US5120842A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Silyl ethers of rapamycin
Assignee: Wyeth LLC
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Filing: 1991-04-01
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Granted: 1992-06-09
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Expires: 2011-04-01
Abstract
Abstract A compound of the structure <IMAGE> wherein R1 is -SiR3R4R5; R2 is hydrogen or -SiR3R4R5; and R3, R4, and R5 are each, independently, alkyl, alkenyl, aralkyl, triphenylmethyl, or phenyl which by virtue of its immunosuppressive activity is useful in treating transplantation rejection, host vs. graft disease, autoimmune diseases and diseases of inflammation; by virtue of its antitumor activity is useful in treating solid tumors; and by virtue of its antifungal activity is useful in treating fungal infections. This invention also provides a method of using rapamycin 42-[O-[(1,1-dimethylethyl)-dimethylsilyl] ether for the preparation of 31-substituted rapamycin derivatives.
Inventors
- 👤 Amedeo A. Failli
- 👤 Robert J. Steffan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 08:58
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/12; C07D498/18; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; A; A61; A61P; A61P29/00; A61P31/00; A61P31/04; A61P31/10; A61P35/00; A61P37/00; A61P37/02; A61P37/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
60 words
A compound of the formula ##STR3## wherein R 1 is --SiR 3 R 4 R 5 ; R 2 is hydrogen or --SiR 3 R 4 R 5 ; and R 3 , R 4 , and R 5 are each, independently, alkyl of 1-8 carbon atoms, alkenyl of 1-8 carbon atoms, phenylalkyl of 7-10 carbon atoms, triphenylmethyl, or phenyl.
Claim 2
Dependent Claim
60 words
A compound of the formula ##STR3## wherein R 1 is --SiR 3 R 4 R 5 ; R 2 is hydrogen or --SiR 3 R 4 R 5 ; and R 3 , R 4 , and R 5 are each, independently, alkyl of 1-8 carbon atoms, alkenyl of 1-8 carbon atoms, phenylalkyl of 7-10 carbon atoms, triphenylmethyl, or phenyl.
Claim 3
Dependent Claim
11 words
A compound of claim 1 in which R 2 is hydrogen.
Claim 4
Dependent Claim
27 words
A compound of claim 1 in which R 2 is hydrogen and R 3 , R 4 , and R 5 are alkyl of 1-8 carbon atoms.
Claim 5
Dependent Claim
22 words
A compound of claim 1 in which R 3 , R 4 , and R 5 are alkyl of 1-8 carbon atoms.
Claim 6
Dependent Claim
9 words
A compound of claim 1 which is rapamycin 42-O-[(1,1-dimethylethyl)dimethylsilyl]ether.
Claim 7
Dependent Claim
9 words
A compound of claim 1 which is rapamycin 31,42-bis-O-[(1,1-dimethylethyl)dimethylsilyl]ether.
Claim 8
Independent Claim
58 words
A method of using rapamycin 42-O-[(1,1-dimethylethyl)-dimethylsilyl]ether for the preparation of a 31-acylated rapamycin which comprises reacting rapamycin 42-[O-[(1,1-dimethylethyl)-dimethylsilyl]ether with an acylating agent to give an intermediate in which the 31-alcohol of rapamycin has reacted with the acylating agent and the 42-position is protected as the 42-[O-[(1,1-dimethylethyl)dimethylsilyl]ether; and subsequent hydrolysis of the 42-silyl ether to provide the 31-acylated rapamycin.
Claim 9
Independent Claim
58 words
A method of using rapamycin 42-O-[(1,1-dimethylethyl)-dimethylsilyl]ether for the preparation of a 31-acylated rapamycin which comprises reacting rapamycin 42-[O-[(1,1-dimethylethyl)-dimethylsilyl]ether with an acylating agent to give an intermediate in which the 31-alcohol of rapamycin has reacted with the acylating agent and the 42-position is protected as the 42-[O-[(1,1-dimethylethyl)dimethylsilyl]ether; and subsequent hydrolysis of the 42-silyl ether to provide the 31-acylated rapamycin.
Claim 10
Dependent Claim
6 words
A compound which is rapamycin 42-[O-[(1,1-Dimethylethyl)dimethylsilyl]ether-31-acetate.
Claim 11
Dependent Claim
6 words
A compound which is rapamycin 42-[O-[(1,1-Dimethylethyl)dimethylsilyl]ether-31-acetate.
Claim 12
Dependent Claim
5 words
A compound which is rapamycin-31-acetate.
Claim 13
Dependent Claim
5 words
A compound which is rapamycin-31-acetate.
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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) | 1995-06-09 | 1995-12-09 | 1996-06-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-06-09 | 1999-12-09 | 2000-06-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-06-09 | 2003-12-09 | 2004-06-09 | $7700.00 | Window Closed / Lapsed |