US4026888A
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Certain derivatives of particular 3-thiolated cephalosporins
Assignee: Bristol Myers Co
•
Filing: 1976-01-30
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Granted: 1977-05-31
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Expires: 1996-01-30
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 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 1,2,3-triazol-5-yl, such group 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. A preferred product has the structure ##STR2##
Inventors
- 👤 Murray A. Kaplan
- 👤 William J. Gottstein
- 👤 Alphonse P. Granatek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:14
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: 64
Claim 1
Independent Claim
85 words
A compound of the formula ##STR37## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt, and R 3 is, 1,2,3-triazol-5-yl, such group being unsubstituted or substituted with one or two lower alkyl groups of one to four carbon atoms.
Claim 2
Dependent Claim
85 words
A compound of the formula ##STR37## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt, and R 3 is, 1,2,3-triazol-5-yl, such group being unsubstituted or substituted with one or two lower alkyl groups of one to four carbon atoms.
Claim 3
Dependent Claim
11 words
A compound 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 carboxyl.
Claim 12
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 2-carboxyphenyl.
Claim 13
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is 3-carboxyphenyl.
Claim 14
Dependent Claim
11 words
A compound of claim 1 wherein R 2 is methanesulfonic acid.
Claim 15
Dependent Claim
11 words
A compound of claim 1 wherein R 2 is methanedisulfonic acid.
Claim 16
Dependent Claim
62 words
A compound of the formula ##STR38## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 17
Dependent Claim
62 words
A compound of the formula ##STR38## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 18
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 19
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is phenyl-2-sulfonic acid.
Claim 20
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is 4-methoxyphenyl-3-sulfonic acid.
Claim 21
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is 4-hydroxyphenyl-3-sulfonic acid.
Claim 22
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 2-carboxymethoxyphenyl.
Claim 23
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 4-carboxymethoxyphenyl.
Claim 24
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 3-hydroxy-4-carboxyphenyl.
Claim 25
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 4-(2'-carboxy)vinylphenyl.
Claim 26
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is carboxyl.
Claim 27
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 2-carboxyphenyl.
Claim 28
Dependent Claim
10 words
A compound of claim 15 wherein R 2 is 3-carboxyphenyl.
Claim 29
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is methanesulfonic acid.
Claim 30
Dependent Claim
11 words
A compound of claim 15 wherein R 2 is methanedisulfonic acid.
Claim 31
Dependent Claim
56 words
A compound of the formula ##STR39## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 32
Dependent Claim
56 words
A compound of the formula ##STR39## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 33
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 34
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is phenyl-2-sulfonic acid.
Claim 35
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is 4-methoxyphenyl-3-sulfonic acid.
Claim 36
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is 4-hydroxyphenyl-3-sulfonic acid.
Claim 37
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 2-carboxymethoxyphenyl.
Claim 38
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 4-carboxymethoxyphenyl.
Claim 39
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 3-hydroxy-4-carboxyphenyl.
Claim 40
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 4-(2'-carboxy)vinylphenyl.
Claim 41
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is carboxyl.
Claim 42
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 2-carboxyphenyl.
Claim 43
Dependent Claim
10 words
A compound of claim 29 wherein R 2 is 3-carboxyphenyl.
Claim 44
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is methanesulfonic acid.
Claim 45
Dependent Claim
11 words
A compound of claim 29 wherein R 2 is methanedisulfonic acid.
Claim 46
Dependent Claim
14 words
The compound of claim 30 having the D configuration wherein R 1 is sodium.
Claim 47
Dependent Claim
14 words
The compound of claim 30 having the D configuration wherein R 1 is potassium.
Claim 48
Dependent Claim
14 words
The compound of claim 30 having the D configuration wherein R 1 is hydrogen.
Claim 49
Dependent Claim
62 words
A compound of the formula ##STR40## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 50
Dependent Claim
62 words
A compound of the formula ##STR40## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 51
Dependent Claim
11 words
A compound of claim 46 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 52
Dependent Claim
58 words
A compound of claim 46 of the formula ##STR41## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 53
Dependent Claim
11 words
A compound of claim 48 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 54
Dependent Claim
14 words
The compound of claim 49 having the D configuration wherein R 1 is sodium.
Claim 55
Dependent Claim
14 words
The compound of claim 49 having the D configuration wherein R 1 is potassium.
Claim 56
Dependent Claim
14 words
The compound of claim 49 having the D configuration wherein R 1 is hydrogen.
Claim 57
Dependent Claim
62 words
A compound of the formula ##STR42## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potasssium salt.
Claim 58
Dependent Claim
62 words
A compound of the formula ##STR42## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potasssium salt.
Claim 59
Dependent Claim
11 words
A compound of claim 53 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 60
Dependent Claim
58 words
A compound of claim 53 of the formula ##STR43## 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, carboxyl, 2-carboxyphenyl, 3-carboxyphenyl, methanesulfonic acid and methanedisulfonic acid in the form of its sodium or potassium salt.
Claim 61
Dependent Claim
11 words
A compound of claim 55 wherein R 2 is 2-furan-5-sulfonic acid.
Claim 62
Dependent Claim
14 words
The compound of claim 56 having the D configuration wherein R 1 is sodium.
Claim 63
Dependent Claim
14 words
The compound of claim 56 having the D configuration wherein R 1 is potassium.
Claim 64
Dependent Claim
14 words
The compound of claim 56 having the D configuration wherein R 1 is hydrogen.
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) | 1980-05-30 | 1980-11-29 | 1981-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-30 | 1984-11-29 | 1985-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-30 | 1988-11-29 | 1989-05-31 | $7700.00 | Window Closed / Lapsed |