ethyl 4-amino-3-chloro-5-methylbenzoate | 500292-98-8

• 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-chloro-5-methylbenzoate
• 英文别名: 4-Amino-3-chloro-5-methylbenzoic acid ethyl ester
• CAS: 500292-98-8
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: MMJZJYVYOKAMKU-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  353.6±37.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 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-chloro-5-methylbenzoate 在 盐酸 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 4-[4-(4-formyl-2-chloro-6-methylphenylamino)pyrimidin-4-ylamino]benzonitrile
  参考文献：
  名称：

  Synthesis of novel diarylpyrimidine analogues of TMC278 and their antiviral activity against HIV-1 wild-type and mutant strains

  摘要：

  Novel diarylpyrimidines (DAPY), which represent next generation of non-nucleoside reverse transcriptase inhibitors (NNRTIs), were synthesized and their activities against human immunodeficiency virus type I (HIV-1) assessed. Modulations at positions 2 and 6 of the left phenyl ring generated interesting derivatives of TMC278 displaying high potency against wild-type and mutant viruses compared to nevirapine and efavirenz. The pharmacokinetic profile of the best newly synthesized DAPY was evaluated and compared with TMC278 now in phase II clinical trials. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.11.014
• 作为产物：
  描述：

  4-氨基-3-甲基苯甲酸乙酯 在 N-氯代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以84%的产率得到ethyl 4-amino-3-chloro-5-methylbenzoate
  参考文献：
  名称：

  Pharmaceutical compositions comprising a basic drug compound, a surfactant, and a physiologically tolerable water soluble acid

  摘要：

  这项发明提供了一种新型的药物组合物，包括一种碱性或酸性药物化合物、表面活性剂和一种生理耐受的水溶性酸或碱，其特点在于酸或碱与药物化合物的比例至少为1:1（按重量计）。

  公开号：

  US09192577B2

文献信息

• Pharmaceutical compositions comprising a basic drug compound, a surfactant, and a physiologically tolerable water soluble acid
  申请人：Vandecruys Roger Petrus Gerebern

  公开号：US09192577B2

  公开（公告）日：2015-11-24

  The invention provides a novel pharmaceutical composition comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base characterized in that the acid respectively base:drug compound ratio is at least 1:1 by weight.

  这项发明提供了一种新型的药物组合物，包括一种碱性或酸性药物化合物、表面活性剂和一种生理耐受的水溶性酸或碱，其特点在于酸或碱与药物化合物的比例至少为1:1（按重量计）。
• Substituted benzamides with activity towards EP4 receptors
  申请人：Almirall, S.A.

  公开号：EP2765128A1

  公开（公告）日：2014-08-13

  The present invention belongs to the field of EP4 receptor ligands. More specifically it refers to compounds of general formula (I) having great affinity and selectivity for the EP4 receptor. The invention also refers to the process for their preparation, to their use as medicament for the treatment and/or prophylaxis of diseases or disorders mediated by the EP4 receptor as well as to pharmaceutical compositions comprising them.

  这项发明属于EP4受体配体领域。更具体地，它涉及具有对EP4受体具有很高亲和力和选择性的一般式(I)化合物。该发明还涉及它们的制备过程，以及它们作为药物用于治疗和/或预防由EP4受体介导的疾病或紊乱，以及包含它们的药物组合物。
• HIV INHIBITING PYRIMIDINES DERIVATIVES
  申请人：Guillemont Jérôme Emile Georges

  公开号：US20120076835A1

  公开（公告）日：2012-03-29

  This invention concerns HIV replication inhibitors of formula the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.

  这项发明涉及公式为N-氧化物、药学上可接受的加合物、季铵盐及其立体化学异构体的HIV复制抑制剂；它们作为药物的使用、它们的制备过程以及包含它们的制药组合物。
• HIV inhibiting pyrimidines derivatives
  申请人：Janssen Pharmaceutica NV

