# US 8,569,288 B2 · Thienotriazolodiazepine derivatives active on apo A

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- Number: US 8,569,288 B2
- Document ID: US8569288B2
- Status: Granted
- Kind: B2
- Application number: 13/126,600
- Filed: 2009-10-29
- Published: 2011-09-22
- Granted: 2013-10-29
- Earliest claimed: 2008-10-30
- Assignees: CircoMed LLC
- Applicants: Herman Kempen; Daniel Bellus; Barbara Staehelin
- Inventors: Herman Kempen; Daniel Bellus; Barbara Staehelin
- Web page: https://patentgrep.com/patent/US8569288B2

## CPC

- C07D 495/14: Ortho-condensed systems
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention relates to new thienotriazolodiazepine derivatives of the formula (1) wherein R1 is CH3, R2 is CH3 or —(CH2)n—R4 or —(CH2)n—O—R4 or —(CH2)n—S—R4 wherein n is 1, 2, 3 or 4 and R4 is CH3, CH2CH3 or CH2CH2OCH3, and R3 is hydrogen or —OCH2O— or —OCH2CH2O— connected to the ortho/meta position or meta/para position of the phenyl ring; or wherein R1 and R2 are hydrogen and R3 is —OCH2O— Or —OCH2CH2O— connected to the ortho/meta position or meta/para position of the phenyl ring; and pharmaceutically acceptable acid addition salts thereof. These compounds and pharmaceutical compositions containing them are useful in the treatment and prevention of atherosclerotic artery diseases, such as myocardial infarction and stroke, and of Alzheimer's disease.

## Claims

### Claim 1

A compound of formula 1
wherein
R1 is CH3, R2 is CH3 or —(CH2)n—R4 or —(CH2)n—O—R4 or —(CH2)n—S—R4 wherein n is 1, 2, 3 or 4 and R4 is CH3, CH2CH3 or CH2CH2OCH3, and R3 is hydrogen or —OCH2O— or —OCH2CH2O— connected to the ortho/meta position or meta/para position of the phenyl ring; or
R1 and R2 are hydrogen and R3 is —OCH2O— Or —OCH2CH2O— connected to the ortho/meta position or meta/para position of the phenyl ring;
and pharmaceutically acceptable acid addition salts thereof.

### Claim 2 (depends on 1)

The compound according to claim 1 of formula 1 wherein R1 is CH3, R2 is CH3 or —(CH2)n—R4 or —(CH2)n—O—R4 or —(CH2)n—S—R4 wherein n is 1, 2, 3 or 4 and R4 is CH3, CH2CH3 or CH2CH2OCH3, and R3 is hydrogen.

### Claim 3 (depends on 1)

The compound according to claim 1 of formula 1 wherein R1 is CH3, R2 is CH3 and R3 is hydrogen.

### Claim 4 (depends on 1)

The compound according to claim 1 of formula 1 wherein
R1 and R2 are hydrogen and R3 is —OCH2O— Or —OCH2CH2O— connected to the ortho/meta position or meta/para position of the phenyl ring.

### Claim 5 (depends on 1)

The compound according to claim 1 of formula 1 wherein
R1 and R2 are hydrogen and R3 is —OCH2O— connected to the meta/para position of the phenyl ring.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a compound of formula 1 according to claim 1, or a pharmaceutically acceptable acid addition salt thereof.

### Claim 7 (depends on 1)

A method of treating a patient afflicted with an atherosclerotic artery disease or with Alzheimer's disease, which method comprises administering an effective amount of the compound of formula 1 according to claim 1 to the patient.