DE1021130B - Herstellung von Foromacidinen - Google Patents

Herstellung von Foromacidinen

Info

Publication number: DE1021130B
Authority: DE; Germany
Prior art keywords: foromacidin; gray; methanol; salts; foromacidins
Prior art date: 1955-05-10
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.): Pending

Application number

DE1956C0012936

Other languages

German (de)

English (en)

Inventor

Dr Ernst Gaeumann

Dr Vladimir Prelog

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1955-05-10

Filing date

1956-04-25

Publication date

1957-12-19

1956-04-25 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1957-12-19 Publication of DE1021130B publication Critical patent/DE1021130B/de

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
229930191122 Foromacidin Natural products 0.000 claims description 36
ACTOXUHEUCPTEW-KWBWCIJSSA-N spiramycin I Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 ACTOXUHEUCPTEW-KWBWCIJSSA-N 0.000 claims description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
MAEJTLFMVPJURI-UHFFFAOYSA-N Foromacidin A Natural products COC1C(O)CC(=O)OC(C)CC=CC=CC(OC2CC(CC(C)O2)N(C)C)C(C)CC(CC=O)C1OC3CC(C)C(OC4CC(C)(O)C(O)C(C)O4)C(C3O)N(C)C MAEJTLFMVPJURI-UHFFFAOYSA-N 0.000 claims description 15
HSZLKTCKAYXVBX-DCAGQSADSA-N [(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2r,5s,6s)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoe Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@@H](O[C@H]2[C@@H]([C@H]([C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@](C)(O)C3)[C@@H](C)O2)N(C)C)O)[C@@H](CC=O)C[C@H]1C)OC)OC(=O)CC)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 HSZLKTCKAYXVBX-DCAGQSADSA-N 0.000 claims description 13
ZPCCSZFPOXBNDL-RSMXASMKSA-N spiramycin II Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)OC(C)=O)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 ZPCCSZFPOXBNDL-RSMXASMKSA-N 0.000 claims description 13
239000003242 anti bacterial agent Substances 0.000 claims description 11
229940088710 antibiotic agent Drugs 0.000 claims description 11
229950006796 spiramycin ii Drugs 0.000 claims description 11
229950003659 spiramycin iii Drugs 0.000 claims description 10
CZINXHNYXCZFKN-UHFFFAOYSA-N Foromacidin C Natural products CCCC(=O)OC1CC(=O)OC(C)CC=CC=CC(OC2CC(CC(C)O2)N(C)C)C(C)CC(CC=O)C(OC3CC(C)C(OC4CC(C)(O)C(O)C(C)O4)C(C3O)N(C)C)C1OC CZINXHNYXCZFKN-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
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238000005984 hydrogenation reaction Methods 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
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241001655322 Streptomycetales Species 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
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241000233866 Fungi Species 0.000 claims 1
230000002538 fungal effect Effects 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 20
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
235000015097 nutrients Nutrition 0.000 description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241000191967 Staphylococcus aureus Species 0.000 description 8
239000008103 glucose Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
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230000003115 biocidal effect Effects 0.000 description 7
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XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
-1 salts Chlorides Chemical class 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
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239000008272 agar Substances 0.000 description 5
238000009826 distribution Methods 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
238000000034 method Methods 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000049 pigment Substances 0.000 description 5
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
238000002211 ultraviolet spectrum Methods 0.000 description 5
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
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 description 4
229930182555 Penicillin Natural products 0.000 description 4
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 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000005903 acid hydrolysis reaction Methods 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
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239000003921 oil Substances 0.000 description 4
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229940049954 penicillin Drugs 0.000 description 4
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235000019260 propionic acid Nutrition 0.000 description 4
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235000019698 starch Nutrition 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000194032 Enterococcus faecalis Species 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
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FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 2
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
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229940074404 sodium succinate Drugs 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229960002920 sorbitol Drugs 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000012137 tryptone Substances 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Zoology (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Biotechnology (AREA)
Pharmacology & Pharmacy (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE1956C0012936 1955-05-10 1956-04-25 Herstellung von Foromacidinen Pending DE1021130B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1218406X		1955-05-10

