# US 11,306,083 B2 · Amide substituted imidazo[4,5-C]quinoline compounds with a branched chain linking group for use as an immune response modifier

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- Number: US 11,306,083 B2
- Document ID: US11306083B2
- Status: Granted
- Kind: B2
- Application number: 15/733,207
- Filed: 2018-12-14
- Published: 2021-04-08
- Granted: 2022-04-19
- Earliest claimed: 2017-12-20
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: George W. Griesgraber
- Web page: https://patentgrep.com/patent/US11306083B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61K 39/39: characterised by the immunostimulating additives, e.g. chemical adjuvants
- A61P 31/12: Antivirals
- 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

## Abstract

Imidazo[4,5-c]quinoline compounds having an alkylamide substituent that is attached at the N-1 position by a branched chain linking group, single enantiomers of the compounds, pharmaceutical compositions containing the compounds, and methods of making the compounds are disclosed. Methods of use of the compounds as immune response modifiers, for inducing cytokine biosynthesis in humans and animals, and in the treatment of diseases including infectious and neoplastic diseases are also disclosed. Formula (I):

## Claims

### Claim 1

A compound of the Formula (I):
wherein:
n is an integer of 0 or 1;
R is selected from the group consisting of halogen, hydroxy, alkyl, alkoxy, and —C(O)—O-alkyl;
X is alkylene, wherein the alkylene group can be optionally interrupted by one or more —O— groups;
R1 is selected from the group consisting of C1-5alkyl and —C1-3alkylene-O—C1-3alkyl;
R2 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, n-butyl, —CH2OCH3, —CH2OCH2CH3, and —CH2CH2OCH3;
R3 is alkyl, wherein the alkyl group can be optionally interrupted by one or more —O— groups;
R4 is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, and isopropyl; or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound or salt of claim 1, wherein X is C1-8alkylene.

### Claim 3 (depends on 1)

The compound or salt of claim 1, wherein X is selected from the group consisting of —CH2—, —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2—, —CH2CH2CH2CH2CH2—, —CH2CH2CH2CH2CH2CH2—, —CH2CH2CH2CH2CH2CH2CH2—, and —CH2CH2CH2CH2CH2CH2CH2CH2—.

### Claim 4 (depends on 1)

The compound or salt of claim 1, wherein R1 is —CH2OCH3 or —CH2OCH2CH3.

### Claim 5 (depends on 1)

The compound or salt of claim 1, wherein R2 is selected from the group consisting of hydrogen, methyl, and ethyl.

### Claim 6 (depends on 1)

The compound or salt of claim 1, wherein R2 is hydrogen.

### Claim 7 (depends on 1)

The compound or salt of claim 1, wherein R3 is C5-19alkyl.

### Claim 8 (depends on 1)

The compound or salt of claim 1, wherein R3 is —CH2(CH2)3-17CH3.

### Claim 9 (depends on 1)

The compound or salt of claim 1, wherein R is selected from the group consisting of hydroxy, F, and Cl.

### Claim 10 (depends on 1)

The compound or salt of claim 1, wherein n is 0.

### Claim 11 (depends on 1)

The compound or salt of claim 1, wherein R4 is hydrogen.

### Claim 12 (depends on 1)

A vaccine adjuvant comprising the compound or salt of claim 1.

### Claim 13 (depends on 1)

A method of inducing biosynthesis of IFN-alpha in a human or animal comprising administering an effective amount of a compound or salt of claim 1 to the human or animal.

### Claim 14 (depends on 1)

A method of inducing biosynthesis of TNF-alpha in a human or animal comprising administering an effective amount of a compound or salt of claim 1 to the human or animal.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount of a compound or salt of claim 1 in combination with a pharmaceutically acceptable carrier.