# US 4,394,505 A · 5-Fluorouracil derivatives

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- Number: US 4,394,505 A
- Document ID: US4394505A
- Status: Granted
- Kind: A
- Application number: 06/369,110
- Filed: 1982-04-16
- Granted: 1983-07-19
- Earliest claimed: 1981-04-28
- Assignees: Shionogi & Co., Ltd.
- Inventors: Susumu Kamata; Wataru Nagata
- Web page: https://patentgrep.com/patent/US4394505A

## CPC

- C07D 239/553: with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
- A61P 35/00: Antineoplastic agents
- C07D 239/60: Three or more oxygen or sulfur atoms
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- 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

Novel 5-fluorouracil derivatives of the following general formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.10 aralkyl, C.sub.1 -C.sub.12 alkanoyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.5 alkanoyloxymethyl, carbamoyl or tri-C.sub.1 -C.sub.5 alkylsilyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.10 aralkyl; X is hydrogen, halogen or C.sub.2 -C.sub.6 alkoxycarbonyl; Y is O, NR' (R' is hydrogen or C.sub.1 -C.sub.5 alkyl), S, SO or SO.sub.2 ; and n is an integer of 1-3. which are orally administrable anti-tumor agents.

## Claims

### Claim 1

A compound of the formula ##STR88## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.6 -C.sub.10 aryl, C.sub.7 -C.sub.10 aralkyl, C.sub.1 -C.sub.12 alkanoyl, C.sub.2 -C.sub.6 alkoxycarbonyl, C.sub.1 -C.sub.5 alkanoyloxymethyl, carbamoyl or tri-C.sub.1 -C.sub.5 alkylsilyl;
R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.10 aralkyl;
X is hydrogen, halogen or C.sub.2 -C.sub.6 alkoxycarbonyl;
Y is O, NR' (R' is hydrogen or C.sub.1 -C.sub.5 alkyl), S, SO or SO.sub.2 ; and
n is an integer of 1-3.

### Claim 2 (depends on 1)

A compound claimed in claim 1, namely dl-8.alpha.-fluoro-2,3,6,7,8,8a.alpha.-hexahydro-5,7-dioxo-3.alpha.-trimet hylacetoxy-5H-oxazolo[3,2-c]pyrimidine.

### Claim 3 (depends on 1)

A compound claimed in claim 1, namely dl-8.alpha.-fluoro-2,3,6,7,8,8a.alpha.-hexahydro-3.alpha.-octanoyloxy-5,7- dioxo-5H-oxazolo[3,2-c]pyrimidine.

### Claim 4 (depends on 1)

A compound claimed in claim 1, namely dl-3.alpha.-acetoxy-8.alpha.-fluoro-2,3,6,7,8,8a.alpha.-hexahydro-5,7-diox o-5H-oxazolo[3,2-c]pyrimidine.

### Claim 5 (depends on 1)

A compound claimed in claim 1, namely dl-9.alpha.-fluoro-3,4,7,8,9,9a.alpha.-hexahydro-6,8-dioxo-4.alpha.-trimet hylacetoxy-2H,6H-[1,3]-oxazino[3,2-c]pyrimidine.