ethyl 4-amino-3-chlorophenylacetate | 25814-07-7

• 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: ethyl 4-amino-3-chlorophenylacetate
• 英文别名: 4-Amino-3-chlor-phenylessigsaeure-aethylester；(4-Amino-3-chloro-phenyl)-acetic acid ethyl ester；ethyl 2-(4-amino-3-chlorophenyl)acetate
• CAS: 25814-07-7
• 化学式: C₁₀H₁₂ClNO₂
• mdl: MFCD18395781
• 分子量: 213.664
• InChiKey: NHGYQADUGSHIGS-UHFFFAOYSA-N

物化性质

• 沸点：
  110-115 °C(Press: 0.001 Torr)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-amino-3-chlorophenylacetate 在 水 、 sodium hydroxide 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以86%的产率得到(4-amino-3-chlorophenyl)acetic acid
  参考文献：
  名称：

  Halogenation of 4-hydroxy/amino-3-methoxyphenyl acetamide TRPV1 agonists showed enhanced antagonism to capsaicin

  摘要：

  As an extension of our analysis of the effect of halogenation on thiourea TRPV1 agonists, we have now modified selected 4-hydroxy(or 4-amino)-3-methoxyphenyl acetamide TRPV1 agonists by 5- or 6-halogenation on the aromatic A-region and evaluated them for potency for TRPV1 binding and regulation and for their pattern of agonism/antagonism (efficacy). Halogenation shifted the functional activity at TRPV1 toward antagonism with a greater extent of antagonism as the size of the halogen increased (I > Br > Cl), as previously observed for the thiourea series. The extent of antagonism was greater for halogenation at the 5-position than at the 6-position, in contrast to SAR for the thiourea series. In this series, compounds 55 and 75 showed the most potent antagonism, with K-i (ant) = 2.77 and 2.19 nM, respectively, on rTRPV1 expressed in Chinese hamster ovary cells. The compounds were thus ca. 40-60-fold more potent than 6'-iodononivamide. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.001
• 作为产物：
  描述：

  ethyl 3-chloro-4-nitrophenylacetate 在 tin(II) chloride dihydrate 、 sodium hydroxide 、 水 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 3.5h， 以60%的产率得到ethyl 4-amino-3-chlorophenylacetate
  参考文献：
  名称：

  Identification of 4-[1-[3-chloro-4-[N’-(5-fluoro-2-methylphenyl)ureido]phenylacetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]benzoic acid as a potent, orally active VLA-4 antagonist

  摘要：

  Optimization of benzoic acid derivatives by introducing substituents into the diphenyl urea moiety led to the identification of compound 201 as a potent VLA-4 antagonist. Compound 201 inhibited eosinophil infiltration into bronchial alveolar lavage fluid in a murine asthma model by oral dosing and its efficacy was comparable to anti-mouse alpha 4 antibody (R1-2). Furthermore, this compound significantly blocked bronchial hyper-responsiveness in the model. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.020

文献信息

• 3-AMINO-INDAZOLE OR 3-AMINO-4,5,6,7-TETRAHYDRO-INDAZOLE DERIVATIVES
  申请人：Benson Gregory Martin

  公开号：US20100076026A1

  公开（公告）日：2010-03-25

  This invention relates to novel indazole derivatives of formula I: wherein R 1 to R 7 are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds are FXR modulators and can be used as medicaments.

  这项发明涉及公式I的新型吲唑衍生物： 其中R1至R7如描述和索赔中所定义，以及其生理上可接受的盐。这些化合物是FXR调节剂，可用作药物。
• [EN] NOVEL EP4 RECEPTOR AGONIST COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS AGONISTES DES RÉCEPTEURS EP4
  申请人：GLAXO GROUP LTD

  公开号：WO2009147165A1

  公开（公告）日：2009-12-10

  A compound selected from the group consisting of: (3-chloro-4-[(5-chloro-2-[(2- chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid; 4-[(5-chloro-2-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid; 3-chloro-4-[(5-chloro-2-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid; (3-chloro-4-[(5-chloro-2-[(3- chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid; 4-[(2-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid; (4-[(5-chloro-2-[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}-2- fluorophenyl)acetic acid; 3-chloro-4-[(2-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid; (3-chloro-4-[(2-[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid; 4-[(2-chloro-6-[(phenylmethyl)oxy]phenyl}carbonyl)amino]phenyl}acetic acid; (4-[(2-chloro-6-[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}phenyl)acetic acid; 4-[(5-chloro-2-[(phenylmethyl)amino]phenyl}carbonyl)amino]phenyl}acetic acid; (4-[(5-chloro-2-[(3-chlorophenyl)methyl]amino}phenyl)carbonyl]amino}phenyl)acetic acid; and (4-[(5-chloro-2-[(2-chlorophenyl)methyl]amino}phenyl)carbonyl]amino}phenyl)acetic acid, or pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising such compounds and the use of such compounds in medicine.

