# US 7,612,067 B2 · Imidazopyridazine compounds

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- Number: US 7,612,067 B2
- Document ID: US7612067B2
- Status: Granted
- Kind: B2
- Application number: 11/817,433
- Filed: 2006-03-20
- Published: 2008-05-15
- Granted: 2009-11-03
- Earliest claimed: 2005-03-21
- Assignees: Eli Lilly and Company
- Inventors: Heather Janelle Barbosa; Elizabeth Aaron Collins; Chafiq Hamdouchi; Erik James Hembre; Philip Arthur Hipskind; Richard Duane Johnston; Jianliang Lu; Michael John Rupp; Takako Takakuwa; Richard Craig Thompson
- Web page: https://patentgrep.com/patent/US7612067B2

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/12: Antidiarrhoeals
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 5/14: of the thyroid hormones, e.g. T3, T4
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/12: Antihypertensives
- A61P 11/06: Antiasthmatics
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 25/30: for treating abuse or dependence
- A61P 25/32: Alcohol-abuse
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/18: for HIV
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel substituted imidazo[1,2-b]pyridazine compounds of Formula (I): pharmaceutical compositions thereof, and the use such compounds as corticotropin releasing factor 1 (CRF1) receptor antagonists in the treatment of psychiatric disorders and neurological diseases.

## Claims

### Claim 1

A compound of Formula I
wherein:
R0 is hydrogen, halo, methyl or ethyl;
R1 and R3 are independently methyl, methoxy, or trifluoromethyl;
R2 is selected from the group consisting of:
R4 is hydrogen, halo, or hydroxy;
R5a and R5b are independently ethyl or n-propyl;
R6 at each occurrence is independently hydrogen, halo, cyano, (C1-C4)alkyl, trifluoromethyl, methoxy, or phenyl;
R7 is hydrogen, halo, methyl, methoxy, dimethylamino,
R8 is selected from the group consisting of hydrogen, halo, cyano, (C1-C4)alkyl, RaRbN—, carbamyl, (C1-C2)alkoxy(C1-C2)alkyl, R11—C(O)—,
R11 is methoxy, methylamino, dimethylamino, or phenyl;
R12 is hydrogen, halo, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy dimethylamino, acetyl, or methylsulfonyl;
R13 is hydrogen, methyl or halo;
R14 is hydrogen or hydroxy;
R15 is methylthio, cyclopropyl, phenyl,
Ra is hydrogen, (C1-C5)alkyl, (C3-C5)cycloalkyl, methoxy(C2-C4)alkyl, acetyl, (C1-C2)alkylsulfonyl, (C3)alkenyl, R15—(CH2)n-, or (C1-C2)alkyl substituted with cyano, formyl, vinyl, or ethynyl;
Rb is hydrogen or (C1-C3)alkyl;
X is —CH2—, —CO—, —O—, —S— or —SO2—;
Y is —CH2— or —O—;
z is S or O;
n is 1 or 2;
Q is hydrogen or methyl;
T is hydrogen or methyl;
J is methyl, trifluoroethyl, or tert-butyl; and
M is methyl or halo;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1 wherein R0 and R4 are hydrogen, R1 and R3 are methyl, and R5a and R5b are ethyl.

### Claim 3 (depends on 2)

The compound according to claim 2, wherein R2 is

### Claim 4 (depends on 3)

The compound according to claim 3, wherein R8 is

### Claim 5 (depends on 4)

The compound according to claim 4 which is N-{4-chloro-5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiazol-2-yl}-morpholine or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 4)

The compound according to claim 4 which is N-{4-chloro-5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiazol-2-yl}-morpholine, hydrochloride salt.

### Claim 7 (depends on 4)

The compound according to claim 4 which is 3-[4-bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-8-(1-ethyl-propyl)-2,6-dimethyl -imidazo[1,2-b]pyridazine or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 4)

The compound according to claim 4 which is 3-[4-chloro-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 4)

The compound according to claim 4 which is 3-[3-chloro-5-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-8-(1-ethyl-propyl)-2,6-dimethyl -imidazo[1,2-b]pyridazine or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent or excipient.