NO812334L - Pyridinylaminofenoler og fremgangsmaate til deres fremstilling - Google Patents
Pyridinylaminofenoler og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO812334L NO812334L NO812334A NO812334A NO812334L NO 812334 L NO812334 L NO 812334L NO 812334 A NO812334 A NO 812334A NO 812334 A NO812334 A NO 812334A NO 812334 L NO812334 L NO 812334L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- phenol
- amino
- nitro
- acid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 15
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 4-pyridinyl Chemical group 0.000 claims description 20
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
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- 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 6
- SPSLZQIUSAWHDY-UHFFFAOYSA-N 2-amino-3-pyridin-4-ylphenol Chemical compound NC1=C(O)C=CC=C1C1=CC=NC=C1 SPSLZQIUSAWHDY-UHFFFAOYSA-N 0.000 description 6
- QVXZQQXMAMYIQG-UHFFFAOYSA-N 2-nitro-5-pyridin-4-ylphenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC(C=2C=CN=CC=2)=C1 QVXZQQXMAMYIQG-UHFFFAOYSA-N 0.000 description 6
- BAXUDFGPSPDCDR-UHFFFAOYSA-N 4-amino-3-pyridin-4-ylphenol Chemical compound NC1=CC=C(O)C=C1C1=CC=NC=C1 BAXUDFGPSPDCDR-UHFFFAOYSA-N 0.000 description 6
- GSNNORMGUIGVTQ-UHFFFAOYSA-N 4-nitro-3-pyridin-4-ylphenol Chemical compound OC1=CC=C([N+]([O-])=O)C(C=2C=CN=CC=2)=C1 GSNNORMGUIGVTQ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 210000003540 papillary muscle Anatomy 0.000 description 6
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- RMRJKEJNNLMCGQ-UHFFFAOYSA-N 2-amino-5-pyridin-4-ylphenol Chemical compound C1=C(O)C(N)=CC=C1C1=CC=NC=C1 RMRJKEJNNLMCGQ-UHFFFAOYSA-N 0.000 description 5
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- 239000003054 catalyst Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
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- 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 4
- DANMQSWQAGVFKV-UHFFFAOYSA-N 4-pyridin-4-ylphenol Chemical compound C1=CC(O)=CC=C1C1=CC=NC=C1 DANMQSWQAGVFKV-UHFFFAOYSA-N 0.000 description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000003177 cardiotonic effect Effects 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
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- 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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- YTJQJGKMRLQBJP-UHFFFAOYSA-N 3-pyridin-3-ylaniline Chemical compound NC1=CC=CC(C=2C=NC=CC=2)=C1 YTJQJGKMRLQBJP-UHFFFAOYSA-N 0.000 description 3
- DKFDPLVNPGJNDE-UHFFFAOYSA-N 4-pyridin-3-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=CN=C1 DKFDPLVNPGJNDE-UHFFFAOYSA-N 0.000 description 3
- GKVYVZSNXXTOMQ-UHFFFAOYSA-N 4-pyridin-4-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=NC=C1 GKVYVZSNXXTOMQ-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 230000001746 atrial effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
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- WBTDXGPMWXJHNB-UHFFFAOYSA-N 2-amino-4-pyridin-2-ylphenol Chemical compound C1=C(O)C(N)=CC(C=2N=CC=CC=2)=C1 WBTDXGPMWXJHNB-UHFFFAOYSA-N 0.000 description 2
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- 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 2