Publications (1)

Publication Number	Publication Date
DE1021130B true DE1021130B (de)	1957-12-19

Family

ID=4563577

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE1956C0012936 Pending DE1021130B (de)	1955-05-10	1956-04-25	Herstellung von Foromacidinen

Country Status (2)

Country	Link
DE (1)	DE1021130B (fr)
FR (1)	FR1218406A (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE934715C (de) *	1954-05-29	1956-07-05	Bayer Ag	Trennen der Komponenten des Actinomycins C

1956
- 1956-04-25 DE DE1956C0012936 patent/DE1021130B/de active Pending
- 1956-05-09 FR FR714165A patent/FR1218406A/fr not_active Expired

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE934715C (de) *	1954-05-29	1956-07-05	Bayer Ag	Trennen der Komponenten des Actinomycins C

Also Published As

Publication number	Publication date
FR1218406A (fr)	1960-05-10

Publication	Publication Date	Title
DE2455230A1 (de)	1975-05-28	Lipiarmycin, verfahren zu seiner herstellung, mikroorganismus zur durchfuehrung des verfahrens und arzneimittel
DE2537902C2 (de)	1982-09-02	Als Rifamycin P, Q, R und U bezeichnete Antibiotika und Verfahren zu deren Herstellung
DE2336811C2 (de)	1984-06-07	Antibiotikum A-2315, Verfahren zu seiner Herstellung und seine Verwendung
CH634853A5 (de)	1983-02-28	Schwefelhaltige metabolite, ihre herstellung und verwendung in arznei- und futtermitteln.
DE1208449B (de)	1966-01-05	Verfahren zur Herstellung des Antibiotikums Ussamycin
DE2725163C2 (fr)	1990-04-05
DE1021130B (de)	1957-12-19	Herstellung von Foromacidinen
DE1617382A1 (de)	1971-04-01	Neues Antibiotikum A 28 829
CH347608A (de)	1960-07-15	Verfahren zur Herstellung eines neuen Antibiotikums
AT200258B (de)	1958-10-25	Verfahren zur Herstellung neuer Antibiotika
AT220290B (de)	1962-03-12	Verfahren zur Herstellung eines neuen Antibiotikums
DE1116864B (de)	1961-11-09	Herstellung und Gewinnung des Antibiotikums Avilamycin
AT216143B (de)	1961-07-10	Verfahren zur Herstellung eines neuen Antibiotikums
CH334468A (de)	1958-11-30	Verfahren zur Herstellung eines neuen Antibiotikums
DE2510868C3 (de)	1980-02-14	Nanaomycin A und Verfahren zur Herstellung der Antibiorica Nanaomycin A und Nanaomycin B
DE2044004C3 (de)	1974-03-07	Verfahren zur Herstellung des Antibiotikumkomplexes Polyfungin
DE1077380B (de)	1960-03-10	Herstellung des Antibiotikums Lemacidin
DE1012032B (de)	1957-07-11	Herstellung von Angolamycin
DE2424707A1 (de)	1975-01-23	Antibiotikum nr. 1998, seine salze mit saeuren, verfahren zu seiner herstellung, mikroorganismen zur durchfuehrung des verfahrens und arzneimittel
DE2825618A1 (de)	1979-01-11	Neue antibiotika, ihre herstellung und verwendung
DE1129259B (de)	1962-05-10	Verfahren zur Herstellung eines neuen Antibiotikums
EP0022425A2 (fr)	1981-01-14	Antibiotiques procédé et intermédiaires pour leur préparation et leur utilisation dans des préparations pharmaceutiques
CH339324A (de)	1959-06-30	Verfahren zur Herstellung eines neuen Antibiotikums
DE1110820B (de)	1961-07-13	Herstellung und Gewinnung des Antibiotikums Mikonomycin
DE1085297B (de)	1960-07-14	Herstellung und Gewinnung des Antibiotikums Holomycin