2-amino-1,3-benzoxazole-6-sulfonyl chloride | 470704-96-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-amino-1,3-benzoxazole-6-sulfonyl chloride
• 英文别名: 2-Amino-6-chlorosulfonylbenzoxazole
• CAS: 470704-96-2
• 化学式: C₇H₅ClN₂O₃S
• 分子量: 232.647
• InChiKey: VLHKDXZNLZSRAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-(2-amino-5-chlorophenyl)hex-5-ynoate 、 2-amino-1,3-benzoxazole-6-sulfonyl chloride 在 吡啶 作用下， 反应 1.0h， 以9%的产率得到methyl 6-[2-[(2-amino-1,3-benzoxazol-6-yl)sulfonylamino]-5-chlorophenyl]hex-5-ynoate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of a Novel Series of Indole Sulfonamide Peroxisome Proliferator Activated Receptor (PPAR) α/γ/δ Triple Activators: Discovery of Lanifibranor, a New Antifibrotic Clinical Candidate

  摘要：

  Here, we describe the identification and synthesis of novel indole sulfonamide derivatives that activate the three peroxisome proliferator activated receptor (PPAR) isoforms. Starting with a PPAR alpha activator, compound 4, identified during a high throughput screening (HTS) of our proprietary screening library, a systematic optimization led to the discovery of lanifibranor (IVA337) 5, a moderately potent and well balanced pan PPAR agonist with an excellent safety profile. In vitro and in vivo, compound 5 demonstrated strong activity in models that are relevant to nonalcoholic steatohepatitis (NASH) pathophysiology suggesting therapeutic potential for NASH patients.

  DOI：

  10.1021/acs.jmedchem.7b01285
• 作为产物：
  描述：

  氯磺酸 、 2-氨基苯并噁唑 、 氯化亚砜 、 、 disodium;carbonate 在 水 、 乙酸乙酯 、 无水氯化钙 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以yielding 7.8 g (90%) of 2-amino-6-chlorosulfonylbenzoxazole (6-3)的产率得到2-amino-1,3-benzoxazole-6-sulfonyl chloride
  参考文献：
  名称：

  BROADSPECTRUM 2-(SUBSTITUTED-AMINO)-BENZOXAZOLE SULFONAMIDE HIV PROTEASE INHIBITORS

  摘要：

  本发明涉及具有以下式N-氧化物，盐，立体异构体，外消旋混合物，前药，酯和其代谢物，其中R1和R8各自为H，可选择性取代的C1-6烷基，C2-6烯基，C3-7环烷基，芳基，Het1，Het2; R1也可以是式（R11aR11b）NC（R10aR10b）CR9—的基团; t为0，1或2; R2为H或C1-6烷基; L为—C（═O）—，—O—C（═O）—，—NR8—C（═O）—，—O—C1-6烷二基-C（═O）—，—NR8—C1-6烷二基-C（═O）—，—S（═O）2—，—O—S（═O）2—，—NR8—S（═O）2; R3为C1-6烷基，芳基，C3-7环烷基，C3-7环烷基C1-4烷基，或芳基C1-4烷基; R4为H，C1-4烷基OC（═O），羧基，氨基C（═O），单烷基或双烷基氨基C（═O），C3-7环烷基，C2-6烯基，C2-6炔基或可选择性取代的C1-6烷基; A为C1-6烷二基，—C（═O）—，—C（═S）—，—S（═O）2—，C1-6烷二基-C（═O）—，C1-6烷二基-C（═S）—或C1-6烷二基-S（═O）2—; R5为H，OH，C1-6烷基，Het1C1-6烷基，Het2C1-6烷基，可选择性取代的氨基C1-6烷基; R6为C1-6烷基氧，Het1，Het1氧，Het2，Het2氧，芳基，芳基氧，C1-6烷氧羰基氨基或氨基; 如果-A-不是C1-6烷二基，则R6也可以是C1-6烷基，Het1C1-4烷基，Het1OC1-4烷基，Het2C1-4烷基，Het2OC1-4烷基，芳基C1-4烷基，芳基OC1-4烷基或氨基C1-4烷基; 其中定义R6中的每个氨基可选择性取代; -A-R6为羟基C1-6烷基; R5和-A-R6与它们所连接的氮原子一起还可以形成Het1或Het2。它进一步涉及它们作为广谱HIV蛋白酶抑制剂的用途，它们的制备过程以及包含它们的制药组合物和诊断试剂盒。它还涉及与另一种抗逆转录病毒药物的组合以及它们作为参考化合物或试剂在测定中的用途。

  公开号：

  US20070135447A1

文献信息

• Indole Compounds, Method of Preparing Them and Uses Thereof
  申请人：BINET Jean

  公开号：US20080153816A1

  公开（公告）日：2008-06-26

  Indole compounds corresponding to the formula (I): as defined in the claims, pharmaceutically acceptable addition salts of such compounds, pharmaceutical compositions containing such compounds, the process for their preparation, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular disease, inflammatory disease and neurodegeneration.

