US4036829A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Lactonyl esters of penicillins
Assignee: Beecham Group PLC
•
Filing: 1976-08-05
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Granted: 1977-07-19
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Expires: 1996-08-05
Abstract
Abstract Lactonyl esters of Penicillins of the formula <IMAGE> WHEREIN R1 is an antibacterially active penicillin-completing side chain; R is hydrogen, methyl or phenyl; and Ra, Rb, Rc, Rd are hydrogen, lower alkyl, lower alkoxy, halo, and nitro, provided that when R is hydrogen and R1 is D- alpha -aminophenylacetamido and Ra, Rb, Rc, and Rd are not all hydrogen are disclosed to possess antibacterial properties.
Inventors
- 👤 Harry Ferres
- 👤 John Peter Clayton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:33
CPC Classifications
C; C07; C07D; C07D499/00; A; A61; A61P; A61P31/00; A61P31/04; C07C; C07C51/00; C07C51/16; C07C51/31; C07D307/00; C07D307/77; C07D307/87; C07D307/88; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/58; C07D333/00; C07D333/50; C07D333/72; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
164 words
A compound of formula (I) or a pharmaceutically acceptable acid addition salt of said compound having a basic nitrogen atom: ##STR35## wherein R is hydrogen, methyl or phenyl; R a , R b , R c and R d are selected from hydrogen, lower alkyl, lower alkoxy, halo and nitro; R 1 is an antibacterially active penicillin-completing side chain selected from phenylacetamido, p-hydroxyphenylacetamido; p-heptylphenylacetamido; phenoxyacetamido; α-phenoxypropionamido; α-phenoxybutyramido; 2,6-dimethoxyphenylacetamido; 3-phenyl-5-methyl-isoxazole-4-carbamido; 3-(2-chlorophenyl)-5-methyl-isoxazole-4-carbamido; 3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbamido; 3-(2-chloro-6-fluorophenyl)-5-methyl-isoxazole-4-carbamido; 2-ethoxy-naphthyl-1-carbamido; o, m or p-aminophenylacetamido; 3-carboxy-quinoxalin-2-carbamido; 2-furylacetamido; 2-thienylacetamido; 3-thienylacetamido; 3-pyridylacetamido; isothiazolylacetamido; 3-hexenamide; 2-biphenylamido; n-hexanamido; n-octanamido; propionamido; α-aminophenylacetamido; α-amino-2-thienylacetamido; α -amino-3-thienylacetamido; α-methyl-aminophenylacetamido; α-amino-2- or -3- or -4-chlorophenylacetamido; α-amino-2-methoxy-phenylacetamido; α -amino-2,4-dichlorophenylacetamido; α -amino-3,4-dichlorophenylacetamido; α -amino-α -methylphenylacetamido; α-amino-4-hydroxyphenylacetamido; α-amino-3-chloro-4-hydroxy-phenylacetamido; α-methylphenylacetamido; α-hydroxyphenylacetamido; α-carboxyphenylacetamido; α-(5-tetrazolyl)phenylacetamido; α-guanidino-2-thienylacetamido; α-guanidino-4-hydroxyphenylacetamido α-guanidino-4-hydroxy-2- or -3-methylphenylacetamido; α-carboxy-3-thienylacetamido; α-sulphaminophenylacetamido; α-sulphamino- 3-thienylacetamido; α-(N-methylsulphamino)-phenylacetamido; α-azidophenylacetamido; 1-aminocyclohexylcarbamido; 1-aminocyclopentylcarbamido; 5-amino-5-carboxypentanamido; α-phenoxyphenylacetamido; α -phenyl-β-sulphaminopropionamido; α-sulphophenylacetamido; α-guanidinophenylacetamido; β-amino-β-cyclohexylpropionamido; α-(benzyloxycarbonyl)-phenylacetamido; or 2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl, (hexahydro-1H-azepin-1-yl)methyleneamino or N,N-dimethylformamidino, provided that when R is hydrogen and R 1 is D-α-aminophenylacetamido R a , R b , R c and R d are not all hydrogen.
