(4-nitrophenyl)ethylamine hydrochloride | 1201633-43-3

• 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: (4-nitrophenyl)ethylamine hydrochloride
• 英文别名: (1R)-(4-nitrophenyl)ethylamine hydrochloride；4-nitrophenylethylamine monohydrochloride；N-Ethyl-4-nitroaniline hydrochloride；N-ethyl-4-nitroaniline;hydrochloride
• CAS: 1201633-43-3
• 化学式: C₈H₁₀N₂O₂*ClH
• 分子量: 202.641
• InChiKey: OTVDILMFUMAOJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (4-nitrophenyl)ethylamine hydrochloride 、 N-乙基-对-硝基苯胺 在 三氟乙酸酐 作用下， 生成 2,2,2-trifluoro-N-(4-nitrophenethyl)acetamide
  参考文献：
  名称：

  Cinnamoylaminoalkyl-substituted benzenesulfonamide derivatives, processes for their preparation, their use, and pharmaceutical preparations comprising them

  摘要：

  本发明涉及公式I的肉桂酰氨基烷基取代的苯磺酰胺衍生物 其中A(1)，A(2)，A(3)，R(1)，R(2)，R(3)，R(4)，X，Y和Z的含义如权利要求所述。公式I的化合物是有价值的药物活性化合物，例如，对心脏肌肉和/或心脏神经中的ATP敏感钾通道具有抑制作用，例如，适用于治疗心血管系统疾病，如冠心病，心律失常，心功能不全或心肌病，或预防心脏猝死，或改善心脏收缩功能降低。本发明还涉及制备公式I化合物的方法，其用途以及包含它们的药物制剂。

  公开号：

  US06350778B1

文献信息

• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF 2-(2-AMINOTHIAZOL-4-YL)-N-[4-(2-[[(2R)-2-HYDROXY-2- PHENYLETHYL]AMINO]-ETHYL)PHENYL]ACETAMIDE<br/>[FR] PROCÉDÉ AMÉLIORÉ DE PRÉPARATION DE 2-(2-AMINOTHIAZOL-4-YL)-N-[4-(2-[[(2R)-2-HYDROXY-2-PHÉNYLÉTHYL] AMINO]-ÉTHYL)PHÉNYL]ACÉTAMIDE
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2015155664A1

  公开（公告）日：2015-10-15

  The present invention relates to an improved process for the preparation of pure 2-(2- amino-1,3-thiazol-4-yl)-N-[4-(2-[(2R)-2-hydroxy-2-phenylethyl]amino]ethylphenyl]- acetamide of formula (1) substantially free of impurities. The present invention relates to the novel process of preparing intermediate (R)-1- Phenyl-2-[[2-(4-nitrophenyl)ethyl]amino]ethanol hydrochloride of formula (2) in high yield, which is useful in the preparation of mirabegron of formula (1). The process also relates to the preparation of pure α –form crystal of 2-(2-Amino- 1,3-thiazol-4-yl)-N-[4-(2-[(2R)-2-hydroxy-2-phenylethyl]amino]ethylphenyl]acetamide Mirabegron (1) without isolation of β-form.

  本发明涉及一种改进的工艺，用于制备纯度高的2-(2-氨基-1,3-噻唑-4-基)-N-[4-(2-[(2R)-2-羟基-2-苯乙基]氨基)乙基苯基]-乙酰胺，其化学式为(1)，基本上不含杂质。本发明涉及一种新的工艺，用于高产率制备中间体(R)-1-苯基-2-[[2-(4-硝基苯基)乙基]氨基]乙醇盐酸盐，其化学式为(2)，该中间体在制备化合物mirabegron的过程中很有用。该工艺还涉及制备纯度高的α-型晶体的2-(2-氨基-1,3-噻唑-4-基)-N-[4-(2-[(2R)-2-羟基-2-苯乙基]氨基)乙基苯基]乙酰胺mirabegron(1)，而无需分离β-型晶体。
• ACETAMIDO-PHENYLTETRAZOLE DERIVATIVES AND METHODS OF USING THE SAME
  申请人：Athenex, Inc.

