N-(3-Cyclopentyloxy-4-methoxy-phenylacetyl)-2-hydroxy-5-chloroaniline | 179314-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-Cyclopentyloxy-4-methoxy-phenylacetyl)-2-hydroxy-5-chloroaniline
• 英文别名: N-(3-cyclopentyloxy-4-methoxyphenylacetyl)-2-hydroxy-5-chloroaniline；N-(5-chloro-2-hydroxyphenyl)-2-(3-cyclopentyloxy-4-methoxyphenyl)acetamide
• CAS: 179314-63-7
• 化学式: C₂₀H₂₂ClNO₄
• 分子量: 375.852
• InChiKey: MNRCRSYCRIHKDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氯丙烯 、 N-(3-Cyclopentyloxy-4-methoxy-phenylacetyl)-2-hydroxy-5-chloroaniline 在 乙酸乙酯 、 甲醇 作用下， 以 乙醇 、 sodium hydroxide 、 甲醇 、 水 为溶剂， 反应 8.0h， 以gave 56.4 g (65%) of the title compound, mp 75-76.5° C.的产率得到N-(3-Cyclopentyloxy-4-methoxyphenyl-acetyl)-2-allyloxy-5-chloroaniline
  参考文献：
  名称：

  Substituted benzoxazoles

  摘要：

  本发明揭示了一种有效的PDE IV抑制剂新化合物。与茶碱或罗利帕姆相比，这些化合物具有更好的PDE IV抑制效果，并且在与PDE III抑制方面具有更好的选择性。

  公开号：

  US05665737A1
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 4-氯-2-氨基苯酚 、 2-(3-cyclopentyloxy-4-methoxyphenyl)acetic acid 以 二氯甲烷 、 水 为溶剂， 以10.7 grams (71%)的产率得到N-(3-Cyclopentyloxy-4-methoxy-phenylacetyl)-2-hydroxy-5-chloroaniline
  参考文献：
  名称：

  Pheynl or benzyl-substituted rolipram-based compounds for and method of

  摘要：

  含有苯基或苄基取代基的Rolipram基PDE IV抑制剂的化学式为：##STR1## 其中X.sub.1和X.sub.2可以相同或不同，且每个都是O或S；R.sub.1选自氢、饱和或不饱和的直链或支链C.sub.2-12烷基、含有3-10个碳原子的环烷基和环烷基-烷基基团；R.sub.2 = R.sub.1或-CH.sub.3；R.sub.3是氢、卤素或饱和或不饱和的直链或支链C.sub.1-12烷基、含有3-7个碳原子的环烷基或环烷基-烷基基团；Z是选择自-CH.sub.2CONH-或-CH.sub.2NHCO-的连接；R.sub.4是苯基或苄基，可以是未取代或取代有一个或多个卤素原子、烷基、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺、取代或未取代的氨基、含有3-10个碳原子的环烷基和环烷基-烷基基团、芳基或芳基-烷基基团，优选含有约6-10个碳原子的杂环基团，其环中含有氮、氧或硫；烷基、烷氧基、环烷基、环烷基-烷基、芳基和芳基-烷基基团是饱和或不饱和的，未取代或取代有卤素原子、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺或取代或未取代的氨基，或一个或多个具有1-3个碳原子的低烷基；但R.sub.4不能取代有多于一个甲氧基。与茶碱或Rolipram相比，具有更好的PDE III抑制选择性。还公开了含有该化合物的制药组合物和治疗方法。

  公开号：

  US05591776A1

文献信息

• Pheynl or benzyl-substituted rolipram-based compounds for and method of
  申请人：Euro-Celtique, S.A.

