You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 28, 2024

Claims for Patent: 5,472,949


✉ Email this page to a colleague

« Back to Dashboard


Summary 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.

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.