Leukotriene antagonists for oral squamous cell carcinoma

A squamous cell carcinoma and solvate technology, which is applied in the direction of antineoplastic drugs, medical preparations containing active ingredients, drug combinations, etc., can solve the problem of increasing the chance of residual or metastatic tumor cell growth, adverse effects of patients' natural immunity, etc. question

Inactive Publication Date: 2000-02-23
ELI LILLY & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] There is growing concern that treatments such as surgery, radiation, and chemotherapy can adversely af

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Disodium 3-[2-[3-[(5-ethyl-2-hydroxy[1,1'-biphenyl]yl-4-yl)oxy]propoxy]-1-oxyfluorene]propionate Salt

[0057] A. Preparation of 3,3-diethoxy-2,3-dihydro-1H-benzofuro[3,2-f][1]benzopyran

[0058] A solution of 2-hydroxyloxyfluorene (5.00 g, 27.2 mmol), triethyl orthoacrylate (10.1 g, 54.3 mmol) and pivalic acid (1.39 g, 13.6 mmol) in toluene (100 mL) was refluxed for 18 hours. The mixture was cooled to room temperature, washed once with water, once with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo to give an orange oil. This material was diluted with hexane and stored at -20°C for 18 hours. The resulting crystals were collected by vacuum filtration to give 5.67 g (67%) of the desired title intermediate, mp 64°C; NMR (CDCl 3 )7.96(d, J=7.8Hz, 1H), 7.57(d, J=8.0Hz, 1H), 7.46(t, J=8Hz, 1H), 7.35(m, 2H), 7.06(d, J=8.8 Hz, 1H), 3.82(q, J=7.2Hz, 2H), 3.73(q, J=6.8Hz, 2H), 3.35(t, J=6.9Hz, 2H), 2.29(t, J=7.0Hz, 2H)...

Embodiment 2

[0075] 7-Carboxy-9-oxo-3-[3-(2-ethyl-5-hydroxy-4-phenylphenoxy)propoxy]-9H-xanthene-4-propionic acid disodium salt Hydrate

[0076] 2-Benzyloxy-1-phenyl-5-ethyl-4-(3-chloro-1-propoxy)benzene (749mg, 1.97mmol), 7-carbonylethoxy-3-hydroxyl-9 A mixture of ethyl oxo-9H-xanthene-4-propionate (729 mg, 1.97 mmol), potassium carbonate (1.36 g, 9.85 mmol) and potassium iodide (33 mg, 0.20 mmol) was refluxed for 24 hours. Dimethylsulfoxide (2 mL) was added and heating continued for 24 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed once with water. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a tan solid. This material was dissolved in ethyl acetate (30 mL), and nitrogen gas was bubbled into the solution thus obtained. To this solution was added 10% palladium on carbon (120 mg), and the suspension thus obtained was hydrogenated at 1 atmosphere. The filtered solution was concentrated i...

Embodiment 3

[0081] 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]phenoxy]benzoic acid sodium salt

[0082] A. 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-(phenylmethoxy)phenoxy]propoxy]phenoxy Base] Preparation of methyl benzoate.

[0083] 2-Benzyloxy-1-(4-fluorophenyl)-5-ethyl-4-(3-chloro-1-propoxy)benzene (20.0g, 50.2mmol) and sodium iodide (75.3g , 502 mmol) in 2-butanol (200 mL) was refluxed for 6 hours. The mixture was then diluted with ether and washed once with water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give a colorless oil. This material was dissolved in dimethylformamide (100 mL) and washed with methyl 2-(3-hydroxy-2-propylphenoxy)benzoate (14.4 g, 50.2 mmol) and potassium carbonate ( 20.8g, 151mmol) for 24 hours. The mixture was diluted with water and extracted twice with ether. The aqueous layer was separated and back extracted once with ethyl acetate. The combined organic layers were dried ...

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PUM

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Abstract

This invention provides methods for the treatment or inhibition of oral squamous cell carcinoma which comprises administering to a mammal in need thereof an effective amount of a compound having activity as a leukotriene B4 antagonist.

Description

Background of the invention [0001] Squamous cell carcinoma is a common head and neck malignancy. It accounts for at least 75% of head and neck cancers in which patients have a high incidence of immunodeficiency and inflammatory symptoms. Although treatment modalities have improved over the past 40 years, the 5-year survival rate of approximately 30% has not improved during this time. [0002] Oral squamous cell carcinoma is associated with excessive smoking and alcohol abuse, both alone and in combination. Other factors associated with mouth cancer include poor dental hygiene and poorly fitting dentures or broken teeth that cause long-term irritation of the mucous membranes. Occupational hazards include long-term exposure of woodworkers to dust and nickel compounds, the former being associated with nasopharyngeal cancer and the latter increasing the risk of paranasal sinus cancer. [0003] Nasopharyngeal carcinoma is associated with the Epstein-Barr virus (EBV), the causati...

Claims

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Application Information

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IPC IPC(8): A61K31/192A61K31/194A61K31/343A61K31/352A61K31/41A61K31/473A61K31/55A61K31/603C07D219/06A61P25/28C07D221/12C07D223/20C07D311/74
CPCA61K31/192A61K31/41A61K31/194A61K31/352A61K31/343A61P25/28A61P35/00A61K31/495
Inventor J·H·弗莱施W·T·杰克森J·S·肖耶尔
Owner ELI LILLY & CO
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