# US 10,479,793 B2 · Imidazopyridazine compounds useful as modulators of IL-12, IL-23 and/or IFN alpha responses

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- Number: US 10,479,793 B2
- Document ID: US10479793B2
- Status: Granted
- Kind: B2
- Application number: 15/776,094
- Filed: 2016-11-17
- Published: 2018-11-15
- Granted: 2019-11-19
- Earliest claimed: 2015-11-18
- Assignees: Bristol-Myers Squibb Company
- Applicants: Bristol-Myers Squibb Company
- Inventors: David S. Weinstein; Ryan M. Moslin; Yanlei Zhang; Daniel S. Gardner; Joseph B. Santella; Charles M. Langevine; Sylwia Stachura
- Web page: https://patentgrep.com/patent/US10479793B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61K 31/5025: ortho- or peri-condensed with heterocyclic ring systems
- A61K 31/53: having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine (melarsoprol A61K31/555 {; with four nitrogen atoms A61K31/495})
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/02: Immunomodulators
- 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

Compounds of formula I or a stereoisomer or pharmaceutically-acceptable salt thereof, are useful in the modulation of IL-12, IL-23 and/or IFNα, by acting on Tyk-2 to cause signal transduction inhibition.

## Claims

### Claim 1

A compound of the formula
wherein
R1 is —NHR2;
R2 is C1-C6 alkyl or C3-C8 cycloalkyl;
R3 is H, C1-C6 alkyl, hydroxy C1-C6 alkyl or mono or bicyclic C3-C8 cycloalkyl;
R4 is H, C1-C6 alkyl, mono or bicyclic C3-C6 cycloalkyl, phenyl, or pyridyl, any of said groups other than H substituted with 0-4 R7;
R5 is H or C1-C4 alkyl;
R7 is H, halo, CN, CF3, C1-C4 alkyl, C1-C4 alkoxy, —CONH C1-C6 alkyl, —CONH halo C1-C6 alkyl, —CONH halo C1-C6 alkoxy, heteroaryl, or aryl, said aryl and heteroaryl groups substituted with 0-2 R8;
R8 is H, halo, CF3, C1-C4 alkyl or C1-C4 alkoxy;
or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

### Claim 2 (depends on 1)

The compound according to claim 1
wherein
R1 is —NHR2;
R2 is CH3 or cyclopropyl;
R3 is H, C1-C6 alkyl, hydroxy C1-C6 alkyl or mono or bicyclic C3-C8 cycloalkyl;
R4 is H, C1-C6 alkyl, mono or bicyclic C3-C6 cycloalkyl, phenyl, or pyridyl, any of said groups other than H substituted with 0-4 R7;
R5 is H or C1-C4 alkyl;
R7 is H, halo, CN, CF3, C1-C4 alkyl, C1-C4 alkoxy, —CONH C1-C6 alkyl, —CONH halo C1-C6 alkyl, —CONH halo C1-C6 alkoxy, heteroaryl, or aryl, said aryl and heteroaryl groups substituted with 0-2 R8;
R8 is H, halo, CF3, C1-C4 alkyl or C1-C4 alkoxy;
or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising one or more compounds according to claim 1 and a pharmaceutically acceptable carrier or diluent.