# US 5,346,898 A · Anti-fungal uracil compounds

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- Number: US 5,346,898 A
- Document ID: US5346898A
- Status: Granted
- Kind: A
- Application number: 07/900,712
- Filed: 1992-06-18
- Granted: 1994-09-13
- Earliest claimed: 1992-06-18
- Assignees: Schering Corporation
- Inventors: Alan B. Cooper; Anil K. Saksena; Raymond Lovey; Viyyoor Girijavallabhan; Ashit Ganguly
- Web page: https://patentgrep.com/patent/US5346898A

## CPC

- C07H 19/06: Pyrimidine radicals
- C07H 19/04: Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Compounds of the formula ##STR1## wherein R.sub.3, R.sub.4, J, K, Z, and Het are as set forth herein are described. The compounds of formula I are useful as agents in the treatment of fungal infections.

## Claims

### Claim 1

A compound of the formula: ##STR125## or pharmaceutically acceptable salts thereof, wherein Het is ##STR126## R is H, COOH; C.sub.1 -C.sub.12 alkyl; CHO; CN; CH.sub.2 OH; or CONH.sub.2 ;
wherein R.sub.3 is ##STR127## wherein R.sub.8 is ##STR128## R.sub.2 is H; OH; F; C.sub.1 -C.sub.6 alkoxy; alkyl; SH; S-alkyl; or SO.sub.2 -alkyl;
R.sub.4 is H; a natural amino acid attached by a peptide bond; or a metabolizable group;
J is OH, H, Br, Cl, or F;
K is OH, H, Br, Cl, or F;
X and Y are the same or different and are independently selected from the group consisting of H; OH; O-C.sub.1 -C.sub.14 alkyl; F; Cl; Br; NO.sub.2, and alkyl;
Z is R.sub.5 NR.sub.6 ; ##STR129## wherein Z' is R.sub.5 NR.sub.6, R.sub.5 is (CH.sub.2).sub.11 CH.sub.3 ;
R.sub.6 is H; OH; O-benzyl; O-aryl; O-C.sub.4 -C.sub.14 alkyl; C.sub.1 -C.sub.12 alkyl; phenyl; substituted phenyl; or CO-R.sub.7 ; and
R.sub.7 is H, C.sub.1 -C.sub.16 alkyl, aryl or alkylaryl; and
n is an integer from 0 to 16.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein Het is uracil.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R.sub.4 is H.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein J and K are both OH.

### Claim 5 (depends on 1)

A compound according to claim 1, selected from the group consisting of
______________________________________ ##STR130## No. ##STR131## Z.OC ______________________________________ ##STR132## CONH(CH.sub.2).sub.11 CH.sub.3 ##STR133## CONH(CH.sub.2).sub.11 CH.sub.3 ##STR134## CONH(CH.sub.2).sub.11 CH.sub.3 ______________________________________
or a pharmaceutically acceptable salt of such a compound.

### Claim 6 (depends on 1)

A compound according to claim 1, having the structural formula ##STR135## or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.

### Claim 8 (depends on 1)

A method for treating a fungal infection in a mammal which comprises administering to the mammal an anti-fungally effective amount of a compound according to claim 1.