US4224442A
Expired / Lapsed
US
⏱️ 0.0 years remaining
7-Ureido acetamido substituted cephalosporin antibiotics
Assignee: Eli Lilly and Co
•
Filing: 1975-03-03
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Granted: 1980-09-23
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Expires: 1995-03-03
Abstract
Abstract Cephalosporin antibiotics of the formula ##STR1## wherein R is ##STR2## and R" is H, C 1 -C 3 alkyl, allyl, propargyl, C 3 -C 6 cycloalkyl, phenyl, benzyl or furfuryl; R' is H or methyl; or R is a cyclic urea group for example, R is ##STR3## R 1 is phenyl, thienyl, or furyl; R 3 is a lower alkyl substituted 1H-tetrazole-5-thio or 1,3,4-thiadiazole-5-thio group and R 4 is hydrogen or an active ester group, e.g., an acetoxymethyl group; are highly active broad spectrum antibiotics especially useful in the treatment of infections attributable to the gram-negative microorganisms.
Inventors
- 👤 Robin D. G. Cooper
- 👤 David K. Herron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:16
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/38
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
110 words
The compound of the formula ##STR60## wherein R is a 3-substituted ureido group represented by the formula ##STR61## wherein R" is hydrogen, C 1 -C 3 alkyl, allyl, propargyl, C 3 -C 6 cycloalkyl, phenyl, benzyl, or furfuryl; R' is hydrogen or methyl; R 1 is phenyl, mono or dihydroxyphenyl, mono or dihalophenyl, monohydroxy substituted mono or dihalophenyl, or ##STR62## R 2 is acetoxy, ##STR63## wherein Z is C 1 -C 4 lower alkyl; R 3 is hydrogen, indanyl, phthalidyl, or an acyloxymethyl group of the formula ##STR64## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 3 is hydrogen, the pharmaceutically acceptable non-toxic salts thereof.
Claim 2
Dependent Claim
110 words
The compound of the formula ##STR60## wherein R is a 3-substituted ureido group represented by the formula ##STR61## wherein R" is hydrogen, C 1 -C 3 alkyl, allyl, propargyl, C 3 -C 6 cycloalkyl, phenyl, benzyl, or furfuryl; R' is hydrogen or methyl; R 1 is phenyl, mono or dihydroxyphenyl, mono or dihalophenyl, monohydroxy substituted mono or dihalophenyl, or ##STR62## R 2 is acetoxy, ##STR63## wherein Z is C 1 -C 4 lower alkyl; R 3 is hydrogen, indanyl, phthalidyl, or an acyloxymethyl group of the formula ##STR64## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 3 is hydrogen, the pharmaceutically acceptable non-toxic salts thereof.
Claim 3
Dependent Claim
9 words
The compound of claim 1 wherein R' is methyl.
Claim 4
Dependent Claim
24 words
A compound of claim 2 of the formula: ##STR65## wherein R 1 is phenyl, hydroxyphenyl, hydroxy-substituted-chlorophenyl or 2-thienyl, and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
31 words
A compound of claim 2 of the formula: ##STR66## wherein R 1 is phenyl, hydroxyphenyl, hydroxy-substituted chlorophenyl or 2-thienyl; R 2 is 1-methyl-1H-tetrazol-5-ylthio or 2-methyl-1,3,4-thiadiazol-5-ylthio, and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
10 words
The compound of claim 4, said compound being 7-[α-(3-methylcarbamoyl-3-methyl-1-ureido)-α-phenylacetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 7
Dependent Claim
11 words
The compound of claim 4, said compound being 7-[α-(3-methylcarbamoyl-3-methyl-1-ureido)-α-(4-hydroxyphenyl) acetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 8
Dependent Claim
10 words
The compound of claim 4, said compound being 7-[α-(3-methylcarbamoyl-3-methyl-1-ureido)-α-phenylacetamido]-3-(5-methyl-1,3,4-thiadiazole-2-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 9
Dependent Claim
10 words
The compound of claim 4, said compound being 7-[α(3-methylcarbamoyl-3-methyl-1-ureido)-α-(4-hydroxyphenyl)acetamido]-3-(5-methyl-1,3,4-thiadiazole-2-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 10
Dependent Claim
10 words
The compound of claim 4 said compound being 7-[α-(3-methylcarbamoyl-3-methyl-1-ureido)-α-(2-thienyl)-acetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 11
Dependent Claim
9 words
The compound of claim 1 wherein R' is hydrogen.