  公开号：US20220106312A1

  公开（公告）日：2022-04-07

  The present disclosure relates to compounds of Formula (IA) and to their prodrugs, pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for the treatment of disorders in which P-glycoprotein and/or cytochrome P450 (e.g. CYP3A4) is modulated (e.g., cancers which have developed multi-drug resistance).

  本公开涉及式（IA）化合物及其前药、药学上可接受的盐、药物组合物、使用方法以及制备方法。本文披露的化合物可用于治疗P-糖蛋白和/或细胞色素P450（例如CYP3A4）被调节的疾病（例如已发展多药耐药性的癌症）。
• Phenethylamino sulfamic acids
  申请人：The Procter & Gamble Company

  公开号：US20040167183A1

  公开（公告）日：2004-08-26

  Compounds of formula (I): 1 are effective in the treatment of protein tyrosine phosphatase (PTPase) mediated disorders such as diabetes.

  公式（I）的化合物在治疗蛋白酪氨酸磷酸酶（PTPase）介导的疾病，如糖尿病方面具有有效性。
• [EN] A PROCESS FOR PREPARATION OF MIRABEGRON AND ALPHA CRYSTALLINE FORM THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DU MIRABÉGRON ET DE SA FORME ALPHA CRISTALLINE
  申请人：MEGAFINE PHARMA P LTD

  公开号：WO2015044965A1

  公开（公告）日：2015-04-02

  An improved process for the preparation of Mirabegron of formula (I) where 4- nitrophenylethylamine of formula (III) or its acid addition salt of formula (IlIa) reacted with compound of formula (XII) in a solvent, optionally in presence of base and/or catalyst to obtain (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide of formula (XIII) followed by reducing (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide of formula (XIII) in a solvent to obtain (R)-2-[2'-(4-nitrophenyl)ethyl]amino]-l-phenylethanol of formula (XIV), optionally converting it into its acid addition salt of formula (XlVa); reducing (R)-2-[2'-(4- nitrophenyl)ethyl]amino]-l -phenylethanol of formula (XIV) or its acid addition salt of formula (XlVa) further in solvent to obtain (R)-2-[[2-(4-aminophenyl)ethyl]-amino]-l -phenylethanol of formula (XV) or its acid addition salt of formula (XVa) respectively; and reacting compound (R)- 2-[[2-(4-aminophenyl)ethyl]-amino]-l-phenylethanol of formula (XV) or its acid addition salt of compound of formula (XVa) with compound of formula (VII) in solvent, optionally in the presence of acid, and/or a catalyst to obtain Mirabegron of formula (I) which is further isolated as its a- crystalline form. The compound of formula (XIV) used in the foregoing process can also be prepared by reacting with a compound of formula (III) or acid addition salt of compound of formula (IlIa) in presence of a solvent, a catalyst and optionally in presence of a base to obtain compound of formula (XIV) optionally converting it into its acid addition salt of formula (XlVa); and the same is used in the above-referred process. The compound of formula (XV) used in the foregoing process can also be prepared by reacting a compound of formula (III) or its acid addition salt of formula (IlIa) with a compound of formula (XVI) in a solvent, optionally in presence of a base, optionally in presence of a catalyst to obtain compound of formula (XVII); and optionally isolate the compound of formula (XVII) followed by reducing the compound of formula (XVII) using reducing agent, in a solvent, optionally in presence of a base, optionally in presence of a catalyst to obtain compound of formula (XV) which is further used in the above- referred process for the preparation of Mirabegron of formula (I) and its a-crystalline form. Another additional single-pot process for preparation of Mirabegron of formula (I) is disclosed, wherein compound of formula (XV) or its acid addition salt of formula (XVa) reacted with compound of formula (XVIII) in presence of a solvent and oxidizing agent, optionally in presence of base, optionally in presence of a catalyst to obtain Mirabegron of formula (I).