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- MCXDTTWQSLJBRA-UHFFFAOYSA-N 3-(2,5-dimethylpyridin-4-yl)phenol Chemical compound C1=NC(C)=CC(C=2C=C(O)C=CC=2)=C1C MCXDTTWQSLJBRA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XWDDSYXASTTYHW-UHFFFAOYSA-N 3-(2,6-diethylpyridin-4-yl)phenol Chemical compound CCC1=NC(CC)=CC(C=2C=C(O)C=CC=2)=C1 XWDDSYXASTTYHW-UHFFFAOYSA-N 0.000 description 2
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- KTNHGZTYCDIWJS-UHFFFAOYSA-N 2-nitro-4-pyridin-3-ylphenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1C1=CC=CN=C1 KTNHGZTYCDIWJS-UHFFFAOYSA-N 0.000 description 1
- DVNJLYRUWKEWGU-UHFFFAOYSA-N 2-nitro-5-pyridin-3-ylphenol Chemical compound C1=C([N+]([O-])=O)C(O)=CC(C=2C=NC=CC=2)=C1 DVNJLYRUWKEWGU-UHFFFAOYSA-N 0.000 description 1
- XTHJCITVHCRQRD-UHFFFAOYSA-N 2-phenylpyridin-3-amine Chemical class NC1=CC=CN=C1C1=CC=CC=C1 XTHJCITVHCRQRD-UHFFFAOYSA-N 0.000 description 1
- HPDNGBIRSIWOST-UHFFFAOYSA-N 2-pyridin-2-ylphenol Chemical class OC1=CC=CC=C1C1=CC=CC=N1 HPDNGBIRSIWOST-UHFFFAOYSA-N 0.000 description 1
- YQZGQXPHGLAEHA-UHFFFAOYSA-N 2-pyridin-2-ylquinoline Chemical class N1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 YQZGQXPHGLAEHA-UHFFFAOYSA-N 0.000 description 1
- DLPSVGYGFVGBJX-UHFFFAOYSA-N 3-(2,3-dimethylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=NC=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1C DLPSVGYGFVGBJX-UHFFFAOYSA-N 0.000 description 1
- ZKEDJJZTQXBGAV-UHFFFAOYSA-N 3-(2,5-dimethylpyridin-4-yl)-2-nitrophenol Chemical compound C1=NC(C)=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1C ZKEDJJZTQXBGAV-UHFFFAOYSA-N 0.000 description 1
- UMNNQUSPGMCOIW-UHFFFAOYSA-N 3-(2,6-diethylpyridin-4-yl)-2-nitrophenol Chemical compound CCC1=NC(CC)=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1 UMNNQUSPGMCOIW-UHFFFAOYSA-N 0.000 description 1
- QVXLSCRBDQLVEN-UHFFFAOYSA-N 3-(2,6-dimethylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=NC(C)=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1 QVXLSCRBDQLVEN-UHFFFAOYSA-N 0.000 description 1
- LPSJKZSFDIMNDD-UHFFFAOYSA-N 3-(2-ethylpyridin-4-yl)-2-nitrophenol Chemical compound C1=NC(CC)=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1 LPSJKZSFDIMNDD-UHFFFAOYSA-N 0.000 description 1
- UKHWYVBXKGJKID-UHFFFAOYSA-N 3-(2-methylpyridin-4-yl)-2-nitrophenol Chemical compound C1=NC(C)=CC(C=2C(=C(O)C=CC=2)[N+]([O-])=O)=C1 UKHWYVBXKGJKID-UHFFFAOYSA-N 0.000 description 1
- KJEUQHGUFMJMMK-UHFFFAOYSA-N 3-(3-methylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=CN=CC=C1C1=CC=CC(O)=C1[N+]([O-])=O KJEUQHGUFMJMMK-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
- BDSBSHZVSVKIHM-UHFFFAOYSA-N 3-pyridin-4-ylaniline Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1 BDSBSHZVSVKIHM-UHFFFAOYSA-N 0.000 description 1
- MSQOVCGRDXRTHY-UHFFFAOYSA-N 5-(2,3-dimethylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=NC=CC(C=2C=C(O)C(=CC=2)[N+]([O-])=O)=C1C MSQOVCGRDXRTHY-UHFFFAOYSA-N 0.000 description 1
- BTHUHWCJEAXPCB-UHFFFAOYSA-N 5-(2,6-diethylpyridin-4-yl)-2-nitrophenol Chemical compound CCC1=NC(CC)=CC(C=2C=C(O)C(=CC=2)[N+]([O-])=O)=C1 BTHUHWCJEAXPCB-UHFFFAOYSA-N 0.000 description 1
