DE2152820A1 - Verfahren zur Entfärbung gewisser antibakterieller Mittel - Google Patents
Verfahren zur Entfärbung gewisser antibakterieller MittelInfo
- Publication number
- DE2152820A1 DE2152820A1 DE19712152820 DE2152820A DE2152820A1 DE 2152820 A1 DE2152820 A1 DE 2152820A1 DE 19712152820 DE19712152820 DE 19712152820 DE 2152820 A DE2152820 A DE 2152820A DE 2152820 A1 DE2152820 A1 DE 2152820A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- pyridylthio
- acetamido
- dimethylformamide
- dimethylacetamide
- 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 23
- 239000003242 anti bacterial agent Substances 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 81
- -1 4-pyridylthio Chemical group 0.000 claims description 36
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 34
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 29
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 27
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 19
- 229960005070 ascorbic acid Drugs 0.000 claims description 19
- 239000011668 ascorbic acid Substances 0.000 claims description 19
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 17
- 235000010323 ascorbic acid Nutrition 0.000 claims description 17
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 claims description 14
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004448 titration Methods 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 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 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/12—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8359970A | 1970-10-23 | 1970-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152820A1 true DE2152820A1 (de) | 1972-06-22 |
Family
ID=22179413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152820 Pending DE2152820A1 (de) | 1970-10-23 | 1971-10-22 | Verfahren zur Entfärbung gewisser antibakterieller Mittel |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3714157A (enExample) |
| JP (1) | JPS523949B1 (enExample) |
| CA (1) | CA932723A (enExample) |
| CH (1) | CH554897A (enExample) |
| DE (1) | DE2152820A1 (enExample) |
| ES (1) | ES396278A1 (enExample) |
| FR (1) | FR2113082A1 (enExample) |
| GB (1) | GB1367169A (enExample) |
| NL (1) | NL7114427A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841706A1 (de) * | 1977-09-27 | 1979-04-05 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 7- eckige klammer auf d(-)- alpha - (4-aethyl -2,3-dioxo-1-piperazincarboxamido)- alpha -(4-hydroxyphenyl)-acetamido eckige klamer zu -3- eckige klammer auf 5-(1-methyl- 1,2,3,4-tetrazolyl)-thiomethyl eckige klammer zu - delta hoch 3 -cephem-4-carbonsaeure und ein pharmazeutisch vertraegliches salz desselben sowie zwischenstufe des verfahrens und zur herstellung der zwischenstufe |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1465694A (en) * | 1973-05-15 | 1977-02-23 | Beecham Group Ltd | Preparation of penicillin salts |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3422100A (en) * | 1967-05-02 | 1969-01-14 | Bristol Myers Co | S-substituted-thioacetamido-cephalosporins |
| US3503967A (en) * | 1968-08-26 | 1970-03-31 | Bristol Myers Co | Process for the preparation of 7 - (alpha-(4 - pyridylthio)acetamido)cephalosporanic acid |
| US3578661A (en) * | 1969-06-02 | 1971-05-11 | Bristol Myers Co | Process for the preparation of 7-(alpha-(4 - pyridylthio)acetamido)cephalosporanic acids |
-
1970
- 1970-10-23 US US00083599A patent/US3714157A/en not_active Expired - Lifetime
-
1971
- 1971-09-16 CA CA123004A patent/CA932723A/en not_active Expired
- 1971-10-20 NL NL7114427A patent/NL7114427A/xx unknown
- 1971-10-21 FR FR7137911A patent/FR2113082A1/fr not_active Withdrawn
- 1971-10-22 CH CH1544571A patent/CH554897A/xx not_active IP Right Cessation
- 1971-10-22 DE DE19712152820 patent/DE2152820A1/de active Pending
- 1971-10-22 GB GB4911371A patent/GB1367169A/en not_active Expired
- 1971-10-22 ES ES396278A patent/ES396278A1/es not_active Expired
- 1971-10-23 JP JP46083702A patent/JPS523949B1/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841706A1 (de) * | 1977-09-27 | 1979-04-05 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 7- eckige klammer auf d(-)- alpha - (4-aethyl -2,3-dioxo-1-piperazincarboxamido)- alpha -(4-hydroxyphenyl)-acetamido eckige klamer zu -3- eckige klammer auf 5-(1-methyl- 1,2,3,4-tetrazolyl)-thiomethyl eckige klammer zu - delta hoch 3 -cephem-4-carbonsaeure und ein pharmazeutisch vertraegliches salz desselben sowie zwischenstufe des verfahrens und zur herstellung der zwischenstufe |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7114427A (enExample) | 1972-04-25 |
| FR2113082A1 (enExample) | 1972-06-23 |
| CA932723A (en) | 1973-08-28 |
| US3714157A (en) | 1973-01-30 |
| ES396278A1 (es) | 1975-09-16 |
| JPS523949B1 (enExample) | 1977-01-31 |
| GB1367169A (en) | 1974-09-18 |
| CH554897A (de) | 1974-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |