4-氯-5-氮杂吲哚-2-甲酸甲酯 | 688357-19-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 4-氯-5-氮杂吲哚-2-甲酸甲酯
• 中文别名: 4-氯-1H-吡咯并[3,2-c]吡啶-2-羧酸甲酯
• 英文名称: methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate
• 英文别名: 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid methyl ester
• CAS: 688357-19-9
• 化学式: C₉H₇ClN₂O₂
• mdl: MFCD09870065
• 分子量: 210.62
• InChiKey: NFEOJQQNFBVATP-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225°
• 沸点：
  400.2±40.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 4-chloro-5-azaindole-2-carboxylate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 4-chloro-5-azaindole-2-carboxylate
CAS number: 688357-19-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H7ClN2O2
Molecular weight: 210.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen chloride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-氯-5-氮杂吲哚-2-甲酸甲酯 在 potassium fluoride 、 二(三叔丁基膦)钯 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 11.0h， 生成 methyl 4-(3-ethoxyphenyl)-1-[2-(4-hydroxyphenoxy)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylate
  参考文献：
  名称：

  [EN] TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF
  [FR] INHIBITEURS DE LA KINASE TRKA, COMPOSITIONS EN CONTENANT ET MÉTHODES ASSOCIÉES

  摘要：

  本发明涉及式I和la化合物，它们是原肌球蛋白相关激酶（Trk）家族蛋白激酶抑制剂，因此可用于治疗疼痛、炎症、癌症、再狭窄、动脉粥样硬化、银屑病、血栓形成、与脱髓鞘或髓鞘形成障碍相关的疾病、紊乱、损伤或功能障碍，或与神经生长因子（NGF）受体TrkA异常活性相关的疾病或紊乱。

  公开号：

  WO2013009582A1
• 作为产物：
  描述：

  2-氯-3-吡啶甲醛 在 sodium methylate 作用下， 以 甲醇 、 均三甲苯 为溶剂， 反应 1.0h， 生成 4-氯-5-氮杂吲哚-2-甲酸甲酯
  参考文献：
  名称：

  取代的 5-、6- 和 7-氮杂吲哚的 Hemetsberger-Knittel 合成

  摘要：

  通过 Hemetsberger-Knittel 反应制备了一系列取代的 5-、6-和 7-氮杂吲哚。一般来说，在更高的温度和更短的反应时间下获得比形成类似吲哚所需的更好的产率，并且在某些情况下，仅在最低温度以下发生分解。生成的模板为后续功能化提供多达五个位点，以实现广泛的化学多样性。

  DOI：

  10.1055/s-2005-872165

文献信息

• Modulators of Cystic Fibrosis Transmembrane Conductance Regulator
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160095858A1

  公开（公告）日：2016-04-07

  The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

  本发明涉及一种具有以下化学式I的化合物： 或其药用可接受的盐，其中R 1 ，R 2 ，R 3 ，W，X，Y，Z，n，o，p和q在此处定义，用于治疗CFTR介导的疾病，如囊性纤维化。本发明还涉及药物组合物、治疗方法和相关工具包。
• [EN] PYRROLO[3,2-C]PYRIDINE DERIVATIVES AS TLR INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-C]PYRIDINE COMME INHIBITEURS DE TLR
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2015088045A1

  公开（公告）日：2015-06-18

  The present invention provides a heterocyclic compound having a TLR7, TLR9, TLR7/8, TLR7/9 or TLR7/8/9 inhibitory action, which is useful as an agent for the prophylaxis or treatment of autoimmune diseases, inflammatory diseases and the like, in particular, systemic lupus erythematosus, Sjogren's syndrome, rheumatoid arthritis, psoriasis, inflammatory bowel disease and the like. The present invention is a compound represented by the formula (1): wherein each symbol is as described in the specification, or a salt thereof.

  本发明提供了一种具有TLR7、TLR9、TLR7/8、TLR7/9或TLR7/8/9抑制作用的杂环化合物，该化合物可用作自身免疫性疾病、炎症性疾病等的预防或治疗剂，特别是系统性红斑狼疮、干燥综合征、类风湿关节炎、牛皮癣、炎症性肠病等。本发明是由式（1）表示的化合物：其中每个符号如说明书中所述，或其盐。
• Method of Treating Pathological Blushing
  申请人：Tobert A. Jonathan

  公开号：US20070299122A1

  公开（公告）日：2007-12-27

  A method of treating pathological blushing is disclosed wherein the patient is administered a DP receptor antagonist. Compositions containing DP antagonists are also included.

  揭示了一种治疗病理性面红的方法，其中患者接受DP受体拮抗剂。还包括含有DP拮抗剂的组合物。
• Method of treating atherosclerosis, dyslipidemias and related conditions
  申请人：——

  公开号：US20040229844A1

  公开（公告）日：2004-11-18

  A method of treating atherosclerosis is disclosed wherein nicotinic acid or another nicotinic acid receptor agonist is administered to the patient in combination with a DP receptor antagonist. The DP receptor antagonist is administered to reduce, prevent or eliminate flushing that may otherwise occur.

  揭示了一种治疗动脉粥样硬化的方法，其中尼古酸或其他尼古酸受体激动剂与DP受体拮抗剂联合给患者使用。DP受体拮抗剂被用来减少、预防或消除可能发生的潮红。
• PYRROLO[3,2-C]PYRIDINE DERIVATIVES AS TLR INHIBITORS
  申请人：TAKEDA PHARMACEUTICAL COMPANY LIMITED

  公开号：US20170008885A1

  公开（公告）日：2017-01-12

  The present invention provides a heterocyclic compound having a TLR7, TLR9, TLR7/8, TLR7/9 or TLR7/8/9 inhibitory action, which is useful as an agent for the prophylaxis or treatment of autoimmune diseases, inflammatory diseases and the like, in particular, systemic lupus erythematosus, Sjogren's syndrome, rheumatoid arthritis, psoriasis, inflammatory bowel disease and the like. The present invention is a compound represented by the formula (1): wherein each symbol is as described in the specification, or a salt thereof.

  本发明提供了一种具有TLR7、TLR9、TLR7/8、TLR7/9或TLR7/8/9抑制作用的杂环化合物，该化合物可用作自身免疫性疾病、炎症性疾病等的预防或治疗剂，特别是系统性红斑狼疮、干燥综合征、类风湿关节炎、牛皮癣、炎症性肠病等。本发明是由式（1）表示的化合物，其中每个符号如说明书中所述，或其盐。