Claim 2
Dependent Claim
164 words
A compound of formula (I) or a pharmaceutically acceptable acid addition salt of said compound having a basic nitrogen atom: ##STR35## wherein R is hydrogen, methyl or phenyl; R a , R b , R c and R d are selected from hydrogen, lower alkyl, lower alkoxy, halo and nitro; R 1 is an antibacterially active penicillin-completing side chain selected from phenylacetamido, p-hydroxyphenylacetamido; p-heptylphenylacetamido; phenoxyacetamido; α-phenoxypropionamido; α-phenoxybutyramido; 2,6-dimethoxyphenylacetamido; 3-phenyl-5-methyl-isoxazole-4-carbamido; 3-(2-chlorophenyl)-5-methyl-isoxazole-4-carbamido; 3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbamido; 3-(2-chloro-6-fluorophenyl)-5-methyl-isoxazole-4-carbamido; 2-ethoxy-naphthyl-1-carbamido; o, m or p-aminophenylacetamido; 3-carboxy-quinoxalin-2-carbamido; 2-furylacetamido; 2-thienylacetamido; 3-thienylacetamido; 3-pyridylacetamido; isothiazolylacetamido; 3-hexenamide; 2-biphenylamido; n-hexanamido; n-octanamido; propionamido; α-aminophenylacetamido; α-amino-2-thienylacetamido; α -amino-3-thienylacetamido; α-methyl-aminophenylacetamido; α-amino-2- or -3- or -4-chlorophenylacetamido; α-amino-2-methoxy-phenylacetamido; α -amino-2,4-dichlorophenylacetamido; α -amino-3,4-dichlorophenylacetamido; α -amino-α -methylphenylacetamido; α-amino-4-hydroxyphenylacetamido; α-amino-3-chloro-4-hydroxy-phenylacetamido; α-methylphenylacetamido; α-hydroxyphenylacetamido; α-carboxyphenylacetamido; α-(5-tetrazolyl)phenylacetamido; α-guanidino-2-thienylacetamido; α-guanidino-4-hydroxyphenylacetamido α-guanidino-4-hydroxy-2- or -3-methylphenylacetamido; α-carboxy-3-thienylacetamido; α-sulphaminophenylacetamido; α-sulphamino- 3-thienylacetamido; α-(N-methylsulphamino)-phenylacetamido; α-azidophenylacetamido; 1-aminocyclohexylcarbamido; 1-aminocyclopentylcarbamido; 5-amino-5-carboxypentanamido; α-phenoxyphenylacetamido; α -phenyl-β-sulphaminopropionamido; α-sulphophenylacetamido; α-guanidinophenylacetamido; β-amino-β-cyclohexylpropionamido; α-(benzyloxycarbonyl)-phenylacetamido; or 2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl, (hexahydro-1H-azepin-1-yl)methyleneamino or N,N-dimethylformamidino, provided that when R is hydrogen and R 1 is D-α-aminophenylacetamido R a , R b , R c and R d are not all hydrogen.
Claim 3
Dependent Claim
19 words
The compound of claim 1 which is 5,6-dimethoxyphthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable non-toxic acid addition salt thereof.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is phenylacetamido.
Claim 5
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is phenoxymethylacetamido.
Claim 6
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is α-aminophenylacetamido.
Claim 7
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is α-guanidino-p-hydroxyphenylacetamido.
Claim 8
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is α-carboxyphenylacetamido.
Claim 9
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is α-azidophenylacetamido.
Claim 10
Dependent Claim
18 words
The compound of claim 1 which is 6-methoxyphthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
18 words
The compound of claim 1 which is 6-chlorophthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
18 words
The compound of claim 1 which is 4,5,6-trimethoxyphthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
18 words
The compound of claim 1 which is 6-bromophthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
18 words
The compound of claim 1 which is 3-methylphthalide 6[D(-)α-aminophenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[D(-)α-amino-3-thienylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
18 words
The compound of claim 1 which is 5,6-dimethoxyphthalide 6[D,L-α-amino-3-thienylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Dependent Claim
10 words
The compound of claim 1 which is 6-nitrophthalide 6[phenylacetamido] penicillanate.
