3-Amino-6-methyl-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetic Acid | 211489-99-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-Amino-6-methyl-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetic Acid
• 英文别名: 2-[3-amino-4-(benzenesulfonyl)-6-methyl-2-oxopyridin-1-yl]acetic acid
• CAS: 211489-99-5
• 化学式: C₁₄H₁₄N₂O₅S
• 分子量: 322.342
• InChiKey: FCMWXULMYUZJDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-aminomethyl-6-methylpyridin-2-ylamine hydrochloride 、 3-Amino-6-methyl-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetic Acid 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-Amino-4-benzenesulfonyl-6-methyl-2-oxo-2H-pyridin-1-yl)-N-(6-amino-2-methyl-pyridin-3-ylmethyl)-acetamide
  参考文献：
  名称：

  3-Amino-4-sulfonylpyridinone acetamide and related pyridothiadiazine thrombin inhibitors

  摘要：

  We describe a series of highly potent and efficacious thrombin inhibitors based on a 3-amino-4-sulfonylpyridinone acetamide template. The functionally dense sulfonyl group stabilizes the aminopyridinone, conformationally constrains the 4-substituent, and forms a hydrogen bond to the insertion loop tyrosine OH. We also describe a related series of fused bicyclic dihydrothiadiazinedioxide derivatives, of which one had improved pharmacokinetics in dogs after oral dosing. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00154-9
• 作为产物：
  描述：

  2-(苯磺酰基)-1,3-苯并噻唑 在 palladium on activated charcoal lithium hydroxide 、 sodium tetrahydroborate 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 生成 3-Amino-6-methyl-2-oxo-4-(phenylsulphonyl)-1,2-dihydropyridine-1-acetic Acid
  参考文献：
  名称：

  3-Amino-4-sulfonylpyridinone acetamide and related pyridothiadiazine thrombin inhibitors

  摘要：

  We describe a series of highly potent and efficacious thrombin inhibitors based on a 3-amino-4-sulfonylpyridinone acetamide template. The functionally dense sulfonyl group stabilizes the aminopyridinone, conformationally constrains the 4-substituent, and forms a hydrogen bond to the insertion loop tyrosine OH. We also describe a related series of fused bicyclic dihydrothiadiazinedioxide derivatives, of which one had improved pharmacokinetics in dogs after oral dosing. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00154-9

文献信息

• Pyridone derivatives, their preparation and their use as synthesis intermediates
  申请人：Sanofi-Synthelabo

  公开号：US06252082B1

  公开（公告）日：2001-06-26

  The invention concerns compounds of formula (I) in which: R is —NO2 or —NHR3, R3 being hydrogen, —COR4 (R4 selected among (C1-C4) alkyl, aryl and aryl (C1-C4) alkyl, —COOR5 (R5 selected among (C1-C4) alkyl and aryl (C1-C4) alkyl), —CONHR6 or SO2R6 (R6 selected among (C1-C5) alkyl, aryl and aryl(C1-C4) alkyl), —SO2NR7R8 (R7 and R8 independently of each other represent hydrogen or (C1-C4) alkyl or form with the nitrogen atom a morpholine group), aryl (C1-C4) alkyl, R1 is a (C1-C4) alkyl group linear or branched, cyclo (C3-C8) alkyl, aryl optionally substituted, aryl (C1-C4) alkyl optionally substituted, heteroaryl, R2 is a hydrogen atom, a (C1-C4) alkyl or arylmethyl group, X is an oxygen or sulphur atom, a —CH2—, —SO2 or —NR1— group and Y is a hydrogen atom or (C1-C6) alkyl. The invention is applicable to synthesis intermediates.

  该发明涉及式(I)的化合物，其中：R为—NO2或—NHR3，其中R3为氢，—COR4（R4在（C1-C4）烷基、芳基和芳基（C1-C4）烷基中选择），—COOR5（R5在（C1-C4）烷基和芳基（C1-C4）烷基中选择），—CONHR6或SO2R6（R6在（C1-C5）烷基、芳基和芳基（C1-C4）烷基中选择），—SO2NR7R8（R7和R8分别独立地代表氢或（C1-C4）烷基，或与氮原子形成吗啡环），芳基（C1-C4）烷基，R1为（C1-C4）直链或支链烷基，环（C3-C8）烷基，芳基可选取代，芳基（C1-C4）烷基可选取代，杂芳基，R2为氢原子，（C1-C4）烷基或芳基甲基基团，X为氧或硫原子，—CH2—、—SO2或—NR1—基团，Y为氢原子或（C1-C6）烷基。该发明适用于合成中间体。
• DERIVES DE PYRIDONE, LEUR PREPARATION ET LEUR UTILISATION COMME INTERMEDIAIRES DE SYNTHESE
  申请人：Sanofi-Synthélabo

