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Details for Patent: 5,710,154

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Details for Patent: 5,710,154

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 groups convertible in vivo into hydroxy moieties, (e.g., a polyether ester, amino acid ester or phosphate ester) 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:08/459,225
Claims:1. A compound represented by the formula I ##STR106## 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 a 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*H(C.sub.2 H.sub.5)C*H(R.sub.4)CH.sub.3, --C*H(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 R.sub.4, --(CH.sub.2).sub.2 --C*H(R.sub.4)C.sub.2 H.sub.5, --C*H(CH.sub.3)CH(R.sub.4)CH.sub.3, --C*H(C.sub.2 H.sub.5)CH.sub.2 R.sub.4 and --CH(CH.sub.3)CH.sub.2 CH.sub.2 R.sub.4

wherein R.sub.4 is a 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 ##STR107## wherein R.sub.5 is ##STR108## wherein R.sub.10 is a group convertible in vivo into OH or a pharmaceutically acceptable salt thereof.

4. A compound represented by the formula IV ##STR109## wherein R.sub.9 =--C*H(C.sub.2 H.sub.5)CH(R.sub.6)CH.sub.3 or --C*H(CH.sub.3)CH(R.sub.6)CH.sub.3

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

5. 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.

6. 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.

7. The pharmaceutical composition of claim 5 wherein the mode of administration is oral or parenteral.

8. A compound of claim I wherein the ester group convertible in vivo into a hydroxy moiety is a polyether ester represented by the formula ##STR110## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, s is an integer from 1 to 6, t is an integer from 1 to 6, and R.sub.8 is R.sub.7 or --CHR.sub.7).sub.s --CO.sub.2 R.sub.7.

9. A compound of claim 11 wherein the ester group convertible in vivo into OH is a phosphate ester represented by the formula ##STR111## wherein z is 0 or 1, R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, f an n are independently an integer from 0 to 6, m is zero or 1 and W is H, CH.sub.2 Ar or ##STR112## and Ar is phenyl, phenyl substituted by halo, nitro, cyano or trihalomethyl.

10. A compound of claim 1 wherein the group convertible in vivo into a hydroxy moiety is a heterocyclic ester represented by the formula ##STR113## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H; w is an integer of from 1 to 5; q and q' are independently 1 to 4 and Y is CHR.sub.7 --O--, NH, NR.sub.7, S, SO or SO.sub.2.

11. A compound of claim 1 wherein the ester group convertible in vivo into hydroxy moiety is an .alpha.-amino acid ester.

12. A compound of claim 3 wherein R.sub.10 the group convertible in vivo into a hydroxy moiety is a polyether ester, a phosphate ester, a sulfate ester, a heterocyclic ester an alkanoate ester, an alkenoate ester, an amino acid ester or an acid ester.

13. A compound of claim 3 wherein R.sub.10, the group convertible in vivo into a hydroxy moiety is a polyether ester represented by the formula ##STR114## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, s is an integer from 1 to 6, t is an integer from 1 to 6, and R.sub.8 is R.sub.7 or --CHR.sub.7).sub.s --CO.sub.2 R.sub.7.

14. A compound of claim 3 wherein the ester group convertible in vivo into OH is a phosphate ester represented by the formula ##STR115## wherein z is 0 or 1, R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, f and n are independently an integer from 0 to 6, m is zero or 1 and W is H, CH.sub.2 Ar or ##STR116## and Ar is phenyl, phenyl substituted by halo, nitro, cyano or trihalomethyl.

15. A compound of claim 3 wherein R.sub.10, the group convertible in vivo into a hydroxy moiety is a heterocyclic ester represented by the formula ##STR117## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H; w is an integer of from 1 to 5; q and q' are independently 1 to 4 and Y is CHR.sub.7,--O--, NH, NR.sub.7, S, SO or SO.sub.2.

16. A compound of claim 3 wherein R.sub.10, the ester group convertible in vivo into a hydroxy moiety is an .alpha.-amino acid ester.

17. A compound of claim 4 wherein R.sub.6, the group convertible in vivo into OH is a polyether ester represented by the formula ##STR118## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, s is an integer from 1 to 6, t is an integer from 1 to 6, and R.sub.8 is R.sub.7 or --CHR.sub.7).sub.s --CO.sub.2 R.sub.7.

18. A compound of claim 4 wherein the ester group convertible in vivo into OH is a phosphate ester represented by the formula ##STR119## wherein z is 0 or 1, R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H, f and n are independently an integer from 0 to 6, m is zero or 1 and W is H, CH.sub.2 Ar or ##STR120## and Ar is phenyl, phenyl substituted by halo, nitro, cyano or trihalomethyl.

19. A compound of claim 4 wherein R.sub.6, the group convertible in vivo into OH is a heterocyclic ester represented by the formula ##STR121## wherein R.sub.7 is a (C.sub.1 -C.sub.6) straight or branched chain alkyl group or H; W is an integer of from 1 to 5; q and q' are independently 1 to 4 and Y is CHR.sub.7,--O--, NH, NR.sub.7, S, SO or SO.sub.2.

20. A compound of claim 4 wherein R.sub.6, the group convertible in vivo into OH is an .alpha.-amino acid ester.
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