Claim 18
Dependent Claim
10 words
The compound of claim 1 which is 5,6-dimethylphthalide 6[phenylacetamido] penicillanate.
Claim 19
Dependent Claim
10 words
The compound of claim 1 which is 6-methoxyphthalide 6[phenylacetamido] penicillanate.
Claim 20
Dependent Claim
10 words
The compound of claim 1 which is 3-phenylphthalide 6[phenylacetamido] penicillanate.
Claim 21
Dependent Claim
10 words
The compound of claim 1 which is 3-methylphthalide 6[phenylacetamido] penicillanate.
Claim 22
Dependent Claim
10 words
The compound of claim 1 which is 3-methylphthalide 6[phenoxyacetamido] penicillanate.
Claim 23
Dependent Claim
10 words
The compound of claim 1 which is 3-phenylphthalide 6[phenoxyacetamido] penicillanate.
Claim 24
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[D(-)α-guanidino-p-hydroxyphenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 25
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[α-guanidino-4-hydroxy-3-methylphenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[α-guanidino-4-hydroxy-2-methylphenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 27
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[α-sulpho-phenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim
18 words
The compound of claim 1 which is phthalide 6[α-carboxy-phenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 29
Dependent Claim
10 words
The compound of claim 1 which is α, β-bis-phthalide 6[α-carboxyphenylacetamido]penicillanate.
Claim 30
Dependent Claim
10 words
The compound of claim 1 which is α, β-bis-phthalide 6[α-carboxy-3-thienylacetamido]penicillanate.
Claim 31
Dependent Claim
8 words
The compound of claim 1 which is α-sulphophenylacetamido.
Claim 32
Dependent Claim
3 words
Phthalide 6[α-azido-phenylacetamido] penicillanate.
Claim 33
Dependent Claim
3 words
Phthalide 6[α-azido-phenylacetamido] penicillanate.
Claim 34
Dependent Claim
11 words
Phthalide 6[β-amino-β-cyclohex-3-enyl-propionamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof;
Claim 35
Dependent Claim
11 words
Phthalide 6[β-amino-β-cyclohex-3-enyl-propionamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof;
Claim 36
Dependent Claim
3 words
Phthalide 6[-(3-o-chlorophenyl-5-methyl-isoxazole-4-carbamido] penicillanate.
Claim 37
Dependent Claim
3 words
Phthalide 6[-(3-o-chlorophenyl-5-methyl-isoxazole-4-carbamido] penicillanate.
Claim 38
Dependent Claim
11 words
Phthalide 6[D(-)α-amino-(p-hydroxy-phenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 39
Dependent Claim
11 words
Phthalide 6[D(-)α-amino-(p-hydroxy-phenylacetamido] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 40
Dependent Claim
11 words
Phthalide 6[(hexahydro-1H-azepin-1-yl)-methyleneamino] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 41
Dependent Claim
11 words
Phthalide 6[(hexahydro-1H-azepin-1-yl)-methyleneamino] penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 42
Dependent Claim
13 words
Phthalide 6-(N,N-dimethylformamidine-N 1 -) penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 43
Dependent Claim
13 words
Phthalide 6-(N,N-dimethylformamidine-N 1 -) penicillanate or a pharmaceutically acceptable acid addition salt thereof.
Claim 44
Dependent Claim
3 words
Phthalide 6[2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl] penicillanate.
Claim 45
Dependent Claim
3 words
Phthalide 6[2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl] penicillanate.
References Cited (Backward Citations)
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US3697507A
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GB1377661A
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US3860579A
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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) | 1980-07-18 | 1981-01-17 | 1981-07-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-18 | 1985-01-17 | 1985-07-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-18 | 1989-01-17 | 1989-07-19 | $7700.00 | Window Closed / Lapsed |