US5294637A
Expired / Lapsed
US
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Fluoro taxols
Assignee: Bristol Myers Squibb Co
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Filing: 1993-05-20
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Granted: 1994-03-15
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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 09:52
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##
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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) | 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 |