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Urea compound, preparation method and application thereof

A compound and urea technology, applied in the field of urea compounds, can solve the problems of high cost, intravenous administration only, and low toxicity

Inactive Publication Date: 2013-06-26
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Complement inhibitors that are relatively mature in research at present are complement regulatory proteins, such as SCR1 and antibodies, which have relatively low toxicity, but are expensive and can only be administered intravenously

Method used

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  • Urea compound, preparation method and application thereof
  • Urea compound, preparation method and application thereof
  • Urea compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0088] Synthesis of Preparation Example 1 Intermediate (S)-1-(3-hydroxyl-4-methoxyphenyl)-3-(1-phenyl-ethyl)-urea

[0089] (1) 3-Benzyloxy-4-methoxy-benzaldehyde

[0090]

[0091] Take isovanillin (3.04g, 20nmol) to a 100ml round bottom flask, add 50ml of acetone, add benzyl bromide (3.42g, 20nmol), anhydrous K 2 CO 3 (11g, 80nmol), heated to reflux for 12 hours, TLC detected that the reaction was complete, the residue obtained after concentration was separated with ethyl acetate and water, the organic phase was washed with water, saturated brine, dried and concentrated to give 3-benzyloxy- 4-methoxy-benzaldehyde 4.7g, yield 98%.

[0092] 1 H NMR (300MHz, CDCl 3 ): δ3.95(s, 3H), 5.18(s, 2H), 6.977-7.006(d, J=8.7Hz, 1H), 7.312-7.40(m, 2H), 7.45-7.47(m, 5H), 9.816(s, 1H).

[0093] (2) 3-Benzyloxy-4-methoxy-benzoic acid

[0094]

[0095] Dissolve 3-benzyloxy-4-methoxy-benzaldehyde (1.08g, 4.46mmol) and sodium dihydrogen phosphate (0.16g, 0.134mmol) in 25ml acetonitri...

preparation Embodiment 2

[0109] Preparation Example 2 (S)-1-(3-butoxy-4-methoxyphenyl)-3-(1-phenyl-ethyl)-urea

[0110]

[0111] (S)-1-(3-hydroxy-4-methoxyphenyl)-3-(1-phenyl-ethyl)-urea (20mg, 0.07mmol), n-butyl bromide 0.1ml, no Mix 80 mg of potassium carbonate in water, catalytic amount of 18-crown-6, and 2 ml of DMF, and stir overnight at room temperature. TLC detects that the reaction is complete. Add water and ethyl acetate to separate layers, extract the aqueous phase with ethyl acetate three times, combine the organic phases with water, wash with saturated brine, dry and concentrate to obtain a white solid (S)-1-(3-butoxy-4- Methoxyphenyl)-3-(1-phenyl-ethyl)-urea 23 mg, yield 96%.

[0112] 1 H NMR (300MHz, CDCl3): δ0.904-0.95(t, 3H), 1.388-1.406(d, J=5.4Hz, 3H), 1.40-1.491(m, 2H), 1.709-1.805(m, 2H) , 3.79(s, 3H), 3.901-3.923(t, 2H), 4.926-4.973(m, 1H), 5.397-5.423(d, J=7.8Hz, 1H), 6.578-6.612(dd, 1H), 6.709 -6.737 (d, J=8.4Hz, 1H), 6.81 (s, 1H), 6.983-6.989 (d, J=1.8Hz, 1H), 7.24-7.31...

preparation Embodiment 3

[0113] Preparation Example 3 (S)-1-(3-pentyloxy-4-methoxyphenyl)-3-(1-phenyl-ethyl)-urea

[0114]

[0115] Except replacing n-butyl bromide with n-pentyl bromide of the corresponding molar number, (S)-1-(3-pentyloxy-4-methoxyphenyl )-3-(1-phenyl-ethyl)-urea.

[0116] 1 H NMR (CDCl3, 300MHz): δ1.38-1.41(t, 3H), 1.388-1.406(d, J=5.4Hz, 3H), 1.40-1.491(m, 2H), 1.709-1.805(m, 2H) , 3.79(s, 3H), 3.901-3.923(t, 2H), 4.926-4.973(m, 1H), 5.397-5.423(d Hz, J=7.8, 1H), 6.578-6.612(dd, 1H), 6.709 -6.737 (d, J=8.4Hz, 1H), 6.81 (s, 1H), 6.983-6.989 (d, J=1.8Hz, 1H), 7.24-7.31 (m, 5H).

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Abstract

The invention relates to an urea compound of the structure shown in a general formula I, a preparation method thereof, a drug composition containing the urea compound and an application of the drug composition in preparation of drugs used for treating inflammatory reaction, immunity hyperfunction and organ transplantation. R1-R7, X, Y and n in the general formula I disclosed in the invention are defined in the specification and claims.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a urea compound, a preparation method thereof, a pharmaceutical composition containing the compound and its use. The compound has complement inhibitory activity and can be applied to the treatment of inflammatory reactions, immune hyperactivity and organ transplantation exclusion etc. Background technique [0002] The complement system is a group of immune-related and activated enzyme-active proteins present on the surface of human and vertebrate serum, interstitial fluid and cell membranes, including more than 20 serum proteins (as the inherent components of complement) and complement regulatory proteins, and Complement active fragments or regulatory protein biological effector receptors that mediate the immune system. [0003] Under physiological conditions, most complement components in serum exist as inactive enzyme precursors. Only under the action of certain activators, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/34C07C273/18C07D207/16C07D213/75C07D213/40C07D303/20A61K31/17A61K31/40A61K31/44A61K31/4406A61K31/4409A61P29/00A61P37/06
CPCA61P29/00A61P37/06C07C275/34C07C2601/14C07D207/06C07D213/40C07D213/75C07D303/23
Inventor 南发俊左建平李佳张梅安娜·布鲁姆唐炜杨筱莹
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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