IP Library Granted Patent US 11,807,635
Granted Patent B2
US 11,807,635 · App. 17/976,291 · Granted Nov 7, 2023

Nitrile derivative that acts as inhibitor of dipeptidyl peptidase 1 and use thereof

Inventors: Yao Li (Sichuan, CN); Zongjun Shi (Sichuan, CN); Guobiao Zhang (Sichuan, CN); Lei Chen (Sichuan, CN); Wenjing Wang (Sichuan, CN); Xiaobo Zhang (Sichuan, CN); Dengyu Zheng (Sichuan, CN); Bo Xu (Sichuan, CN); Xin Liu (Sichuan, CN); Yajun Wang (Sichuan, CN); Fei Ye (Sichuan, CN); Pingming Tang (Sichuan, CN); Jia Ni (Sichuan, CN); Chen Zhang (Sichuan, CN); Pangke Yan (Sichuan, CN)
Assignee: Haisco Pharmaceuticals Pte. Ltd.
C07D413/12C07D267/10C07D413/14C07D417/12C07F9/6527
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Quick Facts
Patent No.
US 11,807,635
App. No.
17/976,291
Granted
Nov 7, 2023
Kind
B2
Abstract

Disclosed is a nitrile derivative compound represented by formula (I), a stereoisomer, a deuterated product, a co-crystal, a solvate or a pharmaceutically acceptable salt thereof, wherein each group is as defined in the description. The compound has dipeptidyl peptidase 1 inhibitory activity and can be used to prepare a drug for treating diseases including obstructive airway diseases, bronchiectasis, cystic fibrosis, asthma, emphysema, and chronic obstructive pulmonary diseases.

Claims (24)

1. A compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof, wherein the compound has a structure of formula (IV):

wherein

Rc is H, halogen, C 1-2 alkyl or C 1-2 alkoxy;

R 1 , R 2 , and R 3 are each independently selected from H, deuterium, F, Cl, Br, methyl, ethyl, methoxy or ethoxy, and the methyl, ethyl, methoxy or ethoxy is optionally substituted with 1-3 groups selected from F, Cl, Br, cyano, hydroxyl, and NH 2 ;

Z is CH or N;

ring G is

or a benzene ring, each of which is optionally substituted with 1-2 R G groups; and

each R G is independently selected from F, Cl, Br, I, methyl, ethyl, propyl, SF 5 and CN, wherein the methyl, ethyl or propyl is optionally further substituted with 1-3 groups selected from deuterium, F, Cl, Br, and I.

2. The compound, or the stereoisomer, deuterated product, co crystal, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein

Z is CH.

3. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein

ring G is

optionally substituted with 1-2 R G groups.

4. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 3 , wherein

each R G is independently selected from methyl, ethyl, propyl, which is optionally further substituted with 1-3 groups selected from deuterium, F, Cl, Br, and I.

5. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 4 , wherein

each R G is independently selected from methyl, ethyl, or propyl.

6. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is selected from one of the following structures:

7. A pharmaceutical composition, comprising the compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , and a pharmaceutically acceptable carrier and/or excipient.

8. A method of treating a disease mediated by dipeptidyl peptidase 1, comprising administering the compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , or the composition according to claim 7 , wherein the disease is selected from obstructive airway diseases, bronchiectasis, cystic fibrosis, asthma, emphysema, and chronic obstructive pulmonary diseases.

9. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is selected from one of the following structures:

10. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is selected from one of the following structures:

11. The compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof according to claim 1 , wherein the compound is selected from one of the following structures:

12. A compound, or the stereoisomer, deuterated product, solvate or pharmaceutically acceptable salt thereof, wherein the compound is selected from one of the following structures:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 11, 2022
From: LI, YAO; SHI, ZONGJUN; ZHANG, GUOBIAO; CHEN, LEI; WANG, WENJING; ZHANG, XIAOBO; ZHENG, DENGYU; XU, BO; LIU, XIN; WANG, YAJUN; YE, FEI; TANG, PINGMING; NI, JIA; ZHANG, CHEN; YAN, PANGKE
To: HAISCO PHARMACEUTICALS PTE. LTD
Reel/Frame 061744/0519 →
Priority Claims (3)
CN 202010871912.1 · Aug 26, 2020 · national
CN 202011129809.6 · Oct 21, 2020 · national
CN 202110167731.5 · Feb 7, 2021 · national
Continuity (2)
Continuation PCTCN2021114500 · Aug 25, 2021
Related Publication 20230121807A1 · Apr 20, 2023
Cited By (5)
US 12,365,673 US 12,421,249 US 12,479,837 US 12,662,474 US 12,679,815