公开(公告)号：US10829474B2

公开(公告)日：2020-11-10

申请号：US16783894

申请日：2020-02-06

Applicant: Takeda Pharmaceutical Company Limited

Inventor： Fumiya Komura ,  Yoshihiro Higuchi

IPC: C07D401/06 ,  C07D401/14 ,  B01J31/22 ,  C07B61/00

Abstract: The present invention provides a production method of heterocyclic compound having an excellent CH24H inhibitory action, which is suitable for industrial production. In the present invention, a 2-halogenonicotinic acid or a reactive derivative thereof or a salt thereof is reacted with 4-benzyl-4-hydroxypiperidine acid addition salt to give a (4-benzyl-4-hydroxypiperidin-1-yl) (2-halogenopyridin-3-yl)methanone or a salt thereof, and then the obtained compound is reacted with pyridine-4-boronic acid or a reactive derivative thereof or a salt thereof in the presence of a metal catalyst and a base to give (4-benzyl-4-hydroxypiperidin-1-yl) (2,4′- bipyridin-3-yl)methanone or a salt thereof.

公开(公告)号：US20200172509A1

公开(公告)日：2020-06-04

申请号：US16783894

申请日：2020-02-06

Applicant: Takeda Pharmaceutical Company Limited

Inventor： Fumiya Komura ,  Yoshihiro Higuchi

IPC: C07D401/06 ,  C07D401/14 ,  B01J31/22

Abstract: The present invention provides a production method of heterocyclic compound having an excellent CH24H inhibitory action, which is suitable for industrial production.In the present invention, a 2-halogenonicotinic acid or a reactive derivative thereof or a salt thereof is reacted with 4-benzyl-4-hydroxypiperidine acid addition salt to give a (4-benzyl-4-hydroxypiperidin-1-yl)(2-halogenopyridin-3-yl)methanone or a salt thereof, and then the obtained compound is reacted with pyridine-4-boronic acid or a reactive derivative thereof or a salt thereof in the presence of a metal catalyst and a base to give (4-benzyl-4-hydroxypiperidin-1-yl) (2,4′-bipyridin-3-yl)methanone or a salt thereof.

公开(公告)号：US11795178B2

公开(公告)日：2023-10-24

申请号：US17694635

申请日：2022-03-14

Applicant: Takeda Pharmaceutical Company Limited

Inventor： Koichiro Fukuoka ,  Kazuhiro Miwa ,  Tsuyoshi Sasaki ,  Fumiya Komura

IPC: C07D495/04 ,  C07D333/38 ,  C07D409/12

CPC classification number: C07D495/04 ,  C07D333/38 ,  C07D409/12

Abstract: The present invention provides a production method of a thienopyrimidine derivative or a salt thereof which has a gonadotropin releasing hormone (GnRH) antagonistic action with high quality in high yield. The present invention provides a method of producing a thienopyrirnidine derivative, which comprises reacting 6-(4-aminophenyl)-1-(2,6-difluorobenzyl)-5-dimethylaminomethyl-3-(6-methoxypyridazin-3-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione or salt thereof, 1,1′-carbonyldiimidazole or a salt thereof and methoxyamine or a salt thereof, and the like.

公开(公告)号：US20150266891A1

公开(公告)日：2015-09-24

申请号：US14432188

申请日：2013-09-27

Applicant: TAKEDA PHARMACEUTICAL COMPANY LIMITED

Inventor： Koichiro Fukuoka ,  Kazuhiro Miwa ,  Tsuyoshi Sasaki ,  Fumiya Komura

IPC: C07D495/04 ,  C07D409/12

CPC classification number: C07D495/04 ,  C07D333/38 ,  C07D409/12

Abstract: The present invention provides a production method of a thienopyrimidine derivative or a salt thereof which has a gonadotropin releasing hormone (GnRH) antagonistic action with high quality in high yield. The present invention provides a method of producing a thienopyrimidine derivative, which comprises reacting 6-(4-aminophenyl)-1-(2,6-difluorobenzyl)-5-dimethyl aminomethyl-3-(6-methoxypyridazin-3-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione or salt thereof, 1,1′-carbonyldiimidazole or a salt thereof and methoxyamine or a salt thereof, and the like.

Abstract translation: 本发明提供具有促进促性腺激素释放激素（GnRH）拮抗作用的噻吩并嘧啶衍生物或其盐的高产率的制造方法。 本发明提供一种噻吩并嘧啶衍生物的制备方法，其包括使6-（4-氨基苯基）-1-（2,6-二氟苄基）-5-二甲基氨基甲基-3-（6-甲氧基哒嗪-3-基）噻吩并 [2,3-d]嘧啶-2,4（1H，3H） - 二酮或其盐，1,1'-羰基二咪唑或其盐和甲氧胺或其盐等。

公开(公告)号：US10562881B2

公开(公告)日：2020-02-18

申请号：US15768037

申请日：2016-10-14

Applicant: Takeda Pharmaceutical Company Limited

Inventor： Fumiya Komura ,  Yoshihiro Higuchi

IPC: C07D401/06 ,  C07D401/14 ,  B01J31/22

Abstract: The present invention provides a production method of heterocyclic compound having an excellent CH24H inhibitory action, which is suitable for industrial production.In the present invention, a 2-halogenonicotinic acid or a reactive derivative thereof or a salt thereof is reacted with 4-benzyl-4-hydroxypiperidine acid addition salt to give a (4-benzyl-4-hydroxypiperidin-1-yl) (2-halogenopyridin-3-yl)methanone or a salt thereof, and then the obtained compound is reacted with pyridine-4-boronic acid or a reactive derivative thereof or a salt thereof in the presence of a metal catalyst and a base to give (4-benzyl-4-hydroxypiperidin-1-yl) (2,4′-bipyridin-3-yl)methanone or a salt thereof.

公开(公告)号：US09758528B2

公开(公告)日：2017-09-12

申请号：US14432188

申请日：2013-09-27

Applicant: Takeda Pharmaceutical Company Limited

Inventor： Koichiro Fukuoka ,  Kazuhiro Miwa ,  Tsuyoshi Sasaki ,  Fumiya Komura

IPC: C07D495/04 ,  C07D333/38 ,  C07D409/12

CPC classification number: C07D495/04 ,  C07D333/38 ,  C07D409/12

Abstract: The present invention provides a production method of a thienopyrimidine derivative or a salt thereof which has a gonadotropin releasing hormone (GnRH) antagonistic action with high quality in high yield. The present invention provides a method of producing a thienopyrimidine derivative, which comprises reacting 6-(4-aminophenyl)-1-(2,6-difluorobenzyl)-5-dimethyl aminomethyl-3-(6-methoxypyridazin-3-yl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione or salt thereof, 1,1′-carbonyldiimidazole or a salt thereof and methoxyamine or a salt thereof, and the like.