DD243501A5 - Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a - Google Patents

Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a Download PDF

Info

Publication number: DD243501A5
Authority: DD; German Democratic Republic
Prior art keywords: aza; deoxo; dihydroerythromycin; product; hexamethylbicyclo
Prior art date: 1985-03-04

Application number

DD86287551A

Other languages

German (de)

English (en)

Inventor

Zlatko Vajtner

Nevenka Lopotar

Gabrijela Kobrehel

Slobodan Djokic

Original Assignee

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Priority date (The priority date 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 date listed.)

1985-03-04

Filing date

1986-03-04

Publication date

1987-03-04

1986-03-04 Application filed by ��@��@��k��k@��@�@��@��k@�K��K�k�� filed Critical ��@��@��k��k@��@�@��@��k@�K��K�k��

1987-03-04 Publication of DD243501A5 publication Critical patent/DD243501A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 4
229960003276 erythromycin Drugs 0.000 claims description 3
IFPNJQLAULGZTH-UHFFFAOYSA-N hexadec-1-en-8-one Chemical compound CCCCCCCCC(=O)CCCCCC=C IFPNJQLAULGZTH-UHFFFAOYSA-N 0.000 abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 4
229910052753 mercury Inorganic materials 0.000 abstract description 4
239000001632 sodium acetate Substances 0.000 abstract description 4
235000017281 sodium acetate Nutrition 0.000 abstract description 4
239000003120 macrolide antibiotic agent Substances 0.000 abstract description 3
229910052757 nitrogen Inorganic materials 0.000 abstract description 3
238000002955 isolation Methods 0.000 abstract description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 3
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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
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
238000006237 Beckmann rearrangement reaction Methods 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
229930006677 Erythromycin A Natural products 0.000 description 1
-1 NaBH 4 Chemical class 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 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
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
230000000694 effects Effects 0.000 description 1
YVTFLQUPRIIRFE-QUMKBVJLSA-N erythronolide A Chemical compound 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@]1(C)O YVTFLQUPRIIRFE-QUMKBVJLSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000007931 macrolactones Chemical group 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000009423 ventilation Methods 0.000 description 1

Classifications

- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F21—LIGHTING
- F21V—FUNCTIONAL FEATURES OR DETAILS OF LIGHTING DEVICES OR SYSTEMS THEREOF; STRUCTURAL COMBINATIONS OF LIGHTING DEVICES WITH OTHER ARTICLES, NOT OTHERWISE PROVIDED FOR
- F21V7/00—Reflectors for light sources
- F21V7/22—Reflectors for light sources characterised by materials, surface treatments or coatings, e.g. dichroic reflectors
- F21V7/24—Reflectors for light sources characterised by materials, surface treatments or coatings, e.g. dichroic reflectors characterised by the material
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/05—Heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/042—Electrodes formed of a single material
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
- C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
- C25B11/042—Electrodes formed of a single material
- C25B11/045—Mercury or amalgam
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
- C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
- C25B9/19—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof with diaphragms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Electrochemistry (AREA)
Materials Engineering (AREA)
Metallurgy (AREA)
General Engineering & Computer Science (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD86287551A 1985-03-04 1986-03-04 Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a DD243501A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU340/85A YU43402B (en)	1985-03-04	1985-03-04	Process for preparation of 11-aza-10-deoxo-10-dihydroeritromycin "a" by using electro-chemical reduction

Publications (1)

Publication Number	Publication Date
DD243501A5 true DD243501A5 (de)	1987-03-04

Family

ID=25549459

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86287551A DD243501A5 (de)	1985-03-04	1986-03-04	Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a

Country Status (6)

Country	Link
AT (1)	AT387391B (pl)
DD (1)	DD243501A5 (pl)
HU (1)	HU195229B (pl)
PL (1)	PL146774B1 (pl)
SU (1)	SU1530096A3 (pl)
YU (1)	YU43402B (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AP44A (en) *	1987-07-09	1989-07-27	Pfizer	Azithromycin dihydrate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2144924C1 (ru) *	1996-06-21	2000-01-27	Зинченко Евгений Яковлевич	Способ получения азитромицина и способы получения промежуточных соединений

