# US 7,608,627 B2 · 6-azaindole compound

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- Number: US 7,608,627 B2
- Document ID: US7608627B2
- Status: Granted
- Kind: B2
- Application number: 11/547,308
- Filed: 2005-04-04
- Published: 2008-03-13
- Granted: 2009-10-27
- Earliest claimed: 2005-04-04
- Assignees: Takeda Pharmaceutical Company Limited
- Inventors: Yoshiaki Horiguchi; Hiroshi Imoto; Mark A. Wolf
- Web page: https://patentgrep.com/patent/US7608627B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/12: Antidiarrhoeals
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A61P 19/10: for osteoporosis
- A61P 21/04: for myasthenia gravis
- 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 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- 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

A compound represented by the formula wherein R1, R2, R3 and R6 are the same or different and each is a hydrogen atom or a substituent; one of R4 and R5 is a hydrogen atom and the other is a group represented by the formula: —C(═X)—R7 wherein X is N—O—R8 or N—NH—R9 wherein R8 and R9 are the same or different and each is a hydrogen atom or a group bonded via a carbon atom; and R7 is a hydrogen atom or a substituent, and the like and a salt thereof have a superior IκB kinase inhibitory activity, and useful as pharmaceutical agents such as agents for preventing or treating diabetes and the like.

## Claims

### Claim 1

A compound represented by the formula
wherein
R1, R2, R3 and R6 are the same or different and each is a hydrogen atom, a halogen atom, an amino group, or a mono- or di-C7-19 aralkylamino group;
R4 is a hydrogen atom; and
R5 is
1) a group represented by the formula: —C(═X)—R7
wherein X is N—O—R8 or N—NH—R9
wherein R8 and R9 are the same or different and each is
(i) a hydrogen atom;
(ii) an amidino group;
(iii) a C1-6 alkyl group optionally having 1 to 3 substituents selected from a hydroxy group, an optionally halogenated C1-6 alkoxy group, a carboxyl group, an amino group, a mono-or di-C1-6 alkylamino group, a 5- to 7-membered heterocyclic group, a C1-6 alkoxy-carbonyl group, a carbamoyl group, a mono- or di-C1-6 alkyl-carbamoyl group, a C6-14 aryl-carbamoyl group, a C1-6 alkoxy-carboxamido group and a 5- to 7-membered heterocyclic oxy group;
(iv) a C7-19 aralkyl group;
(v) a heterocyclic group bonded via a carbon atom and optionally having 1 to 3 C1-6 alkoxy-carbonyl groups; or
(vi) a carbamoyl group, and
R7is
(i) a hydrogen atom or
(ii) a C1-6 alkyl group, a C6-14 aryl group, a C7-19 aralkyl group or a monocyclic aromatic heterocyclic group, each of which may have 1 to 3 substituents selected from a halogen atom, a C1-6 alkyl group and an optionally halogenated C1-6 alkoxy group;
2) a group represented by the formula: —C(═O)—R10
wherein R10
(i) a hydrogen atom;
(ii) a C1-6 alkyl group;
(iii) C6-14 aryl group optionally having 1 to 3 substituents selected from a halogen atom, a C1-6 alkyl group and an optionally halogenated C1-6 alkoxy group;
(iv) a C7-19 aralkyl group; or
(v) a heterocyclic group bonded via a carbon atom;
3) a group represented by the formula: —CH(OH)—R10 wherein R10 is as defined above;
4) a group represented by the formula: —C(═O)—NH—(CH2)n-Ar wherein n is 0, 1 or 2, and Ar is a C6-14 aryl group or a 5 or 6-membered aromatic heterocyclic group;
5) a group represented by the formula: —C(═O)-Het wherein Het is 1-pyrrolidinyl, 1-piperazinyl, 4-morpholinyl or 4-thiomorpholinyl each optionally having 1 to 3 substituents selected from an optionally halogenated C1-6 alkyl group and an optionally halogenated C1-6 alkyl-carbonyl group; or
6) a group represented by the formula: —CH(R12)—NR13R14 wherein R12 is a hydrogen atom, C1-6 alkyl group or a C6-14 aryl group;
R13 and R14 are the same or different and each is
(i) a hydrogen atom,
(ii) a C1-6 alkyl group, a C3-8cycloalkyl group or a C7-19 aralkyl group each optionally having one to three 5- to 7-membered heterocyclic groups,
(iii) a monocyclic non-aromatic heterocyclic group optionally having 1 to 3 C7-19 aralkyl groups, or
(iv) a C1-6 alkyl-carbonyl group, a C6-14 aryl-carbonyl group or an aromatic heterocyclic carbonyl group each optionally having 1 to 3 C1-6 alkoxy-carboxamido groups, or R13 and R14 form, together with the adjacent nitrogen atom, a nitrogen-containing heterocyclic group optionally having 1 to 3 substituents selected from a halogen atom, an optionally halogenated C1-6 alkyl group and an optionally halogenated C1-6 alkoxy group (provided that the nitrogen-containing heterocyclic group is not an oxopyrrolidinyl group or an oxopiperazinyl group),
or a salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R4 is a hydrogen atom, and R5 is a group represented by the formula: —C(═X)—R7 wherein X and R7 are as defined in claim 1.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R4 is a hydrogen atom, and R5 is a group represented by the formula: —C(═O)—R10 wherein R10 is as defined in claim 1.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1, R2 and R3 are each a hydrogen atom.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 or a salt thereof and a pharmacologically acceptable carrier.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R1, R2, R3 and R6 are each a hydrogen atom.

### Claim 7 (depends on 1)

The compound of claim 1,
wherein R1, R2, R3 and R6 are each a hydrogen atom;
R4 is a hydrogen atom; and
R5 a group represented by the formula: —C(═X)—R7 wherein X and R7 are as defined in claim 1.

### Claim 8 (depends on 1)

The compound of claim 1,
wherein R1, R2, R3 and R6 are each a hydrogen atom;
R4 is a hydrogen atom; and
R5 is a group represented by the formula: —C(═O)—R10 wherein R10 is as defined in claim 1.