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[0123] The conjugated anticancer compounds described herein are less toxic and more effective than the corresponding unconjugated anticancer compounds. Therefore the fatty alcohol-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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example 1
Synthesis of linoleyl para-nitrophenyl carbonate
[0187] To a vigorously stirring room temperature solution containing linoleyl alcohol (1.07 g, 4.05 mmol, 1.0 equiv), CH2Cl2 (15 mL), and Et3N (845.9 μL, 6.07 mmol, 1.5 equiv) under an argon atmosphere, was added dropwise a solution containing para-nitrophenyl chloroformate (815.6 mg, 4.05 mmol, 1.0 equiv) and CH2Cl2 (5 mL). After one hour, the reaction appeared to be complete, as monitored by thin layer chromatography. To insure completeness, approximately 50 mg of para-nitrophenyl chloroformate was added, and the reaction allowed to stir an additional 0.5 hr. At this time, the reaction was concentrated to approximately ½ volume, and the supernatant was decanted directly to two (2) Biotage 3.0 gram silica gel samplets (Biotage, Inc., Charlottesville, Va.). The carbonate product was purified on the Biotage Quad 4 Purification System using two 25M 40 gram silica cartridges, eluting with 1:9 EtOAc / hexanes. The product carbonate was isol...
example 2
Synthesis of 2′-linoleyl carbonate paclitaxel
[0188] To a vigorously stirring room temperature solution containing paclitaxel (500 mg, 0.59 mmol, 1.0 equiv), CH2Cl2 (3 mL), and 4-dimethylaminopyridine (78.7 mg, 0.64 mmol, 1.1 equiv) under an argon atmosphere, was added dropwise a solution containing linoleyl, para-nitrophenyl carbonate (as prepared in Example 1) (303.2 mg, 0.70 mmol, 1.2 equiv) and CH2Cl2 (2.0 mL). After stirring 80 minutes, the reaction was shown to be complete by thin layer chromatography. At this time, the reaction solution was added directly to a Biotage 3.0 gram silica samplet. 2′-linoleyl carbonate paclitaxel was purified on the Biotage Quad 4 Purification System using a 25M 40 gram silica cartridges, eluting the first 20 fractions using 1:3 EtOAc / hexanes, and the final 20 fractions using 1:1 EtOAc / hexanes. Yield: 651.5 mg (97.1%); clear glassy white solid.
[0189] Optionally, 2′-linoleyl carbonate paclitaxel may be recrystallized from ethanol at a concentratio...
example 3
Synthesis of a Fatty Alcohol-Adefovir Conjugate Via a Carbamate Linkage
[0191] Adefovir (PMEA) is conjugated to a fatty alcohol using the following procedure:
[0192] wherein Z is methyl or ethyl and ROC(O)T is:
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Abstract
The invention provides conjugates of fatty alcohols and pharmaceutical agents useful in treating cancer, viruses, psychiatric disorders. Compositions, pharmaceutical preparations, and methods of preparation of the fatty alcohols-pharmaceutical agent conjugates are provided.
Description
RELATED APPLICATIONS [0001] This application is a divisional application of U.S. non-provisional application Ser. No. 10 / 107,537, filed Mar. 25, 2002, currently pending, which claims benefit under 35 U.S.C. §119(e) of U.S. provisional Patent Application No. 60 / 278,457, 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 alcohols 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 th...
Claims
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