3,4-dihydro-1-(4-piperidyl)-2(1H)-quinoline hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,4-dihydro-1-(4-piperidyl)-2(1H)-quinoline hydrochloride
• 英文别名: 1-(4-Piperidinyl)-3,4-dihydrocarbostyril hydrochloride；1-(4-Piperidyl)-1,2,3,4-tetrahydro-2-quinolinone hydrochloride；1-piperidin-4-yl-3,4-dihydroquinolin-2-one;hydrochloride
• 化学式: C₁₄H₁₈N₂O*ClH
• 分子量: 266.771
• InChiKey: JMLZUWGVEHXDLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1-(4-piperidyl)-2(1H)-quinoline hydrochloride 在 硫酸 、 potassium carbonate 、 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 15.5h， 生成 N-[3-[4-[[4-(3,4-二氢-2-氧代-1(2H)-喹啉基)-1-哌啶基]羰基]苯氧基]丙基]乙酰胺
  参考文献：
  名称：

  Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihydro-2(1H)-quinolinones

  摘要：

  A series of compounds has been synthesized and demonstrated to be antagonists of V1 receptors both in vitro and in vivo. These compounds are structurally related to the 1-(4-piperidyl)-2(1H)-quinolinones, including OPC-21268, an orally bioavailable AVP V1 antagonist with high V1 specificity. It has been found that the introduction of an acetamide group on the terminal alkoxy chain of 41-44 leads to an increase in oral activity. Certain of these compounds may have efficacy in the study of AVP V1 receptors.

  DOI：

  10.1021/jm00066a010
• 作为产物：
  描述：

  二氢肉桂酰胺 在 platinum(IV) oxide 、 palladium on activated charcoal 盐酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 3,4-dihydro-1-(4-piperidyl)-2(1H)-quinoline hydrochloride
  参考文献：
  名称：

  Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihydro-2(1H)-quinolinones

  摘要：

  A series of compounds has been synthesized and demonstrated to be antagonists of V1 receptors both in vitro and in vivo. These compounds are structurally related to the 1-(4-piperidyl)-2(1H)-quinolinones, including OPC-21268, an orally bioavailable AVP V1 antagonist with high V1 specificity. It has been found that the introduction of an acetamide group on the terminal alkoxy chain of 41-44 leads to an increase in oral activity. Certain of these compounds may have efficacy in the study of AVP V1 receptors.

  DOI：

  10.1021/jm00066a010

文献信息

• [EN] BICYCLIC DERIVATIVES FOR USE IN THE TREATMENT OF ANDROGEN RECEPTOR ASSOCIATED CONDITIONS<br/>[FR] DÉRIVÉS BICYCLIQUES DESTINÉS À ÊTRE UTILISÉS DANS LE TRAITEMENT D'AFFECTIONS ASSOCIÉES AU RÉCEPTEUR DES ANDROGÈNES
  申请人：ASTRAZENECA AB

  公开号：WO2009081197A1

  公开（公告）日：2009-07-02

  The invention concerns bicyclic compounds of Formula (I), wherein the integers X1, X2, X3, Ring A, R4, R5 and m are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of androgen-receptor associated conditions.

  该发明涉及式(I)的双环化合物，其中整数X1、X2、X3、环A、R4、R5和m的定义如描述中所示。本发明还涉及制备这些化合物的方法、含有它们的药物组合物以及它们在制备用于预防或治疗雄激素受体相关疾病的药物中的应用。
• Carbostyril oxytocin receptor antagonists
  申请人：Merck & Co., Inc.

