US4576751A
Expired / Lapsed
US
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β-Lactams
Assignee: F Hoffmann La Roche AG
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Filing: 1982-08-11
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Granted: 1986-03-18
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Expires: 2002-08-11
Abstract
Abstract There is presented optically uniform beta -lactams of the formulae <IMAGE> wherein Z is a readily cleavable acyl group, R1 is amino or a group convertible into amino, R2 is hydrogen or a readily cleavable protecting group and R3 and R4 each are a lower hydrocarbon group which optionally contains oxygen and which is attached via a carbon atom, whereby these groups can also be joined with one another to form a ring, with the proviso that R1 is a readily cleavable acylamino when R2 is hydrogen, and the corresponding optical antipodes, their manufacture and use in the manufacture of antimicrobially-active beta -lactams as well as novel intermediates usable in their manufacture.
Inventors
- 👤 Christian N. Hubschwerlen
- 👤 Gerard Schmid
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 18:21
CPC Classifications
C; C07; C07D; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D317/00; C07D317/08; C07D317/72; C07D205/085; C07D277/00; C07D277/02; C07D277/20; C07D277/32; C07D277/38; C07D277/40; C07D317/10; C07D317/14; C07D317/28; C07D403/00; C07D403/02; C07D403/04; C07D405/00; C07D405/14; C07D493/00; C07D493/12; C07D493/14; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
112 words
An optically uniform 3,4-cis β-lactam of the formula ##STR25## wherein R 1 is amino or a group selected from azido, phthalimido, (lower alkyl)--OCO--CH═C(CH 3 )--NH or Z--NH wherein Z is selected from t-butoxycarbonyl, trichloroethoxycarbonyl, or benzyloxycarbonyl, R 2 is hydrogen or a compound selected from 2,4 or 3,4-di-(lower alkoxy)-benzyl, 2,4 or 3,4-di-(lower alkoxy)-phenyl, di-[4-(lower alkoxy)-phenyl]-methyl or 4-(lower alkoxy)-phenyl and R 3 and R 4 are joined with one another together with the CHO to which they are attached to form a substituted or unsubstituted 5 or 6 membered heterocycle having two oxygen atom with the proviso that R 1 is Z--NH when R 2 is hydrogen, and the corresponding optical antipodes thereof.
Claim 2
Dependent Claim
112 words
An optically uniform 3,4-cis β-lactam of the formula ##STR25## wherein R 1 is amino or a group selected from azido, phthalimido, (lower alkyl)--OCO--CH═C(CH 3 )--NH or Z--NH wherein Z is selected from t-butoxycarbonyl, trichloroethoxycarbonyl, or benzyloxycarbonyl, R 2 is hydrogen or a compound selected from 2,4 or 3,4-di-(lower alkoxy)-benzyl, 2,4 or 3,4-di-(lower alkoxy)-phenyl, di-[4-(lower alkoxy)-phenyl]-methyl or 4-(lower alkoxy)-phenyl and R 3 and R 4 are joined with one another together with the CHO to which they are attached to form a substituted or unsubstituted 5 or 6 membered heterocycle having two oxygen atom with the proviso that R 1 is Z--NH when R 2 is hydrogen, and the corresponding optical antipodes thereof.
Claim 3
Dependent Claim
41 words
Compounds according to claim 1 wherein ##STR26## is a 5- or 6-membered O-heterocycle which contains a further oxygen atom not directly linked with the center of chirality and which can be substituted by lower alkyl, lower alkoxy, oxo or spirocyclo-lower alkyl.
Claim 4
Dependent Claim
17 words
Compounds according to claim 2, wherein the group ##STR27## represents one of the groups selected from ##STR28##
Claim 5
Dependent Claim
3 words
The compound: N-[(3R,4R)-1-(2,4-Dimethoxybenzyl)-4-[(S)-1,4-dioxaspiro[4.5]dec-2-yl]-2-oxo-3-azetidinyl]phthalimide.
Claim 6
Dependent Claim
3 words
The compound: N-[(3R,4R)-1-(2,4-Dimethoxybenzyl)-4-[(S)-1,4-dioxaspiro[4.5]dec-2-yl]-2-oxo-3-azetidinyl]phthalimide.
Claim 7
Dependent Claim
3 words
The compound: N-[3S,4S)-Cis-1-(3,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]-phthalimide.
Claim 8
Dependent Claim
3 words
The compound: N-[3S,4S)-Cis-1-(3,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]-phthalimide.
Claim 9
Dependent Claim
3 words
The compound: Benzyl(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinecarbamate.
Claim 10
Dependent Claim
3 words
The compound: Benzyl(3S,4S)-cis-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinecarbamate.
Claim 11
Dependent Claim
3 words
The compound: Benzyl(3S,4S)-cis-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinecarbamate.
Claim 12
Dependent Claim
3 words
The compound: Benzyl(3S,4S)-cis-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinecarbamate.
Claim 13
Dependent Claim
78 words
An optionally uniform compound of the formula ##STR29## wherein R 10 is azido, phthalimido, amino or the group alkoxycarbonyl--CH═C(CH 3 )--NH-- or Z--NH--, Z is t-butoxycarbonyl, trichloroethoxycarbonyl, or benzyloxycarbonyl, R 20 is hydrogen or the group Z'--, Z' is 2,4- or 3,4-di-(lower alkoxy)benzyl, di-[4-(lower alkoxy)-phenyl]-methyl or 4-(lower alkoxy)-phenyl and R 30 and R 40 together are isopropylidene, with the proviso that R 10 is the group Z--NH-- when R 20 is hydrogen and the corresponding optical antipodes thereof.
Claim 14
Dependent Claim
78 words
An optionally uniform compound of the formula ##STR29## wherein R 10 is azido, phthalimido, amino or the group alkoxycarbonyl--CH═C(CH 3 )--NH-- or Z--NH--, Z is t-butoxycarbonyl, trichloroethoxycarbonyl, or benzyloxycarbonyl, R 20 is hydrogen or the group Z'--, Z' is 2,4- or 3,4-di-(lower alkoxy)benzyl, di-[4-(lower alkoxy)-phenyl]-methyl or 4-(lower alkoxy)-phenyl and R 30 and R 40 together are isopropylidene, with the proviso that R 10 is the group Z--NH-- when R 20 is hydrogen and the corresponding optical antipodes thereof.
Claim 15
Dependent Claim
20 words
The compound of claim 8, wherein R 10 is phthalimido, amino or benzyloxycarbonyl-amino and R 20 is hydrogen or 2,4-dimethoxybenzyl.
Claim 16
Dependent Claim
3 words
The compound: N-[3S,4S)-Cis-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]-phthalimide.
Claim 17
Dependent Claim
3 words
The compound: N-[3S,4S)-Cis-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-3-azetidinyl]-phthalimide.
Claim 18
Dependent Claim
3 words
The compound: (3S,4S)-Cis-3-amino-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone.
Claim 19
Dependent Claim
3 words
The compound: (3S,4S)-Cis-3-amino-1-(2,4-dimethoxybenzyl)-4-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azetidinone.
References Cited (Backward Citations)
US4473502A
Cited
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