  与公式（I）相对应的吲哚化合物，如权利要求中所定义的，这些化合物的药学上可接受的加盐物，含有这些化合物的药物组合物，其制备方法，以及它们作为药理活性物质的用途，特别是在治疗高三酰甘油血症、高脂血症、高胆固醇血症、糖尿病、内皮功能障碍、心血管疾病、炎症性疾病和神经退行性疾病方面。
• Pyrrolopyridine Compounds, Method of Making Them and Uses Thereof
  申请人：Boubia Benaissa

  公开号：US20080200495A1

  公开（公告）日：2008-08-21

  Pyrrolopyridine compounds corresponding to formula (I): as defined in the claims, pharmaceutically acceptable salts thereof, the process for preparing such compounds, pharmaceutical compositions containing such compounds, and their use as pharmacologically active substances, especially in the treatment of hypertriglyceridemia, hyperlipidemia, hypercholesterolemia, diabetes, endothelial dysfunction, cardiovascular diseases, inflammatory diseases and neurodegenerative diseases.

  与公式（I）中定义的吡咯吡啶化合物相应的药用盐，制备这类化合物的方法，含有这类化合物的药物组合物，以及它们作为药理活性物质的用途，特别是在治疗高甘油三酯血症、高脂血症、高胆固醇血症、糖尿病、内皮功能障碍、心血管疾病、炎症性疾病和神经退行性疾病方面。
• Broadspecturm 2-amino-benzoxazole sulfonamide hiv protease inhibitors
  申请人：——

  公开号：US20040106661A1

  公开（公告）日：2004-06-03

  The present invention concerns the compounds having the formula 1 N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein R 1 and R 8 each are H, optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, aryl, Het 1 , Het 2 ; R 1 may also be a radical of formula (R 11a R 11b )NC(R 10a R 10b )CR 9 —; t is 0, 1 or 2; R 2 is H or C 1-6 alkyl; L is —C(═O)—, —O—C(═O)—, —NR 8 —C(═O)—, —C 1-6 alkanediyl-C(═O)—, —NR 8 —C 1-6 alkanediyl-C(═O)—, —S(═O) 2 -, —O—S(═O) 2 —, —NR 9 -S(═O) 2 ; R 3 is C 1-6 alkyl, aryl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, or arylC 1-4 alkyl; R 4 is H, C 1-4 alkylOC(═O), carboxyl, aminoC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl or optionally substituted C 1-6 alkyl; R 5 and R 6 are H or C 1-6 alkyl. It further relates to their use as broadspectrum HIV protease inhibitors, processes for their preparation as well as pharmaceutical compositions and diagnostic kits comprising them. It also concerns combinations thereof with another anti-retroviral agent, and to their use in assays as reference compounds or as reagents.

  本发明涉及具有式1的化合物，其包括N-氧化物、盐、立体异构体、外消旋混合物、前药、酯和其代谢物，其中R1和R8分别为H、可选取代的C1-6烷基、C2-6烯基、C3-7环烷基、芳基、Het1、Het2；R1还可以是公式（R11aR11b）NC（R10aR10b）CR9—的基团；t为0、1或2；R2为H或C1-6烷基；L为—C(═O)—、—O—C(═O)—、—NR8—C(═O)—、—C1-6烷二基-C(═O)—、—NR8—C1-6烷二基-C(═O)—、—S(═O)2-、—O—S(═O)2—、—NR9-S(═O)2；R3为C1-6烷基、芳基、C3-7环烷基、C3-7环烷基C1-4烷基或芳基C1-4烷基；R4为H、C1-4烷基OC(═O)、羧基、氨基C(═O)、单烷基或二烷基氨基C(═O)、C3-7环烷基、C2-6烯基、C2-6炔基或可选取代的C1-6烷基；R5和R6为H或C1-6烷基。本发明还涉及其作为广谱HIV蛋白酶抑制剂的用途，以及它们的制备方法、包含它们的制药组合物和诊断试剂盒。本发明还涉及它们与另一种抗逆转录病毒药物的组合，以及它们作为参考化合物或试剂在测定中的用途。
• Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide hiv protease inhibitors
  申请人：——

