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3-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl)-propylamine | 166810-76-0

中文名称
——
中文别名
——
英文名称
3-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl)-propylamine
英文别名
3-(4-(ethoxycarbonyl)-4-phenylpiperidin-1-yl)propylamine;3-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl) propylamine;3-(4-ethoxycarbonyl-4-phenylpiperidin-1-yl)propylamine;ethyl 1-(3-aminopropyl)-4-phenylpiperidine-4-carboxylate
3-(4-Ethoxycarbonyl-4-phenylpiperidin-1-yl)-propylamine化学式
CAS
166810-76-0
化学式
C17H26N2O2
mdl
——
分子量
290.406
InChiKey
ZXJVTZPFQUNDQN-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    405.4±45.0 °C(Predicted)
  • 密度:
    1.067±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.9
  • 重原子数:
    21
  • 可旋转键数:
    7
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.59
  • 拓扑面积:
    55.6
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Design and Synthesis of Novel α1a Adrenoceptor-Selective Dihydropyridine Antagonists for the Treatment of Benign Prostatic Hyperplasia
    摘要:
    We report the synthesis and evaluation of novel alpha(1a) adrenoceptor subtype-selective antagonists. Systematic modification of the lipophilic 4,4-diphenylpiperidinyl moiety of the dihydropyridine derivatives 1 and 2 provided several highly selective and potent alpha(1a), antagonists. From this series, we identified the 4-(methoxycarbonyl)-4-phenylpiperidine analogue SNAP 5540 (-) [(-)-63] for further characterization. When examined in an isolated human prostate tissue assay, this compound was found to have a K-i of 2.8 nM, in agreement with the cloned human receptor binding data (K-i = 2.42 nM). Further evaluation of the compound in isolated dog prostate tissue showed a K-i of 3.6 nM and confirmed it to be a potent antagonist (K-b = 1.6 nM). In vivo, this compound effectively blocked the phenylephrine-stimulated increase in intraurethral pressure (IUP) in mongrel dogs, at doses which did not significantly affect the arterial pressure (diastolic blood pressure, DBP), with a DBP K-b/IUP K-b ratio of 16. In addition, (-)-63 also showed greater than 40 000-fold selectivity over the rat L-type calcium channel and 200-fold selectivity over several G protein-coupled receptors, including histamine and serotonin subtypes. These findings prove that alpha(1a) adrenoceptor-subtype selective antagonists such as (-)-63 may be developed as uroselective agents for an improved treatment of BPH over nonselective alpha(1) antagonists such as prazosin and terazosin, with fewer side effects.
    DOI:
    10.1021/jm980506g
  • 作为产物:
    描述:
    参考文献:
    名称:
    Design and Synthesis of Novel α1a Adrenoceptor-Selective Dihydropyridine Antagonists for the Treatment of Benign Prostatic Hyperplasia
    摘要:
    We report the synthesis and evaluation of novel alpha(1a) adrenoceptor subtype-selective antagonists. Systematic modification of the lipophilic 4,4-diphenylpiperidinyl moiety of the dihydropyridine derivatives 1 and 2 provided several highly selective and potent alpha(1a), antagonists. From this series, we identified the 4-(methoxycarbonyl)-4-phenylpiperidine analogue SNAP 5540 (-) [(-)-63] for further characterization. When examined in an isolated human prostate tissue assay, this compound was found to have a K-i of 2.8 nM, in agreement with the cloned human receptor binding data (K-i = 2.42 nM). Further evaluation of the compound in isolated dog prostate tissue showed a K-i of 3.6 nM and confirmed it to be a potent antagonist (K-b = 1.6 nM). In vivo, this compound effectively blocked the phenylephrine-stimulated increase in intraurethral pressure (IUP) in mongrel dogs, at doses which did not significantly affect the arterial pressure (diastolic blood pressure, DBP), with a DBP K-b/IUP K-b ratio of 16. In addition, (-)-63 also showed greater than 40 000-fold selectivity over the rat L-type calcium channel and 200-fold selectivity over several G protein-coupled receptors, including histamine and serotonin subtypes. These findings prove that alpha(1a) adrenoceptor-subtype selective antagonists such as (-)-63 may be developed as uroselective agents for an improved treatment of BPH over nonselective alpha(1) antagonists such as prazosin and terazosin, with fewer side effects.
