448780A (en) * | 1982-09-03 | 1984-05-15 | Sterling Drug Inc. | N-(Lower-alkyl)-N'-[5-(pyridinyl)-2-pyridinyl]ureas and cardiotonic use thereof |
| US5580883A (en) * | 1990-03-26 | 1996-12-03 | Takeda Chemical Industries, Ltd. | Aminobenzene compounds to prevent nerve cell degradation |
| US6458018B1 (en) | 1999-04-23 | 2002-10-01 | 3M Innovative Properties Company | Abrasive article suitable for abrading glass and glass ceramic workpieces |
| WO2007026920A2 (en) * | 2005-09-02 | 2007-03-08 | Astellas Pharma Inc. | Amide derivatives as rock inhibitors |
| EP3019475A1 (en) * | 2013-07-08 | 2016-05-18 | Bristol-Myers Squibb Company | Aryl amide kinase inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US445493A (en) * | 1891-01-27 | William boyrer | ||
| US3907798A (en) * | 1966-06-15 | 1975-09-23 | Sterling Drug Inc | Preparation of 4H-pyrido{8 1,2-a{9 pyrimidin-4-ones from cyclic alkylidene 2-pyridylaminomethylenemalonates |
| GB1183046A (en) * | 1966-06-28 | 1970-03-04 | Allen & Hanburys Ltd | Novel Heterocyclic Compounds |
| US3753993A (en) * | 1971-05-17 | 1973-08-21 | Sterling Drug Inc | 1,4-dihydro-4-oxo-7-pyridyl-3-quinoline-carboxylic acid derivatives |
| BE791864A (fr) * | 1971-12-24 | 1973-03-16 | Dufour Claude | Nouveaux composes a fonction amide derives de la pyridine et leur preparation |
| JPS52125176A (en) * | 1976-04-09 | 1977-10-20 | Sterling Drug Inc | Production of substituted quinoline carboxylic acid and intermediate using same |
-
1980
- 1980-05-27 US US06/152,991 patent/US4317827A/en not_active Expired - Lifetime
-
1981
- 1981-05-20 NZ NZ197155A patent/NZ197155A/xx unknown
- 1981-05-21 IL IL62929A patent/IL62929A0/xx unknown
- 1981-05-21 AU AU70901/81A patent/AU7090181A/en not_active Abandoned
- 1981-05-22 GB GB8115762A patent/GB2076815B/en not_active Expired
- 1981-05-22 FI FI811576A patent/FI811576L/fi not_active Application Discontinuation
- 1981-05-25 ZA ZA19813474A patent/ZA813474B/xx unknown
- 1981-05-25 PT PT73083A patent/PT73083B/pt unknown
- 1981-05-26 FR FR8110481A patent/FR2483233A1/fr active Granted
- 1981-05-26 NL NL8102582A patent/NL8102582A/nl not_active Application Discontinuation
- 1981-05-26 NO NO811783A patent/NO811783L/no unknown
- 1981-05-26 CA CA000378281A patent/CA1161440A/en not_active Expired
- 1981-05-26 BE BE1/10237A patent/BE888963A/fr not_active IP Right Cessation
- 1981-05-26 ES ES502493A patent/ES502493A0/es active Granted
- 1981-05-26 DE DE19813120954 patent/DE3120954A1/de not_active Withdrawn
- 1981-05-26 SE SE8103325A patent/SE8103325L/xx unknown
- 1981-05-26 IT IT21967/81A patent/IT1137232B/it active
- 1981-05-26 DK DK229881A patent/DK229881A/da not_active Application Discontinuation
- 1981-05-27 LU LU83396A patent/LU83396A1/fr unknown
- 1981-05-27 AT AT0238481A patent/ATA238481A/de not_active Application Discontinuation
- 1981-05-27 AR AR285465A patent/AR228155A1/es active
- 1981-05-27 JP JP8071181A patent/JPS5711965A/ja active Pending
- 1981-09-29 FR FR8118336A patent/FR2489147A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DE3120954A1 (de) | 1982-02-04 |
| FR2483233A1 (fr) | 1981-12-04 |
| ZA813474B (en) | 1982-06-30 |
| ES8203844A1 (es) | 1982-04-01 |
| GB2076815B (en) | 1984-05-23 |
| DK229881A (da) | 1981-11-28 |
| JPS5711965A (en) | 1982-01-21 |
| AR228155A1 (es) | 1983-01-31 |
| BE888963A (fr) | 1981-11-26 |
| IL62929A0 (en) | 1981-07-31 |
| ES502493A0 (es) | 1982-04-01 |
| IT8121967A0 (it) | 1981-05-26 |
| FR2489147A1 (fr) | 1982-03-05 |
| FI811576L (fi) | 1981-11-28 |
| ATA238481A (de) | 1984-01-15 |
| SE8103325L (sv) | 1981-11-28 |
| GB2076815A (en) | 1981-12-09 |
| LU83396A1 (fr) | 1982-01-20 |
| NL8102582A (nl) | 1981-12-16 |
| PT73083A (en) | 1981-06-01 |
| FR2483233B1 (ja) | 1984-06-15 |
| US4317827A (en) | 1982-03-02 |
| IT1137232B (it) | 1986-09-03 |
| NZ197155A (en) | 1983-11-18 |
| CA1161440A (en) | 1984-01-31 |
| AU7090181A (en) | 1981-12-03 |
| PT73083B (en) | 1982-07-05 |
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