US4152432A
Expired / Lapsed
US
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3-Acetoxymethyl-7-(iminoacetamido)-cephalosporanic acid derivatives
Assignee: Sanofi Aventis France
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Filing: 1977-07-19
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Granted: 1979-05-01
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Expires: 1997-07-19
Abstract
Abstract Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.
Inventors
- 👤 Rene Heymes
- 👤 Andre Lutz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 14:38
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/02; C07D277/20; C07D277/587; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/26; C07D501/34
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
54 words
A compound of the formula ##STR46## wherein R is hydrogen, R' is alkyl of 1 to 4 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal, magnesium and a pharmaceutically acceptable organic amine base and the OR' group is in the syn position.
Claim 2
Dependent Claim
54 words
A compound of the formula ##STR46## wherein R is hydrogen, R' is alkyl of 1 to 4 carbon atoms, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal, magnesium and a pharmaceutically acceptable organic amine base and the OR' group is in the syn position.
Claim 3
Dependent Claim
21 words
A compound of claim 1 wherein A is selected from the group consisting of hydrogen, sodium and an equivalent of diethylamine.
Claim 4
Dependent Claim
9 words
A compound of claim 1 which is 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid.
Claim 5
Dependent Claim
9 words
A compound of claim 1 which is sodium 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-ceph-3-eme-4-carboxylate.
Claim 6
Dependent Claim
13 words
A compound of claim 1 which is the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxylminoacetamido]-ceph-3-eme-4-carboxylic acid.
Claim 7
Dependent Claim
16 words
A compound of claim 1 which is the sodium salt of the acid of claim 5.
Claim 8
Dependent Claim
23 words
A compound of claim 1 which is the crystalline sodium salt of 3-acetoxymethyl 7-[2-(2-amino 4-thiazolyl) 2-methoxy imino acetamido] ceph-3-eme 4-carboxylic acid, syn isomer.
Claim 9
Dependent Claim
21 words
A compound of claim 1 which is the crystalline sodium salt of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid, syn isomer, in hydrated or solvated form.
Claim 10
Dependent Claim
30 words
A compound of claim 1 selected from the group consisting of syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-ethoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid and its alkali metal, alkaline earth metal, magnesium and pharmaceutically acceptable organic amine salts.
Claim 11
Dependent Claim
31 words
A compound of claim 1 selected from the group consisting of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid and its alkali metal, alkaline earth metal magnesium and pharmaceutically acceptable organic amine salts.
Claim 12
Dependent Claim
21 words
An antibiotic composition comprising an antibiotically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 13
Dependent Claim
17 words
A composition of claim 11 wherein A is selected from the group consisting of hydrogen and sodium.
Claim 14
Dependent Claim
15 words
A composition of claim 11 wherein the compound is the syn isomer of 3-acetoxymethyl-7-/2-(2-amino-4-thiazolyl-2-methoxyiminoacetamido/-ceph-3-eme-4-carboxylic acid.
Claim 15
Dependent Claim
19 words
The composition of claim 11 wherein the compound is the sodium salt of the syn isomer of 3-acetoxymethyl-7-/2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido/-ceph-3-eme-4-carboxylic acid.
Claim 16
Dependent Claim
14 words
The composition of claim 11 wherein the compound is the compound of claim 11.
Claim 17
Dependent Claim
14 words
The composition of claim 11 wherein the compound is the compound of claim 12.
Claim 18
Dependent Claim
49 words
The composition of claim 11 wherein the compound is selected from the group consisting of 3-acetoxymethyl 7-[ 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid, its sodium salt and the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid, the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid and their alkali metal, alkaline earth metal, magnesium and pharmaceutically acceptable organic amine salts.
Claim 19
Dependent Claim
27 words
A method of combatting bacterial infections in warm-blooded animals comprising administering internally to warm-blooded animals an antibacterially effective amount of at least one compound of claim 1.
Claim 20
Dependent Claim
17 words
A method of claim 18 wherein A is selected from the group consisting of hydrogen and sodium.
Claim 21
Dependent Claim
36 words
A method of claim 18 wherein the compound is selected from the group consisting of the syn isomer of 3-acetoxymethyl-7-/2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido/-ceph-3-eme-4-carboxylic acid, its sodium salt, its cristalline sodium salt and its hydrated or solvated cristalline sodium salt.
Claim 22
Dependent Claim
43 words
The method of claim 18 wherein the compound is selected from the group consisting of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid, its sodium salt and the syn isomers of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetamido]-ceph-3-eme-4-carboxylic acid, 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid, and their alkali metal, alkaline earth metal, magnesium and pharmaceutically acceptable organic amine salts.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-04-30 | 1982-10-30 | 1983-05-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-04-30 | 1986-10-30 | 1987-05-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-04-30 | 1990-10-30 | 1991-05-01 | $7700.00 | Window Closed / Lapsed |