US3890309A
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Cephalosporin derivatives
Assignee: Takeda Pharmaceutical Co Ltd
•
Filing: 1972-07-12
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Granted: 1975-06-17
•
Expires: 1992-07-12
Abstract
Abstract New cephalosporin derivatives of the formula, WHEREIN R represents the same or different substituent selected from halogen atom, nitro group, lower alkyl group, amino group or carboxylic group, n is an integer from 0 to 3 and X represents hydrogen or halogen atom. These compounds are remarkably effective for inhibiting the growth of a broad range of microorganisms including Proteus morganii and Mycobacterium tuberculosis. Examples thereof include 7-(1''-pyrazolylacetamido)3-(2''''-pyridylthiomethyl)-3-cephem-4-carboxylic acid 1''''-oxide, 7-(4''-nitro-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3cephem-4 -carboxylic acid 1''''-oxide, 7-(4''-chloro-1''pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem -4carboxylic acid 1''''-oxide, 7-(3'',5''-dimethyl-1''pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem -4carboxylic acid 1''''-oxide and 7-(1-pyrazolylacetamido)-3-(4''chloro-2''-pyridylthiomethyl)-3-cephem-4 -carboxylic acid 1''oxide.
Inventors
- 👤 Michihiko Ochiai
- 👤 Osami Aki
- 👤 Akira Morimoto
- 👤 Taiiti Okada
- 👤 Katsutada Masuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:43
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D231/14; C07D231/16; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/36
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
5 words
A COMPOUND OF THE FORMULA,
Claim 2
Dependent Claim
5 words
A COMPOUND OF THE FORMULA,
Claim 3
Dependent Claim
16 words
A compound according to claim 1, wherein the substituent group at the 3-position is 2-pyridylthiomethyl N-oxide.
Claim 4
Dependent Claim
11 words
A compound as claimed in claim 2, namely 7-(1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4-carboxylic acid 1''''-oxide.
Claim 5
Dependent Claim
12 words
A compound as claimed in claim 2, namely 7-(4''-nitro-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4 -carboxylic acid 1''''-oxide.
Claim 6
Dependent Claim
12 words
A compound as claimed in claim 2, namely 7-(4''-chloro-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4 -carboxylic acid 1''''-oxide.
Claim 7
Dependent Claim
12 words
A compound as claimed in claim 2, namely 7-(3'',5''-dimethyl-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem -4-carboxylic acid 1''''-oxide.
Claim 8
Dependent Claim
12 words
A compound as claimed in claim 1, namely 7-(1-pyrazolylacetamido)-3-(4''-chloro-2''-pyridylthiomethyl)-3-cephem-4 -carboxylic acid 1''-oxide.
Claim 9
Dependent Claim
38 words
A compound according to claim 1, wherein R represents the same or different substituent selected from chlorine, bromine, nitro group, lower alkyl group, amino group or carboxyl group, and further wherein X represents hydrogen, chlorine, bromine or fluorine.
Claim 10
Dependent Claim
35 words
A compound according to claim 8, wherein R represents the same or different substituent selected from chlorine, nitro group, lower alkyl group, amino group or carboxyl group, and further wherein X represents hydrogen or chlorine.
Claim 11
Dependent Claim
5 words
A compound of the formula
Claim 12
Dependent Claim
5 words
A compound of the formula
Claim 13
Dependent Claim
29 words
A compound according to claim 10, wherein said compound is a salt having a cation selected from the group consisting of sodium, potassium, magnesium, calcium, aluminum, ammonium, and triethylamine.
Claim 14
Dependent Claim
12 words
A compound according to claim 10, wherein R represents chlorine or bromine.
Claim 15
Dependent Claim
12 words
A compound according to claim 10, wherein R represents an amino group.
Claim 16
Dependent Claim
20 words
A compound according to claim 1, wherein R represents a lower alkyl group having from 1 to 4 carbon atoms.
