Drug therapy for celiac sprue

a celiac sprue and drug therapy technology, applied in the field of celiac sprue drug therapy, can solve the problems of no good treatment for the disease, few patients respond poorly or not at all, and erroneous diagnosis of eczema

Inactive Publication Date: 2008-02-21
THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Itching and burning are severe, and scratching often obscures the primary lesions with eczematization of nearby skin, leading to an erroneous diagnosis of eczema.
At the present time, there is no good therapy for the disease, except to avoid completely all foods containing gluten.
A few patients respond poorly or not at all to gluten withdrawal, either because the diagnosis is incorrect or because the disease is refractory.

Method used

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  • Drug therapy for celiac sprue
  • Drug therapy for celiac sprue
  • Drug therapy for celiac sprue

Examples

Experimental program
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Effect test

example 1

Synthesis of dihydroxyisoxazole Containing tTGase INHIBITORS

[0065] Synthesis of {(S)-1-[(3-Bromo-4,5-dihydro-isoxazol-5-ylmethyl)-carbamoyl]-2-phenyl-ethyl}-carbamic acid benzyl ester (n=0, X═NH, R1=BnO, R2═(S)-Bn, R3═Br) (49). N-Cbz-L-Phe (0.30 g, 1.0 mmol) and HOBt (0.15 g, 1.1 eq) were dissolved in 2 mL DMF. 3-Bromo-5-aminomethyl-4,5-dihydroisoazole (0.18 g, 1.0 eq), prepared following a reported procedure (Rohloff et al. (1992) Tetrahedron Lett. 33(22):3113-3116), was added to the solution cooled in an ice bath followed by EDCI (0.23 g, 1.2 eq). The ice bath was removed and the stirring was continued overnight. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 solution and brine. The organic layer was dried over MgSO4 and filtered. The solvent was removed by evaporation and the residue was purified by SiO2 chromatography to give the title compound as a white solid (0.24 g, 52%).

[0066]1H NMR (CDCl3, 200 MHz): δ=7.34-7.26 (m, 8H), 7.17 (d, 2H, J=7.6 Hz), 6....

example 2

Synthesis of Dioxoindole Containing tTGase Inhibitors

[0111] Synthesis of 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamide. 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonyl chloride (0.10 g, 0.41 mmol), prepared by the reaction of the sodium salt of 5-isatinsulfonic acid with POCl3, was dissolved in 5 mL THF. This solution was cooled in an ice bath and DIEA (0.14 mL, 2.0 eq) was added slowly, followed by n-propylamine (35 uL, 1.0 eq). Stirring was continued for 40 min and the solution was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by SiO2 chromatography to give the title compound (65 mg, 60%).

[0112]1H NMR (CD3CN, 400 MHz): δ=9.17 (br, 1H), 8.02 (d, 1H, J=8.0 Hz), 7.93 (s, 1H), 7.13 (d, 1H, J=8.0 Hz), 5.62-5.58 (m, 1H), 2.85-2.80 (m, 2H), 1.48-1.42 (m, 2H), 0.85 (t, 3H, J=7.2 Hz)

[0113] MS (ESI): m / z=−267.1 [M−H]−

[0114] Synthesis of 2,3-Dioxo-2,3-dihydro-1H-indole...

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Abstract

Administering an effective dose of a tTGase inhibitor to a Celiac or dermatitis herpetiformis patient reduces the toxic effects of toxic gluten oligopeptides, thereby attenuating or eliminating the damaging effects of gluten.

Description

[0001] This application is a continuation of U.S. application Ser. No. 10 / 716,846, which is a continuation in part of International Application US03 / 15343, filed May 14, 2003; which claims priority to U.S. Provisional Application 60 / 380,761 filed May 14, 2002; to U.S. Provisional Application 60 / 392,782 filed Jun. 28, 2002; and to U.S. Provisional application No. 60 / 422,933, filed Oct. 31, 2002, and to U.S. Provisional Application 60 / 428,033, filed Nov. 20, 2002, each of which are herein specifically incorporated by reference.BACKGROUND OF THE INVENTION [0002] In 1953, it was first recognized that ingestion of gluten, a common dietary protein present in wheat, barley and rye causes a disease called Celiac Sprue in sensitive individuals. Gluten is a complex mixture of glutamine- and proline-rich glutenin and prolamine molecules and is thought to be responsible for induction of Celiac Sprue. Ingestion of such proteins by sensitive individuals produces flattening of the normally luxurio...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K38/48A61K31/404A61P1/00C07D261/04A61P17/00A61K31/42A61K38/00C07D413/12
CPCA61K31/42C07D413/12C07D261/04A61K38/005A61P1/00A61P1/12A61P1/14A61P3/00A61P7/06A61P17/00A61P17/02A61P17/04A61P25/00A61P25/14A61P25/16A61P25/28A61P29/00A61P35/00A61P37/00A61P37/08A61P43/00
Inventor KHOSLA, CHAITANCHOI, KIHANG
Owner THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIV
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