US4091213A
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7-Cyclizedamino-3-heterothiomethyl cephalosporin derivatives
Assignee: Bristol Myers Co
•
Filing: 1977-01-10
•
Granted: 1978-05-23
•
Expires: 1997-01-10
Abstract
Abstract Compounds of the formula ##STR1## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, R 2 is carboxyl or 2-furyl or an aliphatic, aromatic or heterocyclic radical to which there is also attached a strongly acidic group in the form of its sodium or potassium salt, and R 3 is tetrazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-3-yl or 1,2,4-triazol-5-yl, each of such groups being unsubstituted or substituted with one or two lower alkyl groups of one to four carbon atoms are prepared by reacting the appropriate aldehyde with the corresponding amphoteric cephalosporin. Preferred products have the structure ##STR2## in which A is --H or --SO 3 Na.
Inventors
- 👤 Murray A. Kaplan
- 👤 William J. Gottstein
- 👤 Alphonse P. Granatek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 12:13
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/54; A61K31/542; A61K31/545; C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/58
Claims Analysis
Total Claims: 81
Claim 1
Independent Claim
87 words
A compound of the formula ##STR28## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt, and R 3 is tetrazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-3-yl or 1,2,4-triazol-5-yl, each of such groups being unsubstituted or substituted with one or two lower alkly groups of one to four carbon atoms.
Claim 2
Dependent Claim
87 words
A compound of the formula ##STR28## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt, and R 3 is tetrazol-5-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-oxadiazol-3-yl or 1,2,4-triazol-5-yl, each of such groups being unsubstituted or substituted with one or two lower alkly groups of one to four carbon atoms.
Claim 3
Dependent Claim
11 words
A compund of claim 1 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 4
Dependent Claim
11 words
A compound of claim 1 wherein R 2 is phenyl-2-sulfonic acid.
Claim 5
Dependent Claim
11 words
A compound of claim 1 wherein R 2 is 4-methoxyphenyl-3-sulfonic acid.
Claim 6
Dependent Claim
11 words
A compound of claim 1 wherein R 2 is 4-hydroxyphenyl-3-sulfonic acid.
Claim 7
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 2-carboxymethoxyphenyl.
Claim 8
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 4-carboxymethoxyphenyl.
Claim 9
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 3-hydroxy-4-carboxyphenyl.
Claim 10
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 4-(2'-carboxy)vinylphenyl.
Claim 11
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 2-carboxyphenyl.
Claim 12
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 3-carboxyphenyl.
Claim 13
Dependent Claim
57 words
A compound of the formula ##STR29## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 14
Dependent Claim
57 words
A compound of the formula ##STR29## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 15
Dependent Claim
11 words
A compound of claim 12 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 16
Dependent Claim
11 words
A compound of claim 12 wherein R 2 is phenyl-2-sulfonic acid.
Claim 17
Dependent Claim
11 words
A compound of claim 12 wherein R 2 is 4-methoxyphenyl-3-sulfonic acid.
Claim 18
Dependent Claim
11 words
A compound of claim 12 wherein R 2 is 4-hydroxyphenyl-3-sulfonic acid.
Claim 19
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 2-carboxymethoxyphenyl.
Claim 20
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 4-carboxymethoxyphenyl.
Claim 21
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 3-hydroxy-4-carboxyphenyl.
Claim 22
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 4-(2'-carboxy)vinylphenyl.
Claim 23
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 2-carboxyphenyl.
Claim 24
Dependent Claim
10 words
A compound of claim 12 wherein R 2 is 3-carboxyphenyl.
Claim 25
Dependent Claim
15 words
A compound of the formula ##STR30## wherein R 1 is hydrogen, sodium or potassium, and
Claim 26
Dependent Claim
15 words
A compound of the formula ##STR30## wherein R 1 is hydrogen, sodium or potassium, and
Claim 27
Dependent Claim
35 words
R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 28
Dependent Claim
35 words
R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 29
Dependent Claim
11 words
A compound of claim 23 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 30
Dependent Claim
11 words
A compound of claim 23 wherein R 2 is phenyl-2-sulfonic acid.
Claim 31
Dependent Claim
11 words
A compound of claim 23 wherein R 2 is 4-methoxyphenyl-3-sulfonic acid.
Claim 32
Dependent Claim
11 words
A compound of claim 23 wherein R 2 is 4-hydroxyphenyl-3-sulfonic acid.
Claim 33
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 2-carboxymethoxyphenyl.
Claim 34
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 4-carboxymethoxyphenyl.
Claim 35
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 3-hydroxy-4-carboxyphenyl.
Claim 36
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 4-(2'-carboxy)vinylphenyl.
Claim 37
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 2-carboxyphenyl.
