Fatty amine drug conjugates

Inactive Publication Date: 2008-06-26
LUITPOLD PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0108]The conjugated anticancer compounds described herein are less toxic and more effective than the corresponding unconjugated anticancer compounds. Therefore the fatty amine-anticancer compound conjugates can be administered in amounts which are equally toxic but more effec

Problems solved by technology

This is particularly the case for toxic agents such as anticancer agents because achieving therapeutic doses effective for treating the cancer is often limited by the toxic side effects of the anticancer agent on no

Method used

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  • Fatty amine drug conjugates
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  • Fatty amine drug conjugates

Examples

Experimental program
Comparison scheme
Effect test

Example

Example 1

Examples of Paclitaxel Conjugates

[0173]The length of the fatty moiety chain is governed by the synthetic procedure. For example, preparation of the fatty amine from the corresponding fatty acid (with an even number of carbons) generally results in a carbon chain with an odd number of carbons. Alternatively, preparation of the fatty amine from the corresponding fatty alcohol (with an even number of carbons) generally results in a carbon chain with an even number of carbons. The following paclitaxel-fatty amine conjugates with an even number and odd number of carbons in the fatty moiety, respectively, are prepared in accordance with the methods of the invention:

Example

Example 2

Preparation of N-Methyl Fatty Amine Conjugates

[0174]The conjugates may be prepared with N-methyl group at the amino moiety of the fatty amine as shown below:

to prevent internal self-immolative destruction. N-methylated fatty amines may be prepared from fatty acids using the procedures described in the Examples and described generally (in Yamada, F., et al. Heterocycles 1986, 24, 1223 and Somei, M., et al. Heterocycles 1987, 26, 895, both hereby incorporated by reference).

Example

Example 3

Synthesis of a Fatty Amine-Adefovir Conjugate Via a Urea Linkage

[0175]Adefovir (PMEA) was conjugated to a fatty amine using the following procedures:

wherein Y is methyl or ethyl, (PhO)2P(O)N3 is diphenylphosphoryl azide, and TMSBr is bromotrimethylsilane. One skilled in the art will appreciate that the number of carbons in the fatty amine moiety of the conjugate is governed by both the starting material and synthetic method chosen.

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Abstract

The invention provides conjugates of fatty amines and pharmaceutical agents useful in treating cancer, viruses, psychiatric disorders. Compositions, pharmaceutical preparations, and methods of preparations of the fatty amine-pharmaceutical agent conjugates are provided.

Description

RELATED APPLICATIONS[0001]This application is a divisional application of U.S. non-provisional application Ser. No. 10 / 108,255, filed Mar. 25, 2002, currently pending, which claims benefit under 35 U.S.C. § 119(e) of U.S. provisional Patent Application No. 60 / 278,552, filed Mar. 23, 2001, the entire contents of both of which are herein incorporated by reference.FIELD OF THE INVENTION[0002]The invention relates to conjugates of fatty amines and pharmaceutical agents such as anticancer, antiviral, and antipsychotic agents useful, for example, in treating cancer, viruses, and psychiatric disorders, and compositions and formulations thereof. Methods for making and using the conjugates also are provided.BACKGROUND OF THE INVENTION[0003]Improving drug selectivity for target tissue is an established goal in the medical arts. In general, it is desirable to deliver a drug selectively to its target, so that dosage and, consequently, side effects can be reduced. This is particularly the case f...

Claims

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Application Information

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IPC IPC(8): A61K31/337C07C271/06C07D493/22A61P35/00A61K31/27A61K31/131A61K31/26A61K31/351A61K31/453A61K31/475A61K31/506A61K31/52A61K31/5513A61K31/664A61K31/7048A61K31/7068A61P1/00A61P1/10A61P1/16A61P3/06A61P3/10A61P5/14A61P7/00A61P7/02A61P9/00A61P9/04A61P13/12A61P15/08A61P15/18A61P17/06A61P17/16A61P25/18A61P25/28A61P31/12A61P35/02A61P43/00C07C265/06C07C271/12C07C275/20C07D209/48C07D243/38C07D305/14C07D309/14C07D405/04C07D473/16C07D473/24C07D491/22C07D519/04C07F9/645C07F9/6524C07F9/6558C07F9/6561C07H15/252C07H17/04C07H19/06
CPCC07C265/06C07C271/12C07C275/20C07D209/48C07D243/38C07D305/14C07H19/06C07D473/24C07D519/04C07F9/65583C07F9/65616C07H15/252C07D405/04A61P1/00A61P1/10A61P1/16A61P13/12A61P15/08A61P15/18A61P17/06A61P17/16A61P25/18A61P25/28A61P31/12A61P35/00A61P35/02A61P3/06A61P43/00A61P5/14A61P7/00A61P7/02A61P9/00A61P9/04A61P3/10
Inventor SWINDELL, CHARLES S.FEGLEY, GLENN G.
Owner LUITPOLD PHARMA INC
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