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US 12,612,427 B2Granted
Aryl glucoside derivative, preparation method therefor and application thereof
AssigneeShanghai Zheye Biotechnology Co. Ltd.
InventorsQiang Zhang, Fengtian Du, Haibo Wang, Na Guo
Life of this patent
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Abstract
Provided are a compound that inhibits sodium-glucose co-transporter 1, and a pharmaceutically acceptable salt and stereoisomer thereof. The compound is used in a pharmaceutical composition and preparation and usage methods, which comprise an application of a drug and composition thereof in the preparation for treating and improving diabetes, cardiovascular and cerebrovascular diseases, weight loss, fatty liver disease, constipation, metabolism-related diseases and tumor treatment.
Claims14
A compound of formula (XA-1), or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof,
- wherein, X, RC and RD are each independently hydrogen, deuterium, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
- R6b, R7b, R6c, R7c, R6d, R7d, R6e and R7e are each independently hydrogen, deuterium, halogen, C1-C6 alkyl or acyl;
- or R6b and R7b, R6c and R7c, R6a and R7d, or R6e and R7e together with the carbon atoms attached therewith form a 3- to 8-membered carbocycle optionally substituted by hydrogen, halogen, C1-C6 alkyl, or halogenated C1-C6 alkyl;
- RA and RB are each independently hydrogen, deuterium, alkyl, deuterated alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, amino, mercapto, nitro, hydroxyl, cyano, oxo, C2-C8 alkenyl, C2-C8 alkynyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, —(CH2)n1Raa, —(CH2)n1ORaa, —SRaa, —(CH2)n1C(O)Raa, —SRaa, —C(O)ORaa, —C(O)Raa, —S(O)m1Raa, —(CH2)n1S(O)m1Raa, —NRaaRbb, —C(O)NRaaRbb, —NRaaC(O)Rbb, or NRaaS(O)m1Rbb;
- Raa and Rbb are each independently hydrogen, deuterium, alkyl, deuterated alkyl, haloalkyl, alkoxy, hydroxyalkyl, haloalkoxy, halogen, cyano, nitro, hydroxy, amino, alkenyl, alkynyl, deuterated alkenyl, deuterated alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of the alkyl, deuterated alkyl, haloalkyl, alkoxy, hydroxyalkyl, haloalkoxy, alkenyl, alkynyl, deuterated alkenyl, deuterated alkynyl, cycloalkyl, heterocyclyl, aryl, or heteroaryl is optionally further substituted by one or more substituents of hydrogen, deuterium, silyl, alkylsilyl, substituted or unsubstituted alkyl, halogen, hydroxy, substituted or unsubstituted amino, oxo, nitro, cyano, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted hydroxyalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
- R3 is H;
- Z is O;
- n1=0, 1, 2, 3, or 4;
- m1=0, 1, 2, 3, or 4;
- p=0, 1, 2, or 3;
- q=0, 1, 2, or 3;
- or
- is represented by any one of the following structures:
- and
- Y is a linking group represented by any one of the following structures:
12 more elements
A compound of formula (I-1), or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof,
- wherein, R1a, R1b and R1c are each independently F, —OR1A, or —NHR1A, wherein each R1A is independently hydrogen, C1-C6 alkyl, or acyl;
- RC and RD are each independently hydrogen, deuterium, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
- or RC and RD together with the nitrogen atoms attached therewith form a 3- to 8-membered heterocycle containing one or more carbon, nitrogen, oxygen or sulfur atoms, and optionally being further substituted by halogen, alkyl, cycloalkyl, aryl, alkoxy, alkenyl, alkynyl, or oxo;
- R2 is —S(O)m—R1A, and m=0, 1, or 2;
- R3, R4, R5, R6, R7, R8 and R9 are each independently hydrogen, deuterium, halogen, C1-C6 alkyl, cycloalkyl, cycloalkylalkyl, acyl, or C2-C8 alkynyl;
- m2=0, 1, 2, or 3;
- n2=0, 1, 2, or 3;
- p=0, 1, 2, 3, 4, or 5;
- X is hydrogen, deuterium, halogen, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
- Z is oxygen or sulfur;
- Y1 is a linking group represented by any one of the following structures:
- wherein, RE, RF, RG and RH are each independently hydrogen, deuterium, halogen, C1-C6 alkyl, or acyl;
- E and J are independently a single bond, —CH2—, oxygen, or —NH—;
- s1=0, 1, 2, 3, 4, or 5;
- s2=0, 1, 2, 3, 4, or 5;
- and
- s3=0, 1, 2, 3, 4, or 5.
14 more elements
Dependencies are inferred from the claim text.