- LQDQJTRWPAEIPI-UHFFFAOYSA-N 5-(2,6-dimethylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=NC(C)=CC(C=2C=C(O)C(=CC=2)[N+]([O-])=O)=C1 LQDQJTRWPAEIPI-UHFFFAOYSA-N 0.000 description 1
- AHNSULBHGLGAAH-UHFFFAOYSA-N 5-(2-ethylpyridin-4-yl)-2-nitrophenol Chemical compound C1=NC(CC)=CC(C=2C=C(O)C(=CC=2)[N+]([O-])=O)=C1 AHNSULBHGLGAAH-UHFFFAOYSA-N 0.000 description 1
- MGFCGQOFIQIJMB-UHFFFAOYSA-N 5-(2-methylpyridin-4-yl)-2-nitrophenol Chemical compound C1=NC(C)=CC(C=2C=C(O)C(=CC=2)[N+]([O-])=O)=C1 MGFCGQOFIQIJMB-UHFFFAOYSA-N 0.000 description 1
- UDHWNSJMVUEMND-UHFFFAOYSA-N 5-(3-methylpyridin-4-yl)-2-nitrophenol Chemical compound CC1=CN=CC=C1C1=CC=C([N+]([O-])=O)C(O)=C1 UDHWNSJMVUEMND-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 229930182843 D-Lactic acid Natural products 0.000 description 1
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 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
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920002472 Starch Polymers 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
- 229930006000 Sucrose Natural products 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 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
- 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
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 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
- 229910052742 iron Inorganic materials 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 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
- WCKATDWEMRLBLE-UHFFFAOYSA-N n-(4-pyridin-2-ylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=CC=N1 WCKATDWEMRLBLE-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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000802 nitrating effect Effects 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
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000005245 right atrium Anatomy 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 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
- 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
- 239000001117 sulphuric acid Substances 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
- 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
- 229960001367 tartaric acid Drugs 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/170,896 US4297363A (en) | 1980-07-21 | 1980-07-21 | 2-Amino-3(4 or 5)-(pyridinyl)phenols and their use as cardiotonics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO812334L true NO812334L (no) | 1982-01-22 |
Family
ID=22621724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO812334A NO812334L (no) | 1980-07-21 | 1981-07-09 | Pyridinylaminofenoler og fremgangsmaate til deres fremstilling |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4297363A (fr) |
| JP (1) | JPS5742672A (fr) |
| AR (1) | AR230434A1 (fr) |
| AT (1) | ATA315781A (fr) |
| AU (1) | AU7284581A (fr) |
| BE (1) | BE889599A (fr) |
| CA (1) | CA1136632A (fr) |
| DE (1) | DE3128364A1 (fr) |
| DK (1) | DK317681A (fr) |
| ES (1) | ES504101A0 (fr) |
| FI (1) | FI812232L (fr) |
| FR (1) | FR2493313A1 (fr) |
| GB (1) | GB2080298B (fr) |
| GR (1) | GR74965B (fr) |
| IL (1) | IL63246A0 (fr) |
| IT (1) | IT1137293B (fr) |
| LU (1) | LU83498A1 (fr) |
| NL (1) | NL8103362A (fr) |
