# US 5,703,079 A · Tetrahydrofuran antifungals

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- Number: US 5,703,079 A
- Document ID: US5703079A
- Status: Granted
- Kind: A
- Application number: 08/460,400
- Filed: 1995-06-02
- Granted: 1997-12-30
- Earliest claimed: 1993-12-21
- Assignees: Schering Corporation
- Inventors: Anil K. Saksena; Viyyoor M. Girijavallabhan; Raymond G. Lovey; Russell E. Pike; Haiyan Wang; Yi-Tsung Liu; Ashit K. Ganguly; Frank Bennett
- Web page: https://patentgrep.com/patent/US5703079A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/10: Antimycotics
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07F 9/65586: {at least one of the hetero rings does not contain nitrogen as ring hetero atom}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## 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 polyetyher ester groups (e.g., a polyether 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.

## Claims

### Claim 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 a hydroxy group or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1 wherein R.sub.1 is a hydroxy-substituted C.sub.4 - or C.sub.5 -alkyl group selected from:
--*CH(C.sub.2 H.sub.5)*CH(R.sub.4)CH.sub.3, --*CH(C.sub.2 H.sub.5)CH.sub.2 CH.sub.2 R.sub.4,
--(CH.sub.2).sub.2 --*CH(R.sub.4)C.sub.2 H.sub.5, --*CH(CH.sub.3)*CH(R.sub.4)CH.sub.3,
--*CH(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 OH and the carbons with the asterisk(*) have the R or S absolute configuration or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R.sub.1 is a C.sub.4 alkyl group substituted by a hydroxy group.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R.sub.1 is a C.sub.5 alkyl group substituted by a hydroxy group.

### Claim 5

A compound represented by formula III ##STR110## wherein R.sub.5 is ##STR111## wherein R.sub.13 is a hydroxy group, or a pharmaceutically acceptable salt thereof.

### Claim 6

A compound represented by the formula IV ##STR112## wherein R.sub.9 =--*CH(C.sub.2 H.sub.5)CH(R.sub.6)CH.sub.3 or --*CH(CH.sub.3)CH(R.sub.6)CH.sub.3
wherein R.sub.6 is OH or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

The pharmaceutical composition of claim 1 wherein the mode of administration is oral or parenteral.