    DOI:
    10.1021/jm980506g
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文献信息

  • 5-(heterocyclic alkyl)-6-aryl-dihydropyrimidines
    申请人:Synaptic Pharmaceutical Corporation
    公开号:US05942517A1
    公开(公告)日:1999-08-24
    This invention is directed to dihydropyrimidine compounds which are selective antagonists for human .alpha..sub.1C receptors and which have the structure: ##STR1## wherein A is aryl; R.sub.1, R.sub.2 and R.sub.3 are alkyl or heteroalkyl; R.sub.4 is heterocyclic alkyl; and X is S, O or NR.sub.3. This invention also relates to use of these compounds for the treatment of benign prostatic hyperplasia and other diseases where antagonism of the human .alpha..sub.1C receptor is useful. The invention further provides pharmaceutical compositions comprising a therapeutically effective amount of such a compound and a pharmaceutically acceptable carrier.
    这项发明涉及选择性拮抗人类α1C受体的二氢嘧啶化合物,其结构为:##STR1##其中A为芳基;R.sub.1、R.sub.2和R.sub.3为烷基或杂原子烷基;R.sub.4为杂环烷基;X为S、O或NR.sub.3。该发明还涉及利用这些化合物治疗良性前列腺增生和其他需要拮抗人类α1C受体的疾病。该发明还提供包含该化合物的治疗有效量和药用可接受载体的药物组合物。
  • Dihydropyridines and new uses thereof
    申请人:Synaptic Pharmaceutical Corporation
    公开号:US05767131A1
    公开(公告)日:1998-06-16
    The invention provides a method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of a compound having the structure: ##STR1## wherein Y is --(CH.sub.2).sub.n --, where n is 1, 2, 3, 4 or 5; --(CH.sub.2).sub.h --O--(CH.sub.2).sub.k --, where h and k are independently the same or different and are 2, 3 or 4; --(CH.sub.2).sub.h --CH.dbd.CH--(CH.sub.2).sub.k --; or --(CH.sub.2).sub.h --C.tbd.C--(CH.sub.2).sub.k --, where h and k are independently the same or different and are 1, 2, 3 or 4; wherein Z is O, NH, or CH.sub.2 ; wherein R.sup.1 is a linear or branched chain alkyl, alkoxyalkyl or arylalkyl group; wherein R.sup.2 and R.sup.4 are independently the same or different and are H, or a linear or branched chain alkyl group; wherein R.sup.3 is H, a linear or branched chain alkyl, alkoxy, alkoxyalkyl or acyl group; and wherein R.sup.5 and R.sup.6 are independently the same or different and are H, OH, Cl, Br, F, NO.sub.2, CN, CF.sub.3, or NH.sub.2, or a linear or branched chain alkyl, alkoxy, alkoxycarbonyl, acyl, alkylsulfoxide, alkylsulfone, or mono- or dialkylamino group. Other active compounds containing one, two or three rings are also disclosed as well as pharmaceutical compositions prepared therefrom and methods of use in the treatment of BPH, inhibition of cholesterol synthesis, and reduction of intraocular pressure.
    该发明提供了一种治疗良性前列腺增生的方法,包括向受试者施用具有以下结构的化合物的治疗有效量: 其中Y为--(CH.sub.2).sub.n --,其中n为1、2、3、4或5;--(CH.sub.2).sub.h --O--(CH.sub.2).sub.k --,其中h和k独立且相同或不同,为2、3或4;--(CH.sub.2).sub.h --CH.dbd.CH--(CH.sub.2).sub.k --;或--(CH.sub.2).sub.h --C.tbd.C--(CH.sub.2).sub.k --,其中h和k独立且相同或不同,为1、2、3或4;其中Z为O、NH或CH.sub.2;其中R.sup.1为线性或支链烷基、烷氧基烷基或芳基烷基;其中R.sup.2和R.sup.4独立且相同或不同,为H,或线性或支链烷基;其中R.sup.3为H、线性或支链烷基、烷氧基、烷氧基烷基或酰基;其中R.sup.5和R.sup.6独立且相同或不同,为H、OH、Cl、Br、F、NO.sub.2、CN、CF.sub.3或NH.sub.2,或线性或支链烷基、烷氧基、烷氧羰基、酰基、烷基亚砜、烷基砜、或单烷基或二烷基氨基基团。还公开了含有一、两个或三个环的其他活性化合物,以及由此制备的药物组合物和在治疗BPH、抑制胆固醇合成和降低眼压中的使用方法。
  • [EN] DIHYDROPYRIMIDINES AND USES THEREOF<br/>[FR] DIHYDROPYRIMIDINES ET LEURS UTILISATIONS
    申请人:SYNAPTIC PHARMACEUTICAL CORPORATION
    公开号:WO1996014846A1
    公开(公告)日:1996-05-23
    (EN) This invention is directed to dihydropyrimidine compounds which are selective antagonists for human $g(a)1C receptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotence, cardiac arrhythmia and for the treatment of any disease where the antagonism of the $g(a)1C receptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.(FR) Cette invention se rapporte à des composés dihydropyrimidine qui sont des antagonistes sélectifs pour les récepteurs $g(a)1C humains, ainsi qu'aux utilisations de ces composés dans la réduction de la pression intraoculaire, l'inhibition de la synthèse du cholestérol, le relâchement des tissus inférieurs des voies urinaires, le traitement de l'hyperplasie prostatique bénigne, l'impuissance, l'arythmie cardiaque et le traitement de toutes maladies pour lesquelles l'antagonisme du récepteur $g(a)1C peut être utile. L'invention se rapporte encore à une composition pharmaceutique comprenant une quantité thérapeutiquement efficace des composés définis ci-dessus et à un excipient pharmaceutiquement acceptable.
