# US 10,766,912 B2 · Silicon-containing compound for resistance to hepatitis C virus infection

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- Number: US 10,766,912 B2
- Document ID: US10766912B2
- Status: Granted
- Kind: B2
- Application number: 16/494,604
- Filed: 2018-03-22
- Published: 2020-01-16
- Granted: 2020-09-08
- Earliest claimed: 2017-03-22
- Assignees: Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
- Applicants: Chia Tai Tianqing Pharmaceutical Group Co., Ltd.
- Inventors: Yinsheng Zhang; Baomin Liu; Yu Huang; Zhengbang Chen; Kuo Gai; Xushi Liu; Xiaojin Wang; Hongjiang Xu
- Web page: https://patentgrep.com/patent/US10766912B2

## CPC

- C07F 7/0816: {said ring comprising Si as a ring atom}
- A61K 31/695: Silicon compounds
- A61P 31/14: for RNA viruses
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a silicon-containing compound for resistance to hepatitis c virus infection, and in particular provides a compound represented by formula I, or a pharmaceutically acceptable salt, or a tautomer, or a stereoisomer, or a deuterated compound thereof and mixture among them, a preparation process therefor, and a pharmaceutical composition comprising the same. The present application also provides a use of the compound, or a pharmaceutically acceptable salt, or a tautomer, or a stereoisomer, or a deuterated compound thereof and mixture among them, and a pharmaceutical composition comprising the same in treatment of hepatitis c virus infection.

## Claims

### Claim 1

A compound of Formula I, a pharmaceutically acceptable salt, a tautomer, a stereoisomer or a deuteride thereof, or a mixture thereof:
wherein:
R1 and R2 are each independently selected from the group consisting of hydroxyl, alkyl, alkoxy and aryl, or R1 and R2 are joined to form a silicon-containing saturated aliphatic ring containing 1, 2 or 3 silicon atoms;
R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen and halogen;
X is selected from the group consisting of the following groups:
Y is selected from the group consisting of the following groups:
R7 and R8 are each independently selected from the group consisting of —CH(alkyl)(alkoxy), —CH(alkyl)2, —CH(alkoxy)2, —C(alkyl)2(alkoxy), —C(alkyl)(alkoxy)2, —C(alkyl)3 and —C(alkoxy)3;
R9 and R10 are each independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, and alkoxyalkyl;
each of Ra and Rb is independently selected from the group consisting of hydrogen, halogen, and alkyl;
each m is independently selected from the group consisting of 0, 1, 2, 3, and 4; and
n is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8.

### Claim 2 (depends on 1)

The compound according to claim 1, which is a compound of Formula Ia, a compound of Formula Ib, a compound of Formula Ic or a compound of Formula Id:
wherein, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, Ra, Rb, X, Y, m and n are as defined in claim 1.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein R1 and R2 are each independently selected from C1-6 alkyl, or R1 and R2 are joined to form a 3- to 8-membered silicon-containing saturated aliphatic ring containing 1 silicon atom.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein R1 and R2 are each independently selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, isobutyl and phenyl, or R1 and R2 are joined to form a 3-, 4-, 5- or 6-membered silicon-containing saturated aliphatic ring, wherein the silicon-containing saturated aliphatic ring contains one silicon atom.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R3, R4, R5 and R6 are each independently selected from the group consisting of hydrogen, fluoro, and chloro.

### Claim 6 (depends on 1)

The compound according to claim 1, X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from the group consisting of

### Claim 7 (depends on 1)

The compound according to claim 1, wherein X is selected from the group consisting of
and Y is selected from the group consisting of
or, X is selected from the group consisting of
and Y is selected from the group consisting of

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R7 and R8 are each independently selected from the group consisting of —CH(CH3)(OCH3), —CH(CH3)2, —CH(OCH3)2, —C(CH3)2(OCH3), —C(CH3)(OCH3)2, —C(CH3)3, —C(OCH3)3, —CH(CH2CH3)(OCH2CH3), —CH(CH3)(OCH2CH3), —CH(CH2CH3)(OCH3), —CH(CH2CH3)2, —CH(CH3)(CH2CH3), —CH(OCH2CH3)2, —CH(OCH2CH3)(OCH3), —C(CH2CH3)2(OCH2CH3), —C(CH3)2(OCH2CH3), —C(CH2CH3)2(OCH3), —C(CH2CH3) (OCH2CH3)2, —C(CH3)(OCH2CH3)2, —C(CH2CH3)(OCH3)2, —C(CH2CH3)3, —C(CH3)(CH2CH3)2, —C(CH3)2(CH2CH3) and —C(OCH2CH3)3.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein R9 and R10 are each independently selected from the group consisting of hydrogen, fluoro, chloro, methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, isobutyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, n-butoxy, isobutoxy, methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R7 and R8 are each independently selected from the group consisting of —CH(CH3)(OCH3) and —CH(CH3)2; and R9 and R10 are each independently selected from the group consisting of hydrogen and methoxymethyl.

### Claim 11 (depends on 1)

The compound according to claim 1, wherein Ra and Rb are each independently selected from the group consisting of hydrogen, fluoro, chloro, methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, and isobutyl.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein R1 and R2 are methyl, or R1 and R2 are joined to form a 4-, 5- or 6-membered silicon-containing saturated aliphatic ring containing 1 silicon atom; one of R3 and R4 is fluoro, and the other is hydrogen, or both R3 and R4 are fluoro; R5 and R6 are hydrogen; X is
Y is
both R7 and R8 are -CH(CH3)(OCH3);
both R9 and Rio are hydrogen or methoxymethyl; and n is 0.

### Claim 13 (depends on 1)

The compound according to claim 1, which is selected from the following compounds:

### Claim 14 (depends on 1)

A pharmaceutical composition, comprising a therapeutically effective amount of the compound according to claim 1, a pharmaceutically acceptable salt, a tautomer, a stereoisomer or a deuteride thereof, or a mixture thereof, and one or more pharmaceutically acceptable carriers.

### Claim 15 (depends on 1)

A method for treating hepatitis C virus infection, comprising administering to a subject in need of such treatment a therapeutically effective amount of the compound according to claim 1, a pharmaceutically acceptable salt, a tautomer, a stereoisomer or a deuteride thereof, or a mixture thereof.

### Claim 16 (depends on 14)

A method for treating hepatitis C virus infection, comprising administering to a subject in need of such treatment a therapeutically effective amount of the pharmaceutical composition according to claim 14.

### Claim 17 (depends on 1)

The compound according to claim 1, wherein one of R3 and R4 is fluoro, and the other is hyrdogen, and R5 and R6 are selected from hydrogen.

### Claim 18 (depends on 1)

The compound according to claim 1, wherein R3 and R4 are selected from fluoro, and R5 and R6 are selected from hydrogen.

### Claim 19 (depends on 1)

The compound according to claim 1, wherein X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from the group consisting of

### Claim 20 (depends on 1)

The compound according to claim 1, wherein X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected from
or X is selected from
and Y is selected fom the group consisting of