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US5380751A Expired / Lapsed US ⏱️ 0.0 years remaining

6,7-modified paclitaxels

Assignee: Bristol Myers Squibb Co
•
Filing: 1993-09-28
•
Granted: 1995-01-10
•
Expires: 2013-09-28
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Abstract

Abstract The present invention provides paclitaxel derivatives of formula I ##STR1## in which R 1 is --COR z in which R Z is RO-- or R; R 2 is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, or a radical of the formula --W--R x in which W is a bond, C 2-6 alkenediyl, or --(CH 2 ) t --, in which t is one to six; and R x is naphthyl, phenyl, or heteroaryl, and furthermore R x can be optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups; R a is --OCOR, H, OH, --OR, --OSO 2 R, --OCONR o R, --OCONHR, --OCOO(CH 2 ) t R, or --OCOOR; R b and R c are both hydroxy or together form a bond with the carbon atoms to which they are attached; and R and R o are independently C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups. Also provided by this invention are pharmaceutical formulations (compositions) and a method of treating mammalian tumors with a compound of formula I.

Inventors

  • 👤 Shu-Hui Chen
  • 👤 Vittorio Farina
  • 👤 Gregory Roth
  • 👤 John Kadow

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 19:46
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; A; A61; A61K; A61K31/00; A61K31/33; A61K31/335; A61P; A61P35/00; C07D305/00; C07D305/14; C07D409/00; C07D409/02; C07D409/12; C07D413/00; C07D413/02; C07D413/12; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804

Claims Analysis

Total Claims: 8
Claim 1
Independent Claim 183 words
A compound of formula I ##STR30## in which R 1 is --COR z in which R z is RO-- or R; R 2 is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, or a radical of the formula --W--R x in which W is a bond, C 2-6 alkenediyl, or --(CH 2 ) t --, in which t is one to six; and R x is naphthyl, or phenyl, and furthermore R x can be optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups; R a is --OCOR, H, OH, --OR, --OSO 2 R, --OCONR o R, --OCONHR, --OCOO(CH 2 ) t R, or --OCOOR; R b and R c are both hydroxy or together form a bond with the carbon atoms to which they are attached; and R and R o are independently C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups.
Claim 2
Dependent Claim 183 words
A compound of formula I ##STR30## in which R 1 is --COR z in which R z is RO-- or R; R 2 is C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl, or a radical of the formula --W--R x in which W is a bond, C 2-6 alkenediyl, or --(CH 2 ) t --, in which t is one to six; and R x is naphthyl, or phenyl, and furthermore R x can be optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups; R a is --OCOR, H, OH, --OR, --OSO 2 R, --OCONR o R, --OCONHR, --OCOO(CH 2 ) t R, or --OCOOR; R b and R c are both hydroxy or together form a bond with the carbon atoms to which they are attached; and R and R o are independently C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C 1-6 alkyl, C 1-6 alkoxy, halogen or --CF 3 groups.
Claim 3
Dependent Claim 40 words
A compound of claim 1 in which R 1 is benzoyl or t-butoxycarbonyl; R 2 is phenyl; R a is acetyloxy; and R b and R c together form a bond with the carbon atoms to which they are attached.
Claim 4
Dependent Claim 8 words
The compound of claim 2 that is 6,7-dehydropaclitaxel.
Claim 5
Dependent Claim 29 words
A compound of claim 1 in which R 1 is benzoyl or t-butoxycarbonyl; R 2 is phenyl; R a is acetyloxy; and R b and R c are hydroxy.
Claim 6
Dependent Claim 8 words
The compound of claim 4 that is 6α-hydroxy-7α-hydroxypaclitaxel.
Claim 7
Dependent Claim 39 words
A pharmaceutical formulation which comprises as an active ingredient a compound as claimed in any one of claims 1 to 5, or a pharmaceutically acceptable salt thereof, associated with one or more pharmaceutically acceptable carriers, excipients or diluents therefor.
Claim 8
Independent Claim 29 words
A method for treating mammalian tumors which comprises administering to a mammal a tumor sensitive amount of a compound as claimed in any one of claims 1 to 5.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1998-01-09 1998-07-11 1999-01-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2002-01-09 2002-07-11 2003-01-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2006-01-09 2006-07-11 2007-01-10 $7700.00 Window Closed / Lapsed

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