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Claims for Patent: 5,472,949

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Claims for Patent: 5,472,949

Title: N.sup.4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine compounds, compositions and methods of using same
Abstract:The invention relates to N.sup.4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine derivatives which are useful as an agent for treating tumors, pharmaceutical compositions including the same, a method of treating tumors and a method of preparing N.sup.4 -(substituted-oxycarbonyl)-5'-deoxy-5-fluorocytidine derivatives for treating tumors. Compounds of formula (I), ##STR1## wherein R.sup.1 is a saturated or unsaturated, straight or branched hydrocarbon radical wherein the number of carbon atoms in the longest straight chain of this hydrocarbon radical ranges from three to seven, or is a radical of the formula --(CH.sub.2)n--.sup.Y wherein Y is a cyclohexyl radical, a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical and wherein when Y is a cyclohexyl radical n is an integer from 0 to 4, and when Y is C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical n is an integer from 2 to 4, and R.sup.2 is a hydrogen atom or a radical easily hydrolyzable under physiological conditions, or a hydrate or solvate thereof. Compounds of formula (I) are useful in the treatment of tumors.
Inventor(s): Arasaki; Motohiro (Kanagawa, JP), Ishitsuka; Hideo (Kanagawa, JP), Kuruma; Isami (Kanagawa, JP), Miwa; Masanori (Kanagawa, JP), Murasaki; Chikako (Kanagawa, JP), Shimma; Nobuo (Kanagawa, JP), Umeda; Isao (Kanagawa, JP)
Assignee: Hoffmann-La Roche Inc. (Nutley, NJ)
Application Number:08/167,392
Patent Claims: 1. A compound of formula (I), ##STR6## wherein R.sup.1 is a saturated straight or branched hydrocarbon radical wherein the number of carbon atoms in the longest straight chain of this hydrocarbon radical ranges from three to seven, or is a radical of the formula --(CH.sub.2)n--.sup.Y wherein Y is a cyclohexyl radical, a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical and wherein when Y is a cyclohexyl radical n is an integer from 0 to 4, and when Y is C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical n is an integer from 2 to 4, and R.sup.2 is a hydrogen atom or a radical easily hydrolyzable under physiological conditions,

or a hydrate or solvate thereof.

2. The compounds according to claim 1, wherein R.sup.1 is selected from the group consisting of n-propyl, 1-isopropyl-2-methylpropyl, 1,1,2-trimethylpropyl, n-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, 2-propylpentyl, n-hexyl, 2-ethylhexyl, n-hetpyl, cyclohexyl, cyclohexylbutyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, phenethyl, 3-phenyl-propyl and 4-phenylbutyl.

3. The compounds according to claim 1, selected from a group consisting of:

5'-deoxy-5-fluoro-N.sup.4 -(propoxycarbonyl)cytidine,

5'-deoxy-5-fluoro-N.sup.4 -(hexyloxycarbonyl)cytidine,

5'-deoxy-5-fluoro-N.sup.4 -(isopentyloxycarbonyl)cytidine,

5'-deoxy-5-fluoro-N.sup.4 -(neopentyloxycarbonyl)cytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(1,1,2-trimethylpropoxy)carbonyl]cytidine,

5'-deoxy-N.sup.4 -[(3,3-dimethylbutoxy)carbonyl]-5-fluorocytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(1-isopropyl-2-methylpropoxy)carbonyl]cytidine,

5'-deoxy-N.sup.4 -[(2-ethylbutyl)oxycarbonyl]-5-fluorocytidine,

N.sup.4 -[(cyclohexylmethoxy)carbonyl]-5'-deoxy-5-fluorocytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(2-phenylethoxy)carbonyl]cytidine,

2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N.sup.4 -(propoxycarbonyl)cytidine,

2',3'-di-O-acetyl-N.sup.4 -(butoxycarbonyl)-5'-deoxy-5-fluorocytidine,

2',3'-di-O-benzoyl-N.sup.4 -(butoxycarbonyl)-5 '-deoxy-5-fluorocytidine,

2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N.sup.4 -(pentyloxycarbonyl)cytidine,

2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N.sup.4 -(isopentyloxycarbonyl)cytidine,

2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N.sup.4 -(hexyloxycarbonyl)cytidine,

2',3'-di-O-acetyl-5'-deoxy-N.sup.4 -[(2-ethylbutyl)oxycarbonyl]-5-fluorocytidine,

2',3'-di-O-acetyl-N.sup.4 -[(cyclohexylmethoxy)carbonyl]-5'-deoxy-5-fluorocytidine,

2',3'-di-O-acetyl-5'-deoxy-5-fluoro-N.sup.4 -[(2-phenylethoxy)carbonyl]cytidine,

5'-deoxy-5-fluoro-N.sup.4 -(isobutoxycarbonyl)cytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(2-propylpentyl)oxycarbonyl]cytidine,

' -deoxy-N.sup.4 -[(2-ethylhexyl)oxycarbonyl]-5'-fluorocytidine,

5'-deoxy-5-fluoro-N.sup.4 -(heptyloxycarbonyl)cytidine,

N.sup.4 -[(2-cyclohexylethoxy)carbonyl]-5'-deoxy-5-fluorocytidine,

N.sup.4 -[(3-cyclohexylpropyl)oxycarbonyl]-5'-deoxy-5-fluorocytidine,

N.sup.4 -(cyclohexyloxycarbonyl)-5'-deoxy-5-fluorocytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(3-phenylpropyl)oxycarbonyl]cytidine,

5'-deoxy-5-fluoro-N.sup.4 -[(2-methoxyethoxy)carbonyl]cytidine,

N.sup.4 -(butoxycarbonyl)-5'-deoxy-5-fluorocytidine and

5'-deoxy-5-fluoro-N.sup.4 -(pentyloxycarbonyl)cytidine.

4. A pharmaceutical composition comprising a therapeutically effective amount of one or more compounds of formula (I) ##STR7## wherein R.sup.1 is a saturated straight or branched hydrocarbon radical wherein the number of carbon atoms in the longest straight chain of the hydrocarbon radical ranges from three to seven, or is a radical of the formula --(CH.sub.2).sub.n --Y wherein Y is a cyclohexyl radical, a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical and wherein when Y is a cyclohexyl radical n is an integer from 0 to 4 and when Y is a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical n is an integer from 2 to 4, and R.sup.2 is a hydrogen atom or a radical easily hydrolyzable under physiological conditions,

or a hydrate or solvate thereof, and an inert carrier.

5. A method of treating tumors comprising administering to a host in need of such treatment an effective amount of a compound of formula (I) ##STR8## wherein R.sup.1 is a saturated straight or branched hydrocarbon radical wherein the number of carbon atoms in the longest straight chain of the hydrocarbon radical ranges from three to seven, or is a radical of the formula --(CH.sub.2).sub.n --Y wherein Y is a cyclohexyl radical, a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical and wherein when Y is a cyclohexyl radical n is an integer from 0 to 4 and when Y is a C.sub.1 -C.sub.4 alkoxy radical or a phenyl radical n is an integer from 2 to 4, and R.sup.2 is a hydrogen atom or a radical easily hydrolyzable under physiological conditions,

or a hydrate or solvate thereof.

6. The compound according to claim 1, 5'-deoxy-5-fluoro-N.sup.4 -(pentyloxycarbonyl)cytidine.
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