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Tosylate salt of trans-n-isobutyl-3-fluoro-3- [3-flu0r0-4- (pyrrolidin-1-yl-methyl) -phenyl] cyclobut anecarboxamide

A technology of cyclobutane carboxamide and toluene sulfonate, applied in the field of toluene sulfonate, can solve the problems of poor performance

Inactive Publication Date: 2011-01-05
PFIZER INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Non-imidazole neuroactive compounds such as β-histamine (Arrang, Eur. J. Pharm. 1985, 111:72-84) have been shown to have certain histamine H 3 Receptor active but poor potency

Method used

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  • Tosylate salt of trans-n-isobutyl-3-fluoro-3- [3-flu0r0-4- (pyrrolidin-1-yl-methyl) -phenyl] cyclobut anecarboxamide
  • Tosylate salt of trans-n-isobutyl-3-fluoro-3- [3-flu0r0-4- (pyrrolidin-1-yl-methyl) -phenyl] cyclobut anecarboxamide
  • Tosylate salt of trans-n-isobutyl-3-fluoro-3- [3-flu0r0-4- (pyrrolidin-1-yl-methyl) -phenyl] cyclobut anecarboxamide

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Embodiment 1

[0104] Trans-N-ethyl-3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)phenyl]-cyclobutanecarboxamide (1) Tosylate

[0105] 3-Fluoro-3-(3-fluoro-4-pyrrolidin-1-ylmethyl-phenyl)-cyclobutanecarboxylic acid isobutyramide (13.8g, 79.0mmol) was dissolved in EtOAc (250mL), and Add p-toluenesulfonic acid (15.2 g, 79.9 mmol) in EtOAc (150 mL). The resulting solution was stirred overnight and the white precipitate was collected and dried under nitrogen purge to obtain 16.5 g of monotoluenesulfonate. The salt was first heated in a mixture of 20 mL MeOH and 40 mL EtOAc. It was then filtered through a nylon filter and EtOAc (250 mL) was added over ~40 min. After stirring for another hour, the resulting white solid was collected and dried under a nitrogen purge. The recrystallization process was repeated twice to obtain 12.19 g of substance, which was determined to be 99.44% pure by HPLC analysis: LRMS m / z C 20 H 28 F 2 N 2 The calculated value of O is 350.2, and the measured value is 351.2(...

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Abstract

The present invention is directed to the tosylate salt of trans-N-isobutyl- 3-fluoro-3-[3-fluoro-4-(pyrrolidin-1-ylmethyl)-phenyl]-cyclobutanecarboxamide Formula (1): to solvates (e.g., hydrates) thereof, to polymorphs thereof, to pharmaceutical compositions thereof and to a method of treating depression, mood disorders, schizophrenia, anxiety disorders, cognitive disorders, Alzheimer's disease, attention-deficit disorder (ADD), attention-deficit hyperactivity disorder (ADHD), psychotic disorders, sleep disorders, obesity, dizziness, epilepsy, motion sickness, respiratory diseases, allergy, allergy-induced airway responses, allergic rhinitis, nasal congestion, allergic congestion, congestion, hypotension, cardiovascular disease, diseases of the Gl tract, hyper- and hypo-motility and acidic secretion of the gastro-intestinal tract comprising administering a therapeutically effective amount thereof.

Description

Technical field [0001] The present invention relates to the tosylate salt of the compound of formula 1 described herein, a pharmaceutical composition comprising the preferred salt, and to the use of the preferred pharmaceutical composition to antagonize histamine-3 (H 3 ) The treatment method of the disease or unhealthy condition that is treated by the recipient. Background technique [0002] Histamine is known to be a mediator in allergic reactions (ie allergies, hay fever, and asthma), which are usually treated with histamine antagonists or "antihistamines." It has also been confirmed that histamine receptors exist in at least two different types, called H 1 And H 2 Receptor. [0003] It is believed that the third histamine receptor (H 3 Receptors) play a role in central nervous system neurotransmission, where it is believed that the H 3 The receptor is placed on the histaminergic nerve endings ( Nature , 302 , S32-S37 (1983)). By selective H 3 The development of receptor agonis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/073A61K31/40A61P1/00A61P11/00A61P25/00
CPCC07D295/073A61P1/00A61P1/04A61P1/08A61P11/00A61P11/02A61P25/00A61P25/08A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P3/04A61P37/08A61P43/00A61P9/00A61P9/02
Inventor 特拉维斯·T·韦杰托德·W·巴特勒
Owner PFIZER INC
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