# US 12,760,018 B2 · Bicyclic compounds

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- Number: US 12,760,018 B2
- Document ID: US12760018B2
- Status: Granted
- Kind: B2
- Application number: 18/302,615
- Filed: 2023-04-18
- Published: 2023-11-30
- Granted: 2026-10-13
- Earliest claimed: 2022-04-20
- Assignees: Aligos Therapeutics, Inc.
- Applicants: Aligos Therapeutics, Inc.
- Inventors: Sandrine Vendeville; David McGowan; Yannick Debing; Pierre Jean-Marie Bernard Raboisson
- Web page: https://patentgrep.com/patent/US12760018B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61K 31/513: having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 31/683: Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
- A61K 31/7072: having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
- A61K 31/708: having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid
- A61K 38/212: {IFN-alpha}
- A61P 31/20: for DNA viruses
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07F 9/6561: containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

## Claims

### Claim 1

A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:
wherein:
R1 is selected from the group consisting of
R2 is selected from the group consisting of
X1A, X1B and X1C are independently selected from the group consisting of hydrogen, halogen, an unsubstituted C1-5 alkyl and an unsubstituted C1-5 haloalkyl;
Y1A is CH, C—CHF2, C—F, C—Cl, C—(NH2), C(NH(unsubstituted C1-5 alkyl)), C(N(unsubstituted C1-5 alkyl)2) or N;
Y2A is CH, C-halogen, C—OCH3, C—(NH2), C(NH(unsubstituted C1-5 alkyl)), C(N(unsubstituted C1-5 alkyl)2) or N;
Y3A is CH or N;
Y4A is CH or N;
Y1B is CH, C—CHF2, C—F, C—Cl, C—(NH2), C(NH(unsubstituted C1-5 alkyl)), C(N(unsubstituted C1-5 alkyl)2) or N;
Y2B is CH, C-halogen, C—OCH3, C—(NH2), C(NH(unsubstituted C1-5 alkyl)), C(N(unsubstituted C1-5 alkyl)2) or N;
Y3B is CH or N;
Y4B is CH or N;
Y1C, Y2C, Y3C and Y4C are each independently CH, C-(halogen) or N;
Y1D is CH, C—CH3, C—OCH3, C-(halogen), C—CHF2, C—CF3 or N;
Y2D is CH, C—CH3, C—OCH3, C-(halogen), C—CHF2, C—CF3 or N;
Y3D is CH, C-(halogen) or N;
Y1E, Y1F and Y1G are each independently CH, C-(halogen) or N;
Y1H, Y2H, Y3H, Y4H, Y5H and Y6H are each independently CH, C-(halogen) or N;
RA1 is hydrogen, an unsubstituted or a substituted C1-5 alkyl or an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, wherein when the C1-5 alkyl and the monocyclic C3-6 cycloalkyl are substituted, the C1-5 alkyl and the C3-6 cycloalkyl are substituted with one or more groups selected from the group consisting of hydroxy, —NH2, an unsubstituted C1-5 alkoxy, an unsubstituted-NH (an unsubstituted C1-5 alkyl), —N(an unsubstituted C1-5 alkyl)2, —C(═O) NH2, —O—P(═O)(OH)2, an unsubstituted 5- or 6-membered monocyclic heterocyclyl and 5- or 6-membered monocyclic heterocyclyl substituted by one or more unsubstituted C1-4 alkyl groups;
RA2 is —CH3 or —CD3;
RA3 is —NH2, —NH (an unsubstituted or a substituted C1-5 alkyl), —N(an unsubstituted or a substituted C1-5 alkyl)2, —NH (an unsubstituted or a substituted C3-6 monocyclic cycloalkyl), an unsubstituted or a substituted 5-membered-monocyclic heteroaryl, an unsubstituted or a substituted 6-membered-monocyclic heteroaryl or an unsubstituted or a substituted 4 to 6-membered-monocyclic heterocyclyl;
RA4 is an unsubstituted or a substituted C1-5 alkyl, an unsubstituted C1-5 haloalkyl or an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, wherein when the C1-5 alkyl and the monocyclic C3-6 cycloalkyl are substituted, the C1-5 alkyl and the C3-6 cycloalkyl are substituted with one or more groups selected from the group consisting of hydroxy, —C(═O) OH and —C(═O) NH2; and
RA5 is selected from the group consisting of hydrogen, halogen, —CN, —OH, —NH2, —C(═O) OH, —CH═CH2, an unsubstituted C1-5 alkyl, and an unsubstituted or a substituted monocyclic C3-6 cycloalkyl, wherein when the monocyclic C3-6 cycloalkyl is substituted, the C3-6 cycloalkyl is substituted with one or more hydroxy groups; and
wherein the compound of Formula (I), or a pharmaceutically acceptable salt thereof, is not:
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is

### Claim 3 (depends on 2)

The compound of claim 2, wherein R2 is

### Claim 4 (depends on 3)

The compound of claim 3, wherein R2 is
Y1A, Y2A, Y3A and Y4A are each CH, or one of Y1A, Y2A, Y3A and Y4A is N.

