# US 8,772,496 B2 · Intermediate and process useful in the preparation of {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 8,772,496 B2
- Document ID: US8772496B2
- Status: Granted
- Kind: B2
- Application number: 12/515,794
- Filed: 2007-12-04
- Published: 2010-03-04
- Granted: 2014-07-08
- Earliest claimed: 2006-12-20
- Assignees: Eli Lilly and Company
- Applicants: Pingyun Chen
- Inventors: Pingyun Chen
- Web page: https://patentgrep.com/patent/US8772496B2

## CPC

- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/06: Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- 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 11/06: Antiasthmatics
- A61P 13/10: of the bladder
- A61P 17/00: Drugs for dermatological disorders
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 213/50: Ketonic radicals
- C07D 213/53: Nitrogen atoms
- C07D 401/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel compounds, (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone benzoate, and (2-chlorophenyl)-[2-(2-hydroxy-2-pyridin-4-yl-vinyl)pyridin-3-yl]methanone toluate, which are useful intermediates for the preparation of the compound of Formula I: (I) The present invention further relates to novel processes for preparing a crystalline compound, which is {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV.

## Claims

### Claim 1

A process for preparing a compound that is {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV, comprising: crystallizing the product from a solvent mixture of isopropyl acetate and heptanes,
wherein the {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV is characterized by at least one of the following:
a) a solid-state 13C nuclear magnetic resonance spectrum comprising peaks at the following chemical shifts: 52.3±0.2 and 195.4±0.2 ppm;
b) an X-ray powder diffraction pattern comprising at least two peaks wherein one peak is 12.1±0.1° and the second peak is selected from the group consisting of 8.3±0.1°, 14.3±0.1°, 16.6±0.1°, 16.9±0.1°, and 18.5±0.1° in 2θ; or
c) an X-ray powder diffraction pattern comprising at least the following peaks: 8.3±0.1°, 12.1±0.1°, 16.6±0.1°, 16.9±0.1°, and 18.5±0.1° in 2θ.

### Claim 2 (depends on 1)

The process of claim 1, wherein the {2-[1-(3,5-bistrifluoromethylbenzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chlorophenyl)-methanone, Form IV is characterized by an X-ray powder diffraction pattern comprising at least the following peaks: 6.8±0.1°, 7.7±0.1°, 8.3±0.1°, 11.2±0.1°, 12.1±0.1°, 12.7±0.1°, 13.5±0.1°, 14.3±0.1°, 14.9±0.1°, 16.2±0.1°, 16.6±0.1°, 16.9±0.1°, 17.4±0.1°, 18.2±0.1°, 18.5±0.1°, 18.9±0.1°, 19.3±0.1°, 19.8±0.1°, 20.3±0.1°, 20.7±0.1°, 21.1±0.1°, 21.4±0.1°, 21.7±0.1°, 21.9±0.1°, 22.1±0.1°, 22.5±0.1°, 22.8±0.1°, 23.4±0.1°, 24.0±0.1°, 24.3±0.1°, 24.9±0.1°, 25.6±0.1°, 25.9±0.1°, 26.4±0.1°, 26.9±0.1°, 27.3±0.1°, 28.1±0.1°, 28.5±0.1°, 29.0±0.1°, 29.3±0.1°, 29.9±0.1°, 30.2±0.1°, 31.3±0.1°, 31.5±0.1°, 32.6±0.1°, 33.3±0.1°, 35.4±0.1°, 36.1±0.1°, 36.4±0.1°, and 36.8±0.1° in 2θ.