CA1169375A - Semisynthetic macrolidic antibiotics, microbiological process for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing them - Google Patents
Semisynthetic macrolidic antibiotics, microbiological process for their preparation and related microorganism, novel intermediate compounds for their preparation and related pharmaceutical compositions containing themInfo
- Publication number
- CA1169375A CA1169375A CA000393832A CA393832A CA1169375A CA 1169375 A CA1169375 A CA 1169375A CA 000393832 A CA000393832 A CA 000393832A CA 393832 A CA393832 A CA 393832A CA 1169375 A CA1169375 A CA 1169375A
- Authority
- CA
- Canada
- Prior art keywords
- fluoroerythronolide
- fluoroerythromycin
- esters
- produced
- chemical equivalent
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims description 69
- 230000008569 process Effects 0.000 title claims description 30
- 239000003242 anti bacterial agent Substances 0.000 title claims description 26
- 229940088710 antibiotic agent Drugs 0.000 title claims description 25
- 244000005700 microbiome Species 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 45
- 230000002906 microbiologic effect Effects 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 238000000855 fermentation Methods 0.000 claims abstract description 35
- 230000004151 fermentation Effects 0.000 claims abstract description 34
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 13
- 241000187747 Streptomyces Species 0.000 claims abstract description 11
- 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 claims description 61
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
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- 239000002253 acid Substances 0.000 claims description 10
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 6
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- 238000002955 isolation Methods 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims 6
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- 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 description 47
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- 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 abstract description 7
- ZFBRGCCVTUPRFQ-HWRKYNCUSA-N erythronolide B Chemical class CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C ZFBRGCCVTUPRFQ-HWRKYNCUSA-N 0.000 abstract description 6
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 abstract description 5
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- 238000003786 synthesis reaction Methods 0.000 abstract description 4
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- 150000001241 acetals Chemical class 0.000 abstract description 3
- 239000011260 aqueous acid Substances 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 150000002373 hemiacetals Chemical class 0.000 abstract 1
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- 239000002775 capsule Substances 0.000 description 14
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- 239000011686 zinc sulphate Substances 0.000 description 2
- 235000009529 zinc sulphate Nutrition 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- XFKCVVFQGHCLIP-UHFFFAOYSA-N 2-ethylbutanedioyl dichloride Chemical compound CCC(C(Cl)=O)CC(Cl)=O XFKCVVFQGHCLIP-UHFFFAOYSA-N 0.000 description 1
- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010003402 Arthropod sting Diseases 0.000 description 1
- 241000182988 Assa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 description 1
- 241000448280 Elates Species 0.000 description 1
- 241001334574 Erythromyces Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
- MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
- 241000206607 Porphyra umbilicalis Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
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- 238000011097 chromatography purification Methods 0.000 description 1
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 230000003111 delayed effect Effects 0.000 description 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- FJGARHPOMSRARC-UHFFFAOYSA-N ethoxyethane;hex-1-ene Chemical compound CCOCC.CCCCC=C FJGARHPOMSRARC-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000009481 moist granulation Methods 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
- C12R2001/48—Streptomyces antibioticus ; Actinomyces antibioticus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