  公开号：EP2298761A1

  公开（公告）日：2011-03-23

  This invention concerns HIV replication inhibitors of formula the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing -a1=a2-a3=a4- and -b1=b2-b3=b4- represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl;n is 0 to 5; m is 1 to 4; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl; substituted C1-6alkyl, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyloxy; substituted C1-6alkyloxyC1-6alkylcarbonyl; R2 is hydroxy, halo, optionally substituted C1-6alkyl, C3-7cycloalkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono-or di(C1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, - S(=O)pR6, -NH-S(=O)pR6, -C(=O)R6, -NHC(=O)H, -C(=O)NHNH2, -NHC(=O)R6 -C(=NH)R6 or a 5-membered heterocycle; X1 is -NR5-, -NH-NH-, -N=N-, -O-, -C(=O)-, C1-4alkanediyl, -CHOH-, -S-, -S(=O)p-, -X2-C1-4alkanediyl- or -C1-4alkanediyl-X2-; R3 is NHR13; NR13R14; -C(=O)-NHR13; -C(=O)-NR13R14; -C(=O)-R15; -CH=N-NH-C(=O)-R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl; substituted C2-6alkynyl; C1-6alkyl substituted with hydroxy and a second substituent; -C(=N-O-R8)-C1-4alkyl; R7; or -X3-R7; R4 is halo, hydroxy, C1-6alkyl, C3-7cycloalkyl, C1-6alkyloxy, cyano, nitro, polyhaloC1-6alkyl, polyhatoC1-6alkyloxy, aminocarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyl, formyl, amino, mono- or di(C1-4alkyl)amino; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及式中的艾滋病毒复制抑制剂 的N-氧化物、药学上可接受的加成盐、季胺及其立体异构体形式，其中含有-a1=a2-a3=a4-和-b1=b2-b3=b4-的环代表苯基、吡啶基、嘧啶基、吡嗪基、哒嗪基；n 为 0 至 5；m 为 1 至 4；R1 为氢；芳基；甲酰基；C1-6烷基羰基；C1-6烷基；C1-6烷氧基羰基；取代的 C1-6烷基、C1-6烷基羰基、C1-6烷氧基羰基、C1-6烷基羰基氧基、C1-6烷基羧基取代的 C1-6 烷氧基 C1-6 烷基羰基；R2 是羟基、卤代、任选取代的 C1-6 烷基、C3-7 环烷基、任选取代的 C2-6 烯基、任选取代的 C2-6 烷炔基、C1-6烷氧基、C1-6烷氧基羰基、羧基、氰基、硝基、氨基、单或双（C1-6烷氧基羰基）烷基羰基、C1-6烷基羰基氧基、C1-6烷基羰基氨基、单或二（C1-6烷基）氨基、多卤代甲基、多卤代甲基氧基、多卤代甲硫基、-S(＝O)pR6、-NH-S(＝O)pR6、-C(＝O)R6、-NHC(＝O)H、-C(＝O)NHNH2、-NHC(＝O)R6 -C(＝NH)R6 或 5 元杂环；X1 是-NR5-、-NH-NH-、-N=N-、-O-、-C(=O)-、C1-4烷二基、-CHOH-、-S-、-S(=O)p-、-X2-C1-4烷二基-或-C1-4烷二基-X2-； R3 是 NHR13；NR13R14；-C(=O)-NHR13；-C(=O)-NR13R14；-C(=O)-R15；-CH=N-NH-C(=O)-R16；取代的 C1-6 烷基；任选取代的 C1-6 烷氧基 C1-6 烷基；取代的 C2-6 烯基；取代的 C2-6 烷炔基；被羟基和第二个取代基取代的 C1-6 烷基；-R4为卤代、羟基、C1-6烷基、C3-7环烷基、C1-6烷氧基、氰基、硝基、多卤代C1-6烷基、多卤代C1-6烷氧基、氨基羰基、C1-6烷氧基羰基、C1-6烷基羰基、甲酰基、氨基、单-或二(C1-4烷基)氨基；它们的医药用途、制备工艺和包含它们的药物组合物。
• HIV REPLICATION INHIBITING PYRIMIDINES
  申请人：Janssen Pharmaceutica NV

