GB1389195A - Antibiotics - Google Patents
AntibioticsInfo
- Publication number
- GB1389195A GB1389195A GB2724274A GB2724274A GB1389195A GB 1389195 A GB1389195 A GB 1389195A GB 2724274 A GB2724274 A GB 2724274A GB 2724274 A GB2724274 A GB 2724274A GB 1389195 A GB1389195 A GB 1389195A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- group
- reacting
- penicillin
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- -1 cephalosporin compounds Chemical class 0.000 abstract 4
- 229930186147 Cephalosporin Natural products 0.000 abstract 3
- 229930182555 Penicillin Natural products 0.000 abstract 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 3
- 229940124587 cephalosporin Drugs 0.000 abstract 3
- 229940049954 penicillin Drugs 0.000 abstract 3
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1389195 Penicillin and cephalosporin compounds GLAXO LABORATORIES Ltd 14 Jan 1972 [29 Jan 1971 1 Oct 1971] 27242/74 Divided out of 1389194 Heading C2C Novel 7#-acylamidoceph-3-em-4-carboxylic acids and 6# - acylamidopenam - 3 - carboxylic acids and non-toxic salts and esters and corresponding 1-oxides thereof, wherein the acylamido group has the structure where R is a hydrogen atom or an organic group and R<SP>a</SP> is a hydrogen atom or an acyl group, the compounds being anti isomers or a mixture of syn and anti isomers containing at least 75% of the anti isomer, are prepared by reacting a 6-aminopenicillanic acid or a 7- aminocephalosporanic acid with an acid of Formula (VI) wherein R and R<SP>a</SP> have the aforesaid meanings, or an N-acylating derivative of the acid (VI), or by reacting a penicillin or cephalosporin compound of Formula (XI) wherein B is >S or >S#O, R<SP>1</SP> is H or a carboxyl-blocking group and Z is a group in which 1 or 2 carbons link the nuclear S atom and the carbon atom bearing the carboxyl group and which, when it contains 2 carbons, has olefinic unsaturation such that the compound (XI) is a ceph-3-em compound, with the aforesaid acid (VI), if necessary followed by separation of the product into the syn and anti isomers. Acids of the Formula (VI) above are prepared by reacting an appropriate glyoxylic acid with hydroxylamine, and if necessary subsequently reacting the product wherein R<SP>a</SP> is hydrogen with an acylating agent to give a product wherein R<SP>a</SP> is an acyl group. The acid (VI) may be converted to the corresponding acid chloride by treatment with PCl 5 . The inventive penicillin and cephalosporin compounds may be mixed with a pharmaceutically acceptable carrier or diluent to give pharmaceutical compositions having antibiotic activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2724274A GB1389195A (en) | 1971-01-29 | 1971-01-29 | Antibiotics |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2724274A GB1389195A (en) | 1971-01-29 | 1971-01-29 | Antibiotics |
| GB2724574 | 1971-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1389195A true GB1389195A (en) | 1975-04-03 |
Family
ID=26258711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2724274A Expired GB1389195A (en) | 1971-01-29 | 1971-01-29 | Antibiotics |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1389195A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503234A (en) * | 1980-07-24 | 1985-03-05 | Lonza Ltd. | Production of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyimino acetic esters |
| GB2173791A (en) * | 1985-04-16 | 1986-10-22 | Ici Plc | Fungicidal cyano oximes |
| US4904811A (en) * | 1986-07-28 | 1990-02-27 | Bayer Aktiengesellschaft | (Z)-2-cyano-2-oximino-acetyl chlorides |
-
1971
- 1971-01-29 GB GB2724274A patent/GB1389195A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503234A (en) * | 1980-07-24 | 1985-03-05 | Lonza Ltd. | Production of 2-(2-aminothiazole-4-yl)-2-(syn)-methoxyimino acetic esters |
| GB2173791A (en) * | 1985-04-16 | 1986-10-22 | Ici Plc | Fungicidal cyano oximes |
| GB2173791B (en) * | 1985-04-16 | 1989-07-05 | Ici Plc | Fungicidal cyano oximes |
| US4904811A (en) * | 1986-07-28 | 1990-02-27 | Bayer Aktiengesellschaft | (Z)-2-cyano-2-oximino-acetyl chlorides |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |