benzyl 4-formyl-1H-pyrrole-2-carboxylate | 185621-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 4-formyl-1H-pyrrole-2-carboxylate
• CAS: 185621-28-7
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: NDEPHKDCOCSLFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-pyrrole-2-carboxylic acid benzyl ester 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以62%的产率得到5-甲酰基-1H-吡咯-2-羧酸苄酯
  参考文献：
  名称：

  N-保护的 5-(胍基羰基)-1H-吡咯-2-羧酸的简便有效的多克合成

  摘要：

  超分子阴离子结合基序的两种通用构件的合成，5-(N-Boc-guanidinocarbonyl)-1H-pyrrole-2-carboxy acid (1) 和 5-(N-Cbz-guanidinocarbonyl)-1H-pyrrole-2报道了-羧酸(2)。使用这些构建块，可以通过使用标准酰胺偶联条件将胍基羰基-吡咯阴离子结合位点轻松引入更复杂的分子中。两种合成都可以在多克规模上进行。产品以纯净形式获得，可以作为固体储存而不会分解。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejoc.200700756

文献信息

• Pyrrole-derivatives as factor Xa inhibitors
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1568698A1

  公开（公告）日：2005-08-31

  The present invention relates to compounds of the formulae I and Ia, wherein R0 ; R1 ; R2 ; R3 ; R4; R22, Q; V, G and M have the meanings indicated in the claims. The compounds of the formulae I and Ia are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formulae I and Ia, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及化合物的公式I和Ia，其中R0; R1; R2; R3; R4; R22，Q; V，G和M具有索赔中指示的含义。公式I和Ia的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，并适用于治疗和预防心血管疾病，如血栓栓塞疾病或再狭窄。它们是血液凝固酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，通常可用于存在因子Xa和/或因子VIIa不良活性或需要抑制因子Xa和/或因子VIIa的治疗或预防的情况。此外，本发明还涉及化合物I和Ia的制备方法，它们的用途，特别是作为药物中的活性成分，以及包含它们的药物制剂。
• Pyrrole-Derivatives as Factor Xa Inhibitors
  申请人：BAUER Armin

  公开号：US20070049573A1

  公开（公告）日：2007-03-01

  The present invention relates to compounds of the formulae (I) and (Ia), wherein R 0 ; R 1 ; R3; R4; R22, Q; V, G and M have the meanings indicated in the claims. The compounds of the formulae (I) and (Ia) are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formulae (I) and (Ia), their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

  本发明涉及公式（I）和（Ia）的化合物，其中R0、R1、R3、R4、R22、Q、V、G和M具有所述权利要求中指示的含义。公式（I）和（Ia）的化合物是有价值的药理活性化合物。它们表现出强烈的抗血栓作用，适用于治疗和预防心血管疾病，如血栓栓塞性疾病或再狭窄。它们是血凝酶酶因子Xa（FXa）和/或因子VIIa（FVIIa）的可逆抑制剂，并且通常可用于存在因子Xa和/或因子VIIa的不良活性或预防其发生的情况下，或者用于治疗或预防需要抑制因子Xa和/或因子VIIa的情况。此外，本发明还涉及制备公式（I）和（Ia）的化合物的方法，它们的使用，特别是作为药物中的活性成分，以及包含它们的制药制剂。
• 5-aryl-1H-pyrrole-3-carbonitrile and a pharmaceutical product using the same
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US10173977B2

  公开（公告）日：2019-01-08

  The present invention provides a production method of a sulfonylpyrrole compound useful as a pharmaceutical product, a production method of an intermediate used for the method, and a novel intermediate. The present invention relates to a method of producing sulfonylpyrrole compound (VIII), which includes reducing compound (III) and hydrolyzing the reduced product to give compound (IV), subjecting compound (IV) to a sulfonylation reaction to give compound (VI), and subjecting compound (VI) to an amination reaction.

  本发明提供了一种可用作医药产品的磺酰基吡咯化合物的生产方法、一种用于该方法的中间体的生产方法以及一种新型中间体。本发明涉及磺酰基吡咯化合物（VIII）的生产方法，其中包括还原化合物（III）并水解还原产物得到化合物（IV），将化合物（IV）进行磺化反应得到化合物（VI），以及将化合物（VI）进行胺化反应。
• Method for producing sulfonyl chloride compound
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US10370357B2

  公开（公告）日：2019-08-06

  An object of the present invention is to provide a production method of an intermediate used in the production method of a sulfonylpyrrole compound useful as a pharmaceutical product. The present invention relates to a method of producing sulfonylpyrrole compound (VI) by reacting a pyridine-3-sulfonic acid compound with phosphorus pentachloride in a solvent of chlorobenzene or trifluoromethylbenzene to give a pyridine-3-sulfonyl chloride compound, reacting the compound without isolation with compound (III) to give compound (IV), and subjecting the compound (IV) to a reductive amination reaction. wherein R2 is a hydrocarbon group etc. and R3 and R4 are each a hydrogen atom etc., wherein R2 is an optionally substituted pyridin-3-yl group, and the other symbols are as defined above, wherein R5 is an alkyl group and the other symbols are as defined above.

  本发明的目的是提供一种用于生产可用作医药产品的磺酰基吡咯化合物的中间体的生产方法。本发明涉及一种磺酰基吡咯化合物(VI)的生产方法，该方法是将吡啶-3-磺酸化合物与五氯化磷在氯苯或三氟甲基苯溶剂中反应，得到吡啶-3-磺酰氯化合物，将该化合物不经分离地与化合物(III)反应，得到化合物(IV)，再将化合物(IV)进行还原胺化反应。 其中 R2 为烃基等，R3 和 R4 各为氢原子等、 其中 R2 是任选取代的吡啶-3-基，其他符号如上定义、 其中 R5 为烷基，其他符号如上定义。
• Aryl Ring Rotation in Porphyrins. A Carbon-13 NMR Spin−Lattice Relaxation Time Study
  作者：Lori Noss、Paul A. Liddell、Ana L. Moore、Thomas A. Moore、Devens Gust

  DOI：10.1021/jp962209y

  日期：1997.1.1

  Overall tumbling and internal rotational motions in porphyrins bearing meso aryl substituents and, in some cases, flanking alkyl groups at the beta-pyrrolic positions have been determined using C-13 spin-lattice relaxation time measurements. In deuteriochloroform solution at 303 K, the overall reorientation of all three porphyrins investigated occurs with diffusion coefficients of similar to 1 x 10(9) s(-1). In porphyrins with only hydrogen at the beta-pyrrolic positions, the meso phenyl rings undergo rotations about their single bonds to the porphyrin with diffusion coefficients of similar to 4 x 10(9) s(-1). Introduction of methyl substituents at the beta-pyrrolic positions adjacent to the phenyl rings reduces these motions, but only to similar to 1 x 10(9) s(-1). Thus, significant internal motions are present in both types of molecules. These motions occur on the time scale of many photoinduced electron and energy transfer processes in porphyrins covalently linked to electron or energy donors or accepters through meso aryl groups. Thus, the internal librational motions may affect rates of photoinduced electron and energy transfer, even in relatively ''rigid'' molecular constructs.