Claim 12
Dependent Claim
10 words
The compound of claim 10 said compound being 7-[α-3-methylcarbamoyl-1-ureido)-α-phenylacetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 13
Dependent Claim
10 words
The compound of claim 10 said compound being 7-[α-(3-methylcarbamoyl-1-ureido)-α-(2-thienyl)-acetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 14
Dependent Claim
10 words
The compound of claim 10 said compound being 7-[α-(3-methylcarbamoyl-1-ureido)-α-(4-hydroxyphenyl)-acetamido]-3-(5-methyl-1,3,4-thiadiazole-2-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 15
Dependent Claim
84 words
A compound of the formula ##STR67## wherein Y is hydrogen, acetyl or methanesulfonyl; n is 2 or 3; R 1 is phenyl, mono or dihydroxyphenyl, mono or dihalophenyl, monohydroxy substituted mono or dihalophenyl, or ##STR68## R 2 is ##STR69## wherein Z is C 1 -C 4 lower alkyl; R 3 is hydrogen, indanyl, phthalidyl, or an acyloxymethyl group of the formula ##STR70## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 3 is hydrogen, the pharmaceutically acceptable non-toxic salts thereof.
Claim 16
Dependent Claim
84 words
A compound of the formula ##STR67## wherein Y is hydrogen, acetyl or methanesulfonyl; n is 2 or 3; R 1 is phenyl, mono or dihydroxyphenyl, mono or dihalophenyl, monohydroxy substituted mono or dihalophenyl, or ##STR68## R 2 is ##STR69## wherein Z is C 1 -C 4 lower alkyl; R 3 is hydrogen, indanyl, phthalidyl, or an acyloxymethyl group of the formula ##STR70## wherein Y' is C 1 -C 4 alkyl or phenyl; and when R 3 is hydrogen, the pharmaceutically acceptable non-toxic salts thereof.
Claim 17
Dependent Claim
40 words
A compound of claim 14 of the formula: ##STR71## wherein R is H--, ##STR72## or CH 3 --SO 2 --; R 1 is phenyl, hydroxyphenyl, hydroxy-substituted-chlorophenyl or 2-thienyl; R 2 is 1-methyl-1H-tetrazol-5-ylthio or 2-methyl-1,3,4-thiadiazol-5-ylthio, and the pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
10 words
The compound of claim 15, said compound being 7-[α-(imidazolidine-2-one-1-ylcarbonylamino)-α-phenyl-acetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 19
Dependent Claim
10 words
The compound of claim 15, said compound being 7-[α-(imidazolidine-2-one-1-ylcarbonylamino)-α-phenyl-acetamido]-3-(5-methyl-1,3,4-thiadiazole-2-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 20
Dependent Claim
10 words
The compound of claim 15, said compound being 7-[α-(imidazolidine-2-one-1-ylcarbonylamino)-α-(4-hydroxyphenyl)acetamido]-3-(1-methyl-1H-tetrazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 21
Dependent Claim
10 words
The compound of claim 15, said compound being 7-[α-(imidazolidine-2-one-1-ylcarbonylamino)-α-(4-hydroxyphenyl)acetamido]-3-(5-methyl-1,3,4-thiadiazole-2-ylthiomethyl)-3-cephem-4-carboxylic acid.
Claim 22
Dependent Claim
16 words
The compound of claim 15 of the formula ##STR73## and the pharmaceutically acceptable non-toxic salts thereof.
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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) | 1983-09-23 | 1984-03-24 | 1984-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-23 | 1988-03-24 | 1988-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-23 | 1992-03-24 | 1992-09-23 | $7700.00 | Window Closed / Lapsed |