GB1221088A - Improvements in or relating to erythromycin oxime acyl derivatives - Google Patents
Improvements in or relating to erythromycin oxime acyl derivativesInfo
- Publication number
- GB1221088A GB1221088A GB3266468A GB3266468A GB1221088A GB 1221088 A GB1221088 A GB 1221088A GB 3266468 A GB3266468 A GB 3266468A GB 3266468 A GB3266468 A GB 3266468A GB 1221088 A GB1221088 A GB 1221088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- erythromycin oxime
- chloride
- erythromycin
- compounds
- oxime
- 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
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\O)/[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 aromatic monocarboxylic acid Chemical class 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 150000002148 esters Chemical class 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
- JDRMYOQETPMYQX-UHFFFAOYSA-M 4-methoxy-4-oxobutanoate Chemical compound COC(=O)CCC([O-])=O JDRMYOQETPMYQX-UHFFFAOYSA-M 0.000 abstract 1
- UZNLHJCCGYKCIL-UHFFFAOYSA-N 6-ethoxy-6-oxohexanoic acid Chemical compound CCOC(=O)CCCCC(O)=O UZNLHJCCGYKCIL-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
1,221,088. Esters of erythromycin oxime. PLIVA PHARMACEUTICAL & CHEMICAL WORKS. 9 July, 1968 [3 Aug., 1967], No. 32664/68. Heading C2A. The invention comprises mono-acyl and bisacyl derivatives of erythromycin oxime, wherein the acyl group is derived from a chloride of an aliphatic or aromatic monocarboxylic acid of formula RCOCl wherein R is C 2 to C 17 alkyl or phenyl, or from a dicarboxylic acid ester chloride of formula ClOC(CH 2 ) n COOR<SP>1</SP>, wherein R<SP>1</SP> is methyl or ethyl and n is 1 to 4. The erythromycin oxime esters are produced by acylating erythromycin oxime with the appropriate acid chloride or acid ester chloride in an inert organic solvent in the presence of an alkali metal salt using an equivalent of the acylating agent and salt for the preparation of the mono compound and two equivalents for the preparation of the bis compound. Typical compounds are the monopropionate, monobenzoate, monomethylsuccinate, monoethyl adipate and the corresponding bis-compounds of erythromycin oxime. These compounds are effective antibiotics. Erythromycin oxime is described in Specification 1,100,504.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU1184667 | 1967-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1221088A true GB1221088A (en) | 1971-02-03 |
Family
ID=25559704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3266468A Expired GB1221088A (en) | 1967-08-03 | 1968-07-09 | Improvements in or relating to erythromycin oxime acyl derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1221088A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2201874A1 (en) * | 1972-10-10 | 1974-05-03 | Abbott Lab | |
| WO1999025723A1 (en) * | 1997-11-17 | 1999-05-27 | Abbott Laboratories | Chemical synthesis of 6-o-alkyl erythromycin a |
-
1968
- 1968-07-09 GB GB3266468A patent/GB1221088A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2201874A1 (en) * | 1972-10-10 | 1974-05-03 | Abbott Lab | |
| WO1999025723A1 (en) * | 1997-11-17 | 1999-05-27 | Abbott Laboratories | Chemical synthesis of 6-o-alkyl erythromycin a |
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