US5489589A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Amino acid derivatives of paclitaxel
Assignee: Bristol Myers Squibb Co
•
Filing: 1994-12-07
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Granted: 1996-02-06
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Expires: 2014-12-07
Abstract
Abstract The present invention concerns water-soluble amino acid derivatives of paclitaxel, their use as antitumor agents, and pharmaceutical compositions containg the compounds.
Inventors
- 👤 Mark D. Wittman
- 👤 John F. Kadow
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:29
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/14; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
164 words
A compound of the formula (I): ##STR30## wherein R 1 or R 2 are independently hydrogen or --(CH 2 O)) n COCH 2 Y; R 6 is hydrogen, C 1-8 alkanoyl or --(CH 2 O) n COCH 2 Y; n is one to six; p is zero or one; R 4 and R 5 are independently C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, or --Z--R 7 ; Z is a direct bond, C 1-8 alkylene or C 2-8 alkenediyl; R 7 is aryl, substituted aryl, C 3-8 cycloalkyl or heteroaryl; R 3 is hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, aryl or heteroaryl; Y is a radical of the formula ##STR31## in which q is one to three; R r is hydrogen or C 1-8 alkyl; and with the proviso at least one of R 1 , R 2 and R 6 is --(CH 2 O) n COCH 2 Y; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
164 words
A compound of the formula (I): ##STR30## wherein R 1 or R 2 are independently hydrogen or --(CH 2 O)) n COCH 2 Y; R 6 is hydrogen, C 1-8 alkanoyl or --(CH 2 O) n COCH 2 Y; n is one to six; p is zero or one; R 4 and R 5 are independently C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, or --Z--R 7 ; Z is a direct bond, C 1-8 alkylene or C 2-8 alkenediyl; R 7 is aryl, substituted aryl, C 3-8 cycloalkyl or heteroaryl; R 3 is hydrogen, C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-8 cycloalkyl, aryl or heteroaryl; Y is a radical of the formula ##STR31## in which q is one to three; R r is hydrogen or C 1-8 alkyl; and with the proviso at least one of R 1 , R 2 and R 6 is --(CH 2 O) n COCH 2 Y; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
31 words
A compound of claim 1 in which R 6 is acetyl; R 2 is hydrogen; R 4 is phenyl; p is zero; R 5 is phenyl; and R 3 is methyl.
Claim 4
Dependent Claim
8 words
The compound of claim 2 that is 7-O-[[[-(4-methyl-1-piperaznyl)acetyl]oxy]methoxy]paclitaxel.
Claim 5
Dependent Claim
8 words
The compound of claim 2 that is 7-O-[-(N,N-diethlaminoacetyl)oxy]methoxy]paclitaxel.
Claim 6
Dependent Claim
8 words
The compound of claim 2 that is 7-O-[[[[-(4-methyl-1-piperazinyl)acetyl]oxy]methoxy]methoxy]paclitaxel.
Claim 7
Dependent Claim
8 words
The compound of claim 2 that is 7-O-[[(morpholinoacetyl)oxy]methoxy]paclitaxel.
Claim 8
Dependent Claim
8 words
The compound of claim 2 that is 7-O-[-(N,N-dimethylaminoacetyl)oxy]methoxy]paclitaxel.
Claim 9
Dependent Claim
31 words
A compound of claim 1 in which R 6 is acetyl; R 1 is hydrogen; R 4 is phenyl; p is zero; R 5 is phenyl; and R 3 is methyl.
Claim 10
Dependent Claim
8 words
The compound of claim 8 that is 2'-O-[[[[-(4-methyl-1-piperazinyl)acetyl]oxy]methoxy]methoxy]paclitaxel.
Claim 11
Dependent Claim
20 words
A pharmaceutical composition which comprises an antitumor effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
27 words
A method for inhibiting tumor growth in a mammalian host which comprises administering to said mammal a tumor-growth inhibiting amount of a compound of a claim 1.
References Cited (Backward Citations)
US4942184A
Cited
US4960790A
Cited
US5059699A
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EP0558959A1
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EP0569281A1
Cited
EP0604910A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1999-02-05 | 1999-08-07 | 2000-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-02-05 | 2003-08-07 | 2004-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-02-05 | 2007-08-07 | 2008-02-06 | $7700.00 | Window Closed / Lapsed |