US4644072A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Intermediates for the production of epipodophyllotoxin and related compounds and processes for the preparation and use thereof
Assignee: Bristol Myers Co
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Filing: 1985-04-12
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Granted: 1987-02-17
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Expires: 2005-04-12
Abstract
Abstract There is provided a novel and efficient stereoselective total synthesis of epipodophyllotoxin and related epipodophyllotoxin compounds of the general formula <IMAGE> wherein R1 and R2 each are independently hydrogen or (lower)alkoxy, or R1 and R2, taken together, is methylenedioxy; R4 and R6 each are independently hydrogen or (lower)alkoxy; and R5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.
Inventors
- 👤 Dolatrai M. Vyas
- 👤 Paul M. Skonezny
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:10
CPC Classifications
C; C07; C07H; C07H3/00; C07D; C07D307/00; C07D307/77; C07D307/92; C07C; C07C51/00; C07C51/347; C07C51/353; C07C51/367; C07C51/377; C07C62/00; C07C62/30; C07C62/32; C07C62/34; C07D261/00; C07D261/20; C07D317/00; C07D317/08; C07D317/44; C07D317/70; C07D493/00; C07D493/02; C07D493/04; C07H17/00; C07H17/04; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
63 words
A compound of the formula ##STR112## wherein R 1 and R 2 each are independently hydrogen or (lower)alkoxy, or R 1 and R 2 , taken together, is methylenedioxy; R 3 is hydrogen or a carboxyl-protecting group; R 4 and R 6 each are independently hydrogen or (lower)alkoxy; and R 5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof.
Claim 2
Dependent Claim
63 words
A compound of the formula ##STR112## wherein R 1 and R 2 each are independently hydrogen or (lower)alkoxy, or R 1 and R 2 , taken together, is methylenedioxy; R 3 is hydrogen or a carboxyl-protecting group; R 4 and R 6 each are independently hydrogen or (lower)alkoxy; and R 5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof.
Claim 3
Dependent Claim
33 words
A compound of claim 1 having the formula ##STR113## wherein R 3 is hydrogen or a carboxyl-protecting group; and R 5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof.
Claim 4
Dependent Claim
61 words
A compound of claim 2 wherein R 3 is hydrogen, (lower)alkyl, phenyl(lower)alkyl, ring substituted phenyl(lower)alkyl or diphenylmethyl; and R 5 is hydrogen, (lower)alkyl, phenyl(lower)alkyl, ring substituted phenyl(lower)alkyl, benzyloxycarbonyl or 2,2,2-trichloroethoxycarbonyl; in which the phenyl ring of R 3 and R 5 may contain one or two substituents independently selected from (lower)alkyl, halogen, (lower)alkoxy and trifluoromethyl; or an acid addition salt thereof.
Claim 5
Dependent Claim
15 words
The compound of claim 3 wherein R 3 is diphenylmethyl; and R 5 is methyl.
Claim 6
Dependent Claim
33 words
A compound of claim 1 having the formula ##STR114## wherein R 3 is hydrogen or a carboxyl-protecting group; and R 5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof.
Claim 7
Dependent Claim
61 words
A compound of claim 5 wherein R 3 is hydrogen, (lower)alkyl, phenyl(lower)alkyl, ring substituted phenyl(lower)alkyl or diphenylmethyl; and R 5 is hydrogen, (lower)alkyl, phenyl(lower)alkyl, ring substituted phenyl(lower)alkyl, benzyloxycarbonyl or 2,2,2-trichloroethoxycarbonyl; in which the phenyl ring of R 3 and R 5 may contain one or two substituents independently selected from (lower)alkyl, halogen, (lower)alkoxy and trifluoromethyl; or an acid addition salt thereof.
Claim 8
Dependent Claim
15 words
The compound of claim 6 wherein R 3 is diphenylmethyl; and R 5 is methyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-02-16 | 1990-08-18 | 1991-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-16 | 1994-08-18 | 1995-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-16 | 1998-08-18 | 1999-02-17 | $7700.00 | Window Closed / Lapsed |