Patent FR1511976A successfully refreshed from Google Patents.
US4024249A
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Heteroarylacetamido cephalosporin
Assignee: Novartis Corp
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Filing: 1975-03-24
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Granted: 1977-05-17
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Expires: 1995-03-24
Abstract
Abstract Novel aminomethyl compounds of the formula ##STR1## wherein X denotes sulphur or oxygen, R denotes hydrogen or an amino protective group, R 1 denotes hydrogen, a free, etherified or esterified hydroxyl group or mercapto group or a substituted ammonium group, R 2 denotes hydroxyl or a carboxyl protective radical which together with the carbonyl grouping of the formula -C(=0)- forms a protected carboxyl group, and their salts, are antibacterial antibiotics or intermediates for the preparation thereof; pharmaceutical preparations containing such active compounds, are useful for combating micro-organisms such as gram-positive or gram-negative bacteria; An illustrative example is 3-acetoxymethyl-7β-[2-(5-aminomethyl-2-thienyl)-acetylamino]-ceph-3-em-4-carboxylic acid.
Inventors
- 👤 Beat Muller
- 👤 Heinrich Peter
- 👤 Peter Schneider
- 👤 Hans Bickel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 15:42
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D307/52; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/22; C07D333/24; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
89 words
A compound of the formula ##STR8## wherein X denotes sulphur or oxygen, R denotes hydrogen or an amino protective group, R 1 denotes a radical --S--R 4 , wherein R 4 is tetrazolyl, thiadiazolyl or tetrazolyl or thiadiazolyl substituted by lower alkyl, or a radical --S--R 5 , wherein R 5 is N-oxido-pyridazinyl or N-oxido-pyridazinyl substituted by lower alkyl, and R 2 denotes hydroxyl or a carboxyl protective radical which together with the carbonyl grouping of the formula --C(=O)-- forms a protected carboxyl group, and their therapeutically acceptable salts.
Claim 2
Dependent Claim
89 words
A compound of the formula ##STR8## wherein X denotes sulphur or oxygen, R denotes hydrogen or an amino protective group, R 1 denotes a radical --S--R 4 , wherein R 4 is tetrazolyl, thiadiazolyl or tetrazolyl or thiadiazolyl substituted by lower alkyl, or a radical --S--R 5 , wherein R 5 is N-oxido-pyridazinyl or N-oxido-pyridazinyl substituted by lower alkyl, and R 2 denotes hydroxyl or a carboxyl protective radical which together with the carbonyl grouping of the formula --C(=O)-- forms a protected carboxyl group, and their therapeutically acceptable salts.
Claim 3
Dependent Claim
158 words
A compound of the formula I according to claim 1, wherein X represents oxygen or sulphur, R denotes hydrogen, lower alkoxycarbonyl which on the carbon atom in α-position to the oxy group carries several aliphatic substituents or is branched, a methoxycarbonyl group substituted by benzoyl, β-halogenoalkoxycarbonyl, phenyl-lower alkoxycarbonyl, phenyl-lower alkoxycarbonyl substituted by lower alkyl, hydroxy, lower alkoxy or nitro, diphenylmethoxycarbonyl, benzyl, triphenylmethyl or diphenylmethoxycarbonyl or benzyl or triphenylmethyl substituted by lower alkoxy, R 1 represents a radical of the formula --S--R 4 , wherein R 4 represents tetrazolyl, thiadiazolyl or tetrazolyl or thiadiazolyl substituted by lower alkyl, or a radical of the formula --S--R 5 , wherein R 5 is N-oxido-pyridazinyl or N-oxido-pyridazinyl substituted by lower alkyl, and R 2 represents hydroxyl, tri-lower alkylsilyloxy, lower alkoxy branched at the α-position or substituted in the α-position by phenyl, phenyl substituted by lower alkoxy or nitro or benzoyl or substituted in the β-position by halogen, and their therapeutically acceptable salts.