  公开号：US20040132791A1

  公开（公告）日：2004-07-08

  The present invention concerns the compounds having the formula 1 N-oxides, salts, stereoisomeric forms, racemic mixtures, prodrugs, esters and metabolites thereof, wherein R 1 and R 8 each are H, optionally substituted C 1-6 alkyl, C 2-6 alkenyl, C 3-7 cycloalkyl, aryl, Het 1 , Het 2 ; R 1 may also be a radical of formula (R 11a R 11b )NC(R 10a R 10b )CR 9 —; t is 0, 1 or 2; R 2 is H br C 1-6 alkyl; L is —C(═O)—, —O—C(═O)—, —NR 8 —C(═O)—, —C 1-6 alkanediyl-C(═O)—, —NR 8 —C 1-6 alkanediyl-C(═O)—, —S(═O) 2 —, —O—S(═O) 2 —, —NR 8 —S(═O) 2 ; R 3 is C 1-6 alkyl, aryl, C 3-7 cycloalkyl, C 3-7 cycloalkylC 1-4 alkyl, or arylC 1-4 alkyl; R 4 is H, C 1-4 alkylOC(═O), carboxyl, aminoC(═O), mono- or di(C 1-4 alkyl)aminoC(═O), C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl or optionally substituted C 1-6 alkyl; A is C 1-6 alkanediyl, —C(═O)—, —C(═S)—, —S(═O) 2 —, C 1-6 alkanediyl-C(═O)—, C 1-6 alkanediyl-C(═S)—or C 1-6 alkanediyl-S(═O) 2 —; R 5 is H, OH, C 1-6 alkyl, Het 1 C 1-6 alkyl, Het 2 C 1-6 alkyl, optionally substituted aminoC 1-6 alkyl; R 6 is C 1-6 alkylO, Het 1 , Het 1 O, Het 2 , Het 2 O, aryl, arylO, C 1-6 alkyloxycarbonylamino or amino; and in case -A- is other than C 1-6 alkanediyl then R 6 may also be C 1-6 alkyl, Het 1 C 1-4 alkyl, Het 1 OC 1-4 alkyl, Het 2 C 1-4 alkyl, Het 2 OC 1-4 alkyl, arylC 1-4 alkyl, arylOC 1-4 alkyl or aminoC 1-4 alkyl; whereby each of the amino groups in the definition of R 6 may optionally be substituted; -A-R 6 is hydroxyC 1-6 alkyl; R 5 and -A-R 6 taken together with the nitrogen atom to which they are attached may also form Het 1 or Het 2 . It further relates to their use as broadspectrum HIV protease inhibitors, processes for their preparation as well as pharmaceutical compositions and diagnostic kits comprising them. It also concerns combinations thereof with another anti-retroviral agent, and to their use in assays as reference compounds or as reagents.

  本发明涉及具有公式1N-氧化物、盐、立体异构体、外消旋混合物、前药、酯和其代谢物的化合物，其中R1和R8各自为H、可选取代的C1-6烷基、C2-6烯基、C3-7环烷基、芳基、Het1、Het2；R1还可以是公式（R11aR11b）NC（R10aR10b）CR9—的基团；t为0、1或2；R2为H、Br或C1-6烷基；L为—C(═O)—、—O—C(═O)—、—NR8—C(═O)—、—C1-6烷二基-C(═O)—、—NR8—C1-6烷二基-C(═O)—、—S(═O)2—、—O—S(═O)2—或—NR8—S(═O)2；R3为C1-6烷基、芳基、C3-7环烷基、C3-7环烷基C1-4烷基或芳基C1-4烷基；R4为H、C1-4烷基OC(═O)、羧基、氨基C(═O)、单烷基或二烷基氨基C(═O)、C3-7环烷基、C2-6烯基、C2-6炔基或可选取代的C1-6烷基；A为C1-6烷二基、—C(═O)—、—C(═S)—、—S(═O)2—、C1-6烷二基-C(═O)—、C1-6烷二基-C(═S)—或C1-6烷二基-S(═O)2—；R5为H、OH、C1-6烷基、Het1C1-6烷基、Het2C1-6烷基、可选取代的氨基C1-6烷基；R6为C1-6烷基O、Het1、Het1O、Het2、Het2O、芳基、芳基O、C1-6烷氧羰基氨基或氨基；如果-A-不是C1-6烷二基，则R6还可以是C1-6烷基、Het1C1-4烷基、Het1OC1-4烷基、Het2C1-4烷基、Het2OC1-4烷基、芳基C1-4烷基、芳基OC1-4烷基或氨基C1-4烷基；其中在R6的定义中的每个氨基可以选择性地被取代；-A-R6为羟基C1-6烷基；R5和-A-R6连同它们附着的氮原子也可以形成Het1或Het2。本发明还涉及它们作为广谱HIV蛋白酶抑制剂的用途，以及它们的制备方法、包含它们的制药组合物和诊断试剂盒。还涉及它们与其他抗逆转录病毒药物的组合使用，以及它们作为参考化合物或试剂在测定中的用途。
• Use of Pyrrolopyridine Compounds for Activating PPAR Receptors and Treatment of Conditions Involving Such Receptors
  申请人：Boubia Benaissa

  公开号：US20090239856A1

  公开（公告）日：2009-09-24

  A method of activating PPAR receptors in a subject, said method comprising administering to said subject an effective PPAR receptor activating amount of a pyrrolopyridine compound corresponding to formula (I): wherein R, R 1 , R 2 , R 3 , R 4 , X, Ar and n have defined meanings, or a pharmaceutically acceptable salt thereof, particularly as part of the treatment of a disorder or disease state selected from the group consisting of atherosclerosis, myocardial infarction, hypertension, and cerebral vascular disease.

  本发明涉及一种激活主体中PPAR受体的方法，该方法包括向该主体投与有效的PPAR受体激活量的与式(I)相对应的吡咯吡啶化合物，其中R、R1、R2、R3、R4、X、Ar和n具有定义的含义，或其药学上可接受的盐，特别用于治疗动脉粥样硬化、心肌梗死、高血压和脑血管疾病等疾病或病态。