# US 7,745,477 B2 · Heteroaryl and benzyl amide compounds

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- Number: US 7,745,477 B2
- Document ID: US7745477B2
- Status: Granted
- Kind: B2
- Application number: 11/698,221
- Filed: 2007-01-25
- Published: 2007-08-09
- Granted: 2010-06-29
- Earliest claimed: 2006-02-07
- Assignees: Hoffman-La Roche Inc.
- Inventors: Aurelia Conte; Holger Kuehne; Thomas Luebbers; Patrizio Mattei; Cyrille Maugeais; Werner Mueller; Philippe Pflieger
- Web page: https://patentgrep.com/patent/US7745477B2

## CPC

- C07C 233/66: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- 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 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 233/65: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C 233/73: of a carbon skeleton containing six-membered aromatic rings
- C07D 213/40: Acylated substituent nitrogen atom
- C07D 213/61: Halogen atoms or nitro radicals
- C07D 213/81: Amides; Imides
- C07D 213/82: in position 3
- C07D 231/16: Halogen atoms or nitro radicals
- C07D 239/28: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07C 2601/02: with a three-membered ring
- C07C 2601/04: with a four-membered ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Compounds of formula I wherein R1, R2, R4, R5, A, B, D and n are as defined, and pharmaceutically acceptable salts thereof, processes for their preparation, their use as pharmaceuticals and pharmaceutical compositions comprising them.

## Claims

### Claim 1

A compound of formula I:
or pharmaceutically acceptable salts thereof, wherein:
R1 is C1-C6alkyl, halo-C1-C6alkyl, halo-C1-C6alkoxy, C3-C8cycloalkyl, halo-C3-C8cycloalkyl or tri-C1-C6alkylsilyl;
R2 is a group:
wherein:
R6 and R7 are independently hydrogen, C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
R8 and R9 are independently hydrogen, C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
X is CR12;
Y is CH;
R12 is halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
R5 is halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
R4 is hydrogen, C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
A is CR10 or N; wherein R10 is hydrogen, C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
B is CR11 or N; wherein R11 is hydrogen; or R11 is C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy, when at least two of R3, R4, R5 and R10 are not hydrogen;
D is CR3 or N; wherein R3 is hydrogen, C1-C6alkyl, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl, OH or halo-C1-C6alkoxy;
wherein -B=A- and -A=D- are not —N═N—; and at least two of R3, R4, R5, R10 and R11 are not hydrogen; and
n is 1, 2 or 3.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R1 is C1-C6alkyl, halo-C1-C6alkyl, C3-C8cycloalkyl, halo-C3-C8cycloalkyl or tri-C1-C6alkylsilyl.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R2 is a group (a).

### Claim 4 (depends on 1)

A compound according to claim 1 wherein R2 is a group (b).

### Claim 5 (depends on 1)

A compound according to claim 1 wherein A is CR10.

### Claim 6 (depends on 1)

A compound according to claim 1 wherein:
A is N;
B is CR11; and
D is CR3.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein:
A is CR10;
B is CR11 or N; and
D is CR3.

### Claim 8 (depends on 1)

A compound according to claim 1 wherein:
R1 is C1-C6alkyl;
R2 is a group:
wherein:
R8 and R9 are independently hydrogen, halo-C1-C6alkyl, halogen, C3-C8cycloalkyl or halo-C1-C6alkoxy;
X is CR12, wherein R12 is halogen or C3-C8cycloalkyl; and Y is CH;
R5 is halogen;
R4 is C1-C6alkyl, halo-C1-C6alkyl or halogen;
A is CR10;
B is CR11 or N;
D is CR3;
R3 is hydrogen;
R10 is halo-C1-C6alkyl or halogen; and
R11 is hydrogen.

### Claim 9 (depends on 5)

A compound of claim 5 wherein R2 is

### Claim 10 (depends on 5)

A compound of claim 5 wherein R2 is

### Claim 11 (depends on 6)

A compound of claim 6 wherein R2 is

### Claim 12 (depends on 6)

A compound of claim 6 wherein R2 is

### Claim 13 (depends on 7)

A compound of claim 7 wherein R2 is

### Claim 14 (depends on 7)

A compound of claim 7 wherein R2 is

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier or adjuvant or mixture thereof.

### Claim 16

N-(4-tert-Butyl-benzyl)-3-chloro-N-[2-(4-chloro-3-ethyl-phenyl)-ethyl]-2-fluoro-5-trifluoromethyl-benzamide or a pharmaceutically acceptable salt thereof.

### Claim 17

N-(4-tert-Butyl-benzyl)-3-chloro-N-[2-(4-chloro-3-ethyl-phenyl)-ethyl]-2-fluoro-5-trifluoromethyl-benzamide.