CN105175326B - 5‑甲基‑2(1h)吡啶酮衍生物及其制备方法和用途 - Google Patents
5‑甲基‑2(1h)吡啶酮衍生物及其制备方法和用途 Download PDFInfo
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- CN105175326B CN105175326B CN201510511401.8A CN201510511401A CN105175326B CN 105175326 B CN105175326 B CN 105175326B CN 201510511401 A CN201510511401 A CN 201510511401A CN 105175326 B CN105175326 B CN 105175326B
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- pyridone
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- NZASCBIBXNPDMH-UHFFFAOYSA-N 3,3-diethyl-1H-pyridine-2,4-dione Chemical class CCC1(CC)C(=O)NC=CC1=O NZASCBIBXNPDMH-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 8
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- -1 methoxyl group Chemical group 0.000 claims description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- SOHMZGMHXUQHGE-UHFFFAOYSA-N 5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1 SOHMZGMHXUQHGE-UHFFFAOYSA-N 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 13
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- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical class CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
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- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
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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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters 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
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (12)
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5362729A (en) * | 1991-09-19 | 1994-11-08 | Farmitalia Carlo Erba S.R.L. | Dihydropyridine derivatives useful in antitumor therapy |
CN1386737A (zh) * | 2002-06-11 | 2002-12-25 | 中南大学湘雅医学院 | 抗纤维化吡啶酮药物及其生产工艺方法 |
CN102786467A (zh) * | 2012-08-15 | 2012-11-21 | 浙江省医学科学院 | 一种n-取代芳基吡啶酮化合物及其制备方法和应用 |
CN103159671A (zh) * | 2011-12-09 | 2013-06-19 | 康普药业股份有限公司 | 一种规模化制备盐酸乐卡地平的方法 |
WO2014159343A1 (en) * | 2013-03-14 | 2014-10-02 | Celtaxsys, Inc. | Method of stimulating immune cell migration |
-
2015
- 2015-08-19 CN CN201510511401.8A patent/CN105175326B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5362729A (en) * | 1991-09-19 | 1994-11-08 | Farmitalia Carlo Erba S.R.L. | Dihydropyridine derivatives useful in antitumor therapy |
CN1386737A (zh) * | 2002-06-11 | 2002-12-25 | 中南大学湘雅医学院 | 抗纤维化吡啶酮药物及其生产工艺方法 |
CN103159671A (zh) * | 2011-12-09 | 2013-06-19 | 康普药业股份有限公司 | 一种规模化制备盐酸乐卡地平的方法 |
CN102786467A (zh) * | 2012-08-15 | 2012-11-21 | 浙江省医学科学院 | 一种n-取代芳基吡啶酮化合物及其制备方法和应用 |
WO2014159343A1 (en) * | 2013-03-14 | 2014-10-02 | Celtaxsys, Inc. | Method of stimulating immune cell migration |
Non-Patent Citations (1)
Title |
---|
Solvent-free, two-step synthesis of some unsymmetrical 4-aryl-1,4-dihydropyridines;Waldo H. Correa等;《Green Chemistry》;20011030(第3期);第296-301页 * |
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