  一种改进的制备Mirabegron的方法，其中式（I）的4-硝基苯乙胺式（III）或其酸加成盐式（IlIa）与式（XII）的化合物在溶剂中反应，可选地在碱和/或催化剂的存在下，得到式（XIII）的（R）-2-羟基-N-[2-（4-硝基苯基）乙基]-2-苯乙酰胺，随后在溶剂中还原式（XIII）的（R）-2-羟基-N-[2-（4-硝基苯基）乙基]-2-苯乙酰胺，以得到式（XIV）的（R）-2-[2'-(4-硝基苯基)乙基]氨基]-1-苯乙醇，可选地将其转化为其酸加成盐式式（XlVa）；然后在溶剂中进一步还原式（XIV）的（R）-2-[2'-(4-硝基苯基)乙基]氨基]-1-苯乙醇或其酸加成盐式式（XlVa），以分别得到式（XV）的（R）-2-[[2-(4-氨基苯基)乙基]氨基]-1-苯乙醇或其酸加成盐式式（XVa）；最后，在溶剂中将化合物（R）-2-[[2-(4-氨基苯基)乙基]氨基]-1-苯乙醇的式（XV）或其酸加成盐式化合物与式（VII）的化合物反应，可选地在酸和/或催化剂的存在下，以得到式（I）的Mirabegron，其进一步作为其α-晶体形式分离。在上述过程中使用的化合物（XIV）也可以通过在溶剂中与式（III）的化合物或式（IlIa）的酸加成盐的存在下，在催化剂和可选的碱的存在下反应以得到化合物的式（XIV），可选地将其转化为其酸加成盐式式（XlVa）；并且在上述提到的过程中使用。在上述过程中使用的化合物（XV）也可以通过在溶剂中与式（XVI）的化合物反应，可选地在碱和/或催化剂的存在下，可选地在催化剂的存在下得到化合物的式（XVII）；并且可选择隔离化合物的式（XVII），随后使用还原剂在溶剂中还原化合物的式（XVII），可选地在碱和/或催化剂的存在下，以得到式（XV）的化合物，该化合物进一步用于上述制备式（I）的Mirabegron及其α-晶体形式的过程中。还披露了另一种额外的单锅制备Mirabegron（I）的方法，其中式（XV）的化合物或其酸加成盐式的式（XVa）在溶剂和氧化剂的存在下，可选地在碱和/或催化剂的存在下与式（XVIII）的化合物反应，以得到式（I）的Mirabegron。
• Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
  申请人：Takasu Toshiyuki

  公开号：US20060115540A1

  公开（公告）日：2006-06-01

  (R)-2-(2-aminothiazol-4-yl)-4′-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetic acid anilide or its salt shows a potent bladder relaxation effect in “isolated rat bladder smooth muscle relaxation test”, dose-dependently lowers the contraction frequency of rhythmic bladder contractions in “rat rhythmic bladder contraction measurement test” and, moreover, prolongs the urination intervals in “urination functions measurement test on cyclophosphamide-induced overactive bladder model rat”. Owing to these effects, the above compound is useful as a remedy for ovaractive bladder.

  (R)-2-(2-氨基噻唑-4-基)-4'-[2-[(2-羟基-2-苯乙基)氨基]乙基]乙酸苯胺或其盐，在“孤立大鼠膀胱平滑肌松弛试验”中显示出强效的膀胱松弛作用，剂量依赖性地降低了“大鼠节律性膀胱收缩测量试验”中节律性膀胱收缩的收缩频率，并且在“环磷酰胺诱导的过度活动性膀胱模型大鼠的排尿功能测量试验”中延长了排尿间隔。由于这些作用，上述化合物可用作治疗过度活动性膀胱的药物。