Claim 38
Dependent Claim
10 words
A compound of claim 23 wherein R 2 is 3-carboxyphenyl.
Claim 39
Dependent Claim
14 words
The compound of claim 24 having the D configuration wherein R 1 is sodium.
Claim 40
Dependent Claim
14 words
The compound of claim 24 having the D configuration wherein R 1 is potassium.
Claim 41
Dependent Claim
14 words
The compound of claim 24 having the D configuration wherein R 1 is hydrogen.
Claim 42
Dependent Claim
57 words
A compound of the formula ##STR31## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 43
Dependent Claim
57 words
A compound of the formula ##STR31## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 44
Dependent Claim
11 words
A compound of claim 37 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 45
Dependent Claim
53 words
A compound of claim 37 of the formula ##STR32## wherein R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 46
Dependent Claim
11 words
A compound of claim 39 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 47
Dependent Claim
14 words
The compound of claim 40 having the D configuration wherein R 1 is sodium.
Claim 48
Dependent Claim
14 words
The compound of claim 40 having the D configuration wherein R 1 is potassium.
Claim 49
Dependent Claim
14 words
The compound of claim 40 having the D configuration wherein R 1 is hydrogen.
Claim 50
Dependent Claim
57 words
A compound of the formula ##STR33## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 51
Dependent Claim
57 words
A compound of the formula ##STR33## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 52
Dependent Claim
11 words
A compound of claim 44 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 53
Dependent Claim
53 words
A compound of claim 44 of the formula ##STR34## wherein R 1 is hydrogen, sodium or potassium, and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 54
Dependent Claim
11 words
A compound of claim 46 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 55
Dependent Claim
14 words
The compound of claim 47 having the D configuration wherein R 1 is sodium.
Claim 56
Dependent Claim
14 words
The compound of claim 47 having the D configuration wherein R 1 is potassium.
Claim 57
Dependent Claim
14 words
The compound of claim 47 having the D configuration wherein R 1 is hydrogen.
Claim 58
Dependent Claim
57 words
A compound of the formula ##STR35## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 59
Dependent Claim
57 words
A compound of the formula ##STR35## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 60
Dependent Claim
11 words
A compound of claim 51 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 61
Dependent Claim
53 words
A compound of claim 51 of the formula ##STR36## wherein R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 62
Dependent Claim
11 words
A compound of claim 53 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 63
Dependent Claim
14 words
The compound of claim 54 having the D configuration wherein R 1 is sodium.
Claim 64
Dependent Claim
14 words
The compound of claim 54 having the D configuration wherein R 1 is potassium.
Claim 65
Dependent Claim
14 words
The compound of claim 54 having the D configuration wherein R 1 is hydrogen.
Claim 66
Dependent Claim
57 words
A compound of the formula ##STR37## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 67
Dependent Claim
57 words
A compound of the formula ##STR37## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 68
Dependent Claim
11 words
A compound of claim 58 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 69
Dependent Claim
53 words
A compound of claim 58 of the formula ##STR38## wherein R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 70
Dependent Claim
11 words
A compound of claim 60 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 71
Dependent Claim
14 words
The compound of claim 61 having the D configuration wherein R 1 is sodium.
Claim 72
Dependent Claim
14 words
The compound of claim 61 having the D configuration wherein R 1 is potassium.
Claim 73
Dependent Claim
14 words
The compouund of claim 61 having the D configuration wherein R 1 is hydrogen.
Claim 74
Dependent Claim
57 words
A compound of the formula ##STR39## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 75
Dependent Claim
57 words
A compound of the formula ##STR39## wherein A is hydrogen, hydroxy, methyl or methoxy, R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 76
Dependent Claim
11 words
A compound of claim 65 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 77
Dependent Claim
53 words
A compound of claim 65 of the formula ##STR40## wherein R 1 is hydrogen, sodium or potassium and R 2 is a member selected from the group consisting of 2-furan-5-sulfonic acid, phenyl-2-sulfonic acid, 4-methoxyphenyl-3-sulfonic acid, 4-hydroxyphenyl-3-sulfonic acid, 2-carboxymethoxyphenyl, 4-carboxymethoxyphenyl, 3-hydroxy-4-carboxyphenyl, 4-(2'-carboxy)vinylphenyl, 2-carboxyphenyl and 3-carboxyphenyl in the form of its sodium or potassium salt.
Claim 78
Dependent Claim
11 words
A compound of claim 67 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 79
Dependent Claim
14 words
The compound of claim 68 having the D configuration wherein R 1 is sodium.
Claim 80
Dependent Claim
14 words
The compound of claim 68 having the D configuration wherein R 1 is potassium.
Claim 81
Dependent Claim
14 words
The compound of claim 68 having the D configuration wherein R 1 is hydrogen.
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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) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |