IE42458L - Syn -7- (2- hydroxyiminoacetamido) -3-¹pyridiniummethyl-cephalosporins. - Google Patents
Syn -7- (2- hydroxyiminoacetamido) -3-¹pyridiniummethyl-cephalosporins.Info
- Publication number
- IE42458L IE42458L IE752786A IE278675A IE42458L IE 42458 L IE42458 L IE 42458L IE 752786 A IE752786 A IE 752786A IE 278675 A IE278675 A IE 278675A IE 42458 L IE42458 L IE 42458L
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- syn isomer
- resulting
- group
- rdurule
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Compounds with antibiotic activity and the formula I <IMAGE> in which the symbols B, R<1>, R<2> and R<3> have the meaning stated in Claim 1, are prepared in the form of the syn isomer or a mixture of syn isomer and anti isomer, where the content of the syn isomer is at least 90%, by reacting a corresponding ceph-3-em-4-carboxylic acid which is substituted in position 3 by a group -CH2X where X is a substituent which can be replaced by the pyridine residue, where appropriate with intermediate protection of the 4-carboxyl group, with an R<3>-substituted pyridine and, if the precursor has an R<1>COCONH group in position 7, converting the resulting compound into the corresponding ceph-3-em compound I by reaction with a hydroxylamine R<2>ONH2. Resulting compounds I in which B is &rdurule& S->O can subsequently be reduced to the corresponding, preferred, compounds in which B is &rdurule& S. In another process, the resulting carboxylic acids (I) are esterified. The compounds are distinguished by an antibiotic activity with a broad spectrum of action, especially by a high activity against Gram-negative microorganisms including those which produce beta -lactamases, and furthermore have a high stability to beta -lactamases produced by some Gram-negative organisms, and to esterases.
[GB1522140A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB55213/74A GB1522140A (en) | 1974-12-20 | 1974-12-20 | Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl cephalosporins methods for their preparation and compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42458L true IE42458L (en) | 1976-06-20 |
| IE42458B1 IE42458B1 (en) | 1980-08-13 |
Family
ID=10473287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2786/75A IE42458B1 (en) | 1974-12-20 | 1975-12-19 | Syn-7-(2-hydroxyiminoacetamido)-3-pyridiniummethyl-cephalosporins, methods for their preparation and compositions containing them |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5191287A (en) |
| AT (1) | AT343804B (en) |
| AU (1) | AU506951B2 (en) |
| BE (1) | BE836872R (en) |
| CA (1) | CA1074297A (en) |
| CH (2) | CH627758A5 (en) |
| DE (1) | DE2557397A1 (en) |
| DK (1) | DK582775A (en) |
| FR (1) | FR2294707A1 (en) |
| GB (1) | GB1522140A (en) |
| IE (1) | IE42458B1 (en) |
| NL (1) | NL7514847A (en) |
| NZ (1) | NZ179598A (en) |
| SE (1) | SE7514475L (en) |
| ZA (1) | ZA757890B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963542A (en) * | 1976-09-08 | 1990-10-16 | Takeda Chemical Industries, Ltd. | Cephalosporin derivatives |
| US4198504A (en) | 1978-11-02 | 1980-04-15 | Bristol-Myers Company | [3-(Pyridinium)-7-(naphthyiridinyl carbonylamino)acetamido]cephalosporanic acid derivatives |
| BE883453A (en) | 1979-05-25 | 1980-11-24 | Glaxo Group Ltd | INTERMEDIATE COMPOUNDS FOR THE PREPARATION OF CEPHALOSPORINS |
| CH645906A5 (en) * | 1979-10-02 | 1984-10-31 | Glaxo Group Ltd | CEPHALOSPORINANTIBIOTICS. |
| DE3006888A1 (en) * | 1980-02-23 | 1981-09-10 | Hoechst Ag, 6000 Frankfurt | CEPHALOSPORINE DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
| US5202315A (en) * | 1989-05-11 | 1993-04-13 | Lucky, Ltd. | Cephalosporin compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1974
- 1974-12-20 GB GB55213/74A patent/GB1522140A/en not_active Expired
-
1975
- 1975-12-19 DE DE19752557397 patent/DE2557397A1/en not_active Withdrawn
- 1975-12-19 ZA ZA757890A patent/ZA757890B/en unknown
- 1975-12-19 IE IE2786/75A patent/IE42458B1/en unknown
- 1975-12-19 BE BE162939A patent/BE836872R/en active
- 1975-12-19 FR FR7539200A patent/FR2294707A1/en active Granted
- 1975-12-19 DK DK582775A patent/DK582775A/en unknown
- 1975-12-19 AT AT970175A patent/AT343804B/en not_active IP Right Cessation
- 1975-12-19 AU AU87744/75A patent/AU506951B2/en not_active Expired
- 1975-12-19 NL NL7514847A patent/NL7514847A/en not_active Application Discontinuation
- 1975-12-19 CA CA242,140A patent/CA1074297A/en not_active Expired
- 1975-12-19 NZ NZ179598A patent/NZ179598A/en unknown
- 1975-12-19 JP JP50150664A patent/JPS5191287A/ja active Pending
- 1975-12-19 CH CH1655375A patent/CH627758A5/en not_active IP Right Cessation
- 1975-12-19 SE SE7514475A patent/SE7514475L/en not_active Application Discontinuation
-
1980
- 1980-05-16 CH CH396880A patent/CH629211A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU506951B2 (en) | 1980-01-31 |
| NL7514847A (en) | 1976-06-22 |
| AU8774475A (en) | 1977-06-23 |
| CH627758A5 (en) | 1982-01-29 |
| GB1522140A (en) | 1978-08-23 |
| AT343804B (en) | 1978-06-26 |
| DE2557397A1 (en) | 1976-06-24 |
| ATA970175A (en) | 1977-10-15 |
| SE7514475L (en) | 1976-06-21 |
| ZA757890B (en) | 1976-11-24 |
| JPS5191287A (en) | 1976-08-10 |
| FR2294707A1 (en) | 1976-07-16 |
| NZ179598A (en) | 1978-04-03 |
| FR2294707B1 (en) | 1978-09-29 |
| CH629211A5 (en) | 1982-04-15 |
| DK582775A (en) | 1976-06-21 |
| BE836872R (en) | 1976-06-21 |
| IE42458B1 (en) | 1980-08-13 |
| CA1074297A (en) | 1980-03-25 |
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