US4362664A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Vinblastine oxazolidinedione disulfides and related compounds
Assignee: Eli Lilly and Co
•
Filing: 1980-12-29
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Granted: 1982-12-07
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Expires: 2000-12-29
Abstract
Abstract Thioalkyl derivatives of vinblastine 3-spiro-5"-oxazolidine-2",4"-dione, mitotic inhibitors.
Inventors
- 👤 Koert Gerzon
- 👤 Jean C. Miller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:14
CPC Classifications
C; C07; C07D; C07D519/00; C07D519/04; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
57 words
A compound of the formula Q--CH.sub.2 --CH.sub.2 --S--S--CH.sub.2 --CH.sub.2 --Z wherein Q is a 3"-oxazolidindionyl radical of the formula: ##STR9## wherein R 2 is CHO or CH 3 ; one of R 3 and R 4 OH or H and the other is ethyl; and Z is Q, NCO or NH--CO 2 --(C 1 -C 3 )alkyl.
Claim 2
Dependent Claim
57 words
A compound of the formula Q--CH.sub.2 --CH.sub.2 --S--S--CH.sub.2 --CH.sub.2 --Z wherein Q is a 3"-oxazolidindionyl radical of the formula: ##STR9## wherein R 2 is CHO or CH 3 ; one of R 3 and R 4 OH or H and the other is ethyl; and Z is Q, NCO or NH--CO 2 --(C 1 -C 3 )alkyl.
Claim 3
Dependent Claim
60 words
An oxazolidinedione of the formula: ##STR10## wherein one of R 3 and R 4 is OH or H and the other is ethyl; R 2 is CH 3 or CHO; R 1 is OH or acetoxy and R is CH 1 --CH 2 --S--S--CH 2 --CH 2 --R 9 wherein R 9 is NCO or NH--CO--O--(C 1 -C 3 )alkyl.
Claim 4
Dependent Claim
60 words
An oxazolidinedione of the formula: ##STR10## wherein one of R 3 and R 4 is OH or H and the other is ethyl; R 2 is CH 3 or CHO; R 1 is OH or acetoxy and R is CH 1 --CH 2 --S--S--CH 2 --CH 2 --R 9 wherein R 9 is NCO or NH--CO--O--(C 1 -C 3 )alkyl.
Claim 5
Dependent Claim
114 words
A process for preparing a compound of the structure Q--CH.sub.2 --CH.sub.2 --SH wherein Q is a 3"-oxazolidinedioxyl radical of the formula ##STR11## wherein R 1 is OH or acetoxy; R 2 is CH 3 or CHO; and one of R 3 and R 4 is H or OH and the other is ethyl, which comprises reducing a compound of the formula Q--CH 2 --CH 2 --S--S--CH 2 --CH 2 --Z, wherein Z is Q, NCO or NH--CO 2 --(C 1 -C 3 )alkyl; and wherein R 1 is acetoxy with zinc and acetic acid; and then, to produce a compound in which R 1 is OH, subjecting the reduced compound to mild alkaline hydrolysis.
Claim 6
Dependent Claim
114 words
A process for preparing a compound of the structure Q--CH.sub.2 --CH.sub.2 --SH wherein Q is a 3"-oxazolidinedioxyl radical of the formula ##STR11## wherein R 1 is OH or acetoxy; R 2 is CH 3 or CHO; and one of R 3 and R 4 is H or OH and the other is ethyl, which comprises reducing a compound of the formula Q--CH 2 --CH 2 --S--S--CH 2 --CH 2 --Z, wherein Z is Q, NCO or NH--CO 2 --(C 1 -C 3 )alkyl; and wherein R 1 is acetoxy with zinc and acetic acid; and then, to produce a compound in which R 1 is OH, subjecting the reduced compound to mild alkaline hydrolysis.
Claim 7
Dependent Claim
61 words
The process which comprises oxidizing a compound of the structure Q--CH 2 --CH 2 --S--H wherein Q is a 3"-oxazolidinedionyl radical of the formula ##STR12## wherein R 2 is CH 3 or CHO; R 1 is OH or acetoxy and one of R 3 and R 4 is H or OH and the other is ethyl; with ferricyanide in hydrochloric acid.
Claim 8
Dependent Claim
61 words
The process which comprises oxidizing a compound of the structure Q--CH 2 --CH 2 --S--H wherein Q is a 3"-oxazolidinedionyl radical of the formula ##STR12## wherein R 2 is CH 3 or CHO; R 1 is OH or acetoxy and one of R 3 and R 4 is H or OH and the other is ethyl; with ferricyanide in hydrochloric acid.
Claim 9
Dependent Claim
11 words
A compound according to claim 1, said compound being vinblastine 3"-(β-[β-(methoxycarbonylamino)-ethyldithio]ethyl)-3-spiro-5"-oxazolidine-2",4"-dione.
Claim 10
Dependent Claim
11 words
A compound according to claim 1, said compound being vinblastine 3"-(β-[β-isocyanatoethyldithio]ethyl)-3-spiro-5"-oxazolidine-2",4"-dione.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-12-06 | 1986-06-07 | 1986-12-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-06 | 1990-06-07 | 1990-12-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-06 | 1994-06-07 | 1994-12-07 | $7700.00 | Window Closed / Lapsed |