  公开号：EP1019376A1

  公开（公告）日：2000-07-19
• US6252082B1
  申请人：——

  公开号：US6252082B1

  公开（公告）日：2001-06-26
• [EN] PYRIDONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS SYNTHESIS INTERMEDIATES<br/>[FR] DERIVES DE PYRIDONE, LEUR PREPARATION ET LEUR UTILISATION COMME INTERMEDIAIRES DE SYNTHESE
  申请人：SANOFI-SYNTHELABO

  公开号：WO1998031671A1

  公开（公告）日：1998-07-23

  (EN) The invention concerns compounds of formula (I) in which: R is -NO2 or -NHR3, R3 being hydrogen, -COR4 (R4 selected among (C1-C4) alkyl, aryl and aryl (C1-C4) alkyl, -COOR5 (R5 selected among (C1-C4) alkyl and aryl (C1-C4) alkyl), -CONHR6 or SO2R6 (R6 selected among (C1-C5) alkyl, aryl and aryl(C1-C4) alkyl), -SO2NR7R8 (R7 and R8 independently of each other represent hydrogen or (C1-C4) alkyl or form with the nitrogen atom a morpholine group), aryl (C1-C4) alkyl, R1 is a (C1-C4) alkyl group linear or branched, cyclo (C3-C8) alkyl, aryl optionally substituted, aryl (C1-C4) alkyl optionally substituted, heteroaryl, R2 is a hydrogen atom, a (C1-C4) alkyl or arylmethyl group, X is an oxygen or sulphur atom, a -CH2-, -SO2- or -NR1- group and Y is a hydrogen atom or (C1-C6) alkyl. The invention is applicable to synthesis intermediates.(FR) Composés de formule (I), où R est -NO2 ou -NHR3, R3 étant hydrogène, -COR4 (R4 choisi parmi (C1-C4)alkyle, aryle et aryl (C1-C4)alkyle), -COOR5 (R5 choisi parmi (C1-C4)alkyle et aryl (C1-C4)alkyle), -CONHR6 ou -SO2R6 (R6 choisi parmi (C1-C5)alkyle, aryle et aryl(C1-C4)alkyle), -SO2NR7R8 (R7 et R8 indépendamment l'un et l'autre hydrogène ou (C1-C4)alkyle ou forment avec l'atome d'azote un groupe morpholine), aryl(C1-C4)alkyle, R1 est un groupe (C1-C4)alkyle droit ou ramifié, cyclo (C3-C8)alkyle, aryle éventuellement substitué, aryl(C1-C4)alkyle éventuellement substitué, hétéroaryle, R2 est un atome d'hydrogène, un groupe (C1-C4)alkyle ou arylméthyle, X est un atome d'oxygène ou de soufre, un groupe -CH2-, -SO2- ou -NR1- et Y est un atome d'hydrogène ou (C1-C6)alkyle. Intermédiaires de synthèse.
• 3-Amino-4-sulfonylpyridinone acetamide and related pyridothiadiazine thrombin inhibitors
  作者：Philip E.J. Sanderson、Kellie J. Cutrona、Kelly L. Savage、Adel M. Naylor-Olsen、Denise J. Bickel、Dennis L. Bohn、Franklin C. Clayton、Julie A. Krueger、S.Dale Lewis、Bobby J. Lucas、Elizabeth A. Lyle、Audrey A. Wallace、Denice C. Welsh、Youwei Yan

  DOI：10.1016/s0960-894x(03)00154-9

  日期：2003.4

  We describe a series of highly potent and efficacious thrombin inhibitors based on a 3-amino-4-sulfonylpyridinone acetamide template. The functionally dense sulfonyl group stabilizes the aminopyridinone, conformationally constrains the 4-substituent, and forms a hydrogen bond to the insertion loop tyrosine OH. We also describe a related series of fused bicyclic dihydrothiadiazinedioxide derivatives, of which one had improved pharmacokinetics in dogs after oral dosing. (C) 2003 Elsevier Science Ltd. All rights reserved.