  从以下组中选择的化合物：（3-氯-4-[(5-氯-2-[(2-氯苯基)甲氧基}苯基)羰基]氨基}苯基）乙酸；4-[(5-氯-2-[(苯甲基)氧基]苯基}羰基)氨基]苯基}乙酸；3-氯-4-[(5-氯-2-[(苯甲基)氧基]苯基}羰基)氨基]苯基}乙酸；（3-氯-4-[(5-氯-2-[(3-氯苯基)甲氧基}苯基)羰基]氨基}苯基）乙酸；4-[(2-[(苯甲基)氧基]苯基}羰基)氨基]苯基}乙酸；（4-[(5-氯-2-[(3-氯苯基)甲氧基}苯基)羰基]氨基}-2-氟苯基）乙酸；3-氯-4-[(2-[(苯甲基)氧基]苯基}羰基)氨基]苯基}乙酸；（3-氯-4-[(2-[(3-氯苯基)甲氧基}苯基)羰基]氨基}苯基）乙酸；4-[(2-氯-6-[(苯甲基)氧基]苯基}羰基)氨基]苯基}乙酸；（4-[(2-氯-6-[(3-氯苯基)甲氧基}苯基)羰基]氨基}苯基）乙酸；4-[(5-氯-2-[(苯甲基)氨基]苯基}羰基)氨基]苯基}乙酸；（4-[(5-氯-2-[(3-氯苯基)甲氨基}苯基)羰基]氨基}苯基）乙酸；和（4-[(5-氯-2-[(2-氯苯基)甲氨基}苯基)羰基]氨基}苯基）乙酸，或其药学上可接受的盐，包含这些化合物的药物组合物以及这些化合物在医学上的用途。
• VLA-4 INHIBITOR
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1757602A1

  公开（公告）日：2007-02-28

  An object of the present invention is to provide a compound which selectively inhibits binding of a ligand and α4β1 integrin (VLA-4), a process for producing the compound, and a medicament containing the compound. A compound represented by the formula (I) etc. orasaltthereof, a process for producing the compound or a salt thereof, a medicament containing the compound or a salt thereof, as well as a preventive and/or a therapeutic agent for a disease caused by cell adhesion, for example, inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory bowel disease and rejection reaction at transplantation, containing the compound or a salt thereof as a primary component. [wherein Y1 represents a divalent aryl group etc. , V1 represents an aryl group etc., and R11 to R14 represent H, OH or a halogen atom etc.]

  本发明的一个目的是提供一种化合物，该化合物选择性地抑制配体与α4β1整合素（VLA-4）的结合，以及包含该化合物的药物的制备过程。化合物的结构如公式（I）所示，或其盐，制备该化合物或其盐的过程，包含该化合物或其盐的药物，以及作为细胞粘附引起的疾病（例如炎症反应、自身免疫疾病、癌症转移、支气管哮喘、鼻阻塞、糖尿病、关节炎、银屑病、多发性硬化症、炎症性肠病和移植排斥反应等）的预防和/或治疗剂，包含该化合物或其盐作为主要成分。【其中Y1代表双价芳基等，V1代表芳基等，R11至R14代表H、OH或卤素原子等】
• [EN] VLA-4 INHIBITOR<br/>[FR] INHIBITEUR DE VLA-4
  申请人：DAIICHI SEIYAKU CO

  公开号：WO2005121135A1

  公开（公告）日：2005-12-22

  A compound which selectively inhibits bonding between a ligand and α4β1 integrin (VLA-4); a process for producing the compound; and a medicine containing the compound. The compound is one represented by, e.g., the formula (I) or a salt thereof. Also provided is a preventive and/or therapeutic agent which contains the compound or salt as a major component and is effective against diseases attributable to cell adhesion, such as, e.g., inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory intestinal disease, and rejection reaction in transplantation. (In the formula, Y1 represents arylene, etc.; V1 represents aryl, etc.; and R11 to R14 each represents H, OH, halogeno, etc.)

  一种选择性抑制配体与α4β1整合素（VLA-4）结合的化合物；一种生产该化合物的方法；以及含有该化合物的药物。该化合物可由例如式（I）或其盐所代表。还提供了一种预防和/或治疗剂，其含有该化合物或盐作为主要成分，并对由细胞粘附引起的疾病具有有效性，例如炎症反应、自身免疫疾病、癌症转移、支气管哮喘、鼻塞、糖尿病、关节炎、牛皮癣、多发性硬化、炎症性肠道疾病和移植排斥反应等（在该式中，Y1代表芳基等；V1代表芳基等；R11至R14分别代表H、OH、卤素等）。
• Vla-4 inhibitors
  申请人：——

  公开号：US20040110945A1

  公开（公告）日：2004-06-10

  The present invention relates to a compound represented by the following formula (I): 1 (wherein, W represents W A —A 1 —W B — (in which, W A is substituted or unsubstituted aryl, etc., A 1 is —NR 1 —, single bond, —C(O)—, etc., and W B is substituted or unsubstituted arylene, etc.), R is single bond, —NH—, —OCH 2 —, alkenylene, etc., X is —C(O)—, —CH 2 —, etc., and M is, for example, the following formula: 2 (in which, R 11 , R 12 and R 13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R 14 is hydrogen or lower alkyl, Y represents —CH 2 —O—, etc., Z is substituted or unsubstituted arylene, etc., A 2 is single bond, etc, and R 10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.

  本发明涉及以下式(I)所表示的化合物：1（其中，W代表WA-A1-WB-（其中，WA是取代或未取代的芳基等，A1是-NR1-，单键，-C（O）-等，WB是取代或未取代的芳烃基等），R是单键，-NH-，-OCH2-，烯烃基等，X是-C（O）-，-CH2-等，M是例如以下公式：2（其中，R11，R12和R13分别独立地代表氢，羟基，氨基，卤素等，R14是氢或低级烷基，Y代表-CH2-O-等，Z是取代或未取代的芳烃基等，A2是单键等，而R10是羟基或低级烷氧基），或其盐；以及含有该化合物的药物。该化合物或其盐选择性地抑制细胞黏附分子与VAL-4的结合，并表现出高的生物利用度，因此可用作预防和/或治疗炎症性疾病、自身免疫性疾病、转移、支气管哮喘、鼻窦狭窄、糖尿病等。