Novel 3-substituted urea derivatives and medicinal use thereof
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A technology of urea derivatives and substituents, which is applied in the field of new 3-substituted urea derivatives and their pharmaceutical applications, and can solve the problems of no discovery
Inactive Publication Date: 2004-01-07
MITSUBISHI TANABE PHARMA CORP
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[0005] However, so far, no drug has been found that can prevent or treat diseases or syndromes caused by inflammation caused by C5a by inhibiting the action of C5a
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preparation Embodiment 1
[0104] To a solution of benzaldehyde (10 mL) in toluene (200 mL) were added 4-octylaniline (22.5 mL) and molecular sieve 4A (20 g) under ice-cooling, and the mixture was stirred at room temperature overnight. Molecular sieve 4A was filtered off from the reaction mixture, and the resulting filtrate was concentrated under reduced pressure. The residue was dissolved in methanol (200 mL), and sodium borohydride (2.3 g) was added under ice-cooling. The mixture was stirred at room temperature for 5 hrs. Methanol was evaporated and water was added to the residue. The mixture was extracted with chloroform, and the organic layer was washed with saturated brine, dried and concentrated under reduced pressure to give benzyl(4-octylphenyl)amine (29 g). 1 H-NMR (CDCl 3 )δ: 0.85 (3H, t, J = 6.6Hz), 1.27-1.30 (10H, m), 1.59 (2H, t, J = 7.3Hz), 2.58 (2H, t, J = 7.3Hz), 4.29 ( 2H, s), 6.56 (2H, d, J = 8.6 Hz), 6.97 (2H, d, J = 8.6 Hz), 7.26-7.38 (5H, m). Preparation Example 2
preparation Embodiment 2
[0105] Use 4-methoxybenzaldehyde (1.0g) and 4-octylaniline (1.4g) as raw materials, react and process in the same manner as Preparation Example 1, to obtain [(4-methoxyphenyl) Methyl](4-octylphenyl)amine (2.2 g). 1 H-NMR (CDCl 3 )δ: 0.90 (3H, t, J = 6.6Hz), 1.22-1.51 (10H, m), 1.54 (2H, t, J = 7.9Hz), 2.48 (2H, t, J = 7.9Hz), 3.79 ( 3H, s), 4.22 (2H, s), 6.57 (2H, d, J=8.6Hz), 6.86 (2H, d, J=8.6Hz), 6.98 (2H, d, J=8.9Hz), 7.28 ( 2H, d, J = 8.9 Hz). Preparation Example 3
preparation Embodiment 3
[0106] Use 4-hydroxybenzaldehyde and 4-octylaniline as raw materials, react and treat in the same manner as Preparation Example 1, to obtain [(4-hydroxymethylphenyl)methyl](4-octylphenyl )amine. Preparation Example 4
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Abstract
The present invention relates to a urea derivative of the formula (1) wherein each symbol is as described in the specification, a pharmaceutically acceptable salt thereof and pharmaceutical use thereof. The compound of the present invention has a C5a receptor antagonistic action and is useful as an agent for the prophylaxis or treatment of diseases or syndromes due to inflammation caused by C5a [e.g., autoimmune diseases such as rheumatism, systemic lupus erythematosus and the like, sepsis, adult respiratory distress syndrome, chronic obstructive pulmonary disease, allergic diseases such as asthma and the like, atherosclerosis, cardiac infarction, brain infarction, psoriasis, Alzheimer's disease and serious organ injury (e.g., pneumonia, nephritis, hepatitis, pancreatitis and the like) due to activation of leukocytes caused by ischemia, trauma, burn, surgical invasion and the like]. In addition, it is useful as an agent for the prophylaxis or treatment of infectious diseases caused by bacteria or virus that invades via a C5a receptor.
Description
technical field [0001] The present invention relates to a urea derivative which exhibits C5a receptor antagonism and is used for the prevention or treatment of autoimmune diseases such as rheumatism and systemic lupus erythematosus, sepsis, adult respiratory distress syndrome, chronic obstructive pulmonary disease , allergic diseases such as asthma, atherosclerosis, myocardial infarction, cerebral infarction, psoriasis, Alzheimer's disease, or leukocyte activation caused by local ischemia, trauma, severe burns, surgical invasion, etc. Serious organ damage (such as pneumonia, nephritis, hepatitis and pancreatitis, etc.), and related to its medicinal salt and its pharmaceutical application. Background technique [0002] When the complement system is activated, proteins of the complement system are enzymatically decomposed and fragments having various physiological activities are produced. One fragment, complement component C5a, is a glycoprotein with a molecular weight of abo...
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