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Substituted phenyl derivatives, producing method and use thereof

一种苯基脲、联苯基的技术，应用在变应性病症和炎症的治疗领域，能够解决未公开氯离子通道阻滞剂应用等问题

Inactive Publication Date: 2003-08-20
NEUROSEARCH AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of chloride channel blockers in the treatment of sickle cell anemia is not disclosed in the literature

Method used

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  • Substituted phenyl derivatives, producing method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13- 3

[0081] Example 13-Trifluoromethylphenyl-4-bromo-2-(5-tetrazolyl)phenylurea

[0082] 3-trifluoromethylphenylisocyanate (0.41ml, 3.0mmol) and 5-(2-amino-5-bromophenyl)tetrazole (0.6g, 2.5mmol) were added in toluene (10ml), at room temperature The reaction mixture was stirred overnight. The precipitate was filtered and washed successively with toluene and petroleum ether to obtain 0.53 g of the desired compound, melting point: 269-270°C.

[0083] The following compounds can be obtained in a similar manner: 3-trifluoromethylphenyl-2-(5-tetrazolyl)phenylurea, melting point: 257-258°C; 3-trifluoromethylphenyl-2-( 5-tetrazolyl)phenylthiourea, melting point > 200°C (decomposition); 3-trifluoromethylphenyl-4-phenyl-2-(5-tetrazolyl)phenylurea, melting point: 260°C ; 4-trifluoromethylphenyl-2-(5-tetrazolyl)phenylurea, melting point: 240°C (decomposition); 3-chlorophenyl-2-(5-tetrazolyl)phenylurea, Melting point: 243°C (decomposition); Phenyl-2-(5-tetrazolyl)phe...

Embodiment 2

[0085] 5-(2-Aminophenyl)tetrazole

[0086] 2-Aminobenzonitrile (9.44g, 80mmol), sodium azide (6.24g, 0.1mol), ammonium chloride (5.12g, 0.1mol) and dimethylformamide (50ml) were mixed and heated at 120°C Heat overnight. The solvent was evaporated and the residue was dissolved in water. The crude product was isolated by filtration and recrystallized from water to give 8.4 g of pure product. Can also be obtained in a similar way: 5-(2-amino-5-bromophenyl) tetrazole 5-(4-amino-3-biphenyl) tetrazole 5-(2-amino-5-nitrobenzene Base) tetrazole 5-(2-amino-4-(2-naphthyl) phenyl) tetrazole 5-(2-amino-4-(3-pyridyl) phenyl) tetrazole 5-(2-amino -4-(1-naphthyl)phenyl)tetrazole 5-(2-amino-4-(4-trifluoromethylphenyl)phenyl)tetrazole 5-(2-amino-4-(3- Furyl)phenyl)tetrazole 5-(2-amino-4-(3-thienyl)phenyl)tetrazole 5-(2-amino-4-(4-trifluoromethylphenyl)phenyl) Tetrazole 5-(2-amino-4-(3-nitrophenyl) phenyl) tetrazole 5-(2-amino-4-(4-ethoxycarbonylphenyl) phenyl) tetrazole 5-( 2...

Embodiment 3

[0088] 2-Amino-4-phenylbenzonitrile

[0089] 2-Amino-5-bromobenzonitrile (1.0g, 5mmol), phenylboronic acid (0.92g, 7.5mmol), tetrakis(triphenylphosphine)palladium (50mg) and potassium carbonate (3.5g, 25mol ) was heated at reflux in dimethoxyethane / water 2:1 (60ml) for 4 hours. After cooling to room temperature, the reaction was diluted with water and extracted with ethyl acetate. The organic phase was dried and the solvent was evaporated. Trituration with petroleum ether afforded 0.89 g of the desired compound. Can be obtained in a similar manner: 2-amino-4-(2-naphthyl)benzonitrile 2-amino-4-(3-pyridyl)benzonitrile 2-amino-4-(1-naphthyl)benzonitrile 2 -Amino-4-(4-trifluoromethylphenyl)benzonitrile 2-amino-4-(3-furyl)benzonitrile 2-amino-4-(3-thienyl)benzonitrile 2-amino-4 -(3-nitrophenyl)benzonitrile 2-amino-4-(4-ethoxycarbonylphenyl)benzonitrile 2-amino-4-(4-diethylaminocarbonylphenyl)benzonitrile 2-amino- 4-(4-Aminocarbonylphenyl)benzonitrile 1-(3-nitro...

