IT1139874B - 8-Fluoro-erythromycin and erythronolide antibiotics - Google Patents
8-Fluoro-erythromycin and erythronolide antibioticsInfo
- Publication number
- IT1139874B IT1139874B IT25344/81A IT2534481A IT1139874B IT 1139874 B IT1139874 B IT 1139874B IT 25344/81 A IT25344/81 A IT 25344/81A IT 2534481 A IT2534481 A IT 2534481A IT 1139874 B IT1139874 B IT 1139874B
- Authority
- IT
- Italy
- Prior art keywords
- erythronolide
- fluoro
- erythromycin
- antibiotics
- fluoroerythronolide
- Prior art date
Links
- 229960001398 flurithromycin Drugs 0.000 title abstract 6
- 239000003242 anti bacterial agent Substances 0.000 title abstract 4
- 229940088710 antibiotic agent Drugs 0.000 title abstract 4
- 229930193775 erythronolide Natural products 0.000 title abstract 2
- ZFBRGCCVTUPRFQ-UHFFFAOYSA-N erythronolide-B Natural products CCC1OC(=O)C(C)C(O)C(C)C(O)C(C)(O)CC(C)C(=O)C(C)C(O)C1C ZFBRGCCVTUPRFQ-UHFFFAOYSA-N 0.000 title abstract 2
- XOEUHCONYHZURQ-HNUBZJOYSA-N flurithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@@](C)(F)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 XOEUHCONYHZURQ-HNUBZJOYSA-N 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=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 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 229930006677 Erythromycin A Natural products 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
8-Fluoro-erythromycin and erythronolide antibiotics of formula (I) and their acid salts, esp. carbonates, are new. The new antibiotics are (85)-8-fluoroerythromycin A (I R is CH3, R1 is OH); (85)-8-fluoroerythromycin B (I R is CH3, R1 is H); (85)-8- fluoroerythromycin C (I R is H, R1 is OH); (85)-8-fluoro- erythromycin D (I R, R1 are H); 3-O-oleandrosyl-5-O-desosaminyl- (85)-8-fluoroerythronolide A (II, R1 is OH) and 3-O-oleandrosyl- 5-O-desoaminyl-(85)-8-fluoroerythronolide B (II R1 is H). The following intermediates are also new (85)-8-fluoro- erythronolide A; (85)-8-fluoro-erythronolide A 6,9,9,11- acetal; 8,9-anhydro-erythronolide A 6,9-hemiacetal; (85)-8- fluoro-3-O-micarosyl-8(S)-fluoroerythronolide B; 3-O-micarosyl- (85)-8-fluoroerythronolide B 6,9;9,11-acetal and 3-O-micarosyl- 8,9-anhydro-erythronolide B 6,9-hemiacetal. These antibiotics have a similar spectrum of activity to that of erythromycin A, but have better stability to acid and may be adm. orally.
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25344/81A IT1139874B (en) | 1981-11-27 | 1981-11-27 | 8-Fluoro-erythromycin and erythronolide antibiotics |
| DE8282200019T DE3268339D1 (en) | 1981-01-09 | 1982-01-08 | Novel semisynthetic macrolidic antibiotics, microbiological processes for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them |
| CH98/82A CH658250A5 (en) | 1981-01-09 | 1982-01-08 | NEW SEMI-SYNTHETIC MACROLIDIC ANTIBIOTICS, MICROBIOLOGICAL PROCEDURES FOR THEIR PREPARATION NEW INTERMEDIATES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR8200187A FR2502155A1 (en) | 1981-01-09 | 1982-01-08 | NOVEL SEMI-SYNTHETIC MACROLIDE ANTIBIOTICS, MICROBIOLOGICAL PROCESS FOR THE PREPARATION THEREOF AND MICROORGANISM THEREFOR, NOVEL INTERMEDIATE PRODUCTS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| US06/338,105 US4439426A (en) | 1981-01-09 | 1982-01-08 | Semisynthetic macrolidic antibiotics, intermediate compounds for their preparation and related pharmaceutical compositions containing them |
| AT82200019T ATE17351T1 (en) | 1981-01-09 | 1982-01-08 | SEMISYNTHETIC MACROLIDS ANTIBIOTICS, PROCESSES FOR THEIR MICROBIOLOGICAL PRODUCTION, THEIR PHARMACEUTICAL COMPOSITIONS, RELATED MICROORGANISMS AND INTERMEDIATE COMPOUNDS FOR THEIR REPRESENTATION. |
| FI820057A FI72346C (en) | 1981-01-09 | 1982-01-08 | SAETT ATT FRAMSTAELLA NYA CHEAP SYNTHETIC MACROIDANTIBIOTICS. |
| CA000393832A CA1169375A (en) | 1981-01-09 | 1982-01-08 | Semisynthetic macrolidic antibiotics, microbiological process for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them |
| EP82200019A EP0056291B1 (en) | 1981-01-09 | 1982-01-08 | Novel semisynthetic macrolidic antibiotics, microbiological processes for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them |
| FI834570A FI80688C (en) | 1981-01-09 | 1983-12-13 | NY MELLANPRODUKT (8S) -8- FLUORERYTRONOLID A SOM AER ANVAENDBAR VID FRAMSTAELLNING AV HALVSYNETETISKA MACROLIDANTIBIOTIKA. |
| US06/570,833 US4540662A (en) | 1981-01-09 | 1984-01-16 | Semisynthetic macrolidic antibiotics, intermediate compounds for their preparation and related pharmaceutical compositions containing compounds for their preparation and related pharmaceutical compositions containing them |
| CA000452649A CA1189856A (en) | 1981-01-09 | 1984-04-24 | Semisynthetic macrolidic antibiotics, microbiological processes for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25344/81A IT1139874B (en) | 1981-11-27 | 1981-11-27 | 8-Fluoro-erythromycin and erythronolide antibiotics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IT8125344A0 IT8125344A0 (en) | 1981-11-27 |
| IT1139874B true IT1139874B (en) | 1986-09-24 |
Family
ID=11216415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT25344/81A IT1139874B (en) | 1981-01-09 | 1981-11-27 | 8-Fluoro-erythromycin and erythronolide antibiotics |
Country Status (1)
| Country | Link |
|---|---|
| IT (1) | IT1139874B (en) |
-
1981
- 1981-11-27 IT IT25344/81A patent/IT1139874B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IT8125344A0 (en) | 1981-11-27 |
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