US4338439A
Expired / Lapsed
US
⏱️ 0.0 years remaining
7-[2-[(Substituted benzoyl]amino]acetamido]cephalosporins
Assignee: Eli Lilly and Co
•
Filing: 1978-12-07
•
Granted: 1982-07-06
•
Expires: 1998-12-07
Abstract
Abstract Cephalosporin antibiotics of the formula ##STR1## wherein R is cyclohexadienyl, phenyl or substituted phenyl, 2-thienyl, 3-thienyl, 2-furyl or 3-furyl; R 1 is a substituted phenyl having 1 to 4 hydroxy substituents or 1 to 3 amino substituents; and wherein Q is halo, methoxy, methyl or a group of the formula --CH 2 R 2 wherein R 2 is alkanoyloxy, carbamoyloxy, alkoxy, halo, pyridinium or substituted pyridinium or a group of the formula --SR 3 wherein R 3 is alkyl, phenyl, substituted phenyl or a 5 or 6 membered-heteroaryl group having from 1 to 4 heteroatoms selected from the group consisting of O, S, and N; are highly active broad spectrum antibiotics especially useful in the treatment of infections attributable to the gram-negative microorganisms.
Inventors
- 👤 David K. Herron
- 👤 William H. W. Lunn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:38
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/59
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
225 words
A compound of the formula ##STR75## wherein Q is methyl or a group of the formula --CH 2 R 2 whereiin R 2 is (a) C 2 -C 4 alkanoyloxy; (b) C 1 -C 4 alkoxy; or (c) pyridinium or monosubstituted pyridinium wherein the substituent is selected from the group consisting of C 1 -C 4 alkyl, halo, hydroxy, hydroxymethyl, trifluoromethyl, carbamoyl, C 1 -C 4 alkylcarbamoyl, carboxy, cyano, and acetyl; and R is cyclohexadienyl, phenyl or phenyl substituted with 1 or 2 groups selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, hydroxy, protected hydroxy, nitro, cyano, methanesulfonamido and trifluoromethyl; or R is 2-thienyl, 3-thienyl, 2-furyl or 3-furyl; and R 1 is a group of the formula ##STR76## wherein X is 1, 2, or 3, and y is 1 or 2, and wherein A is substituent selected from the group consisting of hydrogen, halo, C 1 -C 4 alkoxy, amino, protected amino, hydroxy, protected hydroxy, C 1 -C 4 alkyl, nitro, cyano, methanesulfonamido and trifluoromethyl, and R 6 is hydrogen or an amino protecting group; and R 0 is hydrogen, indanyl, phthalidyl or an acyloxymethyl group of the formula ##STR77## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 0 is hydrogen, the pharmaceutical acceptable nontoxic salts of the acids represented thereby.
Claim 2
Dependent Claim
225 words
A compound of the formula ##STR75## wherein Q is methyl or a group of the formula --CH 2 R 2 whereiin R 2 is (a) C 2 -C 4 alkanoyloxy; (b) C 1 -C 4 alkoxy; or (c) pyridinium or monosubstituted pyridinium wherein the substituent is selected from the group consisting of C 1 -C 4 alkyl, halo, hydroxy, hydroxymethyl, trifluoromethyl, carbamoyl, C 1 -C 4 alkylcarbamoyl, carboxy, cyano, and acetyl; and R is cyclohexadienyl, phenyl or phenyl substituted with 1 or 2 groups selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, hydroxy, protected hydroxy, nitro, cyano, methanesulfonamido and trifluoromethyl; or R is 2-thienyl, 3-thienyl, 2-furyl or 3-furyl; and R 1 is a group of the formula ##STR76## wherein X is 1, 2, or 3, and y is 1 or 2, and wherein A is substituent selected from the group consisting of hydrogen, halo, C 1 -C 4 alkoxy, amino, protected amino, hydroxy, protected hydroxy, C 1 -C 4 alkyl, nitro, cyano, methanesulfonamido and trifluoromethyl, and R 6 is hydrogen or an amino protecting group; and R 0 is hydrogen, indanyl, phthalidyl or an acyloxymethyl group of the formula ##STR77## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 0 is hydrogen, the pharmaceutical acceptable nontoxic salts of the acids represented thereby.
Claim 3
Dependent Claim
26 words
The compound of claim 1 wherein Q is a group of the formula --CH 2 R 2 wherein R 2 is C 2 -C 4 alkanoyloxy.
Claim 4
Dependent Claim
23 words
The compound of claim 1 or claim 2 wherein R o is hydrogen and R 1 is a group of the formula ##STR78##
Claim 5
Dependent Claim
23 words
The compound of claim 1 or claim 2 wherein R o is hydrogen and R 1 is a group of the formula ##STR79##
Claim 6
Dependent Claim
9 words
The compound of claim 1 wherein Q is methyl.
Claim 7
Dependent Claim
18 words
The compound of claim 1 wherein Q is a group of the formula --CH 2 R 2 .
Claim 8
Dependent Claim
10 words
The compound of claim 6 wherein R 2 is acetoxy.
Claim 9
Dependent Claim
10 words
The compound of claim 6 wherein R 2 is methoxy.
Claim 10
Dependent Claim
13 words
The compound of claim 6 wherein R 2 is pyridinium or substituted pyridinium.
Claim 11
Dependent Claim
19 words
The compound of claim 6 wherein R 1 is a group of the formula ##STR80## wherein A is hydrogen.
Claim 12
Dependent Claim
39 words
The compound of claim 10 wherein R 1 is a group of the formula ##STR81## wherein X is 2 or 3 and wherein at least two of the hydroxy substituents are bonded to the phenyl at adjacent carbon atoms.
Claim 13
Dependent Claim
15 words
The compound of claim 11 wherein R is phenyl, 3-hydroxyphenyl, 4-hydroxyphenyl, 3-methanesulfonamidophenyl, 2-thienyl or 1,4-cyclohexadienyl.
Claim 14
Dependent Claim
11 words
The compound of claim 12 wherein R is phenyl or 4-hydroxyphenyl.
Claim 15
Dependent Claim
13 words
The compound of claim 13 wherein R 1 is 2,3-dihydroxyphenyl, 3,4-dihydroxyphenyl, or 3,4,5-trihydroxyphenyl.
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) | 1985-07-05 | 1986-01-04 | 1986-07-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-05 | 1990-01-04 | 1990-07-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-05 | 1994-01-04 | 1994-07-06 | $7700.00 | Window Closed / Lapsed |