5-<4-(hydroxymethyl)phenyl>-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine | 131833-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 5-<4-(hydroxymethyl)phenyl>-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine
• 英文别名: 5-(p-hydroxymethylphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine；[4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)phenyl]methanol
• CAS: 131833-71-1
• 化学式: C₁₄H₁₆N₂O
• 分子量: 228.294
• InChiKey: HNWGYDJRCZATGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-<4-(hydroxymethyl)phenyl>-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 60.0 ℃ 、275.79 kPa 条件下， 反应 4.0h， 以63%的产率得到5-(4-methylphenyl)-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine hydrochloride
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038
• 作为产物：
  描述：

  5-<4-(ethoxycarbonyl)phenyl>-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以95%的产率得到5-<4-(hydroxymethyl)phenyl>-5,6,7,8-tetrahydroimidazo<1,5-a>pyridine
  参考文献：
  名称：

  Fadrozole hydrochloride: a potent, selective, nonsteroidal inhibitor of aromatase for the treatment of estrogen-dependent disease

  摘要：

  A new class of potent, selective, nonsteroidal inhibitors of aromatase have been discovered. The most potent member of this series is fadrozole hydrochloride, CGS 16949 A, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile monohydrochloride, 26a. In addition, the 6,7-dihydropyrrolo[1,2-c]imidazole (21a) and the 6,7,8,9-tetrahydroimidazo[1,5-a]azepine (21b) analogues were synthesized and evaluated. CGS 16949 A's ability to selectively inhibit aromatase (IC50 = 4.5nM) over other cytochrome P-450 enzymes and suppress estrogen production when administered orally make it a suitable candidate to test the potential of an aromatase inhibitor in estrogen-dependent diseases including breast cancer.

  DOI：

  10.1021/jm00106a038

文献信息

• Substituted imidazo[5-a]pyridine derviatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US05428160A1

  公开（公告）日：1995-06-27

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidised etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidised etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3, or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明涉及一种式子I的化合物：##STR1## 其中R.sub.1代表氢，低烷基，取代的低烷基，硝基，卤素，自由的，醚化或酯化的羟基，自由的，醚化，氧化醚化或酯化的巯基，未取代的，单取代或双取代的氨基，铵离子，自由的或功能修饰的磺酸基，自由的或功能修饰的甲酰基，C.sub.2-C.sub.20-酰基，氰基，自由的或功能修饰的羧基；R.sub.2代表氢，低烷基，取代的低烷基，卤素；自由的，醚化或酯化的羟基；自由的，醚化，氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基；其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，而R.sub.1和R.sub.2如上述式I中所定义，并且它们的盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；这些化合物用于治疗响应于例如哺乳动物中的芳香化酶抑制的情况的用途；制备这些化合物的过程和中间体。
• Substituted imidazo[1,5-A]pyridine derivatives and other substituted
  申请人：Ciba-Geigy Corporation

  公开号：US04728645A1

  公开（公告）日：1988-03-01

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidized etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 -C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidized etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明揭示了式I的化合物：##STR1## 其中R.sub.1代表氢、低碳基、取代的低碳基、硝基、卤素、自由、醚化或酯化的羟基、自由、醚化、氧化醚化或酯化的巯基、未取代的、单取代或双取代的氨基、铵离子、自由或功能修饰的磺酸基、自由或功能修饰的甲酰基、C.sub.2-C.sub.20酰基、氰基、自由或功能修饰的羧基；R.sub.2代表氢、低碳基、取代的低碳基、卤素；自由、醚化或酯化的羟基；自由、醚化、氧化醚化或酯化的巯基；自由或功能修饰的羧基或酰基。其7,8-二氢衍生物；以及式I*的化合物：##STR2## 其中n表示0、1、2、3或4，R.sub.1和R.sub.2如上所述，以及其盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；使用这些化合物治疗对哺乳动物的芳香化酶抑制等反应性疾病的方法；制备这些化合物的过程和中间体。
• Substituted imidazo[1,5-a]pyridine derivatives and other substituted
  申请人：Ciba-Geigy Corp.