Claim 17
Dependent Claim
30 words
A compound according to claim 10, wherein R represents a substituted lower alkyl group substituted with a member selected from the group consisting of hydroxy, nitro, amino, halogen and carboxyl.
Claim 18
Dependent Claim
12 words
A compound according to claim 10, wherein R represents a carboxyl group.
Claim 19
Dependent Claim
10 words
A compound according to claim 10, wherein R represents amide.
Claim 20
Dependent Claim
10 words
A compound according to claim 10, wherein X represents hydrogen.
Claim 21
Dependent Claim
18 words
A compound according to claim 10, wherein X represents a halogen atom selected from chlorine, bromine and fluorine.
Claim 22
Dependent Claim
9 words
A compound according to claim 1, namely 7-(1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4-carboxylate 1''''-oxide.
Claim 23
Dependent Claim
12 words
A compound according to claim 1, namely sodium of 7-(4''-nitro-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4 -carboxylate 1''''-oxide.
Claim 24
Dependent Claim
12 words
A compound according to claim 1, namely sodium 7-(4''-chloro-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4 -carboxylic acid 1''''-oxide.
Claim 25
Dependent Claim
12 words
A compound according to claim 1, namely sodium 7-(3'', 5''-dimethyl-1''-pyrazolylacetamido)-3-(2''''-pyridylthiomethyl)-3-cephem-4 -carboxylate 1''''-oxide.
Claim 26
Dependent Claim
37 words
A compound according to claim 1, wherein R represents the same or different substituent selected from chlorine, bromine, a nitro group, an amino group or a carboxyl group, and wherein X represents hydrogen, chlorine, bromine, or fluorine.
Claim 27
Dependent Claim
10 words
A compound according to claim 24, wherein R represents chlorine.
Claim 28
Dependent Claim
10 words
A compound according to claim 24, wherein X represents chlorine.
Claim 29
Dependent Claim
22 words
A compound according to claim 1, wherein the acyl group in the formula is 1-pyrazolyl-acetyl, 3,5-dimethyl-1-pyrazolylacetyl, 4-chloro-1-pyrazolyl-acetyl, 4-nitropyrazolylacetyl, 4-amino-1-pyrazolylacetyl, 4-hydroxymethyl-1-pyrazolylacetyl and 4-methyl-1-pyrazolylacetyl.
Claim 30
Dependent Claim
37 words
A compound according to claim 10, wherein R represents the same or different substituent selected from chlorine, bromine, an amino group, methyl, a carboxyl group, and an amide and wherein X represents hydrogen, chlorine, bromine or fluorine.
Claim 31
Dependent Claim
68 words
A compound according to claim 10, wherein R represents the same or different substituent selected from the group consisting of chlorine, bromine, an amino group, lower alkyl having 1 to 4 carbon atoms, a carboxyl group, a substituted lower alkyl group substituted with a hydroxy group, nitro group, amino group, halogen atom or carboxyl group, and an amide, and further wherein X represents hydrogen, chlorine, bromine or fluorine.
Claim 32
Dependent Claim
28 words
A compound according to claim 29, wherein said substituted lower alkyl group is substituted with a hydroxy group, a nitro group, an amino group, or a carboxyl group.
Claim 33
Dependent Claim
63 words
A compound according to claim 29, wherein R represents the same or different substituents selected from the group consisting of chlorine, bromine, an amino group, lower alkyl, a carboxyl group, an amide, and a substituted lower alkyl group substituted with a hydroxy group, a nitro group, an amino group, or a carboxyl group, and further wherein X represents hydrogen, chlorine, bromine, or fluorine.
Claim 34
Dependent Claim
16 words
A compound according to claim 31, wherein said lower alkyl groups have from 1-4 carbon atoms.
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) | 1978-06-16 | 1978-12-16 | 1979-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-06-16 | 1982-12-16 | 1983-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-06-16 | 1986-12-16 | 1987-06-17 | $7700.00 | Window Closed / Lapsed |