Claim 4
Dependent Claim
81 words
A compound of the formula I ##STR9## wherein X is oxygen or sulphur, R denotes hydrogen, tert.-butoxycarbonyl, tert.-pentoxycarbonyl, phenacyloxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2-iodoethoxycarbonyl, benzyloxy- or 4-nitrobenzyloxycarbonyl, diphenylmethoxycarbonyl, 4,4'-dimethoxydiphenylmethoxycarbonyl, benzyl, p-methoxybenzyl or trityl, R 1 denotes a radical --S--R 4 , wherein R 4 is tetrazolyl, thidiazolyl, 1-methyl-1H-tetrazol-5-yl or 5-methyl-1,3,4-thiadiazol-2-yl, or a radical --S--R 5 , wherein R 5 is N-oxido-pyridazinyl or 6-methyl-1-oxido-pyridazin-3-yl, and R 2 is hydroxy, trimethylsilyloxy, tert.-butoxy, benzyloxy, 4-methoxybenzyloxy, 4-nitrobenzyloxy, diphenylmethoxy, 4,4'-dimethoxydiphenylmethoxy, phenacyl, 2,2,2-trichloroethoxy or 2-iodoethoxy, and their therapeutically acceptable salts.
Claim 5
Dependent Claim
81 words
A compound of the formula I ##STR9## wherein X is oxygen or sulphur, R denotes hydrogen, tert.-butoxycarbonyl, tert.-pentoxycarbonyl, phenacyloxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2-iodoethoxycarbonyl, benzyloxy- or 4-nitrobenzyloxycarbonyl, diphenylmethoxycarbonyl, 4,4'-dimethoxydiphenylmethoxycarbonyl, benzyl, p-methoxybenzyl or trityl, R 1 denotes a radical --S--R 4 , wherein R 4 is tetrazolyl, thidiazolyl, 1-methyl-1H-tetrazol-5-yl or 5-methyl-1,3,4-thiadiazol-2-yl, or a radical --S--R 5 , wherein R 5 is N-oxido-pyridazinyl or 6-methyl-1-oxido-pyridazin-3-yl, and R 2 is hydroxy, trimethylsilyloxy, tert.-butoxy, benzyloxy, 4-methoxybenzyloxy, 4-nitrobenzyloxy, diphenylmethoxy, 4,4'-dimethoxydiphenylmethoxy, phenacyl, 2,2,2-trichloroethoxy or 2-iodoethoxy, and their therapeutically acceptable salts.
Claim 6
Dependent Claim
18 words
A compound as claimed in claim 3 being 7β-[2-(5-tert.-butoxycarbonylaminomethyl-2-thienyl)-acetylamino]-3-[(1-methyl-1H-tetrazol-5-ylthio)-methyl]-ceph-3-em-4-carboxylic acid diphenylmethyl ester or a therapeutically acceptable salt thereof.
Claim 7
Dependent Claim
16 words
A compound as claimed in claim 3 being 7β-[2-(5-aminomethyl-2-thienyl)-acetylamino]-3-[(1-methyl-1H-tetrazol-5-ylthio)-methyl]-ceph-3-em-4-carboxylic acid or a therapeutically acceptable salt thereof.
Claim 8
Dependent Claim
16 words
A compound as claimed in claim 3 being 7β-[2-(5-aminomethyl-2-thienyl)-acetylamino]-3-[(5-methyl-1,3,4-thiadiazol-2-ylthio)-methyl]-ceph-3-em-4-carboxylic acid or a therapeutically acceptable salt thereof.
Claim 9
Dependent Claim
16 words
A compound as claimed in claim 3 being 7β-[2-(5-aminomethyl-2-thienyl)-acetylamino]-3-[(6-methyl-1-oxido-pyridazin-3-ylthio)-methyl]-ceph-3-em-4-carboxylic acid or a therapeutically acceptable salt thereof.
Claim 10
Dependent Claim
22 words
An antibiotic pharmaceutical composition comprising a therapeutically effective amount of a compound as claimed in claim 3 together with a pharmaceutical carrier.
References Cited (Backward Citations)
US3488730A
Cited
US3382241A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-16 | 1980-11-15 | 1981-05-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-16 | 1984-11-15 | 1985-05-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-16 | 1988-11-15 | 1989-05-17 | $7700.00 | Window Closed / Lapsed |