US4155912A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-Methylpenem-3-carboxylic acid antibiotics
Assignee: Bristol Myers Co
•
Filing: 1977-12-14
•
Granted: 1979-05-22
•
Expires: 1997-12-14
Abstract
Abstract There is described the preparation of novel 2-penem-3-carboxylic acid compounds having the formula ##STR1## and easily cleavable esters and carboxylic acid salts thereof. The compounds of formula I, particularly the dextrorotatory isomers thereof, are potent antibacterial agents or are of use as intermediates in the preparation of such agents.
Inventors
- 👤 Marcel Menard
- 👤 Gilles Caron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 21:22
CPC Classifications
C; C07; C07D; C07D499/00; C07D499/88; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/09; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/568
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
23 words
A compound of the formula ##STR35## wherein R is hydrogen or an easily removable ester protecting group, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
23 words
A compound of the formula ##STR35## wherein R is hydrogen or an easily removable ester protecting group, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
56 words
A compound according to claim 1 having the formula ##STR36## wherein R 1 is p-nitrobenzyl or the residue of a physiologically cleavable ester group, said ester being selected from the group consisting of indanyl, phthalidyl, methoxymethyl, glycyloxymethyl, phenylglycyloxymethyl, thienylglycyloxymethyl and acyloxymethyl of the formula ##STR37## in which Y is C 1 -C 4 alkyl or phenyl.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 wherein R 1 is p-nitrobenzyl.
Claim 5
Dependent Claim
50 words
A compound according to claim 2 wherein R 1 is the residue of a physiologically cleavable ester group, said ester being selected from the group consisting of indanyl, phthalidyl, methoxymethyl, glycyloxymethyl, phenylglycyloxymethyl, thienylglycycloxymethyl and acyloxymethyl of the formula ##STR38## in which Y is C 1 -C 4 alkyl or phenyl.
Claim 6
Dependent Claim
30 words
A compound according to claim 2 wherein R 1 is indanyl, phthalidyl, methoxymethyl or acyloxymethyl of the formula ##STR39## in which Y is C 1 -C 4 alkyl or phenyl.
Claim 7
Dependent Claim
16 words
A compound according to claim 2 wherein R 1 is methoxymethyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl or indanyl.
Claim 8
Dependent Claim
15 words
The acid of claim 1 having the formula ##STR40## or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
10 words
The acid of claim 7, said acid being 2-methylpenem-3-carboxylic acid.
Claim 10
Dependent Claim
9 words
The sodium salt of the acid of claim 7.
Claim 11
Dependent Claim
9 words
The potassium salt of the acid of claim 7.
Claim 12
Dependent Claim
75 words
The dextrorotatory optical isomer of the compound having the formula ##STR41## wherein R 1 is hydrogen or the residue of a physiologically cleavable ester selected from the group consisting of indanyl, phthalidyl, methoxymethyl, glycyloxymethyl, phenylglycyloxymethyl, thienylglycyloxymethyl and acyloxymethyl of the formula ##STR42## in which Y is C 1 -C 4 alkyl or phenyl or, when R 1 is hydrogen, a pharmaceutically acceptable salt thereof, said isomer being substantially free of the corresponding levorotatory optical isomer.
Claim 13
Dependent Claim
75 words
The dextrorotatory optical isomer of the compound having the formula ##STR41## wherein R 1 is hydrogen or the residue of a physiologically cleavable ester selected from the group consisting of indanyl, phthalidyl, methoxymethyl, glycyloxymethyl, phenylglycyloxymethyl, thienylglycyloxymethyl and acyloxymethyl of the formula ##STR42## in which Y is C 1 -C 4 alkyl or phenyl or, when R 1 is hydrogen, a pharmaceutically acceptable salt thereof, said isomer being substantially free of the corresponding levorotatory optical isomer.
Claim 14
Dependent Claim
29 words
The compound of claim 11 wherein R 1 is indanyl, phthalidyl, methoxymethyl or acyloxymethyl of the formula ##STR43## in which Y is C 1 -C 4 alkyl or phenyl.
Claim 15
Dependent Claim
15 words
The compound of claim 11 wherein R 1 is methoxymethyl, pivaloyloxymethyl, acetoxymethyl, phthalidyl or indanyl.
Claim 16
Dependent Claim
15 words
The acid of claim 11 having the formula ##STR44## or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
10 words
The acid of claim 11, said acid being (+)-2-methylpenem-3-carboxylic acid.
Claim 18
Dependent Claim
9 words
The sodium salt of the acid of claim 11.
Claim 19
Dependent Claim
9 words
The potassium salt of the acid of claim 11.
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) | 1982-05-21 | 1982-11-20 | 1983-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-21 | 1986-11-20 | 1987-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-21 | 1990-11-20 | 1991-05-22 | $7700.00 | Window Closed / Lapsed |