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1,5-bis(tert-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine | 259809-53-5

中文名称
——
中文别名
——
英文名称
1,5-bis(tert-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine
英文别名
1,5-bis(t-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine;ditert-butyl 2-(hydroxymethyl)-6,7-dihydro-4H-pyrrolo[3,2-c]pyridine-1,5-dicarboxylate
1,5-bis(tert-butoxycarbonyl)-2-hydroxymethyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine化学式
CAS
259809-53-5
化学式
C18H28N2O5
mdl
——
分子量
352.431
InChiKey
ZVZCLEKNLBFUJK-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:
    484.3±55.0 °C(Predicted)
  • 密度:
    1.18±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    1.8
  • 重原子数:
    25
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.67
  • 拓扑面积:
    81
  • 氢给体数:
    1
  • 氢受体数:
    5

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:
    Synthesis and Conformational Analysis of a Non-Amidine Factor Xa Inhibitor That Incorporates 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine as S4 Binding Element
    摘要:
    Our exploratory study was based on the concept that a non-amidine factor Xa (fXa) inhibitor is suitable for an orally available anticoagulant. We synthesized and evaluated a series of N-(6-chloronaphthalen-2-yl)sulfonylpiperazine derivatives incorporating various fused-bicyclic rings containing an aliphatic amine expected to be S4 binding element. Among this series, 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine type 61 displayed orally potent anti-fXa activity and evident prolongation of prothrombin time (PT) with the moderate bioavailability in rats. The X-ray crystal analysis afforded an obvious binding mode that 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine and 6-chloronaphthalene respectively bound to S4 and S1 subsites. In this X-ray study, we discovered a novel intramolecular S-O close contact. Ab initio energy calculations of model compounds deduced that conformers with the most close S-O proximity were most stable. The Mulliken population analysis proposed that this energy profile was caused by both of electrostatic S-O affinity and N-O repulsion. The results of these calculations and X-ray analysis suggested a possibility that the restricted conformation effected the affinity to S4 subsite of fXa.
    DOI:
    10.1021/jm049884d
  • 作为产物:
    参考文献:
    名称:
    Synthesis and Conformational Analysis of a Non-Amidine Factor Xa Inhibitor That Incorporates 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine as S4 Binding Element
    摘要:
    Our exploratory study was based on the concept that a non-amidine factor Xa (fXa) inhibitor is suitable for an orally available anticoagulant. We synthesized and evaluated a series of N-(6-chloronaphthalen-2-yl)sulfonylpiperazine derivatives incorporating various fused-bicyclic rings containing an aliphatic amine expected to be S4 binding element. Among this series, 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine type 61 displayed orally potent anti-fXa activity and evident prolongation of prothrombin time (PT) with the moderate bioavailability in rats. The X-ray crystal analysis afforded an obvious binding mode that 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine and 6-chloronaphthalene respectively bound to S4 and S1 subsites. In this X-ray study, we discovered a novel intramolecular S-O close contact. Ab initio energy calculations of model compounds deduced that conformers with the most close S-O proximity were most stable. The Mulliken population analysis proposed that this energy profile was caused by both of electrostatic S-O affinity and N-O repulsion. The results of these calculations and X-ray analysis suggested a possibility that the restricted conformation effected the affinity to S4 subsite of fXa.
    DOI:
    10.1021/jm049884d
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文献信息

  • NOVEL SULFONYL DERIVATIVES
    申请人:DAIICHI PHARMACEUTICAL CO., LTD.
    公开号:EP1104754A1
    公开(公告)日:2001-06-06
    Sulfonyl derivatives represented by the following general formula (I): Q1-Q2-T1-Q3-SO2-QA and drugs containing the same (wherein Q1 is an optionally substituted, saturated or unsaturated, five- or six-membered cyclic hydrocarbon group, a five- or six-membered heterocyclic group, or the like; Q2 is a single band, oxygen, sulfur, C1-C6 alkylene or the like; QA is optionally substituted arylalkenyl, heteroarylalkenyl or the like; and T1 is carbonyl or the like). These compounds have potent FXa-inhibitory effects and promptly exert satisfactory and persistent antithrombotic effects through oral administration, thus being useful as anticoagulant agents little accompanied with side effects.
    以下是通用公式(I)所代表的磺酰衍生物:Q1-Q2-T1-Q3-SO2-QA以及含有这些衍生物的药物(其中Q1是可选择地取代的饱和或不饱和的五元或六元环烃基团,五元或六元杂环基团等;Q2是单键,氧,硫,C1-C6烷基或类似物;QA是可选择地取代的芳基烯烃基团,杂环芳基烯烃基团或类似物;T1是羰基或类似物)。这些化合物具有强大的FXa抑制作用,并通过口服迅速产生令人满意且持久的抗血栓作用,因此可作为几乎不伴随副作用的抗凝血剂。
  • Novel sulfonyl derivatives
    申请人:DAIICHI PHARMACEUTICAL CO., LTD.
    公开号:US20040082611A1
    公开(公告)日:2004-04-29
    Described in the present invention are a sulfonyl derivative represented by the following formula (I): Q 1 -Q 2 -T 1 -Q 3 -SO 2 -Q A (I) [wherein Q 1 represents a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group, 5- or 6-membered heterocyclic group, dicyclic fused ring or tricyclic fused ring group which may have a substituent; Q 2 represents a single bond, an oxygen atom, a sulfur atom, a linear or branched C 1-6 alkylene group or the like; Q A represents an arylalkenyl group which may have a substituent or a heteroarylalkenyl group which may have a substituent; and T 1 represents a carbonyl group or the like] and a medicament comprising the same. The compound has strong FXa inhibitory action, provides prompt, sufficient and long-lasting anti-thrombus effects when orally administered, and has low side effects and is therefore useful as an excellent anticoagulant.
    本发明描述了一种由以下式(I)表示的磺酰基衍生物: Q1-Q2-T1-Q3-SO2-QA(I) [其中,Q1表示饱和或不饱和的5-或6-环烃基、5-或6-杂环基、二环融合环或三环融合环基,可能具有取代基;Q2表示单键、氧原子、硫原子、线性或支链的C1-6烷基等;QA表示可能具有取代基的芳基烯基或杂芳基烯基;T1表示羰基基团或类似物],以及包含该化合物的药物。该化合物具有强烈的FXa抑制作用,口服后提供快速、充分和持久的抗血栓效果,并且具有低副作用,因此可用作优秀的抗凝剂。
  • Novel ethylenediamine derivatives
    申请人:Nakamoto Yumi
    公开号:US20070129371A1
    公开(公告)日:2007-06-07
    A compound represented by the following formula (1): Q 1 —Q 2 —T o —N(R 1 )—Q 3 —N(R 2 )—T 1 —Q 4 ( 1 ) [wherein, R 1 and R 2 are hydrogen atoms or the like; Q 1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may have a substituent, or the like; Q 2 is a single bond or the like; Q 3 represents the following group: —C(R 3a )(R 4a )—C(R 3b )(R 4b )}m 1 —C(R 3c )(R 4c )}m 2 —C(R 3d )(R 4d )}m 3 —C(R 3e )(R 4e )}m 4 —C (R 3f )(R 4f )— (in which, R 3a to R 4e represent hydrogen or the like); T 0 represents a carbonyl group or the like; and T 1 represents —COCONR— or the like]; or salt thereof, solvate thereof, or N-oxide thereof. The compound is useful as a preventive and/or therapeutic agent for cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.
    以下化合物公式(1)表示的化合物:Q1-Q2-To-N(R1)-Q3-N(R2)-T1-Q4(1)[其中,R1和R2是氢原子或类似物;Q1是饱和或不饱和的5或6元环烃基,可以具有取代基或类似物;Q2是单键或类似物;Q3表示以下基团:-C(R3a)(R4a)-C(R3b)(R4b)}m1-C(R3c)(R4c)}m2-C(R3d)(R4d)}m3-C(R3e)(R4e)}m4-C(R3f)(R4f)-(其中,R3a到R4e代表氢或类似物);T0表示羰基基团或类似物;T1表示-COCONR-或类似物];或其盐,溶剂化合物或N-氧化物。该化合物可用作预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥漫性血管内凝血综合征、瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征(SIRS)、多器官功能障碍综合征(MODS)、体外循环期间的血栓形成或采血时的血液凝固。
  • Sulfonyl derivatives
    申请人:Daiichi Pharmaceutical Co., Ltd.
    公开号:US06747023B1
    公开(公告)日:2004-06-08
    Described in the present invention are a sulfonyl derivative represented by the following formula (I): Q1—Q2—T1—Q3—SO2—QA  (I) [wherein Q1 represents a saturated or unsaturated 5- or 6-membered cyclic hydrocarbon group, 5- or 6-membered heterocyclic group, dicyclic fused ring or tricyclic fused ring group which may have a substituent; Q2 represents a single bond, an oxygen atom, a sulfur atom, a linear or branched C1-6 alkylene group or the like; QA represents an arylalkenyl group which may have a substituent or a heteroarylalkenyl group which may have a substituent; and T1 represents a carbonyl group or the like] and a medicament comprising the same. The compound has strong FXa inhibitory action, provides prompt, sufficient and long-lasting anti-thrombus effects when orally administered, and has low side effects and is therefore useful as an excellent anticoagulant.
    本发明涉及一种磺酰基衍生物,其由以下式(I)表示:Q1-Q2-T1-Q3-SO2-QA(I)[其中,Q1代表饱和或不饱和的5-或6-成员环烃基,5-或6-成员杂环基,二环融合环或三环融合环基,可以有取代基;Q2代表单键,氧原子,硫原子,线性或支链C1-6烷基或类似物;QA代表芳基烯基,可以有取代基,或杂环芳基烯基,可以有取代基;T1代表羰基或类似物],以及包含该化合物的药物。该化合物具有强烈的FXa抑制作用,在口服时提供迅速,充分和持久的抗血栓效果,并且副作用低,因此是一种优秀的抗凝剂。
  • NOVEL ETHYLENEDIAMINE DERIVATIVES
    申请人:DAIICHI PHARMACEUTICAL CO., LTD.
    公开号:EP1577302A1
    公开(公告)日:2005-09-21
    A compound represented by the following formula (1):Q1-Q2-To-N(R1)-Q3-N(R2)-T1-Q4 [wherein, R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may have a substituent, or the like; Q2 is a single bond or the like; Q3 represents the following group: -C(R3a)(R4a)-C(R3b)(R4b)}m1-C(R3c)(R4c)}m2-C(R3d)(R4d)}m3-C(R3e)(R4e)}m4-C(R3f)(R4f)- (in which, R3a to R4e represent hydrogen or the like); T0 represents a carbonyl group or the like; and T1 represents -COCONR- or the like]; or salt thereof, solvate thereof, or N-oxide thereof. The compound is useful as a preventive and/or therapeutic agent for cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.
    下式(1)代表的化合物:Q1-Q2-To-N(R1)-Q3-N(R2)-T1-Q4 [其中,R1 和 R2 是氢原子或类似物;Q1 是饱和或不饱和的 5 或 6 位环烃基团,该基团可具有取代基或类似物;Q2 是单键或类似物;Q3 代表以下基团:-C(R3a)(R4a)-C(R3b)(R4b)}m1-C(R3c)(R4c)}m2-C(R3d)(R4d)}m3-C(R3e)(R4e)}m4-C(R3f)(R4f)-(其中,R3a 至 R4e 代表氢或类似物);T0 代表羰基或类似物;T1 代表 -COCONR- 或类似物];或其盐、其溶液或其 N-氧化物。 该化合物可用作脑梗塞、脑栓塞、心肌梗塞、心绞痛、肺梗塞、肺栓塞、布格氏病、深静脉血栓形成、弥散性血管内凝血综合征的预防和/或治疗剂、瓣膜或关节置换术后血栓形成、血管成形术后血栓形成和再闭塞、全身炎症反应综合征(SIRS)、多器官功能障碍综合征(MODS)、体外循环过程中血栓形成或抽血时血液凝固。
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