### Claim 5 (depends on 4)

The compound of claim 4, wherein RA1 is a C1-5 alkyl substituted with one or more groups selected from the group consisting of hydroxy, —NH2, an unsubstituted C1-5 alkoxy, an unsubstituted-NH (an unsubstituted C1-5 alkyl), —N(an unsubstituted C1-5 alkyl)2, —C(═O) NH2, —O—P(═O)(OH)2, an unsubstituted 5- or 6-membered monocyclic heterocyclyl and 5- or 6-membered monocyclic heterocyclyl substituted by one or more unsubstituted C1-4 alkyl groups; or RAL is a monocyclic C3-6 cycloalkyl substituted with one or more groups selected from the group consisting of hydroxy, —NH2, an unsubstituted C1-5 alkoxy, an unsubstituted-NH (an unsubstituted C1-5 alkyl), —N(an unsubstituted C1-5 alkyl)2, C(═O) NH2, —O—P(═O)(OH)2, an unsubstituted 5- or 6-membered monocyclic heterocyclyl and 5- or 6-membered monocyclic heterocyclyl substituted by one or more unsubstituted C1-4 alkyl groups.

### Claim 6 (depends on 3)

The compound of claim 3, wherein R2 is
Y1B, Y2B, Y3B and Y4B are each CH, or one of Y1B, Y2B, Y3B and Y4B is N.

### Claim 7 (depends on 3)

The compound of claim 3, wherein R2 is
Y1C, Y2C, Y3C and Y4C are each CH, or one of Y1C, Y2C, Y3C and Y4C is N; RA3 is —NH2, —NH (an unsubstituted or a substituted C1-5 alkyl), —NH (an unsubstituted or a substituted C3-6 monocyclic cycloalkyl), an unsubstituted or a substituted 5-membered-monocyclic heteroaryl, an unsubstituted or a substituted 4-membered-monocyclic heterocyclyl, an unsubstituted or a substituted 5-membered-monocyclic heterocyclyl or an unsubstituted or a substituted 6-membered-monocyclic heterocyclyl.

### Claim 8 (depends on 2)

The compound of claim 2, wherein R2 is

### Claim 9 (depends on 8)

The compound of claim 8, wherein R2 is
and RA4 is an unsubstituted C1-5 alkyl.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R2 is selected from the group consisting of:

### Claim 11

A compound selected from the group consisting of:
or a pharmaceutically acceptable salt of any of the foregoing.

### Claim 12 (depends on 1)

The compound of claim 1 selected from the group consisting of:
or a pharmaceutically acceptable salt of any of the foregoing.

### Claim 13 (depends on 1)

A pharmaceutical composition comprising an effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof, and excipient.

### Claim 14 (depends on 11)

A method for treating hepatitis B in a subject comprising administering to the subject in need thereof an effective amount of a compound of claim 11, or a pharmaceutically acceptable salt thereof, suffering from hepatitis B.

### Claim 15 (depends on 11)

The compound of claim 11 selected from the group consisting of:
or a pharmaceutically acceptable salt of any of the foregoing.

### Claim 16 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 17 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 19 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 20 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 21 (depends on 11)

The compound of claim 11, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 22 (depends on 15)

The compound of claim 15, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 23 (depends on 15)

The compound of claim 15, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 24 (depends on 15)

The compound of claim 15, wherein the compound is
or a pharmaceutically acceptable salt thereof.

### Claim 25 (depends on 9)

The compound of claim 9, wherein R2 is
and RA5 is hydrogen.

### Claim 26 (depends on 25)

The compound of claim 25, wherein Y1D is CH or C-(halogen); Y2D is N; and Y3D is CH, C—CH3, C—OCH3, C-(halogen), C—CHF2 or C—CF3.

### Claim 27 (depends on 25)

The compound of claim 25, wherein Y1D is CH or C-(halogen); Y2D is CH, C—CH3, C—OCH3, C-(halogen), C—CHF2 or C—CF3; and Y3D is CH, C—CH3, C—OCH3, C-(halogen), C—CHF2 or C—CF3.