  公开号：US05591776A1

  公开（公告）日：1997-01-07

  Rolipram-based PDE IV inhibitors containing phenyl- or benzyl-substituted moieties of the formula: ##STR1## wherein X.sub.1 and X.sub.2 may be the same or different and each is O or S; R.sub.1 is selected from the group consisting of hydrogen, saturated or unsaturated straight-chain or branched C.sub.2-12 alkyl groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety; R.sub.2 =R.sub.1 or --CH.sub.3 ; R.sub.3 is hydrogen, halogen, or a saturated or unsaturated straight-chain or branched C.sub.1-12 alkyl group, a cycloalkyl or cycloalkyl-alkyl groups containing from 3 to 7 carbon atoms in the cycloalkyl moiety; Z is a linkage selected from --CH.sub.2 CONH-- or --CH.sub.2 NHCO--, and R.sub.4 is a phenyl or benzyl which may be unsubstituted or substituted with one or more halogen atoms, alkyl groups, hydroxyl groups, cyano groups, carboxyl groups, alkoxy groups, alkoxycarbonyl, amido, carboxamido, substituted or unsubstituted amino groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety, aryl or aralkyl groups preferably containing from about 6 to about 10 carbon atoms, or heterocyclic groups containing nitrogen, oxygen or sulfur in the ring; the alkyl, alkoxy, cycloalkyl, cycloalkylalkyl, aryl, and aryl-alkyl groups being saturated or unsaturated, unsubstituted or substituted by halogen atoms, hydroxyl groups, cyano groups, carboxyl groups, alkoxy groups, alkoxycarbonyl, carboxamido or substituted or unsubstituted amino groups, or one or more lower alkyl groups having from 1 to 3 carbon atoms; provided that R.sub.4 cannot be substituted with more than one methoxy group. compared to theophylline or rolipram as well as with improved selectivity with regard to PDE III inhibition. Pharmaceutical compositions containing the same and methods of treatment are also disclosed.

  含有苯基或苄基取代基的Rolipram基PDE IV抑制剂的化学式为：##STR1## 其中X.sub.1和X.sub.2可以相同或不同，且每个都是O或S；R.sub.1选自氢、饱和或不饱和的直链或支链C.sub.2-12烷基、含有3-10个碳原子的环烷基和环烷基-烷基基团；R.sub.2 = R.sub.1或-CH.sub.3；R.sub.3是氢、卤素或饱和或不饱和的直链或支链C.sub.1-12烷基、含有3-7个碳原子的环烷基或环烷基-烷基基团；Z是选择自-CH.sub.2CONH-或-CH.sub.2NHCO-的连接；R.sub.4是苯基或苄基，可以是未取代或取代有一个或多个卤素原子、烷基、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺、取代或未取代的氨基、含有3-10个碳原子的环烷基和环烷基-烷基基团、芳基或芳基-烷基基团，优选含有约6-10个碳原子的杂环基团，其环中含有氮、氧或硫；烷基、烷氧基、环烷基、环烷基-烷基、芳基和芳基-烷基基团是饱和或不饱和的，未取代或取代有卤素原子、羟基、氰基、羧基、烷氧基、烷氧羰基、酰胺、羧酰胺或取代或未取代的氨基，或一个或多个具有1-3个碳原子的低烷基；但R.sub.4不能取代有多于一个甲氧基。与茶碱或Rolipram相比，具有更好的PDE III抑制选择性。还公开了含有该化合物的制药组合物和治疗方法。
• Substituted benzoxazoles
  申请人：Euro-Celtique, S.A.

  公开号：US05665737A1

  公开（公告）日：1997-09-09

  Novel compounds which are effective PDE IV inhibitors are disclosed. The compounds possess improved PDE IV inhibition as compared to theophylline or rolipram, with improved selectivity with regard to, e.g., PDE III inhibition.

  本发明揭示了一种有效的PDE IV抑制剂新化合物。与茶碱或罗利帕姆相比，这些化合物具有更好的PDE IV抑制效果，并且在与PDE III抑制方面具有更好的选择性。
• Heterocyclic compounds for inhibiting phosphodiesterase IV
  申请人：Euro-Celtique, S.A.

