US4068080A
Expired / Lapsed
US
⏱️ 0.0 years remaining
O-2-Isocephem-4-carboxylic acid derivatives as antibacterial agents
Assignee: Bristol Myers Co
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Filing: 1976-08-19
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Granted: 1978-01-10
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Expires: 1996-08-19
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 halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carbonyl 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
2026-11-06 01:26
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: 10
Claim 1
Independent Claim
135 words
A compound having the formula ##STR162##wherein Z is etherified hydroxyl of the formula --OR 3 in which R 3 is benzyl or a 5- or 6-membered heterocyclic radical containing 1-4 atoms selected from N, O and S, said heterocyclic radical being optionally substituted by one or more substituents selected from halogen, amino, nitro, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl, trifluoromethyl, phenyl, benzyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, di C 1 -C 4 alkylamino or alkoxyalkyl of up to 4 carbon atoms and R" is hydrogen or an easily cleavable ester carboxyl-protecting group selected from benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl or acetoxymethyl, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
135 words
A compound having the formula ##STR162##wherein Z is etherified hydroxyl of the formula --OR 3 in which R 3 is benzyl or a 5- or 6-membered heterocyclic radical containing 1-4 atoms selected from N, O and S, said heterocyclic radical being optionally substituted by one or more substituents selected from halogen, amino, nitro, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkenyl, trifluoromethyl, phenyl, benzyl, C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, di C 1 -C 4 alkylamino or alkoxyalkyl of up to 4 carbon atoms and R" is hydrogen or an easily cleavable ester carboxyl-protecting group selected from benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, trichloroethyl, trimethylsilyl, phenacyl, acetonyl, (lower)alkyl, triphenylmethyl, methoxymethyl, indanyl, phthalidyl, pivaloyloxymethyl or acetoxymethyl, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
21 words
A compound of claim 1 wherein R 3 is benzyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-oxadiazolyl, 1,2,3,4-tetrazolyl, 2-methyl-1,3,4-thiadiazol-5-yl, 2-methyl-1,3,4-oxadiazol-5 -yl or 1-N-methyltetrazolyl.
Claim 4
Dependent Claim
15 words
An acid of claim 2 wherein R" is hydrogen, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
9 words
An acid of claim 2 wherein R" is hydrogen.
Claim 6
Dependent Claim
14 words
A compound of claim 2 wherein R" is pivaloyloxymethyl, methoxymethyl, indanyl, phthalidyl or acetoxymethyl.
Claim 7
Dependent Claim
14 words
The acid of claim 2 wherein R 3 is benzyl and R" is hydrogen.
Claim 8
Dependent Claim
14 words
The acid of claim 2 wherein R 3 is 1-N-methyltetrazol-5-yl and R" is hydrogen.
Claim 9
Dependent Claim
14 words
The ester of claim 2 wherein R 3 is 1-N-methyltetrazol-5-yl and R" is p-nitrobenzyl.
Claim 10
Dependent Claim
14 words
The ester of claim 2 wherein R 3 is benzyl and R" is benzyl.
References Cited (Backward Citations)
US3835130A
Cited
GB1377715A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-09 | 1981-07-11 | 1982-01-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-09 | 1985-07-11 | 1986-01-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-09 | 1989-07-11 | 1990-01-10 | $7700.00 | Window Closed / Lapsed |