- Y10S435/888—Streptomyces antibioticus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19082A/81 | 1981-01-09 | ||
| IT8119082A IT1190651B (it) | 1981-01-09 | 1981-01-09 | Antibiotici macrolidici semisintetici,procedimento microbiologico per la loro preparazione e relatico microorganismo,intermedio per la loro preparazione e composizioni farmaceutiche che li contengono |
| IT25344A/81 | 1981-11-27 | ||
| IT25346/81A IT1139875B (it) | 1981-11-27 | 1981-11-27 | Antibiotici macrolidici semisintetici,procedimento microbiologico per la loro preparazione,intermedio per la loro preparazione e composizioni farmaceutiche che li contengono |
| IT25346A/81 | 1981-11-27 | ||
| IT25344/81A IT1139874B (it) | 1981-11-27 | 1981-11-27 | Preparazione di antibiotici macrolidici semisintetici,procedimento microbiologico e intermedio per la loro preparazione |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452649A Division 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1169375A true CA1169375A (en) | 1984-06-19 |
Family
ID=27272929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000393832A Expired 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 |
Country Status (7)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1195299B (it) * | 1981-11-27 | 1988-10-12 | Pierrel Spa | Procedimento chimico di sintesi per la preparazione di antibiotici macrolidici |
| IT1163796B (it) * | 1983-07-18 | 1987-04-08 | Pierrel Spa | Procedimento per la preparazione di (8s)-8-fluoroeritromicina |
| GB8333624D0 (en) * | 1983-12-16 | 1984-01-25 | Lepetit Spa | Antibiotics l 17054 and l 17392 |
| IT1196041B (it) * | 1984-03-08 | 1988-11-10 | Pierrel Spa | Emichetali di (8s)-8-fluoroeritromicine,il procedimento per la loro preparazione e le formulazioni adatte alla somministrazione orale che contengono i prodotti |
| JPS6187625A (ja) * | 1984-10-05 | 1986-05-06 | Satoshi Omura | 消化管収縮運動促進剤 |
| CA2292359C (en) | 1999-01-28 | 2004-09-28 | Pfizer Products Inc. | Novel azalides and methods of making same |
| WO2001079520A1 (en) * | 2000-04-13 | 2001-10-25 | Biotica Technology Limited | Hybrid glycosylated products and their production and use |
| KR100903485B1 (ko) | 2007-09-17 | 2009-06-18 | (주) 제노텍 | 케토라이드류 항생물질의 전구체인 5-ｏ-데소사미닐에리스로노라이드 ａ의 조합생합성방법 및 재조합 균주개발 |
| CN105418706B (zh) * | 2015-10-27 | 2019-05-17 | 华南理工大学 | 一种大环内酯类抗菌化合物及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1341022A (en) * | 1970-04-13 | 1973-12-19 | Lilly Industries Ltd | Erythromycylamine compounds |
| US3697547A (en) * | 1970-12-18 | 1972-10-10 | Abbott Lab | Erythronolide b derivatives |
| US3816397A (en) * | 1972-06-15 | 1974-06-11 | Abbott Lab | 11,12-epoxyerythromycins |
| US3855200A (en) * | 1973-04-23 | 1974-12-17 | Polska Akademia Nauk Instytut | Process for preparing 8-hydroxyerthromycin a and intermediates therefor |
| US3992264A (en) * | 1974-02-04 | 1976-11-16 | Hoffmann-La Roche Inc. | Antibiotic 1745A/X and methods for the production thereof |
| JPS53144589A (en) * | 1977-05-21 | 1978-12-15 | Taisho Pharmaceut Co Ltd | Erythromycin a derivatives |
| US4440857A (en) * | 1980-07-29 | 1984-04-03 | Eli Lilly And Company | Process for preparing mycarosyltylactone |
| IT1169013B (it) * | 1981-01-09 | 1987-05-20 | Pierrel Spa | Composti macrolidici ad attivita' antibiotica, procedimento e microorganismo per la loro preparazione e relative composizioni farmaceutiche |
-
1982
- 1982-01-08 EP EP82200019A patent/EP0056291B1/en not_active Expired
- 1982-01-08 CA CA000393832A patent/CA1169375A/en not_active Expired
- 1982-01-08 US US06/338,105 patent/US4439426A/en not_active Expired - Lifetime
- 1982-01-08 FR FR8200187A patent/FR2502155A1/fr active Granted
- 1982-01-08 FI FI820057A patent/FI72346C/fi not_active IP Right Cessation
- 1982-01-08 DE DE8282200019T patent/DE3268339D1/de not_active Expired
- 1982-01-08 CH CH98/82A patent/CH658250A5/it not_active IP Right Cessation
-
1984
- 1984-01-16 US US06/570,833 patent/US4540662A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0056291A2 (en) | 1982-07-21 |
| US4439426A (en) | 1984-03-27 |
| DE3268339D1 (en) | 1986-02-20 |
| EP0056291B1 (en) | 1986-01-08 |
| EP0056291A3 (en) | 1982-10-27 |
| US4540662A (en) | 1985-09-10 |
| FR2502155B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-10-19 |
| FI820057L (fi) | 1982-07-10 |
| FI72346C (fi) | 1987-05-11 |
| FI72346B (fi) | 1987-01-30 |
| FR2502155A1 (fr) | 1982-09-24 |
| CH658250A5 (it) | 1986-10-31 |
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