| NO (1) | NO812334L (fr) |
| NZ (1) | NZ197601A (fr) |
| PT (1) | PT73363B (fr) |
| SE (1) | SE431747B (fr) |
| ZA (1) | ZA814635B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5964376A (en) * | 1997-02-07 | 1999-10-12 | Kenosha; William J. | Inverted bottle support and dispenser apparatus and methods of making and using the same thereof |
| JP6896673B2 (ja) | 2018-03-23 | 2021-06-30 | 株式会社東芝 | 半導体装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753993A (en) * | 1971-05-17 | 1973-08-21 | Sterling Drug Inc | 1,4-dihydro-4-oxo-7-pyridyl-3-quinoline-carboxylic acid derivatives |
| US3907808A (en) * | 1971-05-17 | 1975-09-23 | Sterling Drug Inc | 1,4-Dihydro-4-oxo-7-pyridyl-3-quinolinecarboxylic acid derivatives |
-
1980
- 1980-07-21 US US06/170,896 patent/US4297363A/en not_active Expired - Lifetime
-
1981
- 1981-07-02 NZ NZ197601A patent/NZ197601A/xx unknown
- 1981-07-07 IL IL63246A patent/IL63246A0/xx unknown
- 1981-07-09 NO NO812334A patent/NO812334L/no unknown
- 1981-07-09 FR FR8113544A patent/FR2493313A1/fr not_active Withdrawn
- 1981-07-09 ZA ZA814635A patent/ZA814635B/xx unknown
- 1981-07-13 BE BE1/010269A patent/BE889599A/fr not_active IP Right Cessation
- 1981-07-13 GB GB8121529A patent/GB2080298B/en not_active Expired
- 1981-07-14 AU AU72845/81A patent/AU7284581A/en not_active Abandoned
- 1981-07-14 IT IT22931/81A patent/IT1137293B/it active
- 1981-07-14 PT PT73363A patent/PT73363B/pt unknown
- 1981-07-15 FI FI812232A patent/FI812232L/fi not_active Application Discontinuation
- 1981-07-15 NL NL8103362A patent/NL8103362A/nl not_active Application Discontinuation
- 1981-07-16 DK DK317681A patent/DK317681A/da not_active Application Discontinuation
- 1981-07-16 AT AT813157A patent/ATA315781A/de not_active Application Discontinuation
- 1981-07-17 SE SE8104433A patent/SE431747B/sv unknown
- 1981-07-17 DE DE19813128364 patent/DE3128364A1/de not_active Withdrawn
- 1981-07-17 JP JP56112058A patent/JPS5742672A/ja active Pending
- 1981-07-20 CA CA000382047A patent/CA1136632A/fr not_active Expired
- 1981-07-20 ES ES504101A patent/ES504101A0/es active Granted
- 1981-07-20 LU LU83498A patent/LU83498A1/fr unknown
- 1981-07-21 AR AR286156A patent/AR230434A1/es active
- 1981-08-13 GR GR65550A patent/GR74965B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8301923A1 (es) | 1983-01-01 |
| US4297363A (en) | 1981-10-27 |
| ES504101A0 (es) | 1983-01-01 |
| IT1137293B (it) | 1986-09-03 |
| IL63246A0 (en) | 1981-10-30 |
| GB2080298B (en) | 1984-01-18 |
| NZ197601A (en) | 1983-12-16 |
| PT73363A (en) | 1981-08-01 |
| AU7284581A (en) | 1982-01-28 |
| DE3128364A1 (de) | 1982-07-15 |
| SE8104433L (sv) | 1982-01-22 |
| PT73363B (en) | 1982-09-23 |
| AR230434A1 (es) | 1984-04-30 |
| NL8103362A (nl) | 1982-02-16 |
| SE431747B (sv) | 1984-02-27 |
| DK317681A (da) | 1982-01-22 |
| ZA814635B (en) | 1982-07-28 |
| GR74965B (fr) | 1984-07-12 |
| CA1136632A (fr) | 1982-11-30 |
| GB2080298A (en) | 1982-02-03 |
| JPS5742672A (en) | 1982-03-10 |
| ATA315781A (de) | 1984-02-15 |
| BE889599A (fr) | 1982-01-13 |
| FR2493313A1 (fr) | 1982-05-07 |
| LU83498A1 (fr) | 1982-02-17 |
| FI812232L (fi) | 1982-01-22 |
| IT8122931A0 (it) | 1981-07-14 |
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