  公开号：EP3808743A1

  公开（公告）日：2021-04-21

  This invention concerns HIV replication inhibitors of formula the N-oxides, the pharmaceutically acceptable addition salts, the quaternary amines and the stereochemically isomeric forms thereof, wherein the ring containing -a1=a2-a3=a4- and -b1=b2-b3=b4- represents phenyl, pyridyl, pyrimidinyl, pirazinyl, pyridazinyl;n is 0 to 5; m is 1 to 4; R1 is hydrogen; aryl; formyl; C1-6alkylcarbonyl; C1-6alkyl; C1-6alkyloxycarbonyl; substituted C1-6alkyl, C1-6alkylcarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyloxy; substituted Cl-6alkyloxyCl-6alkylcarbonyl; R2 is hydroxy, halo, optionally substituted C1-6alkyl, C3-7cycloalkyl, optionally substituted C2-6alkenyl, optionally substituted C2-6alkynyl, C1-6alkyloxy, C1-6alkyloxycarbonyl, carboxyl, cyano, nitro, amino, mono- or di(C1-6alkyl)amino, polyhalomethyl, polyhalomethyloxy, polyhalomethylthio, -S(=O)pR6, -NH-S(=O)pR6, -C(=O)R6, -NHC(=O)H, -C(=O)NHNH2, -NHC(=O)R6, -C(=NH)R6 or a 5-membered heterocycle; X1 is -NR5-, -NH-NH-, -N=N-, -O-, -C(=O)-, C1-4alkanediyl, -CHOH-, -S-, -S(=O)p-, -X2-C1-4alkanediyl- or -C1-4alkanediyl-X2-; R3 is NHR13; NR13R14; -C(=O)-NER13; -C(=O)-NR13R14; -C(=O)-R15; -CH=N-NH-C(=O)-R16; substituted C1-6alkyl; optionally substituted C1-6alkyloxyC1-6alkyl; substituted C2-6alkenyl; substituted C2-6alkynyl; C1-6alkyl substituted with hydroxy and a second substituent; -C(=N-O-R8)-C1-4alkyl; R7; or -X3-R7; R4 is halo, hydroxy, C1-6alkyl, C3-7cycloalkyl, C1-6alkyloxy, cyano, nitro, polyhaloC1-6alkyl, polyhaloC1-6alkyloxy, aminocarbonyl, C1-6alkyloxycarbonyl, C1-6alkylcarbonyl, formyl, amino, mono- or di(C1-4alkyl)amino; their use as a medicine, their processes for preparation and pharmaceutical compositions comprising them.

  本发明涉及式中的艾滋病毒复制抑制剂 的N-氧化物、药学上可接受的加成盐、季胺及其立体异构体形式，其中含有-a1=a2-a3=a4-和-b1=b2-b3=b4-的环代表苯基、吡啶基、嘧啶基、吡嗪基、哒嗪基；取代的C1-6烷氧基Cl-6烷基羰基；R2 是羟基、卤代、任选取代的 C1-6 烷基、C3-7 环烷基、任选取代的 C2-6 烯基、任选取代的 C2-6 烷炔基、C1-6烷氧基、C1-6烷氧基羰基、羧基、氰基、硝基、氨基、单或双（C1-6烷氧基羰基）、C1-6烷氧基羰基、C1-6烷基羧基、C1-6烷基羰基氨基、单-或二(C1-6烷基)氨基、多卤甲基、多卤甲基氧基、多卤甲基硫代、-S(＝O)pR6、-NH-S(＝O)pR6、-C(＝O)R6、-NHC(＝O)H、-C(＝O)NHNH2、-NHC(＝O)R6、-C(＝NH)R6 或 5 元杂环；X1 是-NR5-、-NH-NH-、-N=N-、-O-、-C(=O)-、C1-4烷二基、-CHOH-、-S-、-S(=O)p-、-X2-C1-4烷二基-或-C1-4烷二基-X2-； R3 是 NHR13；NR13R14；-C(=O)-NER13；-C(=O)-NR13R14；-C(=O)-R15；-CH=N-NH-C(=O)-R16；取代的 C1-6 烷基；任选取代的 C1-6 烷氧基 C1-6 烷基；取代的 C2-6 烯基；取代的 C2-6 烷炔基；被羟基和第二个取代基取代的 C1-6 烷基；-R4为卤代、羟基、C1-6烷基、C3-7环烷基、C1-6烷氧基、氰基、硝基、多卤代C1-6烷基、多卤代C1-6烷氧基、氨基羰基、C1-6烷氧基羰基、C1-6烷基羰基、甲酰基、氨基、单-或二(C1-4烷基)氨基；它们的医药用途、制备工艺和包含它们的药物组合物。