IP Library Granted Patent US 9,562,029
Granted Patent B2
US 9,562,029 · App. 14/129,316 · Granted Feb 7, 2017

C-glycoside derivatives

Inventor: Frank Wu (Shandong Province, CN)
Assignee: XUANZHU PHARMA CO., LTD.
C07D309/10C07D307/77C07D307/94C07D311/96C07D407/12
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,562,029
App. No.
14/129,316
Granted
Feb 7, 2017
Kind
B2
Abstract

The present invention involves a compound represented by general formula (I), a derivative thereof and a use thereof: wherein R 1 , R 2 , R 3 , R 4 , R 5a , R 5b , R 5c and X are defined as in the description.

Claims (60)

1. A compound represented by general formula (I), a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 and R 2 each independently represent hydrogen, —OH, —OR 6 , alkyl, —CF 3 , —OCHF 2 , —OCF 3 , halogen, —CN, C 2-6 alkynyl, C 2-6 alkenyl, cycloalkyl, C 2-4 alkenyl-C 1-4 alkyl, C 2-4 alkynyl-C 1-4 alkyl, C 2-4 alkenyl-C 1-4 alkoxy, C 2-4 alkynyl-C 1-4 alkoxy, C 3-7 cycloalkyl-C 1-4 alkyl, —NR 7 R 7a , carbonyl, —COOR 6a , —COOH, —COR 7b , —CH(OH)R 7c , —CH(OR 6g )R 7d , —CONR 7 R 7a , —NHCOR 6b , —NHSO 2 R 6c , —NHSO 2 aryl, aryl, —SR 6d , —SOR 6e , —SO 2 R 6f , —SO 2 aryl, or

R 1 and R 2 together with carbon atoms attached thereto form a ring or a 3-14 membered heterocyclic ring containing 1-4 heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 3 represents OR 8 , a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group, or a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl, or aryl-(C 1-3 alkyl)carbonyl;

R 8 represents a 6 membered fused-ring group;

R 6 , R 6a , R 6b , R 6c , R 6d , R 6e and R 6f respectively represent alkyl or cycloalkyl, or alkyl or cycloalkyl in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 7 , R 7a , R 7b , R 7c and R 7d respectively represent hydrogen, alkyl, aryl, alkylaryl or cycloalkyl, or R 7 and R 7a together with the nitrogen attached thereto form a 3-14 membered heterocyclyl containing 1-4 heteroatoms selected from N, O, S, SO and/or SO 2 ;

X represents a chemical bond, NH, O, S, SO, SO 2 or an alkylene, said alkylene can be further substituted by one or more substituents, which comprise halogen, hydroxyl, C 1-4 alkyl, cycloalkyl, C 1-4 alkoxy, C 1-4 alkyl that is substituted by halogen;

wherein the alkyl, the cycloalkyl, the aryl, the heterocyclyl, the spiro-ring group, the bridged-ring group, and the fused-ring group, as mentioned above, can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, alkyl, alkoxy, aminosulfonyl, carbamoyl, C 1-4 alkoxy that is substituted by halogen, and C 1-4 alkyl that is substituted by halogen, hydroxyl, amino, and/or carboxyl.

2. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 represents hydrogen, —OH, —OR 6 , alkyl, —CF 3 , —OCHF 2 , —OCF 3 , halogen or —CN;

R 2 represents hydrogen;

R 3 represents OR 8 , a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group, or a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen, (C 1-18 -alkly)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl, or aryl-(C 1-3 alkyl)carbonyl;

R 8 represents a 6 membered fused-ring group;

X represents a chemical bond or an alkylene, said alkylene can be further substituted by one or more substituents, which comprise halogen, hydroxyl, C 1-4 alkyl, C 1-4 alkoxy, and C 1-4 alkyl that is substituted by halogen;

wherein the alkyl, the aryl, the spiro-ring group, the bridged-ring group, and the fused-ring group can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, alkyl, alkoxy, aminosulfonyl, carbamoyl, C 1-4 alkoxy that is substituted by halogen, and C 1-4 alkyl that is substituted by halogen, hydroxyl, amino, and/or carboxyl.

3. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 represents hydrogen, —OH, —OR 6 , alkyl, —CF 3 , —OCHF 2 , —OCF 3 , halogen or —CN;

R 2 represents hydrogen;

R 3 represents OR 8 , a 7-12 membered spiro-ring group, or a 5-12 membered spiro-ring group, a 5-12 membered bridged-ring group or a 6-14 membered fused-ring group in which one or more carbon atoms are replaced with one or more heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 8 represents a 6 membered fused-ring group;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen;

X is methylene;

wherein the spiro-ring group and the fused-ring group can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, alkyl, alkoxy, aminosulfonyl, carbamoyl, C 1-4 alkoxy that is substituted by halogen, and C 1-4 alkyl that is substituted by halogen, hydroxyl, amino, and/or carboxyl.

4. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 represents halogen or —CN;

R 2 represents hydrogen;

R 3 represents OR 8 or a 7-12 membered spiro-ring group;

R 8 represents a 6 membered fused-ring group;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen;

X is methylene;

wherein the spiro-ring group and the fused-ring group can be further substituted by one or more substituents, which comprise halogen, hydroxyl, amino, carboxyl, C 1-6 alkyl, C 1-6 alkoxy, aminosulfonyl, and carbamoyl.

5. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 represents halogen or —CN;

R 2 represents hydrogen;

R 3 represents OR 8 , a 7-10 membered spiro-ring group or a 7-10 membered spiro-ring group containing 1-2 heteroatoms selected from N, O, S, SO and/or SO 2 ;

R 8 represents 6 membered fused-ring group;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen;

X is methylene.

6. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein,

R 1 represents halogen;

R 2 represents hydrogen;

R 3 represents OR 8 or a 7-10 membered spiro-ring group;

R 8 represents a 6 membered fused-ring group;

R 4 , R 5a , R 5b and R 5c respectively represent hydrogen;

X is methylene.

7. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof:

wherein R 3 is selected from:

8. The compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof, wherein said compound is selected from the group consisting of:

9. A pharmaceutical composition, which contains the compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof, and one or more pharmaceutically acceptable carriers and/or diluents, and is in any pharmaceutically acceptable dosage form.

10. A method for the treatment of insulin-dependent diabetes mellitus, non-insulin-dependent diabetes mellitus, and various diabetes-associated diseases, comprising the administration of a therapeutically effective amount of the compound according to claim 1 , a pharmaceutically acceptable salt thereof or a stereoisomer thereof as sodium glucose co-transporter inhibitor to a subject in need thereof.

11. The method according to claim 10 , wherein the diabetes-associated disease is insulin resistance disease or obesity.

Assignments (3)
CHANGE OF NAME Recorded Sep 15, 2023
From: JI LIN HUI SHENG BIO-PHARMACEUTICAL CO., LTD
To: HUISHENG BIOPHARMACEUTICAL CO., LTD.
Reel/Frame 064915/0971 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2021
From: XUANZHU PHARMA CO., LTD.
To: JI LIN HUI SHENG BIO-PHARMACEUTICAL CO., LTD.; BEIJING HUIZHIHENG BIOTECHNOLOGY CO., LTD.
Reel/Frame 056110/0855 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2014
From: WU, FRANK
To: XUANZHU PHARMA CO., LTD.
Reel/Frame 031934/0745 →
Priority Claims (2)
CN 2011 1 0188186 · Jun 25, 2011 · national
CN 2011 1 0435397 · Dec 22, 2011 · national
Continuity (1)
Related Publication 20140128331A1 · May 8, 2014