公开(公告)号：US09487485B2

公开(公告)日：2016-11-08

申请号：US14770914

申请日：2014-02-27

Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITED

Inventor： Keisuke Majima

IPC: C07D213/71 ,  C07D401/12

CPC classification number: C07D401/12 ,  A61K9/2018 ,  A61K9/2866 ,  C07D213/71

Abstract: An object of the present invention is to provide a production method of an intermediate used in the production method of a sulfonylpyrrole compound useful as a pharmaceutical product. The present invention relates to a method of producing sulfonylpyrrole compound (VI) by reacting a pyridine-3-sulfonic acid compound with phosphorus pentachloride in a solvent of chlorobenzene or trifluoromethylbenzene to give a pyridine-3-sulfonyl chloride compound, reacting the compound without isolation with compound (III) to give compound (IV), and subjecting the compound (IV) to a reductive amination reaction. wherein R2 is a hydrocarbon group etc. and R3 and R4 are each a hydrogen atom etc., wherein R1 is an optionally substituted pyridin-3-yl group, and the other symbols are as defined above, wherein R5 is an alkyl group and the other symbols are as defined above.

Abstract translation: 本发明的目的是提供用作药物产品的磺酰基吡咯化合物的制造方法中使用的中间体的制造方法。 本发明涉及通过在氯苯或三氟甲基苯的溶剂中使吡啶-3-磺酸化合物与五氯化磷反应生成磺酰基吡咯化合物（VI）的方法，得到吡啶-3-磺酰氯化合物，使化合物不分离 与化合物（III）反应，得到化合物（IV），并使化合物（IV）进行还原胺化反应。 其中R 2是烃基等，R 3和R 4各自是氢原子等，其中R 1是任选取代的吡啶-3-基，其它符号如上所定义，其中R 5是 烷基，其它符号如上所定义。

公开(公告)号：US10370357B2

公开(公告)日：2019-08-06

申请号：US15899055

申请日：2018-02-19

Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITED

Inventor： Keisuke Majima

IPC: C07D401/12 ,  C07D213/71 ,  A61K9/28 ,  A61K9/20

Abstract: An object of the present invention is to provide a production method of an intermediate used in the production method of a sulfonylpyrrole compound useful as a pharmaceutical product. The present invention relates to a method of producing sulfonylpyrrole compound (VI) by reacting a pyridine-3-sulfonic acid compound with phosphorus pentachloride in a solvent of chlorobenzene or trifluoromethylbenzene to give a pyridine-3-sulfonyl chloride compound, reacting the compound without isolation with compound (III) to give compound (IV), and subjecting the compound (IV) to a reductive amination reaction. wherein R2 is a hydrocarbon group etc. and R3 and R4 are each a hydrogen atom etc., wherein R2 is an optionally substituted pyridin-3-yl group, and the other symbols are as defined above, wherein R5 is an alkyl group and the other symbols are as defined above.

公开(公告)号：US09932322B2

公开(公告)日：2018-04-03

申请号：US15266307

申请日：2016-09-15

Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITED

Inventor： Keisuke Majima

IPC: C07D401/12 ,  C07D213/71 ,  A61K9/28 ,  A61K9/20

CPC classification number: C07D401/12 ,  A61K9/2018 ,  A61K9/2866 ,  C07D213/71

Abstract: An object of the present invention is to provide a production method of an intermediate used in the production method of a sulfonylpyrrole compound useful as a pharmaceutical product. The present invention relates to a method of producing sulfonylpyrrole compound (VI) by reacting a pyridine-3-sulfonic acid compound with phosphorus pentachloride in a solvent of chlorobenzene or trifluoromethylbenzene to give a pyridine-3-sulfonyl chloride compound, reacting the compound without isolation with compound (III) to give compound (IV), and subjecting the compound (IV) to a reductive amination reaction. wherein R2 is a hydrocarbon group etc. and R3 and R4 are each a hydrogen atom etc., wherein R1 is an optionally substituted pyridin-3-yl group, and the other symbols are as defined above, wherein R5 is an alkyl group and the other symbols are as defined above.