US5539103A
Expired / Lapsed
US
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β-lactams as taxol intermediates N-acylated
Assignee: Florida State University
•
Filing: 1994-12-07
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Granted: 1996-07-23
•
Expires: 2014-12-07
Abstract
Abstract β-lactam compounds which are reacted with a metal alkoxide for preparing N-acyl, N-sulfonyl and phosphoryl substituted isoserine esters.
Inventors
- 👤 Robert A. Holton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 17:36
CPC Classifications
C; C07; C07D; C07D407/00; C07D407/02; C07D407/12; A; A61; A61P; A61P35/00; A61P35/02; C07C; C07C227/00; C07C227/22; C07C231/00; C07C231/12; C07C233/00; C07C233/64; C07C233/81; C07C233/82; C07C233/87; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D305/00; C07D305/14; C07D409/00; C07D409/02; C07D409/12; C07F; C07F7/00; C07F7/003; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07C2601/00; C07C2601/12; C07C2601/14; C07C2601/16; C07C2603/00; C07C2603/56; C07C2603/58; C07C2603/60; C07C2603/62; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
35 words
A cis diastereomer of a β-lactam having the formula ##STR50## wherein R 1 is hydroxy; R 3 is furyl, thienyl, or ##STR51## R 5 is --COR 10 ; and R 10 and Ph are phenyl.
Claim 2
Dependent Claim
35 words
A cis diastereomer of a β-lactam having the formula ##STR50## wherein R 1 is hydroxy; R 3 is furyl, thienyl, or ##STR51## R 5 is --COR 10 ; and R 10 and Ph are phenyl.
Claim 3
Dependent Claim
71 words
A cis diastereomer of a β-lactam having the formula ##STR52## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR53## R 5 is --COR 10 , --COOR 10 , or --COSR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, or heteroaromatic; and Ph is phenyl.
Claim 4
Dependent Claim
71 words
A cis diastereomer of a β-lactam having the formula ##STR52## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR53## R 5 is --COR 10 , --COOR 10 , or --COSR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, or heteroaromatic; and Ph is phenyl.
Claim 5
Dependent Claim
23 words
A β-lactam having the formula ##STR54## wherein R 10 is tert-butoxy, R 3 is phenyl, and R 6 is a hydroxy protecting group.
Claim 6
Dependent Claim
23 words
A β-lactam having the formula ##STR54## wherein R 10 is tert-butoxy, R 3 is phenyl, and R 6 is a hydroxy protecting group.
Claim 7
Dependent Claim
59 words
A cis diastereomer of a β-lactam having the formula ##STR55## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR56## R 5 is --COR 10 or --COOR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is alkyl; and Ph is phenyl.
Claim 8
Dependent Claim
59 words
A cis diastereomer of a β-lactam having the formula ##STR55## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR56## R 5 is --COR 10 or --COOR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is alkyl; and Ph is phenyl.
Claim 9
Dependent Claim
60 words
A cis diastereomer of a β-lactam having the formula ##STR57## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR58## R 5 is --COR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is phenyl, heteroaromatic, or substituted phenyl; and Ph is phenyl.
Claim 10
Dependent Claim
60 words
A cis diastereomer of a β-lactam having the formula ##STR57## wherein R 1 is --OR 6 ; R 3 is hydrogen, alkyl, alkenyl, alkynyl, phenyl, naphthyl, substituted phenyl, heteroaromatic, ##STR58## R 5 is --COR 10 ; R 6 is alkenyl, alkynyl, aryl, heteroaromatic, or a hydroxy protecting group; R 10 is phenyl, heteroaromatic, or substituted phenyl; and Ph is phenyl.
Claim 11
Dependent Claim
75 words
The diastereomer of claim 2 wherein R 6 is a hydroxy protecting group; R 3 is alkyl, phenyl, heteroaromatic, alkenyl, or substituted phenyl wherein the phenyl substituent is Cl, Br, F, CH 3 O-- or NO 2 ; and R 5 is --COR 10 or --COOR 10 wherein R 10 is alkyl, alkenyl, alkynyl, phenyl, naphthyl, heteroaromatic, or substituted phenyl wherein the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 12
Dependent Claim
24 words
The diastereomer of claim 2 having the formula ##STR59## wherein R 1 , R 3 and R 5 are as defined in claim 2.
