DE1543831B1 - Verfahren zur Herstellung von Erythromycinglutamat - Google Patents
Verfahren zur Herstellung von ErythromycinglutamatInfo
- Publication number
- DE1543831B1 DE1543831B1 DE19661543831 DE1543831A DE1543831B1 DE 1543831 B1 DE1543831 B1 DE 1543831B1 DE 19661543831 DE19661543831 DE 19661543831 DE 1543831 A DE1543831 A DE 1543831A DE 1543831 B1 DE1543831 B1 DE 1543831B1
- Authority
- DE
- Germany
- Prior art keywords
- erythromycin
- glutamate
- water
- soluble
- activity
- 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.)
- Withdrawn
Links
- KNOXLRZTEFJWPE-OFWBJVIESA-N (2s)-2-aminopentanedioic acid;(3r,4s,5s,6r,7r,9r,11r,12r,13s)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclote Chemical compound OC(=O)[C@@H](N)CCC(O)=O.O([C@@H]1[C@@H](C)C(=O)OC([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 KNOXLRZTEFJWPE-OFWBJVIESA-N 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 3
- 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 claims description 74
- 229960003276 erythromycin Drugs 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 5
- 235000013922 glutamic acid Nutrition 0.000 claims description 5
- 239000004220 glutamic acid Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 10
- 230000003115 biocidal effect Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- TYQXKHPOXXXCTP-CSLYCKPJSA-N erythromycin A 2'-propanoate 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)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 TYQXKHPOXXXCTP-CSLYCKPJSA-N 0.000 description 7
- 229950001028 erythromycin propionate Drugs 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 244000052616 bacterial pathogen Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000036765 blood level Effects 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 229960004822 erythromycin phosphate Drugs 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 229930195712 glutamate Natural products 0.000 description 4
- 229940049906 glutamate Drugs 0.000 description 4
- -1 lauryl sulfate thiocyanate Chemical compound 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- AOJBACHWNDMRQP-UHFFFAOYSA-N n,n-diethyl-4-methylbenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(C)C=C1 AOJBACHWNDMRQP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 3
- 235000013923 monosodium glutamate Nutrition 0.000 description 3
- 230000001717 pathogenic effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- AFMZWSYYPCLGPM-YZPBMOCRSA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;sulfa Chemical compound NS(O)(=O)=O.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 AFMZWSYYPCLGPM-YZPBMOCRSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- 206010061372 Streptococcal infection Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- AWMFUEJKWXESNL-JZBHMOKNSA-N erythromycin estolate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O.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)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AWMFUEJKWXESNL-JZBHMOKNSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 239000004223 monosodium glutamate Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PGNYNCTUBKSHHL-UHFFFAOYSA-N 2,3-diaminobutanedioic acid Chemical compound OC(=O)C(N)C(N)C(O)=O PGNYNCTUBKSHHL-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000446313 Lamella Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 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
- 239000012984 antibiotic solution Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000009548 growth disturbance Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR23308A FR1465403A (fr) | 1965-07-02 | 1965-07-02 | Nouveau sel d'érythromycine et procédé de préparation |
| FR33299A FR4966M (enExample) | 1965-07-02 | 1965-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543831B1 true DE1543831B1 (de) | 1971-01-07 |
Family
ID=26164530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543831 Withdrawn DE1543831B1 (de) | 1965-07-02 | 1966-06-30 | Verfahren zur Herstellung von Erythromycinglutamat |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE682981A (enExample) |
| CH (1) | CH469807A (enExample) |
| DE (1) | DE1543831B1 (enExample) |
| FR (2) | FR1465403A (enExample) |
| GB (1) | GB1084830A (enExample) |
| LU (1) | LU51440A1 (enExample) |
