2-n-butoxy-5-iodopyridine-3-carboxylic acid | 334490-71-0

• 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
• 英文名称: 2-n-butoxy-5-iodopyridine-3-carboxylic acid
• 英文别名: 2-n-butoxy-5-iodonicotinic acid；2-Butoxy-5-iodonicotinic Acid；5-Iodo-2-butoxynicotinic acid；2-butoxy-5-iodopyridine-3-carboxylic acid
• CAS: 334490-71-0
• 化学式: C₁₀H₁₂INO₃
• 分子量: 321.115
• InChiKey: GODXSVXXWPBSEV-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±42.0 °C(Predicted)
• 密度：
  1.683±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-n-butoxy-5-iodopyridine-3-carboxylic acid 在 吡啶 、 草酰氯 、 双(三甲基硅烷基)氨基钾 、 caesium carbonate 、 N,N-二甲基甲酰胺 、 正丁醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 5-(2-butoxy-5-iodo-3-pyridinyl)-3-ethyl-2-[2-(4-morpholinyl)ethyl]-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
  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：

  2-n-butoxypyridine-3-carboxylic acid 在 三氟乙酸酐 作用下， 以 乙酸乙酯 、 三氟乙酸 为溶剂， 以68%的产率得到2-n-butoxy-5-iodopyridine-3-carboxylic acid
  参考文献：
  名称：

  Pharmaceutically active compounds

  摘要：

  提供了化合物的结构式IA和结构式IB，其中R1、R2、R3、Het1和X的含义如描述中所示，这些化合物在治疗和预防需要抑制环状鸟苷3′,5′-单磷酸磷酸二酯酶（例如cGMP PDE5）的医疗状况方面是有用的。

  公开号：

  US06440982B1

文献信息

• [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。
• 2-(2-Alkoxy-5-heterocyclylsulphonylphenyl)purin-6-ones as phosphodiesterase inhibitors
  申请人：Pfizer Limited

  公开号：EP1092718A1

  公开（公告）日：2001-04-18

  There is provided compounds of formula IA and of formula IB, wherein R1, R2, R3, Het1 and X have meanings given in the description, which are useful in the curative and prophylactic treatment of medical conditions for which inhibition of a cyclic guanosine 3',5'-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.

  提供了式 IA 和式 IB 的化合物、 其中 R1、R2、R3、Het1 和 X 具有描述中给出的含义，可用于治疗和预防需要抑制环鸟苷-3',5'-单磷酸磷酸二酯酶（如 cGMP PDE5）的病症。
• BONE METABOLISM IMPROVING AGENTS
  申请人：The Nisshin OilliO, Ltd.

  公开号：EP1380293A1

  公开（公告）日：2004-01-14

  Compounds of general formula (I): wherein R1, R2, R3, R4, X, Y and A have the meanings given herein 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.

  通式(I)化合物： 其中 R1、R2、R3、R4、X、Y 和 A 具有本文给出的含义，这些化合物可用于治疗和预防需要抑制环鸟苷-3',5'-单磷酸磷酸二酯酶（如 cGMP PDE5）的病症。
• Imidazo[5,1-f][1,2,4]triazine derivatives
  申请人：Pfizer Limited

  公开号：EP1092719B1

  公开（公告）日：2003-05-28
• 5-(2-SUBSTITUTED-5-HETEROCYCLYLSULPHONYLPYRID-3-YL)-DIHYDROPYRAZOLO[4,3-D]PYRIMIDIN-7-ONES AS PHOSPHODIESTERASE INHIBITORS
  申请人：Pfizer Limited

  公开号：EP1222190A1

  公开（公告）日：2002-07-17