# US 4,393,052 A · Antitumor anthracycline glycosides, their preparation, intermediates therefor, and compositions and use thereof

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- Number: US 4,393,052 A
- Document ID: US4393052A
- Status: Granted
- Kind: A
- Application number: 06/316,058
- Filed: 1981-10-29
- Granted: 1983-07-12
- Earliest claimed: 1980-11-01
- Assignees: Farmitalia Carlo Erba S.p.A.
- Inventors: Alberto Bargiotti; Giuseppe Cassinelli; Sergio Penco; Federico Arcamone; Annamaria Casazza
- Web page: https://patentgrep.com/patent/US4393052A

## CPC

- C07H 15/04: attached to an oxygen atom of the saccharide radical
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- C07H 13/04: having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H 15/252: Naphthacene radicals, e.g. daunomycins, adriamycins
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Novel antitumor anthracycline glycosides are prepared by condensing daunomycinone with 2,3,4,6-tetradeoxy-4-C-methylene-3-trifluoroacetamido-L-threo-hexopyranosy l chloride; 2,3,4,6-tetradeoxy-4-C-methylene-3-trifluoroacetamido-L-arabino-hexopyrano syl chloride or 2,3,6-trideoxy-4-C-trifluoroacetamidomethyl-3-trifluoroacetamido-3-O-trifl uoroacetyl-L-lyxo-hexopyranosyl chloride.

## Claims

### Claim 1

An anthracycline glycoside of the formula I: ##STR5## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen or trifluoroacetyl; R.sub.3 is methyl, hydroxymethyl, aminomethyl or trifluoroacetylaminomethyl; and R.sub.4 is hydrogen or hydroxy, with the proviso that when R.sub.4 is hydroxy, R.sub.3 is aminomethyl; or R.sub.3 and R.sub.4 together form methylene, and pharmaceutically acceptable acid addition salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein the salt is the hydrochloride.

### Claim 3 (depends on 1)

A compound according to claim 1 which is 4'-deoxy-4'-C-methylene-daunorubicin hydrochloride.

### Claim 4 (depends on 1)

A compound according to claim 1 which is 4'-deoxy-4'-epi-C-methyl-daunorubicin hydrochloride.

### Claim 5 (depends on 1)

A compound according to claim 1 which is 4'-deoxy-4'-epi-C-methyl-doxorubicin hydrochloride.

### Claim 6 (depends on 1)

A compound according to claim 1 which is 4'-C-aminomethyl-daunorubicin hydrochloride.

### Claim 7 (depends on 1)

A compound according to claim 1 which is 4'-C-aminomethyl-doxorubicin hydrochloride.

### Claim 8

A sugar compound selected from the group consisting of ##STR6##

### Claim 9 (depends on 1)

A pharmaceutical composition for treating P388 ascitic leukemia comprising a therapeutically effective amount of a compound according to claim 1 in combination with a carrier therefor.

### Claim 10 (depends on 1)

A method of inhibiting the growth of P388 ascitic leukemia comprising administering to a mammal afflicted therewith, a therapeutically effective amount of a compound according to claim 1.