  公开号：US05356904A1

  公开（公告）日：1994-10-18

  A method of inhibiting oxytocin from acting at its receptor site by administering oxytocin receptor antagonist compounds of the formula ##STR1## wherein X is oxygen or sulfur; Y is hydrogen or lower alkyl; R.sup.A is ##STR2##

  通过给予公式为##STR1##的催产素受体拮抗剂化合物，抑制催产素在其受体位点的作用方法。其中X为氧或硫；Y为氢或较低的烷基；R.sup.A为##STR2##
• Carbostyril derivatives and pharmaceutical composition containing the
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US05300513A1

  公开（公告）日：1994-04-05

  Novel carbostyril derivatives of the formula: ##STR1## wherein X is 0 or S; Y is H or alkyl; R.sup.A is a group of the ##STR2## wherein n is 1 or 2, A is alkylene, R.sup.1 is benzoyl having optionally 1-3 substituents, R.sup.2A is ##STR3## is (i) alkoxy, (ii) substituted or unsubstituted 5- or 6-membered heterocylic group, (iii) alkenylthio, (iv) pyrrolidinyl-alkyl--S--, (v) pyrrolidinyl-alkyl--SO--, (vi) pyrrolidinyl-alkyl--SO.sub.2 --, (vii) --O--B--NR.sup.4 R.sup.5 [B is alkylene having optionally OH, R.sup.4 is H, R.sup.5 is tricyclo[3.3.1.1]decanyl, tricyclo[3.3.1.1]decanylalkyl, etc., or R.sup.4 and R.sup.5 may together form a group of ##STR4## (R.sup.6 is substituted or unsubstituted amino)] or (viii) substituted alkoxy; m is 1 to 3]}, which have excellent vasopressin antagonistic activities and are useful as vasodilator, hypotensive agent, water diuretics, platelet agglutination inhibitor, and a vasopressin antagonistic composition containing the compound as the active ingredient.

  化合物的结构式为：##STR1## 其中X为0或S；Y为H或烷基；R.sup.A为##STR2##中的一种基团其中n为1或2，A为烷基，R.sup.1为具有可选1-3个取代基的苯甲酰基，R.sup.2A为##STR3##是(i)烷氧基，(ii)取代或未取代的5-或6-成员杂环基团，(iii)烯基硫，(iv)吡咯烷基-烷基--S--，(v)吡咯烷基-烷基--SO--，(vi)吡咯烷基-烷基--SO.sub.2 --，(vii)--O--B--NR.sup.4 R.sup.5 [B为烷基，可选OH，R.sup.4为H，R.sup.5为三环[3.3.1.1]癸基，三环[3.3.1.1]癸基烷基等，或R.sup.4和R.sup.5可以共同形成##STR4##的基团（R.sup.6为取代或未取代的氨基）}或(viii)取代烷氧基；m为1到3。这些化合物具有出色的抗加压素活性，可用作扩血管剂、降压剂、利尿剂、抑制血小板凝聚剂以及含有该化合物作为活性成分的抗加压素组合物。
• BICYCLIC DERIVATIVES FOR USE IN THE TREATMENT OF ANDROGEN RECEPTOR ASSOCIATED CONDITIONS-155
  申请人：Bradbury Robert Hugh

  公开号：US20100016279A1

  公开（公告）日：2010-01-21

  The invention concerns bicyclic compounds of Formula I wherein the integers X 1 , X 2 , X 3 , Ring A, R 4 , R 5 and m are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of androgen-receptor associated conditions.

  本发明涉及公式I的双环化合物，其中整数X1、X2、X3、环A、R4、R5和m如描述中所定义。本发明还涉及制备这种化合物的方法、包含它们的制药组合物以及它们在制造用于预防或治疗与雄激素受体相关疾病的药物中的应用。
• Bicyclic derivatives for use in the treatment of androgen receptor associated conditions-155
  申请人：AstraZeneca AB

  公开号：US08003649B2

  公开（公告）日：2011-08-23

  The invention concerns bicyclic compounds of Formula I wherein the integers X1, X2, X3, Ring A, R4, R5 and m are as defined in the description. The present invention also relates to processes for the preparation of such compounds, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of androgen-receptor associated conditions.

  本发明涉及式I的双环化合物，其中整数X1、X2、X3、环A、R4、R5和m的定义如描述中所述。本发明还涉及制备此类化合物的方法、含有它们的制药组合物以及它们在制造用于预防或治疗雄激素受体相关疾病的药物中的应用。