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Generated: October 17, 2017

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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 phosphate ester groups (e.g., a phosphate ester 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:08/459,145
Claims:1. A compound represented by the formula I ##STR109## 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 to C.sub.5) alkyl group substituted by an ester or an ether group 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: --H(C.sub.2 H.sub.5)H(R.sub.4)CH.sub.3, --H(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 R.sub.4, --(CH.sub.2).sub.2 H(R.sub.4)C.sub.2 H.sub.5, --H(CH.sub.3)H(R.sub.4)CH.sub.3, --H(C.sub.2 H.sub.5)CH.sub.2 R.sub.4 and --H(CH.sub.3)CH.sub.2 Ch.sub.2 R.sub.4

wherein R.sub.4 is an ester group or an ether group 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 ##STR110## wherein R.sub.5 is ##STR111## wherein R.sub.12 is an ester group or an ether group or a pharmaceutically acceptable salt thereof.

4. A compound represented by the formula IV ##STR112## wherein R.sub.9 =--H(C.sub.2 H.sub.5)CH(R.sub.6)CH.sub.3 or --H(CH.sub.3)CH(R.sub.6)CH.sub.3 wherein R.sub.6 is an ester group or an ether group.

5. A compound of claim 4 which is ##STR113## or a pharmaceutically acceptable salt thereof.

6. A compound of claim 1 wherein the ester group is a polyether ester, a phosphate ester, a heterocyclic ester, an alkanoate ester, an alkenoate ester, an amino acid acid ester, an acid ester, or a sulfate ester.

7. A compound of claim 1 wherein R.sub.1 is a straight or branched chain (C.sub.4 -C.sub.5) alkyl group substituted by an ester group.

8. A compound of claim 4 wherein the ester group is a polyether ester, a phosphate ester, a heterocyclic ester, an alkanoate ester, an alkenoate ester, an amino acid acid ester, an acid ester, or a sulfate ester.

9. 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.

10. 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.

11. The pharmaceutical composition of claim 9 wherein the mode of administration is oral or parenteral.
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