1985
- 1985-03-04 YU YU340/85A patent/YU43402B/xx unknown
1986
- 1986-03-03 PL PL1986258216A patent/PL146774B1/pl unknown
- 1986-03-03 AT AT0053686A patent/AT387391B/de not_active IP Right Cessation
- 1986-03-04 SU SU864027117A patent/SU1530096A3/ru active
- 1986-03-04 HU HU86896A patent/HU195229B/hu unknown
- 1986-03-04 DD DD86287551A patent/DD243501A5/de unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AP44A (en) *	1987-07-09	1989-07-27	Pfizer	Azithromycin dihydrate

Also Published As

Publication number	Publication date
YU43402B (en)	1989-06-30
YU34085A (en)	1987-12-31
ATA53686A (de)	1988-06-15
HU195229B (en)	1988-04-28
SU1530096A3 (ru)	1989-12-15
HUT41045A (en)	1987-03-30
PL146774B1 (en)	1989-03-31
AT387391B (de)	1989-01-10

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20060305

Publication	Publication Date	Title
DE3012533C2 (pl)	1988-09-29
DE69810842T2 (de)	2003-11-20	Herstellung von Azithromycin
DE2642837A1 (de)	1977-04-07	Anthracyclinglycoside
DD211565A5 (de)	1984-07-18	Verfahren zur herstellung von 4"-epi-erythromycin a und derivaten hiervon als brauchbare antibakterielle mittel
DE69025505T2 (de)	1996-09-19	Tylosin-Derivate
DD243501A5 (de)	1987-03-04	Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a
DE2929058C2 (de)	1986-03-06	N,N,N-Trimethylammonium-methylsulfate der Polyenmakrolidmethylester und Verfahren zu deren Herstellung
DE2514185A1 (de)	1975-10-09	Halogenierte antibiotika und verfahren zu deren herstellung
DE69921996T2 (de)	2005-11-24	Neue vinca-alkaloidderivate und verfahren zur herstellung
DE60026718T2 (de)	2006-11-16	Einstufiges verfahren zur herstellung von 7,16-deoxy-2-aza-10-o-cladinosil-12-o-desosaminil-4,5-dihydroxi-6-ethyl-3,5,9,11,13,15-hexamethylbicycle(11.2.11)hexadeca-1(2)-en-8-ona undeine neue form von 9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a
CH624126A5 (pl)	1981-07-15
DE69824590T2 (de)	2005-06-30	Solvate von erythromycin a oxim
DE2756057C2 (pl)	1988-09-29
AT392922B (de)	1991-07-10	Verfahren zur herstellung eines neuen stabilen homogenen rhodium-hydrierungs-katalysators und dessen anwendung
DE2804509C2 (de)	1982-12-02	4"-Amino-oleandomycin-Derivate und diese Verbindungen enthaltende antibakterielle Mittel
DE2302935A1 (de)	1973-08-02	Semi-synthetische antibiotika mit makrocyclischer lactonstruktur
CH615197A5 (en)	1980-01-15	Process for the preparation of antibiotic compounds
DE69908288T2 (de)	2004-04-08	Verfahren zur Herstellung von UCN-01
DE60204826T2 (de)	2006-04-27	Verfahren zur Herstellung von Natriumsalz der D-6-[(alpha-4-(Ethyl-2,3-dioxo-1-piperazinocarbonyl-amino)phenylacetamido]-penicillansäure
DE3028758C2 (de)	1982-09-23	Verfahren zur Herstellung von Anisaldehyd
DE69725287T2 (de)	2004-07-29	Indolderivate und wurzelbildende mittel, die diese als aktive bestandteile enthalten
DE69910810T2 (de)	2004-08-19	Natriumsalz von 3-(4-cinnamyl-1-piperazinyl)-iminomethyl-rifamycin sv und verfahren zu seiner herstellung
DE1196650B (de)	1965-07-15	Verfahren zur Herstellung von 6-Methylen-6-desoxy-6-desmethyl-5-oxytetracyclin
DE1593961C (pl)
DE928833C (de)	1955-06-13	Verfahren zur Herstellung von Normal- bzw. Allopregnan-3, 11, 20-trion

DD243501A5 - Verfahren zur herstellung von 11-aza-10-deoxo-10-dihydroerythramycin a - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=25549459

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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