US5294637A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Fluoro taxols
Assignee: Bristol Myers Squibb Co
•
Filing: 1993-05-20
•
Granted: 1994-03-15
•
Expires: 2013-05-20
Abstract
Abstract This invention relates to a fluorinated taxol of formula I <IMAGE> I in which R1 is -CORz in which Rz is RO- or R; Rg is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or a radical of the formula -W-Rx in which W is a bond, C2-6 alkenediyl, or -(CH2)t-, in which t is one to six; and Rx is naphthyl, furyl, thienyl or phenyl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or -CF3 groups; R2 is -OCOR, H, OH, -OR, -OSO2R, -OCONRoR, -OCONHR, -OCOO(CH2)tR, or -OCOOR; and R and Ro are independently C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or -CF3 groups. Further provided by this invention are pharmaceutical formulations and useful intermediates for the fluorinated taxols of formula I. A method of treating mammalian tumors using a compound of formula I is also provided.
Inventors
- 👤 Shu-Hui Chen
- 👤 Vittorio Farina
- 👤 Joydeep Kant
- 👤 Dolatrai M. Vyas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:39
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; C07D305/00; C07D305/14; C07D409/00; C07D409/02; C07D409/12; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F9/00; C07F9/02; C07F9/547; C07F9/655; C07F9/6551; C07F9/65512; C07F9/6558; C07F9/65586; H; H05; H05K; H05K1/00; H05K1/16; H10; H10W; H10W70/00; H10W70/01; H10W70/04; H10W70/047; H05K1/02; H05K1/03; H05K1/0306; H05K1/09; H05K1/092; H05K3/00; H05K3/40; H05K3/403
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
163 words
A compound of formula I ##STR52## in which R 1 is --COR z in which R z is RO-- or R; R g 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, furyl, thienyl 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 2 is --OCOR, H, OH, --OR, --OSO 2 R, --OCONR o R, --OCONHR, --OCOO(CH 2 ) t R, or --OCOOR; 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
163 words
A compound of formula I ##STR52## in which R 1 is --COR z in which R z is RO-- or R; R g 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, furyl, thienyl 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 2 is --OCOR, H, OH, --OR, --OSO 2 R, --OCONR o R, --OCONHR, --OCOO(CH 2 ) t R, or --OCOOR; 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
34 words
A compound of claim 1 in which R 1 is t-butoxycarbonyl or C 6 H 5 CO--; R 2 is --OCOCH 3 , H, or OH; and R g is phenyl, 2-thienyl or 2-furyl.
Claim 4
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluorotaxol.
Claim 5
Dependent Claim
8 words
A compound of claim 2 that is N-debenzoyl-N-t-butoxycarbonyl-7-α-fluorotaxol.
Claim 6
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-10-desacetyloxytaxol.
Claim 7
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-10-desacetyltaxol.
Claim 8
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-3'-dephenyl-3'-(2-furyl)-N-debenzoyl-N-t-butoxycarbonyltaxol.
Claim 9
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-3'-dephenyl-3'-(2-thienyl)-N-debenzoyl-N-t-butoxycarbonyltaxol.
Claim 10
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-3'-dephenyl-3'-(2-thienyl)taxol.
Claim 11
Dependent Claim
8 words
A compound of claim 2 that is 7-α-fluoro-3'-dephenyl-3'-(2-furyl)taxol.
Claim 12
Dependent Claim
33 words
A pharmaceutical formulation which comprises as an active ingredient a compound as claimed in any one of claims 1 to 10 associated with one or more pharmaceutically acceptable carriers, excipients or diluents therefor.
Claim 13
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 10.
Claim 14
Dependent Claim
7 words
The fluorobaccatin III of formula IV ##STR53##
Claim 15
Dependent Claim
7 words
The fluorobaccatin III of formula IV ##STR53##
References Cited (Backward Citations)
US4814470A
Cited
US4876399A
Cited
US4960790A
Cited
EP0400971A2
Cited
US5015744A
Cited
US5136060A
Cited
EP0522958A1
Cited
EP0524093A1
Cited
WO1993002064A1
Cited
EP0534707A1
Cited
EP0534709A1
Cited
EP0534708A1
Cited
WO1993006093A1
Cited
WO1993006079A1
Cited
WO1993006094A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-03-14 | 1997-09-13 | 1998-03-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-03-14 | 2001-09-13 | 2002-03-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-03-14 | 2005-09-13 | 2006-03-15 | $7700.00 | Window Closed / Lapsed |