5-乙酰基-2-乙氧基烟酸 | 335078-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-乙酰基-2-乙氧基烟酸
• 英文名称: 5-acetyl-2-ethoxynicotinic acid
• 英文别名: 5-acetyl-2-ethoxypyridine-3-carboxylic acid
• CAS: 335078-23-4
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: QXTWBDGHBJEDID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-乙酰基-2-乙氧基烟酸 在 caesium carbonate 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 3-[4-{[(5-acetyl-2-ethoxy-3-pyridinyl)carbonyl]amino}-3-(aminocarbonyl)-5-propyl-1H-pyrazol-1-yl]-1-azetidinecarboxylate
  参考文献：
  名称：

  A Novel Series of Potent and Selective PDE5 Inhibitors with Potential for High and Dose-Independent Oral Bioavailability

  摘要：

  Sildenafil ( 5-[ 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl) phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[ 4,3-d] pyrimidin-7-one), a potent and selective phosphodiesterase type 5 ( PDE5) inhibitor, provided the first oral treatment for male erectile dysfunction. The objective of the work reported in this paper was to combine high levels of PDE5 potency and selectivity with high and dose-independent oral bioavailability, to minimize the impact on the C-max of any interactions with coadministered drugs in the clinic. This goal was achieved through identification of a lower clearance series with a high absorption profile, by replacing the 5'-piperazine sulfonamide in the sildenafil template with a 5'-methyl ketone. This novel series provided compounds with low metabolism in human hepatocytes, excellent caco-2 flux, and the potential for good aqueous solubility. The in vivo oral and iv pharmacokinetic profiles of example compounds confirmed the high oral bioavailability predicted from these in vitro screens. 5-( 5-Acetyl-2-butoxy-3-pyridinyl)-3-ethyl-2-( 1-ethyl-3-azetidinyl)-2,6-dihydro-7H-pyrazolo[ 4,3-d] pyrimidin-7-one ( 2) was selected for progression into the clinic.

  DOI：

  10.1021/jm060113e
• 作为产物：
  描述：

  5-溴-2-乙氧基烟酸 、 乙烯基正丁醚 在 palladium diacetate 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙腈 为溶剂， 反应 38.0h， 以63%的产率得到5-乙酰基-2-乙氧基烟酸
  参考文献：
  名称：

  Pyrazolopyrimidine derivatives

  摘要：

  本发明提供了一个式（I）的化合物：其中Q是一个式的基团：这些化合物抑制环鸟苷3',5'-磷酸二酯酶（cGMP PDEs）。更重要的是，这些化合物是强效且选择性地抑制类型5环鸟苷3',5'-磷酸二酯酶，并因此在多种治疗领域中具有用途。特别是，目前的化合物对于治疗哺乳动物性功能障碍具有价值。

  公开号：

  EP1241170A3

文献信息

• Pyrazolopyrimidine derivatives
  申请人：Pfizer Limited

  公开号：EP1241170A3

  公开（公告）日：2003-03-12

  The present invention provides a compound of formula (I): where Q is a group of formula:These compounds inhibit cyclic guanosine 3',5'-monophosphate phosphodiesterases (cGMP PDEs). More notably, the compounds are potent and selective inhibitors of the type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases and have utility therefore in a variety of therapeutic areas. In particular, the present compounds are of value for the curative or prophylactic treatment of mammalian sexual disorders.

  本发明提供了一个式（I）的化合物：其中Q是一个式的基团：这些化合物抑制环鸟苷3',5'-磷酸二酯酶（cGMP PDEs）。更重要的是，这些化合物是强效且选择性地抑制类型5环鸟苷3',5'-磷酸二酯酶，并因此在多种治疗领域中具有用途。特别是，目前的化合物对于治疗哺乳动物性功能障碍具有价值。
• Process for the preparation of pyrazolo[4,3-d]pyrimidin-7-ones and intermediates thereof
  申请人：Pfizer Limited

  公开号：EP1176147A1

  公开（公告）日：2002-01-30

  A process is provided for the preparation of compounds of formula (I) herein comprising reacting a compound of formula (II), (III), (IV) or (V) in the presence of -OR3 and a hydroxide trapping agent or in the case of compounds of formula (IV) reacting in the presence of an auxiliary base and a hydroxide trapping agent (i.e. -OR3 is substituted by the auxiliary base), wherein X is a leaving group and R1 to R4 are as defined.

  提供一种用于制备式（I）化合物的方法，包括在-OR3和氢氧化物捕获剂的存在下，反应式（II）、（III）、（IV）或（V）化合物，或者在辅助碱和氢氧化物捕获剂的存在下反应式（IV）化合物（即-OR3被辅助碱取代），其中X是离去基团，R1至R4如所定义。
• Process for the preparation of pyrazolo[4,3-d]pyrimidin-7-one compounds and intermediates thereof
  申请人：——

  公开号：US20020038024A1

  公开（公告）日：2002-03-28

  A process is provided for the preparation of compounds of formula (I) herein comprising reacting a compound of formula (II), (III), (IV) or (V) in the presence of − OR 3 and a hydroxide trapping agent or in the case of compounds of formula (IV) reacting in the presence of an auxiliary base and a hydroxide trapping agent (i.e. − OR 3 is substituted by the auxiliary base), wherein X is a leaving group and R 1 to R 4 are as defined.

  提供一种制备式(I)化合物的方法，包括在−OR3和羟基捕捉剂的存在下，反应式(II)、(III)、(IV)或(V)的化合物，或在式(IV)化合物的情况下，在辅助碱和羟基捕捉剂的存在下反应(即−OR3被辅助碱取代)，其中X是离去基团，R1到R4如定义。
• [EN] 5-(2-SUBSTITUTED-5-HETEROCYCLYLSULPHONYLPYRID-3-YL)-DIHYDROPYRAZOLO[4,3-D]PYRIMIDIN-7-ONES AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] PYRIMIDINE-7-ONES 5-(2-SUBSTITUTEES-5-HETEROCYCLYLSULPHONYLPYRIDE-3-YL)-DIHYDROPYRAZOLO[4,3-D] SERVANT D'INHIBITEURS DE LA PHOSPHODIESTERASE
  申请人：PFIZER LTD

  公开号：WO2001027112A1

  公开（公告）日：2001-04-19

  There is provided compounds of formula (I) wherein R?1, R2, R3, R4¿ and X have meanings given in the description, which are useful in the curative and prophylactic treatment of a medical condition for which inhibition of a cyclic guanosine 3',5'-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.

  提供了式（I）的化合物，其中R?1，R2，R3，R4¿和X具有在说明中给出的含义，这些化合物在治疗和预防需要抑制环磷酸鸟苷3'，5'-单磷酸磷酸二酯酶（例如cGMP PDE5）的医疗状况中是有用的。
• Pharmaceutically active compounds
  申请人：Maw Nigel Graham

  公开号：US20050107412A1

  公开（公告）日：2005-05-19

  The present invention provides a compound of formula (I): where Q is a group of formula: These compounds inhibit cyclic guanosine 3′,5′-monophosphate phosphodiesterases (cGMP PDEs). More notably, the compounds are potent and selective inhibitors of the type 5 cyclic guanosine 3′,5′-monophosphate phosphodiesterases and have utility therefore in a variety of therapeutic areas. In particular, the present compounds are of value for the curative or prophylactic treatment of mammalian sexual disorders.

  本发明提供了一种公式（I）的化合物：其中Q是公式的一个基团：这些化合物抑制环状鸟苷酸3′，5′-单磷酸磷酸二酯酶（cGMP PDEs）。更值得注意的是，这些化合物是强效和选择性的第5型环状鸟苷酸3′，5′-单磷酸磷酸二酯酶抑制剂，因此在各种治疗领域中具有实用价值。特别地，本化合物对哺乳动物性功能障碍的治疗或预防具有价值。