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Abstract

A compound having formula (I) or a pharmaceutically acceptable salt thereof wherein one of R<1>, R<2> and R<3> is a cyclic or heterocyclic acidic functional group having a pKa value below 8 or a group which is convertible in vivo to such a group; R<4>, R<5> and the two other substitutents R<1>, R<2> and R<3> are each independently selected from hydrogen; alkyl; alkoxy; hydroxy; halogen; trifluoromethyl; cyano; nitro; amino; alkylamino; -COOR<7>; -NHSO2-alkyl; -SO2N(R<7>)2; -SO2OR<7>; -CO-R<7>; aryl, biphenyl, phenylamino, phenoxy or heteroaryl, wherein the aryl, biphenyl, phenylamino, phenoxy or heteroaryl group may be substituted one or more times with substituents selected from alkyl, hydroxy, alkoxy, halogen, trifluoromethyl, cyano, nitro, amino and alkylamino; aryl and heteroaryl, or R<3> and R<4> or R<4> and R<5> together form a cyclic structure and the other substituents R<1>, R<2>, R<3>, R<4> and R<5> is as defined above; and R<7> is hydrogen, alkyl, amino or phenyl; Y is -CO-, -CS-, -SO2-, or -C(=N-R<8>)-, wherein R<8> is hydrogen, alkyl, or cyano; X is -NH-, -CH2-NH-, or -SO2-NH-; Z is NR<6>, O, -CH=CH-, -N=CH-, or -CH=N-; R<6> is hydrogen, or alkyl; R<11>, R<12>, R<13>, R<14> and R<15> are each independently selected from hydrogen; alkyl; alkoxy; hydroxy; halogen; trifluoromethyl; cyano; nitro; amino; alkylamino; -COOR<7>; -NHSO2-alkyl; -SO2N(R<7>)2; -SO2OR<7>; -CO-R<7>.

Description

[0001] The present invention relates to novel substituted phenyl derivatives which are potent chloride channel blockers and are thus suitable for the treatment of sickle cell anemia, ischemia and tumor secondary It is also suitable for reducing intraocular pressure in the treatment of diseases such as glaucoma. Background technique [0002] Chloride channels have a variety of specific cellular functions. Thus, chloride channels contribute to the normal function of skeletal and smooth muscle cells. Chloride channel blockers are known to be effective in the treatment of cerebral edema secondary to ischemia or tumors, diarrhea, hypertension (diuretic), osteoporosis, and are suitable for reducing intraocular pressure. The compounds according to the invention are also suitable for the treatment of allergic disorders and inflammation, and for promoting the healing of wounds. [0003] The use of chloride channel blockers in the treatment of sickle cell anem...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12A61K31/41A61K31/4196A61K31/4245A61K31/4427A61P1/04A61P1/12A61P3/00A61P7/06A61P9/00A61P9/12A61P19/10A61P27/06A61P29/00A61P37/08C07C233/55C07C271/58C07C275/40C07C275/42C07C309/51C07C311/08C07C311/21C07C311/47C07C311/60C07C335/22C07D249/10C07D257/04C07D271/10C07D401/10C07D405/10C07D409/10
CPCC07C311/47C07C271/58C07C233/55C07C335/22C07C311/60C07C309/51C07C275/42C07C311/21C07C311/08C07C275/40A61P1/04A61P1/12A61P19/10A61P27/06A61P29/00A61P3/00A61P37/08A61P43/00A61P7/06A61P9/00A61P9/12
Inventor P·克里斯托菲森O·比德森
Owner NEUROSEARCH AS
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