| NL (1) | NL6609205A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2502627A1 (fr) * | 1981-02-02 | 1982-10-01 | Refarmed Sa | Derives thioliques de l'erythromycine a activite therapeutique, procede de preparation et produits pharmaceutiques dans lesquels ils apparaissent |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830982A (en) * | 1955-06-03 | 1958-04-15 | Abbott Lab | Water-soluble salt of erythromycin |
| BE647805A (enExample) * | 1963-05-31 | 1964-11-12 |
-
1965
- 1965-07-02 FR FR23308A patent/FR1465403A/fr not_active Expired
- 1965-09-30 FR FR33299A patent/FR4966M/fr not_active Expired
-
1966
- 1966-06-16 CH CH871366A patent/CH469807A/fr unknown
- 1966-06-22 BE BE682981D patent/BE682981A/xx unknown
- 1966-06-29 LU LU51440A patent/LU51440A1/xx unknown
- 1966-06-30 DE DE19661543831 patent/DE1543831B1/de not_active Withdrawn
- 1966-06-30 GB GB2935266A patent/GB1084830A/en not_active Expired
- 1966-07-01 NL NL6609205A patent/NL6609205A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2830982A (en) * | 1955-06-03 | 1958-04-15 | Abbott Lab | Water-soluble salt of erythromycin |
| BE647805A (enExample) * | 1963-05-31 | 1964-11-12 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH469807A (fr) | 1969-03-15 |
| BE682981A (enExample) | 1966-12-22 |
| FR4966M (enExample) | 1967-05-08 |
| FR1465403A (fr) | 1967-01-13 |
| NL6609205A (enExample) | 1967-01-03 |
| LU51440A1 (enExample) | 1966-08-29 |
| GB1084830A (en) | 1967-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2130113C3 (de) | Gentamicin B, Gentamicin B1 und Gentamicin X, Verfahren zu deren Gewinnung und diese Gentamicine enthaltende pharmazeutische Zubereitungen | |
| DE1166199B (de) | Verfahren zur Herstellung von 7-Aminocephalosporansaeurederivaten | |
| DE2641388C3 (de) | 3',4'-Didesoxykanamycin B-N-methansulfonsäuren und deren Alkalimetallsalze sowie diese Verbindungen enthaltende pharmazeutische Präparate | |
| DE1543831C (de) | Verfahren zur Herstellung von Erythromy cinglutamat | |
| DE2001731C3 (de) | Erythromycinasparaginat, Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Mittel | |
| DE1543831B1 (de) | Verfahren zur Herstellung von Erythromycinglutamat | |
| DE2316705C3 (de) | 9-Acyl -3' '-thiomethoxymethyl-SF-837-Macrolid-Antibiotika, Verfahren zur Herstellung derselben sowie diese enthaltende pharmazeutische Mittel | |
| DE1237107B (de) | Verfahren zur Herstellung von Tetracyclinfusidat, des Salzes der Fusidinsaeure mit Tetracyclin | |
| AT267061B (de) | Verfahren zur Herstellung eines neuen Erythromycinsalzes | |
| DE1216280B (de) | Verfahren zur Herstellung der N-Alkansulfon-oder N-Alkansulfinsaeuren von Neomycin, Framycetin, Dihydrostreptomycin oder Kanamycin | |
| DE1593015C3 (de) | N.N'-Dimethyl-NJ'i'-di-detracyclinomethyl)-äthylendiamin und dessen Salze mit pharmakologisch unbedenklichen Mineral- und organischen Säuren sowie Verfahren zu deren Herstellung | |
| DE2336397A1 (de) | Alkylester von polyen-antibiotika | |
| DE2057188B2 (de) | Erythromycyl B amin und Ver fahren zu dessen Herstellung | |
| DE941640C (de) | Verfahren zur Herstellung von Saeure-Additionssalzen des Erythromycins oder Carbomycins | |
| DE1545708C (de) | N- eckige Klammer auf 3-(5-Nitrofurfuryliden-methyl)-6-pyridazinyl eckige Klammer zu -N,N-dimethylformamidin und seine Salze | |
| DE1793628C (de) | Erythromycinoxim und Verfahren zu dessen Herstellung | |
| DE972336C (de) | Verfahren zur Gewinnung von stabilen, besonders fuer die Oraltherapie geeigneten Penicillinen | |
| DE1938437C3 (de) | Verfahren zur Herstellung von Levorinnatriumsalz | |
| AT239440B (de) | Verfahren zur Herstellung von neuen Derivaten der 6-Amino-Penicillansäure | |
| AT230539B (de) | Verfahren zur Herstellung von neuen Produkten mit antibiotischer Wirkung | |
| DE822993C (de) | Verfahren zur Herstellung asymmetrischer Arsenobenzolverbindungen | |
| DE2621615C3 (de) | Dihydromocimycin, seine Salze, Verfahren zu seiner Herstellung und seine Verwendung als Futtermittelzusatz | |
| DE958241C (de) | Verfahren zur Herstellung und Gewinnung einer antibiotisch wirkenden Verbindung | |
| AT234903B (de) | Verfahren zur Herstellung von Kanamycin-N, N'-dimethansulfonsäure | |
| DE2529538A1 (de) | Neues erythromycinsalz, verfahren zu seiner herstellung und pharmazeutische zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |