NO803911L - 3-acylamino-5-(pyridinyl)-2(1h)-pyridinoner og fremgangsmaate til fremstilling derav - Google Patents
3-acylamino-5-(pyridinyl)-2(1h)-pyridinoner og fremgangsmaate til fremstilling deravInfo
- Publication number
- NO803911L NO803911L NO803911A NO803911A NO803911L NO 803911 L NO803911 L NO 803911L NO 803911 A NO803911 A NO 803911A NO 803911 A NO803911 A NO 803911A NO 803911 L NO803911 L NO 803911L
- Authority
- NO
- Norway
- Prior art keywords
- pyridinyl
- pyridinone
- acid
- acyl
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 24
- 125000002252 acyl group Chemical group 0.000 claims abstract description 12
- -1 2-acetoxypropanoyl Chemical group 0.000 claims abstract description 9
- 239000012458 free base Substances 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 17
- TTWBWFIZXPABQE-UHFFFAOYSA-N [1-oxo-1-[(2-oxo-5-pyridin-4-yl-1h-pyridin-3-yl)amino]propan-2-yl] acetate Chemical compound N1C(=O)C(NC(=O)C(OC(C)=O)C)=CC(C=2C=CN=CC=2)=C1 TTWBWFIZXPABQE-UHFFFAOYSA-N 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
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- 239000000203 mixture Substances 0.000 description 8
- ALSFHERXNZCXOY-UHFFFAOYSA-N 3-oxo-n-(2-oxo-5-pyridin-4-yl-1h-pyridin-3-yl)butanamide Chemical compound N1C(=O)C(NC(=O)CC(=O)C)=CC(C=2C=CN=CC=2)=C1 ALSFHERXNZCXOY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 210000003540 papillary muscle Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
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- 230000003177 cardiotonic effect Effects 0.000 description 5
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000001746 atrial effect Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 3
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- 238000006243 chemical reaction Methods 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
- 239000012043 crude product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 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 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 2
- QBKPCIBWNCIMFR-UHFFFAOYSA-N 2-hydroxy-n-(2-oxo-5-pyridin-4-yl-1h-pyridin-3-yl)acetamide Chemical compound N1C(=O)C(NC(=O)CO)=CC(C=2C=CN=CC=2)=C1 QBKPCIBWNCIMFR-UHFFFAOYSA-N 0.000 description 2
- LHWAVCJDVQZDFB-UHFFFAOYSA-N 3-amino-5-pyridin-3-yl-1h-pyridin-2-one Chemical compound N1C(=O)C(N)=CC(C=2C=NC=CC=2)=C1 LHWAVCJDVQZDFB-UHFFFAOYSA-N 0.000 description 2
- ILNCTSNICWCSFX-UHFFFAOYSA-N 3-oxo-n-(2-oxo-5-pyridin-3-yl-1h-pyridin-3-yl)butanamide Chemical compound N1C(=O)C(NC(=O)CC(=O)C)=CC(C=2C=NC=CC=2)=C1 ILNCTSNICWCSFX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- UGPVJKBUVLXYON-UHFFFAOYSA-N [2-oxo-2-[(2-oxo-5-pyridin-4-yl-1h-pyridin-3-yl)amino]ethyl] acetate Chemical compound N1C(=O)C(NC(=O)COC(=O)C)=CC(C=2C=CN=CC=2)=C1 UGPVJKBUVLXYON-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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000000496 cardiotonic agent Substances 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 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
- 238000001704 evaporation Methods 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
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- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 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
- 239000000463 material Substances 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 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
- 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 1
- OTIZLYDEBSAMGZ-UHFFFAOYSA-N 3-amino-5-pyridin-2-yl-1h-pyridin-2-one Chemical class N1C(=O)C(N)=CC(C=2N=CC=CC=2)=C1 OTIZLYDEBSAMGZ-UHFFFAOYSA-N 0.000 description 1
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- 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
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 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
- RCLXKQDHQBWEBJ-UHFFFAOYSA-N [1-oxo-1-[(2-oxo-5-pyridin-3-yl-1h-pyridin-3-yl)amino]propan-2-yl] acetate Chemical compound N1C(=O)C(NC(=O)C(OC(C)=O)C)=CC(C=2C=NC=CC=2)=C1 RCLXKQDHQBWEBJ-UHFFFAOYSA-N 0.000 description 1
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- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
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- 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
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/106,764 US4271168A (en) | 1979-12-26 | 1979-12-26 | Selected 3-acylamino-5-[4(or 3)-pyridinyl]-2(1H)-pyridinones |
Publications (1)
Publication Number | Publication Date |
---|---|