  公开号：US05889014A1

  公开（公告）日：1999-03-30

  Novel compounds which are effective PDE IV inhibitors are disclosed. The compounds have the formula: ##STR1## wherein: R.sub.1 and R.sub.2 may be the same or different and each is selected from the group consisting of hydrogen, saturated or unsaturated straight-chain or branched C.sub.1-12 alkyl groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety; R.sub.3 is hydrogen, halogen, or a saturated or unsaturated straight-chain or branched C.sub.1-12 alkyl group, a cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 7 carbon atoms in the cycloalkyl moiety; R.sub.4 is a phenyl or benzyl or a 6-membered heteroaryl which may be unsubstituted or substituted with one or more halogen atoms, alkyl groups, nitro groups, hydroxyl groups, cyano groups, carboxyl groups, alkoxy group, alkoxycarbonyl, amido, carboxamido, substituted or unsubstituted amino groups, cycloalkyl and cycloalkyl-alkyl groups containing from 3 to 10 carbon atoms in the cycloalkyl moiety, aryl or aralkyl groups preferably containing from about 6 to about 10 carbon atoms, or heterocyclic groups containing nitrogen, oxygen or sulfur in the ring; said alkyl, cycloalkyl, cycloalkyl-alkyl, aryl, and arylalkyl groups being unsubstituted or substituted by halogen atoms, hydroxyl groups, cyano groups, carboxyl groups, alkoxy groups, alkoxycarbonyl, carboxamido or substituted or unsubstituted amino groups, or one or more lower alkyl groups having from 1 to 3 carbon atoms; Z is selected from the group consisting of --CH.sub.2 CO--, --NHCH.sub.2 --, --CH.sub.2 NH--, --CH.sub.2 CONH--, --CH.sub.2 NHCO--, --CH.sub.2 COCH.sub.2 --, --COCH.sub.2 --, --C(.dbd.NOC(.dbd.O)NHQ)--, and --C(.dbd.NQ)NH--; X.sub.1 and X.sub.2 may be the same or different and each is O or S; wherein Q is R.sub.4 or hydrogen except that when Z.dbd.C(.dbd.NOCONHQ)--, R.sub.4 is not benzyl and R.sub.1 and R.sub.2 are both not hydrogen.

  揭示了有效的PDE IV抑制剂的新化合物。该化合物具有以下结构式：##STR1## 其中：R.sub.1和R.sub.2可以相同或不同，且每个都选自氢，饱和或不饱和的直链或支链C.sub.1-12烷基，含有3至10个碳原子的环烷基和环烷基-烷基基团；R.sub.3是氢，卤素或饱和或不饱和的直链或支链C.sub.1-12烷基，含有3至7个碳原子的环烷基和环烷基-烷基基团；R.sub.4是苯基或苄基或一个6元杂环，可以是未取代或取代有一个或多个卤素原子，烷基，硝基，羟基，氰基，羧基，烷氧基，烷氧羰基，酰胺，羧酰胺，取代或未取代氨基，含有3至10个碳原子的环烷基和环烷基-烷基基团，芳基或芳基烷基基团，最好含有约6至10个碳原子，或含有氮，氧或硫的杂环基团；所述的烷基，环烷基，环烷基-烷基，芳基和芳基烷基基团可以未取代或取代有卤素原子，羟基，氰基，羧基，烷氧基，烷氧羰基，酰胺或取代或未取代的氨基基团，或具有1至3个碳原子的一个或多个较低烷基基团；Z选自--CH.sub.2 CO--，--NHCH.sub.2 --，--CH.sub.2 NH--，--CH.sub.2 CONH--，--CH.sub.2 NHCO--，--CH.sub.2 COCH.sub.2 --，--COCH.sub.2 --，--C(.dbd.NOC(.dbd.O)NHQ)--和--C(.dbd.NQ)NH--的群；X.sub.1和X.sub.2可以相同或不同，且每个都是O或S；其中Q是R.sub.4或氢，但当Z.dbd.C(.dbd.NOCONHQ)--时，R.sub.4不是苄基，且R.sub.1和R.sub.2都不是氢。
• US06153630
  申请人：——

  公开号：——

  公开（公告）日：——
• NOVEL BENZOXAZOLES
  申请人：Euroceltique S.A.

  公开号：EP0785927A1

  公开（公告）日：1997-07-30