US4572801A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production
Assignee: Takeda Pharmaceutical Co Ltd
•
Filing: 1983-05-31
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Granted: 1986-02-25
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Expires: 2003-05-31
Abstract
Abstract Disclosed are compounds of the general formula: ##STR1## wherein R 1 is a hydrogen atom or a lower alkyl group and R 2 is a hydrogen atom or an ester residue, said derivative having the (3S,4S)-configuration; and pharmaceutically acceptable salts and esters thereof. The compounds have antimicrobial and/or β-lactamase-inhibitory activity and are of value as drugs for human beings and domesticated animals.
Inventors
- 👤 Taisuke Matsuo, deceased
- 👤 Michihiko Ochiai
- 👤 Shoji Kishimoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 18:59
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D205/085; C07D205/09; C07D205/095; C07D257/00; C07D257/02; C07D257/04; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/38; C07D277/44; C07D277/46; C07D277/587; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D401/00; C07D401/02; C07D401/06; C07D403/00; C07D403/02; C07D403/04; C07D413/00; C07D413/14; C07D417/00; C07D417/02; C07D417/12; C07D417/14; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812; C07F7/10; C07F9/00; C07F9/02; C07F9/547; C07F9/6558; C07F9/65583
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
75 words
A member selected from the group consisting of a 1-sulfo-2-azetidinone compound of the formula ##STR14## wherein R 1 is hydrogen or lower alkyl and R 2 is hydrogen or an ester residue selected from the group consisting of α-(C 1-4 )-alkoxy(C 1-4 )alkyl, (C 1-4 )alkylthiomethyl, pivaloyloxymethyl, α-acetoxyethyl, α-(C 1-4 )-alkoxycarbonyloxy(C 1-4 )-alkyl, tert-butyl, benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, p-nitrophenyl, β-trimethylsilylethyl, β,β,β-trichloroethyl, tert-butyldimethylsilyl and isopropyldimethylsilyl, said compound having the (3S,4S)-configuration, and a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
75 words
A member selected from the group consisting of a 1-sulfo-2-azetidinone compound of the formula ##STR14## wherein R 1 is hydrogen or lower alkyl and R 2 is hydrogen or an ester residue selected from the group consisting of α-(C 1-4 )-alkoxy(C 1-4 )alkyl, (C 1-4 )alkylthiomethyl, pivaloyloxymethyl, α-acetoxyethyl, α-(C 1-4 )-alkoxycarbonyloxy(C 1-4 )-alkyl, tert-butyl, benzhydryl, benzyl, p-nitrobenzyl, p-methoxybenzyl, p-nitrophenyl, β-trimethylsilylethyl, β,β,β-trichloroethyl, tert-butyldimethylsilyl and isopropyldimethylsilyl, said compound having the (3S,4S)-configuration, and a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
12 words
A compound as claimed in claim 1, wherein R 1 is hydrogen.
Claim 4
Dependent Claim
15 words
A compound as claimed in claim 1, wherein lower alkyl is (C 1-4 ) alkyl.
Claim 5
Dependent Claim
15 words
A compound as claimed in claim 3, wherein the (C 1-4 ) alkyl is methyl.
Claim 6
Dependent Claim
12 words
A compound as claimed in claim 1, wherein R 2 is hydrogen.
Claim 7
Dependent Claim
31 words
A compound as claimed in claim 1, wherein the pharmaceutically acceptable salt is a salt with a non-toxic cation with respect to at least one of the sulfo and carboxyl groups.
Claim 8
Dependent Claim
17 words
A compound as claimed in claim 6, wherein the salt with a non-toxic cation is di-sodium salt.
Claim 9
Dependent Claim
30 words
A compound as claimed in claim 1, wherein the ester residue R 2 is α-(C 1-4 )alkoxy(C 1-4 )alkyl, (C 1-4 )alkylthiomethyl, pivaloyloxymethyl, α-acetoxyethyl or α-(C 1-4 )alkoxycarbonyloxy-(C 1-4 )alkyl.
Claim 10
Dependent Claim
11 words
A compound as claimed in claim 1, which is (3S,4S)-cis-3-[2-(2-amino-4-thiazolyl)-(Z)-2-carboxymethoxyiminoacetamido]-4-carbamoyloxymethyl-2-azetidinone-1-sulfonic acid.
Claim 11
Dependent Claim
13 words
A compound as claimed in claim 1, which is (3S,4s)-cis-3-[2-(2-amino-4-thiazolyl)-(Z)-2-carboxymethoxyiminoacetamido]-4-carbamoyloxymethyl-2-azetidinone-1-sulfonic acid disodium salt.
Claim 12
Dependent Claim
11 words
A compound as claimed in claim 1, which is (3S,4S)-cis-3-[2-(2-amino-4-thiazolyl)-(Z)-2-(1-carboxy-1-methylethoxyimino)acetamido]-4-carbamoyloxymethyl-2-azetidinone-1-sulfonic acid.
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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) | 1989-02-24 | 1989-08-26 | 1990-02-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-24 | 1993-08-26 | 1994-02-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-24 | 1997-08-26 | 1998-02-25 | $7700.00 | Window Closed / Lapsed |