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Oxypiperidine derivatives and methods of use thereof

A solvate and medicament technology, applied in the field of oxygen piperidine derivatives as histamine receptor antagonists, can solve problems such as nausea/diarrhea, lactic acidosis and the like

Inactive Publication Date: 2010-11-03
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, biguanides can induce lactic acidosis and nausea / diarrhea

Method used

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  • Oxypiperidine derivatives and methods of use thereof
  • Oxypiperidine derivatives and methods of use thereof
  • Oxypiperidine derivatives and methods of use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0386] Preparation of Compound 4

[0387]

[0388] Step A

[0389] To a stirred solution of 4-hydroxypyridine (2 g, 21.03 mmol) in 70 mL of anhydrous THF was added 4-hydroxypiperidine (5.29 g, 26.28 mmol) at room temperature. Triphenylphosphine (6.9 g, 26.31 mmol) was then added followed by diisopropylazodicarboxylate (5.2 mL, 26.41 mmol) dropwise. The reaction was heated to 55°C and allowed to stir at this temperature for approximately 15 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The resulting oily residue was treated with 1.0M aqueous HCl (30 mL) and washed with CH 2 Cl 2 (30 ml x 2) wash the acidic solution. Merged CH 2 Cl 2 Wash with 1.0M aqueous HCl (10 mL) and H 2 O (20 mL) was re-extracted and discarded. The combined aqueous fractions were basified to pH~12 using 1.0M aqueous NaOH, and the basic solution was washed with CH 2 Cl 2 (50ml x4) extraction. The combined organic extracts were washed with brine, ...

Embodiment 2

[0401] Preparation of intermediate compound 2B

[0402]

[0403] Step A

[0404] Using the procedure described in Example 1, Step C, bis-N-heterocycloalkyl ether 1B (196 mg, 0.689 mmol) was converted to compound 2A (155 mg, 58%).

[0405] Step B

[0406] Using the procedure described in Example 1, Step D, amide 2A (155 mg) was converted to compound 2B (96.4 mg, 86.5%).

Embodiment 3 and 4

[0408] Preparation of intermediate compounds 3A and 4A

[0409] Using the procedure described in Example 2, except using the acids specified in the table below, compound IB was converted to intermediate compounds 3A and 4A.

[0410]

[0411]

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PUM

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Abstract

The present invention relates to novel Oxypiperidine Derivatives, pharmaceutical compositions comprising the Oxypiperidine Derivatives and the use of the Oxypiperidine Derivatives for treating or preventing treating allergy, an allergy-induced airway response, congestion, hypotension, a cardiovascular disease, a gastrointestinal disorder, obesity, a sleep disorder, pain, diabetes, a diabetic complication, impaired glucose tolerance, impaired fasting glucose or a central nervous system (CNS) disorder.

Description

technical field [0001] The present invention relates to novel oxygen piperidine derivatives, pharmaceutical compositions containing the oxygen piperidine derivatives and the use of the oxygen piperidine derivatives for the treatment or prevention of allergies, airway reactions induced by allergies, congestion, hypotension, cardiac Use for vascular disease, gastrointestinal disorders, obesity, sleep disturbance, pain, diabetes, diabetic complications, impaired glucose tolerance, impaired fasting glucose, or central nervous system (CNS) disorders. Background technique [0002] histamine receptor H 1 、H 2 and H 3 is the fully recognized form. h 1 Receptors are receptors that mediate responses antagonized by conventional antihistamines. h 1 Receptors are found, for example, in the ileum, skin and bronchial smooth muscle of humans and other mammals. by H 2 Receptor-mediated responses to histamine-stimulated gastric acid secretion in mammals and chronotropic effects in iso...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D417/14A61K31/506A61K31/4523A61P1/00A61P25/00A61P3/04A61P3/10A61P37/08
CPCC07D401/14C07D417/14A61P1/00A61P1/04A61P1/12A61P1/18A61P3/00A61P3/04A61P3/10A61P9/00A61P9/02A61P9/04A61P9/06A61P9/10A61P11/00A61P25/00A61P25/04A61P25/06A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/28A61P37/08A61P43/00
Inventor J·朝R·G·亚斯兰尼安J·郑
Owner SCHERING AG
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