DE1114187B - Verfahren zur Herstellung einer reinen, stabilen 4-Epitetracyclinverbindung - Google Patents
Verfahren zur Herstellung einer reinen, stabilen 4-EpitetracyclinverbindungInfo
- Publication number
- DE1114187B DE1114187B DEF30711A DEF0030711A DE1114187B DE 1114187 B DE1114187 B DE 1114187B DE F30711 A DEF30711 A DE F30711A DE F0030711 A DEF0030711 A DE F0030711A DE 1114187 B DE1114187 B DE 1114187B
- Authority
- DE
- Germany
- Prior art keywords
- epitetracycline
- methanol
- pure
- compound
- stable
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 4-epitetracycline compound Chemical class 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 44
- NWXMGUDVXFXRIG-PMXORCKASA-N (4r,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-PMXORCKASA-N 0.000 claims description 23
- 229930101283 tetracycline Natural products 0.000 claims description 8
- 239000004098 Tetracycline Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229960002180 tetracycline Drugs 0.000 claims description 7
- 235000019364 tetracycline Nutrition 0.000 claims description 7
- 150000003522 tetracyclines Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YCIHPQHVWDULOY-DXDJYCPMSA-N (4r,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydron;chloride Chemical compound Cl.C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O YCIHPQHVWDULOY-DXDJYCPMSA-N 0.000 description 1
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 1
- ACTFDRRTVUIDFZ-ZZEGOUJXSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;trihydrate Chemical compound O.O.O.C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O ACTFDRRTVUIDFZ-ZZEGOUJXSA-N 0.000 description 1
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002423 tetracycline trihydrate Drugs 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/195—Antibiotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30711A DE1114187B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung einer reinen, stabilen 4-Epitetracyclinverbindung |
| CH269361A CH394165A (de) | 1960-03-09 | 1961-03-07 | Verfahren zur Herstellung einer reinen, stabilen 4-Epitetracyclinverbindung |
| SE239561A SE220344C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1960-03-09 | 1961-03-07 | |
| GB8297/61A GB956974A (en) | 1960-03-09 | 1961-03-07 | A pure, stable 4-epitetracycline compound and process for its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30711A DE1114187B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung einer reinen, stabilen 4-Epitetracyclinverbindung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1114187B true DE1114187B (de) | 1961-09-28 |
Family
ID=7093881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30711A Pending DE1114187B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung einer reinen, stabilen 4-Epitetracyclinverbindung |
Country Status (4)
-
1960
- 1960-03-09 DE DEF30711A patent/DE1114187B/de active Pending
-
1961
- 1961-03-07 GB GB8297/61A patent/GB956974A/en not_active Expired
- 1961-03-07 SE SE239561A patent/SE220344C1/sv unknown
- 1961-03-07 CH CH269361A patent/CH394165A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE220344C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-05-07 |
| GB956974A (en) | 1964-04-29 |
| CH394165A (de) | 1965-06-30 |
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