NO803911L true NO803911L (no) | 1981-06-29 |
Family
ID=22313122
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO803911A NO803911L (no) | 1979-12-26 | 1980-12-22 | 3-acylamino-5-(pyridinyl)-2(1h)-pyridinoner og fremgangsmaate til fremstilling derav |
Country Status (25)
Country | Link |
---|---|
US (1) | US4271168A (es) |
JP (1) | JPS56103164A (es) |
KR (1) | KR830004291A (es) |
AR (1) | AR230435A1 (es) |
AT (1) | AT373876B (es) |
AU (1) | AU6556680A (es) |
BE (1) | BE886766A (es) |
CA (1) | CA1131231A (es) |
DE (1) | DE3048635A1 (es) |
DK (1) | DK550480A (es) |
ES (1) | ES498144A0 (es) |
FI (1) | FI803973L (es) |
FR (1) | FR2472563A1 (es) |
GB (1) | GB2066251B (es) |
IE (1) | IE50523B1 (es) |
IL (1) | IL61690A (es) |
IT (1) | IT1134860B (es) |
LU (1) | LU83032A1 (es) |
NL (1) | NL8006824A (es) |
NO (1) | NO803911L (es) |
NZ (1) | NZ195878A (es) |
PH (1) | PH15974A (es) |
PT (1) | PT72264B (es) |
SE (1) | SE8009134L (es) |
ZA (1) | ZA807864B (es) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS587411A (ja) * | 1981-07-07 | 1983-01-17 | Mitsui Toatsu Chem Inc | 薄肉射出成形用プロピレン/エチレン共重合体の製造方法 |
US4432979A (en) * | 1981-10-26 | 1984-02-21 | William H. Rorer, Inc. | Pyridone compounds |
BE896678A (fr) * | 1982-05-18 | 1983-11-07 | Sandoz Sa | Nouveaux derives de la 2 (1h)-pyridinone, leur preparation et leur utilisation comme medicaments. |
IT8367883A0 (it) * | 1982-08-23 | 1983-08-22 | Rorer Int Overseas | Composti cardiotonici del 2 piridone 5 biciclico eteroaril sostituito e relative composizioni farmaceutiche |
US4666913A (en) * | 1985-11-22 | 1987-05-19 | William H. Rorer, Inc. | Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses |
US8101770B2 (en) | 2004-12-16 | 2012-01-24 | Vertex Pharmaceuticals Incorporated | Pyridones useful as inhibitors of kinases |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
-
1979
- 1979-12-26 US US06/106,764 patent/US4271168A/en not_active Expired - Lifetime
-
1980
- 1980-12-11 IL IL61690A patent/IL61690A/xx unknown
- 1980-12-12 IE IE2619/80A patent/IE50523B1/en unknown
- 1980-12-16 NL NL8006824A patent/NL8006824A/nl not_active Application Discontinuation
- 1980-12-17 ZA ZA00807864A patent/ZA807864B/xx unknown
- 1980-12-18 PH PH25005A patent/PH15974A/en unknown
- 1980-12-18 NZ NZ195878A patent/NZ195878A/xx unknown
- 1980-12-19 FI FI803973A patent/FI803973L/fi not_active Application Discontinuation
- 1980-12-19 BE BE1/10084A patent/BE886766A/fr not_active IP Right Cessation
- 1980-12-19 AU AU65566/80A patent/AU6556680A/en not_active Abandoned
- 1980-12-22 PT PT72264A patent/PT72264B/pt unknown
- 1980-12-22 IT IT26876/80A patent/IT1134860B/it active
- 1980-12-22 NO NO803911A patent/NO803911L/no unknown
- 1980-12-22 FR FR8027218A patent/FR2472563A1/fr active Pending
- 1980-12-23 SE SE8009134A patent/SE8009134L/xx not_active Application Discontinuation
- 1980-12-23 CA CA367,452A patent/CA1131231A/en not_active Expired
- 1980-12-23 LU LU83032A patent/LU83032A1/fr unknown
- 1980-12-23 AR AR283770A patent/AR230435A1/es active
- 1980-12-23 AT AT0629380A patent/AT373876B/de not_active IP Right Cessation
- 1980-12-23 GB GB8041225A patent/GB2066251B/en not_active Expired
- 1980-12-23 DE DE19803048635 patent/DE3048635A1/de not_active Withdrawn
- 1980-12-23 DK DK550480A patent/DK550480A/da not_active Application Discontinuation
- 1980-12-24 KR KR1019800004918A patent/KR830004291A/ko unknown
- 1980-12-24 ES ES498144A patent/ES498144A0/es active Granted
- 1980-12-26 JP JP18947780A patent/JPS56103164A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
LU83032A1 (fr) | 1981-07-23 |
NL8006824A (nl) | 1981-07-16 |
ES8201136A1 (es) | 1981-12-01 |
FI803973L (fi) | 1981-06-27 |
SE8009134L (sv) | 1981-06-27 |
DK550480A (da) | 1981-06-27 |
ATA629380A (de) | 1983-07-15 |
IE50523B1 (en) | 1986-04-30 |
BE886766A (fr) | 1981-06-19 |
ZA807864B (en) | 1981-12-30 |
PH15974A (en) | 1983-05-11 |
PT72264B (en) | 1981-11-05 |
CA1131231A (en) | 1982-09-07 |
IL61690A (en) | 1983-11-30 |
DE3048635A1 (de) | 1981-09-17 |
GB2066251B (en) | 1983-10-19 |
FR2472563A1 (fr) | 1981-07-03 |
ES498144A0 (es) | 1981-12-01 |
IT1134860B (it) | 1986-08-20 |
PT72264A (en) | 1981-01-01 |
AU6556680A (en) | 1981-07-02 |
KR830004291A (ko) | 1983-07-09 |
IE802619L (en) | 1981-06-26 |
JPS56103164A (en) | 1981-08-18 |
IT8026876A0 (it) | 1980-12-22 |
IL61690A0 (en) | 1981-01-30 |
GB2066251A (en) | 1981-07-08 |
US4271168A (en) | 1981-06-02 |
AR230435A1 (es) | 1984-04-30 |
NZ195878A (en) | 1982-11-23 |
AT373876B (de) | 1984-02-27 |
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