    这项发明涉及选择性拮抗人类$g(a)1C受体的二氢嘧啶化合物。该发明还涉及使用这些化合物降低眼内压、抑制胆固醇合成、放松下尿路组织、治疗良性前列腺增生、阳痿、心律失常以及治疗任何需要拮抗$g(a)1C受体的疾病。该发明还提供了一种制药组合物,包括上述定义的化合物的治疗有效量和药用载体。
  • [EN] DIDHYDROPYRIMIDINES AND USES THEREOF<br/>[FR] DIHYDROPYRIMIDINES ET LEURS EMPLOIS
    申请人:SYNAPTIC PHARMACEUTICAL CORPORATION
    公开号:WO1997042956A1
    公开(公告)日:1997-11-20
    (EN) This invention is directed to dihydropyrimidine compounds which are selective antagonists for human $g(a)1A receptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotency, cardiac arrhythmia and for the treatment of any disease where the antagonism of the $g(a)1A receptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.(FR) L'invention concerne des composés de dihydropyrimidine qui sont des antagonistes sélectifs de récepteurs humains $g(a)1A. L'invention concerne également les emplois desdits composés pour abaisser la pression intraoculaire, inhiber la synthèse du cholestérol, soulager le tissu du bas appareil urinaire, ainsi que pour traiter l'hyperplasie prostatique bénigne, l'impuissance, l'arythmie cardiaque et toute autre maladie pour laquelle l'antagonisme du récepteur $g(a)1A peut être utile. L'invention décrit en outre une composition pharmaceutique contenant une dose thérapeutiquement efficace des composés susmentionnés et un excipient pharmaceutiquement admissible.
    (中) 本发明涉及二氢嘧啶化合物,其是人类$g(a)1A受体的选择性拮抗剂。本发明还涉及使用这些化合物降低眼压、抑制胆固醇合成、放松下尿路组织、治疗良性前列腺增生、阳痿、心律失常以及治疗任何可能有用的$g(a)1A受体拮抗剂的疾病。本发明还提供了一种药物组合物,包括上述定义化合物的治疗有效量和药用载体。
  • Dihydropyrimidines and uses thereof
    申请人:Synaptic Pharmaceutical Corporation
    公开号:US20020010186A1
    公开(公告)日:2002-01-24
    This invention is directed to dihydropyrimidine compounds which are selective antagonists for human &agr; 1A receptors. This invention is also related to uses of these compounds for lowering intraocular pressure, inhibiting cholesterol synthesis, relaxing lower urinary tract tissue, the treatment of benign prostatic hyperplasia, impotency, cardiac arrhythmia and for the treatment of any disease where the antagonism of the &agr; 1A receptor may be useful. The invention further provides a pharmaceutical composition comprising a therapeutically effective amount of the above-defined compounds and a pharmaceutically acceptable carrier.
    这项发明涉及二氢嘧啶化合物,它们是人类α1A受体的选择性拮抗剂。此发明还涉及使用这些化合物降低眼压、抑制胆固醇合成、放松下尿路组织、治疗良性前列腺增生、阳痿、心律失常和治疗任何需要拮抗α1A受体的疾病。该发明还提供一种制药组合物,包括上述定义化合物的治疗有效量和药学可接受的载体。
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