3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine | 181283-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine
• 英文别名: methyl 3-amino-5-chloro-thieno[3,2-b]pyridine-2-carboxylate；3-Amino-5-chlorothieno[3,2-b]pyridine-2-carboxylic acid methyl ester；methyl 3-amino-5-chlorothieno[3,2-b]pyridine-2-carboxylate
• CAS: 181283-58-9
• 化学式: C₉H₇ClN₂O₂S
• 分子量: 242.686
• InChiKey: WYGHRSSHGYFGQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine 在 potassium tert-butylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 23.25h， 生成 6-Methoxy-2-[2-(6-methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-4H-9-thia-2,4,5-triaza-fluorene-1,3-dione
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)

  摘要：

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

  DOI：

  10.1021/jm990567u
• 作为产物：
  描述：

  3-chloro-2-cyanopyridine-N-oxide 在 sodium methylate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 3-amino-2-carbomethoxy-5-chlorothieno[3,2-b]pyridine
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)

  摘要：

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

  DOI：

  10.1021/jm990567u

文献信息

• Tricyclic substituted hexahydrobenz [e]isoindole alpha-1 adrenergic
  申请人：Abbott Laboratories

  公开号：US05597823A1

  公开（公告）日：1997-01-28

  The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a tricyclic heterocyclic ring system; which is an .alpha.-1 adrenergic antagonist and is useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 receptors and treating BPH.

  本发明涉及一种具有以下结构的化合物##STR1##及其药用可接受的盐，其中W是一个三环杂环环系统；它是一种α-1肾上腺素受体拮抗剂，对治疗BPH有用；还公开了α-1拮抗剂组合物和拮抗α-1受体并治疗BPH的方法。
• Benzopyranopyrrole and benzopyranopyridine .alpha.-1 adenergic compounds
  申请人：Abbott Laboratories

  公开号：US05891882A1

  公开（公告）日：1999-04-06

  The present invention relates to a compound of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are .alpha.-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are .alpha.-1 antagonist compositions and a method for antagonizing .alpha.-1 adrenoreceptors and tr

  这项发明涉及一种具有以下结构的化合物##STR1##及其药用可接受的盐，其中W是一个双环杂环环系统。这些化合物是α-1肾上腺素受体拮抗剂，对于治疗BPH很有用；还披露了α-1拮抗剂组合物和拮抗α-1肾上腺素受体的方法。
• 3-phenylpyrrolidine alpha-1 adrenergic compounds
  申请人：Abbott Laboratories

  公开号：US06133275A1

  公开（公告）日：2000-10-17

  Compounds having the formula are .alpha..sub.1 adrenoreceptor antagonists. Processes for making these compounds, synthetic intermediates employed in these processes and a method for inhibiting .alpha..sub.1 adrenoreceptors and treating benign prostatic hyperplasia (also called benign prostatic hypertrophy or BPH) and other urological diseases such as BOO (bladder outlet obstruction), neurogenic bladder and gynecological syndromes such as dysmenorrhea are disclosed.

  具有该化学式的化合物是α1肾上腺素受体拮抗剂。本文揭示了制备这些化合物的方法、用于这些方法的合成中间体，以及一种抑制α1肾上腺素受体、治疗良性前列腺增生（也称为良性前列腺肥大或BPH）以及其他泌尿系统疾病，如膀胱出口梗阻（BOO）、神经源性膀胱和妇科综合症，如痛经的方法。
• [EN] BENZOPYRANOPYRROLE AND BENZOPYRANOPYRIDINE ALPHA-1 ADRENERGIC COMPOUNDS<br/>[FR] COMPOSES ALPHA-1 ADRENERGIQUES A BASE DE BENZOPYRANOPYRROLE ET DE BENZOPYRANOPYRIDINE
  申请人：ABBOTT LABORATORIES

  公开号：WO1998024791A1

  公开（公告）日：1998-06-11

  (EN) The present invention relates to a compound of formula (I) and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are $g(a)-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are $g(a)-1 antagonist compositions and a method for antagonizing $g(a)-1 adrenoreceptors and treating BPH.(FR) La présente invention concerne un composé de la formule (I) ainsi que les sels de celui-ci, acceptables sur le plan pharmacologique. Dans cette formule W représente un système de noyau hétérocyclique bicyclique. Ces composés sont des antagonistes $g(a)-1 adrénergiques et ils sont utiles dans le traitement de l'hyperplasie prostatique bénigne. L'invention concerne également des compositions antagonistes $g(a)-1 adrénergiques ainsi qu'un procédé destiné à antagoniser les adrénorécepteurs $g(a)-1 et à traiter l'hyperplasie prostatique bénigne.

  本发明涉及一种公式(I)的化合物及其药学上可接受的盐，其中W是一个双环杂环环系统。这些化合物是$g(a)-1肾上腺素受体拮抗剂，可用于治疗BPH；还披露了$g(a)-1拮抗剂组合物和拮抗$g(a)-1肾上腺素受体和治疗BPH的方法。
• [EN] 3-PHENYLPYRROLE ALPHA-1 ADRENERGIC COMPOUNDS<br/>[FR] COMPOSES DE 3-PHENYLPYRROLE [ALPHA-1]-ADRENERGIQUES
  申请人：ABBOTT LABORATORIES

  公开号：WO1999057122A1

  公开（公告）日：1999-11-11

  (EN) Compounds having formula (I) are $g(a)1 adrenoreceptor antagonists. Processes for making these compounds, synthetic intermediates employed in these processes and a method for inhibiting $g(a)1 adrenoreceptors and treating benign prostatic hyperplasia (also called benign prostatic hypertrophy or BPH) and other urological diseases such as BOO (bladder outlet obstruction), neurogenic bladder and gynecological syndromes such as dysmenorrhea are disclosed.(FR) L'invention concerne des composés de la formule (I) qui sont des antagonistes de l'adrénorécepteur alpha-1. On décrit des procédés de production desdits composés, des intermédiaires synthétiques utilisés dans lesdits procédés et un procédé d'inhibition des adrénorécepteurs alpha-1 et de traitement de l'hyperplasie prostatique bénigne (également appelée hypertrophie prostatique ou BPH) ou d'autres maladies urologiques, telles que l'obstruction à la sortie de la vessie (BOO), la vessie neurogène ou les syndromes gynécologiques comme la dysménorrhée.

  化学式为（I）的化合物是$g(a)1肾上腺素受体拮抗剂。公开了制备这些化合物的过程、用于这些过程的合成中间体以及一种抑制$g(a)1肾上腺素受体和治疗良性前列腺增生（也称良性前列腺肥大或BPH）和其他泌尿系统疾病，如膀胱出口梗阻（BOO）、神经源性膀胱和妇科综合症，如痛经的方法。