Claim 13
Dependent Claim
20 words
The diastereomer of claim 4 wherein the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 14
Dependent Claim
20 words
The diastereomer of claim 5 wherein the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 15
Dependent Claim
13 words
The diastereomer of claim 2 wherein R 6 is a hydroxy protecting group.
Claim 16
Dependent Claim
16 words
The diastereomer of claim 10 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic.
Claim 17
Dependent Claim
22 words
The diastereomer of claim 10 wherein R 5 is --COR 10 or --COOR 10 wherein R 10 is alkyl, phenyl or heteroaromatic.
Claim 18
Dependent Claim
13 words
The diastereomer of claim 7 wherein R 6 is a hydroxy protecting group.
Claim 19
Dependent Claim
16 words
The diastereomer of claim 13 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic.
Claim 20
Dependent Claim
22 words
The diastereomer of claim 13 wherein R 5 is --COR 10 or --COOR 10 wherein R 10 is alkyl, phenyl or heteroaromatic.
Claim 21
Dependent Claim
10 words
The diastereomer of claim 10 wherein R 10 is heteroaromatic.
Claim 22
Dependent Claim
13 words
The diastereomer of claim 4 wherein R 6 is a hydroxy protecting group.
Claim 23
Dependent Claim
31 words
The diastereomer of claim 17 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic and the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 24
Dependent Claim
24 words
An diastereomer of claim 4 having the formula ##STR60## wherein R 1 , R 3 and R 5 are as defined in claim 4.
Claim 25
Dependent Claim
24 words
An diastereomer of claim 1 having the formula ##STR61## wherein R 1 , R 3 and R 5 are as defined in claim 1.
Claim 26
Dependent Claim
13 words
The diastereomer of claim 5 wherein R 6 is a hydroxy protecting group.
Claim 27
Dependent Claim
31 words
The diastereomer of claim 21 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic and the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 28
Dependent Claim
12 words
The diastereomer of claim 1 wherein R 3 is furyl or thienyl.
Claim 29
Dependent Claim
24 words
An diastereomer of claim 5 having the formula ##STR62## where R 1 , R 3 and R 5 are as defined in claim 5.
Claim 30
Dependent Claim
31 words
The diastereomer of claim 26 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic and the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 31
Dependent Claim
13 words
The diastereomer of claim 24 wherein R 6 is a hydroxy protecting group.
Claim 32
Dependent Claim
13 words
The diastereomer of claim 19 wherein R 6 is a hydroxy protecting group.
Claim 33
Dependent Claim
31 words
The diastereomer of claim 27 wherein R 3 is alkyl, alkenyl, phenyl, substituted phenyl or heteroaromatic and the phenyl substituent is alkoxy, protected hydroxy, halogen, alkyl, aryl, alkenyl, nitro, or amino.
Claim 34
Dependent Claim
17 words
The diastereomer of claim 4 wherein R 3 is alkyl, alkenyl, alkynyl, phenyl, substituted phenyl, or heteroaromatic.
Claim 35
Dependent Claim
39 words
The diastereomer of claim 4 wherein R 6 is a hydroxy protecting group, and R 3 is alkyl, phenyl, heteroaromatic, alkenyl, or substituted phenyl wherein the phenyl substituent is Cl, Br, F, CH 3 O-- or NO 2 .
Claim 36
Dependent Claim
17 words
The diastereomer of claim 5 wherein R 3 is alkyl, alkenyl, alkynyl, phenyl, substituted phenyl, or heteroaromatic.
Claim 37
Dependent Claim
39 words
The diastereomer of claim 5 wherein R 6 is a hydroxy protecting group, and R 3 is alkyl, phenyl, heteroaromatic, alkenyl, or substituted phenyl wherein the phenyl substituent is Cl, Br, F, CH 3 O-- or NO 2 .
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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) | 1999-07-23 | 2000-01-22 | 2000-07-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-07-23 | 2004-01-22 | 2004-07-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-07-23 | 2008-01-22 | 2008-07-23 | $7700.00 | Window Closed / Lapsed |