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Methods and compositions for delivery of catecholic butanes for treatment of tumors

A technology of catechol butane and composition, which is applied in the field of release and composition of catechol butane for treating tumors, and can solve problems such as not being an ideal treatment method and uncomfortable injection points

Inactive Publication Date: 2006-10-18
THE JOHN HOPKINS UNIV SCHOOL OF MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Also, intratumoral injection or direct injection of the drug into the infected tissue may not be an ideal treatment
The patient's injection site is sometimes uncomfortable

Method used

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  • Methods and compositions for delivery of catecholic butanes for treatment of tumors
  • Methods and compositions for delivery of catecholic butanes for treatment of tumors
  • Methods and compositions for delivery of catecholic butanes for treatment of tumors

Examples

Experimental program
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preparation example Construction

[0153] Preparation of Catechol Butane

[0154] The catechol butane of the present invention can be prepared by any conventional method. For example, these compounds can be prepared as described in US Patent 5,008,294.

[0155] Preparation of NDGA compounds

[0156] NDGA compounds and formulations thereof can be prepared by any method conventional in the art. For example, NDGA compounds may be disclosed by U.S. Patent 5,008,294 (Jordan et al., issued April 16, 1991); U.S. Patent 6,291,524 (Huang et al., issued September 18, 2001); Hwu, J.R. et al. (1998); or Prepared as described by McDonald, R.W. et al. (2001).

[0157] In one embodiment of the invention, an NDGA compound, 4-O-methyl NDGA, also known as meso-1,4-bis(3,4-dimethoxyphenyl)-2, 3-Dimethylbutane (meso-1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane), or M 4 N was prepared by preparing a solution containing NDGA and potassium hydroxide in methanol in a reaction vial. Dimethyl sulfate was then added to the react...

Embodiment 1

[0245] Example 1. Preparation of a preliminary batch of 4-O-methyl-NDGA

[0246] 4-O-methyl NDGA, referred to herein as M 4 N, synthesized by reacting NDGA with an excess of dimethyl sulfate in the presence of a base such as potassium hydroxide. The product was isolated by adding water to precipitate the product. The reaction product was passed through a basic alumina plug to remove trace phenolic impurities, mainly different species of 2-O-methyl and 3-O-methyl substituted NDGA. As the solution of the reaction mixture passed through the alumina plug, the solvent was removed on a rotary evaporator to form a solid product. The product was triturated with 2-propanol, filtered and dried in a vacuum oven to yield crude 4-O-methyl NDGA. Crystallization from 2-propanol will give 4-O-methyl NDGA purity greater than or equal to 99.66%.

[0247] Step 1: Synthesis of crude preparation of 4-O-methyl-NDGA

[0248] Set up a 22 L flask equipped with a mechanical stirrer, condenser and ...

Embodiment 2

[0253] Embodiment 2 Preparation of PLGA nanoparticles containing NDGA compounds

[0254] The NDGA compound can be prepared as a nanoparticle preparation by conventional methods in the art. For example, the nanoparticles can be prepared as described by Lamprecht, A. et al. (2001a) and as follows.

[0255] The biodegradable polymer poly(DL-lactide-co-glycolide) 50 / 50 (PLGA) (molecular weight (mol.wt.) 5,000 or 20,000) can be purchased from Waco (Osaka, Japan). Approximately 40 mg of an NDGA compound can be dissolved in 4 ml of dichloropropane containing 250 mg of the polymer poly(DL-lactide-glycolide) 50 / 50 (molecular weight 5,000 or 20,000). This solution can then be poured into 8 ml of aqueous polyvinyl alcohol (Polyvinyl Alcohol) solution (1%) and treated with a sonicator (ultrasonifier) ​​(ultrasonifier UR-200P; Tomy Seiko (Tomy Seiko) Co., Ltd., Tokyo, Japan) Homogenize for 3 min in an ice bath. Ethylene dichloride can be evaporated under reduced pressure and the polymer...

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Abstract

The present invention provides kits, methods and compositions for treating tumors and other proliferative diseases such as tumors. The compositions herein contain a formulation of substantially pure at least one catechol butane, including, for example, the NDGA compound in a pharmaceutically acceptable carrier or excipient. The catecholbutane, such as NDGA or a derivative thereof, is administered to one or more subjects in need of treatment by a route other than direct injection into or topical application to the diseased tissue. Figure 1 shows the systemic distribution of M4N to different organs 3 hours after intravenous and intraperitoneal injection.

Description

[0001] Cross References to Related Applications [0002] This application claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application 60 / 472,188, entitled "Methods and Compositions for the Release of NDGA Derivatives for the Treatment of Cancer," filed May 20, 2003; Priority is claimed to U.S. Provisional Application 60 / 472,299, filed May 20, 2003, entitled "Methods and Compositions for the Release of NDGA for the Treatment of Cancer"; Priority is claimed to U.S. Provisional Application 60 / 472,008, filed May 20, 2003, entitled "Compositions and Methods for Treating Neurodegenerative Diseases, Disorders, and Conditions" NDGA Compositions and Methods" claiming priority to U.S. Provisional Application 60 / 472,144; U.S. Provisional Application 60 / 472, filed May 20, 2003, entitled "NDGA Derivatives for the Treatment of Hypertension, Diabetes, and Obesity" 472,282 claims priority, the contents of all of which are incorporated herein by reference in their entirety. techni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/05
Inventor 茹智·C·黄理查德·帕克张智川梁钰川大卫·莫尔德伊莱恩·林乔纳森·赫勒尼尔·弗雷泽
Owner THE JOHN HOPKINS UNIV SCHOOL OF MEDICINE
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