US4502990A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof
Assignee: Pfizer Inc
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Filing: 1983-06-06
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Granted: 1985-03-05
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Expires: 2003-06-06
Abstract
Abstract A process for the preparation of beta-lactamase inhibiting 6-alpha-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives. R- and S-1-(ethoxycarbonyloxy)ethyl 6-alpha-(aminomethyl)penicillanate 1,1-dioxide are specifically described.
Inventors
- 👤 Wayne E. Barth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 18:14
CPC Classifications
C; C07; C07D; C07D499/00; A; A61; A61P; A61P31/00; A61P31/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
70 words
A process for the preparation of a compound of the formula ##STR7## wherein R 5 is a conventional carboxy protecting group removable by hydrogenolysis, or a conventional ester forming radical which is hydrolyzable under physiological conditions, which comprises reacting a compound of the formula ##STR8## with substantially 2 molar equivalents of methylmagnesium bromide and then 1 molar equivalent of benzyl N-(acetoxymethyl)carbamate at -50° to -100° C. in an ethereal solvent.
Claim 2
Dependent Claim
70 words
A process for the preparation of a compound of the formula ##STR7## wherein R 5 is a conventional carboxy protecting group removable by hydrogenolysis, or a conventional ester forming radical which is hydrolyzable under physiological conditions, which comprises reacting a compound of the formula ##STR8## with substantially 2 molar equivalents of methylmagnesium bromide and then 1 molar equivalent of benzyl N-(acetoxymethyl)carbamate at -50° to -100° C. in an ethereal solvent.
Claim 3
Dependent Claim
38 words
A process of claim 1 wherein R 5 is: benzyl benzhydryl gamma-butyrolacton-4-yl, --CHR 2 OCOR 3 , or --CHR 2 OCOOR 3 wherein R 2 is hydrogen or methyl and R 3 is (C 1 -C 6 )alkyl.
Claim 4
Dependent Claim
10 words
The process of claim 2 wherein R 5 is benzyl.
Claim 5
Dependent Claim
10 words
The process of claim 2 wherein R 5 is pivaloyloxymethyl.
Claim 6
Dependent Claim
12 words
The process of claim 2 wherein R 5 is R- or S-1-(2-ethoxycarbonyloxy)ethyl.
Claim 7
Dependent Claim
10 words
The process of claim 5 wherein R 5 has R-stereochemistry.
Claim 8
Dependent Claim
10 words
The process of claim 5 wherein R 5 has S-stereochemistry.
Claim 9
Dependent Claim
31 words
A Grignard reagent of the formula ##STR9## wherein R 5 is a conventional carboxy protecting group removable by hydrogenolysis; or a conventional ester forming radical which is hydrolyzable under physiological conditions.
Claim 10
Dependent Claim
31 words
A Grignard reagent of the formula ##STR9## wherein R 5 is a conventional carboxy protecting group removable by hydrogenolysis; or a conventional ester forming radical which is hydrolyzable under physiological conditions.
Claim 11
Dependent Claim
39 words
A compound of claim 8 wherein R 5 is: benzyl; benzhydryl; gamma-butyrolacton-4-yl; --CHR 2 OCOR 3 ; or --CHR 2 OCOOR 3 ; wherein R 2 is hydrogen or methyl and R 3 is (C 1 -C 6 )alkyl.
Claim 12
Dependent Claim
10 words
The compound of claim 9 wherein R 5 is benzyl.
Claim 13
Dependent Claim
10 words
The compound of claim 9 wherein R 5 is pivaloyloxymethyl.
Claim 14
Dependent Claim
12 words
The compound of claim 9 wherein R 5 is R- or S-1-(2-ethoxycarbonyloxy)ethyl.
Claim 15
Dependent Claim
10 words
The compound of claim 12 wherein R 5 has R-stereochemistry.
Claim 16
Dependent Claim
10 words
The compound of claim 12 wherein R 5 has S-stereochemistry.
Claim 17
Dependent Claim
5 words
R- or S-1-(Ethoxycarbonyloxy)ethyl 6-alpha-(benzyloxycarbonylaminomethyl)penicillanate 1,1-dioxide.
Claim 18
Dependent Claim
5 words
R- or S-1-(Ethoxycarbonyloxy)ethyl 6-alpha-(benzyloxycarbonylaminomethyl)penicillanate 1,1-dioxide.
Claim 19
Dependent Claim
7 words
The compound of claim 15 having R-stereo-chemistry.
Claim 20
Dependent Claim
7 words
The compound of claim 15 having S-stereo-chemistry.
Claim 21
Dependent Claim
13 words
R- or S-1-(Ethoxycarbonyloxy)ethyl 6-alpha-(aminomethyl)penicillanate 1,1-dioxide, or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
13 words
R- or S-1-(Ethoxycarbonyloxy)ethyl 6-alpha-(aminomethyl)penicillanate 1,1-dioxide, or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
7 words
The compound of claim 18 having R-stereo-chemistry.
Claim 24
Dependent Claim
7 words
The compound of claim 18 having S-stereo-chemistry.
References Cited (Backward Citations)
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US4237051A
Cited
US4309347A
Cited
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Cited
US4287181A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-03-04 | 1988-09-03 | 1989-03-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-04 | 1992-09-03 | 1993-03-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-04 | 1996-09-03 | 1997-03-05 | $7700.00 | Window Closed / Lapsed |