4-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde | 1333472-89-1

• 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-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde
• CAS: 1333472-89-1
• 化学式: C₁₀H₈N₂OS
• 分子量: 204.252
• InChiKey: USWUGTKXFNKMQE-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以90%的产率得到2-[4-(Diethoxymethyl)phenyl]-5-methyl-1,3,4-thiadiazole
  参考文献：
  名称：

  [EN] OPTICALLY ACTIVE PDE10 INHIBITOR
  [FR] INHIBITEUR DE PDE10 OPTIQUEMENT ACTIF

  摘要：

  本发明涉及(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的纯对映体，具体而言，(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮。本发明还涉及(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的晶体结构，(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的药物组合物，使用(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮抑制PDE10的方法，以及在(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的生产中使用的过程和特定个体中间体。

  公开号：

  WO2015167968A1
• 作为产物：
  描述：

  2-溴-5-甲基-1,3,4-噻二唑 、 4-甲酰基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 以85%的产率得到4-(5-methyl-1,3,4-thiadiazol-2-yl)benzaldehyde
  参考文献：
  名称：

  [EN] SOLID STATE FORMS OF A PDE10 INHIBITOR
  [FR] FORMES SOLIDES D'UN INHIBITEUR DE PDE10

  摘要：

  该发明涉及一种新的可变水合物晶体形式，1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮，其制备方法，药物组合物以及其在抑制PDE10方面的用途。

  公开号：

  WO2017079678A1

文献信息

• PDE10 INHIBITORS AND RELATED COMPOSITIONS AND METHODS
  申请人：Cutshall Neil S.

  公开号：US20110224202A1

  公开（公告）日：2011-09-15

  Compounds that inhibit PDE10 are disclosed that have utility in the treatment of a variety of conditions, including (but not limited to) psychotic, anxiety, movement disorders and/or neurological disorders such as Parkinson's disease, Huntington's disease, Alzheimer's disease, encephalitis, phobias, epilepsy, aphasia, Bell's palsy, cerebral palsy, sleep disorders, pain, Tourette's syndrome, schizophrenia, delusional disorders, drug-induced psychosis and panic and obsessive-compulsive disorders. Pharmaceutically acceptable salts, stereoisomers, solvates and prodrugs of the compounds are also provided. Also disclosed are compositions containing a compound in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for inhibiting PDE10 in a warm-blooded animal in need of the same.

  揭示了抑制PDE10的化合物，对治疗多种疾病有用，包括（但不限于）精神病、焦虑、运动障碍和/或神经系统疾病，如帕金森病、亨廷顿病、阿尔茨海默病、脑炎、恐惧症、癫痫、失语症、贝尔氏面瘫、脑瘫、睡眠障碍、疼痛、抽动综合征、精神分裂症、妄想症、药物诱发的精神病、恐慌和强迫症。还提供了这些化合物的药用盐、立体异构体、溶剂合物和前药。还揭示了含有化合物与药用载体组合的组合物，以及与使用有关的方法，用于在需要的温血动物中抑制PDE10。
• [EN] PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF A PDE10 INHIBITOR<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION D'UN INHIBITEUR DE LA PDE10
  申请人：OMEROS CORP

  公开号：WO2015167969A1

  公开（公告）日：2015-11-05

  The present invention is directed to an improved process for the preparation of compounds of Formula (II) and Formula (III), which are useful in the inhibition of PDE10. In particular, the present invention is directed to an improved process for the preparation of 1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, which is useful in the inhibition of PDE10.

  本发明涉及一种改进的工艺，用于制备式（II）和式（III）化合物，这些化合物在抑制PDE10方面是有用的。具体地，本发明涉及一种改进的工艺，用于制备1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮，这在抑制PDE10方面是有用的。
• PDE10 inhibitors and related compositions and methods
  申请人：Omeros Corporation

  公开号：US08343970B2

  公开（公告）日：2013-01-01

  Compounds that inhibit PDE10 are disclosed that have utility in the treatment of a variety of conditions, including (but not limited to) psychotic, anxiety, movement disorders and/or neurological disorders such as Parkinson's disease, Huntington's disease, Alzheimer's disease, encephalitis, phobias, epilepsy, aphasia, Bell's palsy, cerebral palsy, sleep disorders, pain, Tourette's syndrome, schizophrenia, delusional disorders, drug-induced psychosis and panic and obsessive-compulsive disorders. Pharmaceutically acceptable salts, stereoisomers, solvates and prodrugs of the compounds are also provided. Also disclosed are compositions containing a compound in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for inhibiting PDE10 in a warm-blooded animal in need of the same.

  本文披露了抑制PDE10的化合物，具有治疗多种疾病的效用，包括（但不限于）精神病、焦虑、运动障碍和/或神经系统疾病，如帕金森病、亨廷顿病、阿尔茨海默病、脑炎、恐惧症、癫痫、失语症、贝尔氏面瘫、脑性瘫痪、睡眠障碍、疼痛、抽动症、精神分裂症、妄想性障碍、药物诱导的精神病、恐慌和强迫症。此外，还提供了该化合物的药物可接受的盐、立体异构体、溶剂化物和前药。还披露了含有化合物和药物可接受的载体的组合物，以及与之相关的方法，用于抑制需要同样的温血动物中的PDE10。
• OPTICALLY ACTIVE PDE10 INHIBITOR
  申请人：OMEROS CORPORATION

  公开号：US20160024070A1

  公开（公告）日：2016-01-28

  The present invention is directed to a pure enantiomer of 1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, in particular, (S)-1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-y1)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone. The present invention is also directed a crystal structure of (S)-1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, a pharmaceutical composition of (S)-1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, a method of inhibiting PDE10 with (S)-1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, and a process and particular individual intermediates used in the production of (S)-1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone.

  本发明涉及一种1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的纯对映体，特别是(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮。本发明还涉及(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的晶体结构、(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的药物组合物、使用(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮抑制PDE10的方法，以及用于生产(S)-1-(5-(4-氯-3,5-二甲氧基苯基)呋喃-2-基)-2-乙氧基-2-(4-(5-甲基-1,3,4-噻二唑-2-基)苯基)乙酮的特定中间体的过程。
• PROCESSES AND INTERMEDIATES FOR THE PREPARATION OF A PDE10 INHIBITOR
  申请人：Omeros Corporation

  公开号：US20160024069A1

  公开（公告）日：2016-01-28

  The present invention is directed to an improved process for the preparation of compounds of Formula (II) and Formula (III), which are useful in the inhibition of PDE10. In particular, the present invention is directed to an improved process for the preparation of 1-(5-(4-chloro-3,5-dimethoxyphenyl)furan-2-yl)-2-ethoxy-2-(4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl)ethanone, which is useful in the inhibition of PDE10.

  本发明涉及一种改进的制备公式（II）和公式（III）化合物的方法，该化合物在抑制PDE10方面有用。具体而言，本发明涉及一种改进的制备1-（5-（4-氯-3,5-二甲氧基苯基）呋喃-2-基）-2-乙氧基-2-（4-（5-甲基-1,3,4-噻二唑-2-基）苯基）乙酮的方法，该化合物在抑制PDE10方面有用。