  公开号：US04889861A1

  公开（公告）日：1989-12-26

  Disclosed are compounds of formula I ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl, substituted lower alkyl, nitro, halogen, free, etherified or esterified hydroxy, free, etherified, oxidized etherified or esterified mercapto, unsubstituted, mono- or disubstituted amino, ammonio, free or functionally modified sulfo, free or functionally modified formyl, C.sub.2 --C.sub.20 -acyl, cyano, free or functionally modified carboxy; and R.sub.2 represents hydrogen, lower alkyl, substituted lower alkyl, halogen; free, etherified or esterified hydroxy; free, etherified, oxidized etherified or esterified mercapto; free or functionally modified carboxy, or acyl; the 7,8-dihydro derivatives thereof; and compounds of the formula I* ##STR2## wherein n denotes 0, 1, 2, 3 or 4, and R.sub.1 and R.sub.2 are as defined above under formula I and salts thereof; e.g. as aromatase inhibitors; pharmaceutical compositions containing these compounds; the use of these compounds for the treatment of conditions responsive to e.g. aromatase inhibition in mammals; processes and intermediates for preparing these compounds.

  本发明涉及式I的化合物，其中R.sub.1代表氢、低烷基、取代的低烷基、硝基、卤素、自由、醚化或酯化羟基、自由、醚化、氧化醚化或酯化巯基、未取代的、单取代或双取代的氨基、铵离子、自由或功能修饰的磺酸基、自由或功能修饰的甲酰基、C.sub.2-C.sub.20酰基、氰基、自由或功能修饰的羧基；R.sub.2代表氢、低烷基、取代的低烷基、卤素；自由、醚化或酯化羟基；自由、醚化、氧化醚化或酯化巯基；自由或功能修饰的羧基或酰基；其7,8-二氢衍生物；以及式I*的化合物，其中n表示0、1、2、3或4，R.sub.1和R.sub.2在式I下定义，以及它们的盐；例如作为芳香化酶抑制剂；含有这些化合物的制药组合物；这些化合物用于治疗哺乳动物对芳香化酶抑制等条件的用途；以及制备这些化合物的过程和中间体。
• Verwendung von bicyclischen Imidazol-Verbindungen zur Behandlung von Hyperaldosteronismus
  申请人：CIBA-GEIGY AG

  公开号：EP0366609A2

  公开（公告）日：1990-05-02

  Die Erfindung betrifft die Verwendung von gewissen bicyclischen Imidazol-­Verbindungen, wie 5-(p-Cyanphenyl)-5,6,7,8-tetrahydroimidazo[1,5-a]-­pyridin, oder pharmazeutisch verwendbaren, nicht-toxischen Salzen davon zur Behandlung von Hyperaldosteronismus, bzw. ein Verfahren zur Behand­lung von Hyperaldosteronismus unter Verwendung von solchen Verbindungen, bzw. die Verwendung dieser Verbindungen zur Herstellung von pharmazeu­tischen Präparaten für die Behandlung von Hyperaldosteronismus.

  本发明涉及某些双环咪唑化合物，如5-(对氰基苯基)-5,6,7,8-四氢咪唑并[1,5-a]-吡啶，或其药学上可接受的无毒盐用于治疗高醛固酮症，或使用此类化合物治疗高醛固酮症的方法，或使用这些化合物制造治疗高醛固酮症的药物组合物。
• Aromatase inhibition to enhance assisted reproduction
  申请人：ARES TRADING S.A.

  公开号：EP1759734A2

  公开（公告）日：2007-03-07

  The use of at least one aromatase inhibitor in the production of a medicament for improving the implantation and pregnancy rates for a female undergoing assisted reproduction treatment, which comprises one or more daily doses of an aromatase inhibitor (Al) for administration during assisted reproduction cycles or ovarian stimulation cycles, wherein the doses of AI are selected from amounts effective to reduce serum estradiol levels. Also disclosed are related pharmaceutical preparations and packages.

  使用至少一种芳香化酶抑制剂生产一种药物，用于提高接受辅助生殖治疗的女性的着床率和妊娠率，该药物包括一种或多种每日剂量的芳香化酶抑制剂（Al），用于在辅助生殖周期或卵巢刺激周期期间给药，其中AI的剂量选自有效降低血清雌二醇水平的量。还公开了相关的药物制剂和包装。