US4011216A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Δ2,3-0-2-Isocephem-4-carboxylic acid and derivatives thereof as antibacterial agents
Assignee: Bristol Myers Co
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Filing: 1975-04-11
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Granted: 1977-03-08
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Expires: 1995-04-11
Abstract
Abstract There is described the stereoselective total synthesis of novel Δ 2 ,3 -1,4-morpholine-2-carboxylic acids possessing a fused β-lactam ring in the 1, 6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is hydroxyl esterified with a carboxylic acid residue and X is amino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.
Inventors
- 👤 Marcel Menard
- 👤 Gary M. F. Lim
- 👤 Terry T. Conway
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 08:28
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; A; A61; A61P; A61P31/00; A61P31/04; C07C; C07C59/00; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/28
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
59 words
A compound of the formula ##STR168## wherein Z is [halo, hydroxyl, hydroxyl esterified with a carboxylic acid or a sulfonic acid group or etherified 4.00CH hydroxyl] esterified hydroxyl of the formula --OCOR.sub.2 wherein R 2 is hydrogen, amino or (lower)alkyl and R" is hydrogen or an easily cleavable ester carboxyl-protecting group, or carboxylic acid or acid addition salts thereof.
Claim 2
Dependent Claim
59 words
A compound of the formula ##STR168## wherein Z is [halo, hydroxyl, hydroxyl esterified with a carboxylic acid or a sulfonic acid group or etherified 4.00CH hydroxyl] esterified hydroxyl of the formula --OCOR.sub.2 wherein R 2 is hydrogen, amino or (lower)alkyl and R" is hydrogen or an easily cleavable ester carboxyl-protecting group, or carboxylic acid or acid addition salts thereof.
Claim 3
Dependent Claim
18 words
A compound of claim 1 wherein R" is hydrogen, or a carboxylic acid or acid addition salt thereof.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein R" is hydrogen.
Claim 5
Dependent Claim
30 words
A compound of claim 1 wherein R" is benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl or acetoxymethyl, or an acid addition salt thereof.
Claim 6
Dependent Claim
19 words
A compound of claim 1 wherein R 2 is hydrogen, or a carboxylic acid or acid addition salt thereof.
Claim 7
Dependent Claim
14 words
The acid of claim 1 wherein R 2 is hydrogen and R" is hydrogen.
Claim 8
Dependent Claim
19 words
A compound of claim 1 wherein R 2 is amino, or a carboxylic acid or acid addition salt thereof.
Claim 9
Dependent Claim
14 words
The acid of claim 1 wherein R 2 is amino and R" is hydrogen.
Claim 10
Dependent Claim
25 words
A compound of the formula ##STR169## wherein R" is hydrogen or an easily cleavable ester carboxyl-protecting group, or carboxylic acid or acid addition salts thereof.
Claim 11
Dependent Claim
25 words
A compound of the formula ##STR169## wherein R" is hydrogen or an easily cleavable ester carboxyl-protecting group, or carboxylic acid or acid addition salts thereof.
Claim 12
Dependent Claim
18 words
An acid of claim 9 wherein R" is hydrogen, or a carboxylic acid or acid addition salt thereof.
Claim 13
Dependent Claim
30 words
An ester of claim 9 wherein R" is benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl or acetoxymethyl, or an acid addition salt thereof.
Claim 14
Dependent Claim
20 words
An ester of claim 9 wherein R" is pivaloyloxymethyl, methoxymethyl, indanyl, phthalidyl or acetoxymethyl, or an acid addition salt thereof.
Claim 15
Dependent Claim
9 words
The acid of claim 9 wherein R" is hydrogen.
References Cited (Backward Citations)
DE1914366A1
Cited
DE2355209A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-07 | 1980-09-06 | 1981-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-07 | 1984-09-06 | 1985-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-07 | 1988-09-06 | 1989-03-08 | $7700.00 | Window Closed / Lapsed |