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Halogenated phenols for diagnostics, antioxidant protection and drug delivery

a technology of antioxidant protection and phenols, applied in the direction of drug compositions, biological material analysis, biological testing, etc., can solve problems such as aging and diseas

Inactive Publication Date: 2013-01-17
IPE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to a method for creating compounds that can be linked to a halogenated phenol ring, which can be used for targeted release and delivery at high FROS sites in the body. The method involves modifying existing drug compounds by adding a halogenated phenol ring to their structure. The invention covers a wide range of drug compounds that can be modified, including alkylating agents, cyclophosphamide, ifosfamide, and nitrogen mustards. The method can also involve cleavage of a ether, thioether, or nitrogen linkage to release the active compound. The resulting compounds can have various hydroxyl, keto, carboxyl, sulfhydryl, amino, or alcohol groups attached to the halogenated phenol ring.

Problems solved by technology

These reactive FROS can also be detrimental to one's health and cause damage to cells and tissues, including genetic mutations, which may ultimately lead to aging and disease.

Method used

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  • Halogenated phenols for diagnostics, antioxidant protection and drug delivery
  • Halogenated phenols for diagnostics, antioxidant protection and drug delivery
  • Halogenated phenols for diagnostics, antioxidant protection and drug delivery

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 1-Acetyl-4-Iodo-Indoxyl

[0262]N-Acetyl-3-Iodo-2-Methyl Aniline.

[0263]Charge a 5 L, 3 neck flask equipped with a mantle, stirrer, condenser, with 708 grams (5M) 3-Iodo-2-Methyl Aniline, followed by 700 ml glacial acetic acid. Add in a stream of 520 grams (5.1M) acetic anhydride and allow the solution to come to a gentle reflux for an hour. The solution is allowed to cool and poured in a stream in a large container of 8 L ice water. The product will crystallize immediately and is filtered and squeezed under vacuum and air-dried. Yield was 900 grams (Theoretical yield=918 g).

[0264]N-Acetyl-6-Iodo Anthranilic Acid.

[0265]Charge a 22 L flask equipped with a stirrer, thermometer, condenser and heating mantle with 616 grams Magnesium Sulphate (heptahydrate) followed by 10 L water, and 800 grams N-Acetyl-3-Iodo-2-Methyl-Aniline. The mixture is stirred and heated to 85° C., over about an hour, and heat is stopped. Potassium Permanganate (1200 grams, 8 mol) is added in portions ove...

example 1a

Synthesis of 1-Acetyl-4,5-Diiodo-Indoxyl

[0274]N-(3-Iodo-2-Carboxy-Phenyl) Glycine—Potassium Salt of Example 1 was iodinated in the 4-position by suspension (35.7 grams, 0.1 mol) in 150 ml 1.0 N HCl and cooled to about 20° C. A second solution of 100 ml 1.0 N HCl containing ICl (20 grams, 0.125 mol) was added to the suspension with stirring and reacted for 6 hours at about 20 C. The settled product was collected by filtration and re-crystallized from ethanol / water to yield 28.2 graam (84%), m.p. 182-186 C. The Diiodo indoxyl product is produced in the subsequent steps described in Example 1, starting with ring closure and acetylation in acetic anhydride.

example 2

Synthesis of 1-Acetyl-5-Br-4-Cl-Indoxyl

[0275]1-Acetyl-5-Br-4-Cl-Indoxyl was synthesized according to the methods described in Example 1 above for 5-Iodo-Indoxyl, by utilizing 2-Methyl-3-Chloro-Aniline as the starting material and including a bromination step. Specifically, the resulting N-(3-Chloro-2-Carboxy-Phenyl) Glycine (267.6 grams, 1.0 mol) is brominated by mixing with 550 cc glacial acetic acid, followed by addition of 52 cc of liquid Bromine to the vigorously stirred suspension. Bromination is exothermic and results in complete solution followed by precipitation of the product during the last 10 cc of Bromine addition. The reaction was diluted with 2 L of ice water and the brominated product was isolated by filtration and air dried to yield about 240 grams. Melting Point (m.p.) 176-178 C. The remaining procedures described in Example 1 result in the desired 1-Acetyl-5-Br-4-Cl-Indoxyl.

[0276]Other syntheses of ring substituted indoxyl and indigo compounds are described, for ex...

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Abstract

The present invention provides compositions and methods of their administration for the protection of cells and tissues from damage caused by FROS in the body of an individual. Compositions comprising halogenated phenol compounds are provided that scavenge or consume FROS in the body. These FROS scavenging compounds may not only protect cells and tissues from damage, but also treat disease and / or alleviate the symptoms of disease associated with high FROS levels. Sunscreen compositions comprising FROS-scavenging compounds of the present invention are further provided to reduce the damaging effects of sunlight on the skin of an individual.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of priority to U.S. Provisional Patent Application No. 61 / 507,670, entitled “Halogenated Phenol Ethers for Diagnostics and Drug Delivery,” filed on Jul. 14, 2011, the entire contents and disclosure of which are incorporated herein by reference.BACKGROUND[0002]1. Field of the Invention[0003]The present invention relates generally to compositions and methods for scavenging free radicals and / or oxidative species in the body of an individual to protect cells and tissues from damage that may lead to disease.[0004]2. Related Art[0005]The presence of elevated levels of free radicals and / or oxidative species (FROS) in the body of an individual may be associated with abnormal conditions or physiology that may be associated with injury, inflammation and / or disease. These reactive FROS can also be detrimental to one's health and cause damage to cells and tissues, including genetic mutations, which may ultimately l...

Claims

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Application Information

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IPC IPC(8): C07C43/257A61P31/00A61K8/34A61P29/00A61K31/09A61Q17/04
CPCC07C43/295Y10T436/145555C07C323/52C07C229/36C07C233/25C07D475/08C07D489/02C07D499/897C07D209/36A61K49/006A61K49/0438A61K47/48023A61K51/0446G01N33/52C07J1/0022C07J5/0053C07C217/60A61P29/00A61P31/00A61P35/00A61P35/04
Inventor LATHAM, KEITH R.
Owner IPE