A Scalable Synthesis of an Azabicyclooctanyl Derivative, a Novel DPP-4 Inhibitor

被引：23

作者：

Fei, Zhongbo ^{[2
]}

Wu, Quanbing ^{[2
]}

Zhang, Fei ^{[2
]}

Cao, Yudong ^{[2
]}

Liu, Chuanqin ^{[2
]}

Shieh, Wen-Chung ^{[1
]}

Xue, Song ^{[1
]}

McKenna, Joe ^{[1
]}

Prasad, Kapa ^{[1
]}

Prashad, Mahavir ^{[1
]}

Baeschlin, Daniel ^{[3
]}

Namoto, Kenji ^{[3
]}

机构：

[1] Novartis Pharmaceut, Chem & Analyt Dev, E Hanover, NJ 07936 USA

[2] Suzhou Novartis Pharma Technol Co Ltd, Chem & Analyt Dev, Changshu 215537, Jiangsu, Peoples R China

[3] Novartis Inst Biomed Res, Ctr Prote Chem, CH-4002 Basel, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 22期

关键词：

D O I：

10.1021/jo801830x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthetic strategy to a chiral azabicycclooctanyl derivative (1), a potent DPP-4 inhibitor, starting from a commercially available nortropine is described. The stereogenic center of 1 was established employing a modified protocol of Ellman's diastereoselective addition of a benzylic nucleophile to tert-butanesulfinimme. Other key steps include Corey-Chaykovsky reaction, Meinwald rearrangement, and CDMT-promoted amide bond formation involving a sterically hindered amine 2.

引用

页码：9016 / 9021

页数：6

共 50 条

[31] DPP-4 INHIBITOR THERAPY IN PATIENTS AFTER PANCREATIC TRANSPLANT
Ergin, Ahmet B.
Poggio, Emilio
Krishnamurthi, Venkatesh
Jaber, Tania
Hatipoglu, Betul A.
ENDOCRINE PRACTICE, 2015, 21 (06) : 567 - 573
[32] Onglyza®, new inhibitor of DPP-4, now available and repaid
不详
CORRESPONDANCES EN METABOLISMES HORMONES DIABETES ET NUTRITION, 2010, 14 (09): : 309 - 309
[33] Teneligliptin: a DPP-4 inhibitor for the treatment of type 2 diabetes
Kishimoto, Miyako
DIABETES METABOLIC SYNDROME AND OBESITY-TARGETS AND THERAPY, 2013, 6 : 187 - 195
[34] DPP-4 inhibitors
Ahren, Bo
BEST PRACTICE & RESEARCH CLINICAL ENDOCRINOLOGY & METABOLISM, 2007, 21 (04) : 517 - 533
[35] DPP-4 inhibitor (sitagliptin)-induced seronegative rheumatoid arthritis
Padron, Simonette
Rogers, Everett
Beckler, Michelle Demory
Kesselman, Marc
BMJ CASE REPORTS, 2019, 12 (08)
[36] Safety and efficacy of teneligliptin: a novel DPP-4 inhibitor for hemodialysis patients with type 2 diabetes
Hideo Otsuki
Takeo Kosaka
Kenzo Nakamura
Fumihiko Shimomura
Yoshitaka Kuwahara
Takuji Tsukamoto
International Urology and Nephrology, 2014, 46 : 427 - 432
[37] The safety of DPP-4 inhibitor and SGLT2 inhibitor combination therapies
Molina-Vega, Maria
Munoz-Garach, Araceli
Fernandez-Garcia, Jose C.
Tinahones, Francisco J.
EXPERT OPINION ON DRUG SAFETY, 2018, 17 (08) : 815 - 824
[38] Safety and efficacy of teneligliptin: a novel DPP-4 inhibitor for hemodialysis patients with type 2 diabetes
Otsuki, Hideo
Kosaka, Takeo
Nakamura, Kenzo
Shimomura, Fumihiko
Kuwahara, Yoshitaka
Tsukamoto, Takuji
INTERNATIONAL UROLOGY AND NEPHROLOGY, 2014, 46 (02) : 427 - 432
[39] Saxagliptin, a new DPP-4 inhibitor for the treatment of type 2 diabetes mellitus: novel aspects
Pedrianes Martin, P.
de Pablos Velasco, P. L.
AVANCES EN DIABETOLOGIA, 2010, 26 (06): : 446 - 448
[40] Synthesis and biological evaluation of triazole based uracil derivatives as novel DPP-4 inhibitors
Li, Qing
Han, Li
Zhang, Bin
Zhou, Jinpei
Zhang, Huibin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (40) : 9598 - 9611

← 1 2 3 4 5 →