← Back to Patent Explorer
US5635531A Expired / Lapsed US ⏱️ 0.0 years remaining

3'-aminocarbonyloxy paclitaxels

Assignee: Bristol Myers Squibb Co
•
Filing: 1996-07-08
•
Granted: 1997-06-03
•
Expires: 2016-07-08
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The present invention concerns novel paclitaxel derivatives, their use as antitumor agents, and pharmaceutical formulations.

Inventors

  • 👤 Shu-Hui Chen

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 21:28
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; C07D305/00; C07D305/14

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 360 words
A compound of formula I, or a pharmaceutically acceptable salt thereof ##STR59## wherein R 1 is hydroxy, --OC(O)R x or --OC(O)OR x ; R 2 is hydrogen, hydroxy, methoxy, --OC(O)R x or --OC(O)OR x ; R 2' is hydrogen, hydroxy or fluoro; R 6' is hydrogen or hydroxy; R 6 is hydrogen, or R 2 and R 6 together can form oxirane ring or a bond; R 3 is hydrogen, hydroxy, C 1-6 alkyloxy, --OCONR 14 R 15 , --OC(O)R x or --OC(O)OR x ; R 8 is methyl or hydroxymethyl, or R 8 and R 2 together form cyclopropane ring; R 9 is hydroxy or --OC(O)R x ; with the proviso that when R 8 and R 2 form cyclopropane ring, R 2' is hydrogen; when R 2 and R 6 form oxirane ring or double bond, R 2' and R 6' are hydrogen; when R 2 is hydroxy, methoxy, --OC(O)R x or --OC(O)OR x , R 2' is hydrogen; when R 2' is fluoro, R 2 is hydrogen; one of R 7 or R 7' is hydrogen and the other is hydroxy, --OC(O)R x or --OC(O)OR x , or R 7 and R 7' together form an oxo group; R 14 and R 15 are independently C 1-6 alkyl, hydrogen, aryl or substituted aryl; R 4 and R 5 are independently C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, or --Z--R 10 ; Z is a direct bond, C 1-6 alkyl or C 2-6 alkenyl; R 10 is aryl, substituted aryl, C 3-6 cycloalkyl or heteroaryl; R 11 is --OC(O)R y or --OC(O)OR y ; R 12 is hydrogen or hydroxy; R y is C 3-6 cycloalkyl or C 1-6 alkyl; R x is C 3-6 cycloalkyl, C 2-6 alkenyl or C 1-6 alkyl, all are optionally substituted with one to six same or different halogen atoms; or R x is a radical of the formula ##STR60## wherein D is a bond or C 1-6 alkyl; and R a , R b and R c are independently hydrogen, nitro, cyano, azido, amino, C 1-6 alkylamino, di-C 1-6 alkylamino, halogen, C 1-6 alkyl, hydroxy or C 1-6 alkoxy.
Claim 2
Dependent Claim 360 words
A compound of formula I, or a pharmaceutically acceptable salt thereof ##STR59## wherein R 1 is hydroxy, --OC(O)R x or --OC(O)OR x ; R 2 is hydrogen, hydroxy, methoxy, --OC(O)R x or --OC(O)OR x ; R 2' is hydrogen, hydroxy or fluoro; R 6' is hydrogen or hydroxy; R 6 is hydrogen, or R 2 and R 6 together can form oxirane ring or a bond; R 3 is hydrogen, hydroxy, C 1-6 alkyloxy, --OCONR 14 R 15 , --OC(O)R x or --OC(O)OR x ; R 8 is methyl or hydroxymethyl, or R 8 and R 2 together form cyclopropane ring; R 9 is hydroxy or --OC(O)R x ; with the proviso that when R 8 and R 2 form cyclopropane ring, R 2' is hydrogen; when R 2 and R 6 form oxirane ring or double bond, R 2' and R 6' are hydrogen; when R 2 is hydroxy, methoxy, --OC(O)R x or --OC(O)OR x , R 2' is hydrogen; when R 2' is fluoro, R 2 is hydrogen; one of R 7 or R 7' is hydrogen and the other is hydroxy, --OC(O)R x or --OC(O)OR x , or R 7 and R 7' together form an oxo group; R 14 and R 15 are independently C 1-6 alkyl, hydrogen, aryl or substituted aryl; R 4 and R 5 are independently C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, or --Z--R 10 ; Z is a direct bond, C 1-6 alkyl or C 2-6 alkenyl; R 10 is aryl, substituted aryl, C 3-6 cycloalkyl or heteroaryl; R 11 is --OC(O)R y or --OC(O)OR y ; R 12 is hydrogen or hydroxy; R y is C 3-6 cycloalkyl or C 1-6 alkyl; R x is C 3-6 cycloalkyl, C 2-6 alkenyl or C 1-6 alkyl, all are optionally substituted with one to six same or different halogen atoms; or R x is a radical of the formula ##STR60## wherein D is a bond or C 1-6 alkyl; and R a , R b and R c are independently hydrogen, nitro, cyano, azido, amino, C 1-6 alkylamino, di-C 1-6 alkylamino, halogen, C 1-6 alkyl, hydroxy or C 1-6 alkoxy.
Claim 3
Dependent Claim 34 words
A compound as claimed claim 1 which has the formula ##STR61## in which R 17 is methyl or hydrogen; and R 3 , R 4 and R 5 are as defined in claim 1.
Claim 4
Dependent Claim 36 words
A compound as claimed in claim 2 in which R 3 is hydroxy or acetyloxy, R 4 is C 1-6 alkyl or C 3-6 cycloalkyl, R 5 is furyl or phenyl, and R 17 is hydrogen.
Claim 5
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is acetyloxy, R 4 is t-butyl, and R 5 is phenyl.
Claim 6
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is acetyloxy, R 4 is t-butyl, and R 5 is 2-furyl.
Claim 7
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is hydroxy, R 4 is t-butyl, and R 5 is phenyl.
Claim 8
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is hydroxy, R 4 is t-butyl, and R 5 is 2-furyl.
Claim 9
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is acetyloxy, R 4 is isopropyl, and R 5 is phenyl.
Claim 10
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is acetyloxy, R 4 is isopropyl, and R 5 is 2-furyl.
Claim 11
Dependent Claim 22 words
A compound as claimed in claim 3 in which R 3 is acetyloxy, R 4 is cyclobutyl, and R 5 is 2-furyl.
Claim 12
Dependent Claim 37 words
A compound as claimed in claim 2 in which R 3 is hydroxy or acetyloxy, R 4 is C 1-6 alkyl or C 3-6 cycloalkyl, and R 5 is furyl or phenyl, and R 17 is methyl.
Claim 13
Dependent Claim 22 words
A compound as claimed in claim 11 in which R 3 is acetyloxy, R 4 is t-butyl, and R 5 is 2-furyl.
Claim 14
Dependent Claim 22 words
A compound as claimed in claim 11 in which R 3 is acetyloxy, R 4 is cyclobutyl, and R 5 is 2-furyl.
Claim 15
Dependent Claim 23 words
A pharmaceutical formulation which comprises an antitumor effective amount of a compound of formula I as claimed in any one of claims 1-13.
Claim 16
Independent Claim 34 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 formula I as claimed in any one of claims 1-13.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2000-06-02 2000-12-02 2001-06-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2004-06-02 2004-12-02 2005-06-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2008-06-02 2008-12-02 2009-06-03 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag