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Details for Patent: 5,714,490

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Details for Patent: 5,714,490

Title: Tetrahydrofuran antifungals
Abstract:A compound represented by the formula I ##STR1## wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl; R.sub.1 is a straight or branched chain (C.sub.3 to C.sub.8) alkyl group substituted by one or two amino acid ester groups (e.g., an amino acid ester group convertible in vivo into a hydroxy group) thereof or a pharmaceutically acceptable salt thereof and pharmaceutical compositions thereof useful for treating and/or preventing fungal infections are disclosed.
Inventor(s): Saksena; Anil K. (Upper Montclair, NJ), Girijavallabhan; Viyyoor M. (Parsippany, NJ), Lovey; Raymond G. (West Caldwell, NJ), Pike; Russell E. (Stanhope, NJ), Wang; Haiyan (Dayton, NJ), Liu; Yi-Tsung (Morris Township, NJ), Ganguly; Ashit K. (Upper Montclair, NJ), Bennett; Frank (Piscataway, NJ)
Assignee: Schering Corporation (Kenilworth, NJ)
Filing Date:Jun 02, 1995
Application Number:08/458,543
Claims:1. A compound represented by the formula I ##STR107## wherein X is independently both F or both Cl or one X is independently F and the other is independently Cl;

R.sub.1 is a straight or branched chain (C.sub.4 -C.sub.5) alkyl group substituted by an amino acid ester group convertible in vivo into a hydroxy moiety

or a pharmaceutically acceptable salt thereof.

2. A compound of claim 1 wherein R.sub.1 is a C.sub.4 - or C.sub.5 -alkyl group selected from:

--C.sup.* H(C.sub.2 H.sub.5)C.sup.* H(R.sub.4)CH.sub.3, --C.sup.* H(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 R.sub.4,

--(CH.sub.2).sub.2 --C.sup.* H(R.sub.4)C.sub.2 H.sub.5, --C.sup.* H(CH.sub.3)CH(R.sub.4)CH.sub.3,

--C.sup.* H(C.sub.2 H.sub.5)CH.sub.2 R.sub.4 and --C.sup.* H(CH.sub.3)CH.sub.2 CH.sub.2 R.sub.4

wherein R.sub.4 is amino acid ester group convertible in vivo into OH and the carbons with the asterisk (*) have the R or S absolute configuration or a pharmaceutically acceptable salt thereof.

3. A compound represented by formula III ##STR108## wherein R.sub.5 is ##STR109## wherein R.sub.11 is an amino acid ester group convertible in vivo into a hydroxy group, or a pharmaceutically acceptible salt thereof.

4. A compound represented by the formula IV ##STR110## wherein R.sub.9 =--C.sup.* H(C.sub.2 H.sub.5)CH(R.sub.6)CH.sub.3 or --C.sup.* H(CH.sub.3)CH(R.sub.6)CH.sub.3

wherein R.sub.6 is an amino acid ester group convertible in vivo into OH or a pharmaceutically acceptable salt thereof.

5. A compound of claim 4 wherein R.sub.6 is a dipeptide ester.

6. A compound of claim 5 wherein the dipeptide ester is the ester of glycylglycine, i.e. --OCOCH.sub.2 NHCOCH.sub.2 NH.sub.2.

7. A compound of claim 4 wherein R.sub.6 is the ester of L-glycine, i.e. --OCOCH.sub.2 NH.sub.2.

8. A compound of claim 4 wherein R.sub.6 is the ester of 2,4-diaminobutanoic acid, i.e., --COCH(NH.sub.2)CH.sub.2 CH.sub.2 NH.sub.2.

9. The compound of claim 4 wherein R.sub.6 is an ester of leucine., i.e., --OCOCH(NH.sub.2)CH.sub.2 CH(CH.sub.3).sub.2.

10. The compound of claim 4 wherein R.sub.6 is an ester of isoleucine, i.e., --OCOCH(NH.sub.2)(CH.sub.2)CHC.sub.2 H.sub.5.

11. The compound of claim 4 wherein R.sub.6 is an ester of valine, i.e., --OCOCH(NH.sub.2)CH(CH.sub.3).sub.2.

12. The compound of claim 4 wherein R.sub.6 is an ester of ##STR111##

13. A pharmaceutical composition for treating or preventing fungal infection comprising an antifungally effective amount of a compound of claim 1 together with a pharmaceutically acceptable carrier therefor.

14. A method of treating and/or preventing fungal infections in a mammal afflicted with same which comprises administering an antifungally effective amount of a compound of claim 1 sufficient for such treating or preventing.

15. The pharmaceutical composition of claim 13 wherein the mode of administration is oral or parenteral.

16. A compound represented by the formula ##STR112## wherein R.sub.11 is an amino ester group convertible in vivo into a hydroxy group;

or a pharmaceutically acceptable salt thereof.

17. A compound of claim 16 wherein R.sub.11 is --OCOCH.sub.2 NH.sub.2 or a pharmaceutically acceptable salt thereof.

18. A compound of claim 16 wherein R.sub.11 is a natural (L) .alpha.-amino acid ester or a pharmaceutically acceptable salt thereof.

19. A pharmaceutical composition for treating or preventing a fungal infection comprising an antifungally effective amount of the compound of claim 16 together with a pharmceutically acceptable carrier therefor.

20. A method of treating and/or preventing a fungal infection in a mammal afflicted with same which comprises administering an antifungally effective amount of the compound of claim 16 sufficient for such treating or preventing.
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