DE2111522A1 - Verfahren zur Reinigung von Cephalexin - Google Patents
Verfahren zur Reinigung von CephalexinInfo
- Publication number
- DE2111522A1 DE2111522A1 DE19712111522 DE2111522A DE2111522A1 DE 2111522 A1 DE2111522 A1 DE 2111522A1 DE 19712111522 DE19712111522 DE 19712111522 DE 2111522 A DE2111522 A DE 2111522A DE 2111522 A1 DE2111522 A1 DE 2111522A1
- Authority
- DE
- Germany
- Prior art keywords
- acetonitrile
- cephalexin
- solvate
- solution
- water
- 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
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 title claims description 51
- 229940106164 cephalexin Drugs 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 27
- 238000000746 purification Methods 0.000 title description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 183
- 239000012453 solvate Substances 0.000 claims description 40
- 239000000243 solution Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 4
- -1 2,2,2-trichloroethoxycarbonyl Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 239000003929 acidic solution Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 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 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229930186147 Cephalosporin Natural products 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000003643 water by type Substances 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1175470 | 1970-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2111522A1 true DE2111522A1 (de) | 1971-09-30 |
Family
ID=9992094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712111522 Pending DE2111522A1 (de) | 1970-03-11 | 1971-03-10 | Verfahren zur Reinigung von Cephalexin |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT302528B (enrdf_load_stackoverflow) |
| BE (1) | BE764055A (enrdf_load_stackoverflow) |
| CH (1) | CH559754A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2111522A1 (enrdf_load_stackoverflow) |
| DK (1) | DK127188B (enrdf_load_stackoverflow) |
| FR (1) | FR2084422A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1327048A (enrdf_load_stackoverflow) |
| NL (1) | NL7103177A (enrdf_load_stackoverflow) |
| SE (1) | SE380268B (enrdf_load_stackoverflow) |
| ZA (1) | ZA711555B (enrdf_load_stackoverflow) |
-
1971
- 1971-03-10 NL NL7103177A patent/NL7103177A/xx unknown
- 1971-03-10 BE BE764055A patent/BE764055A/xx unknown
- 1971-03-10 DK DK111171AA patent/DK127188B/da unknown
- 1971-03-10 DE DE19712111522 patent/DE2111522A1/de active Pending
- 1971-03-10 SE SE7103090A patent/SE380268B/xx unknown
- 1971-03-10 CH CH353671A patent/CH559754A5/xx not_active IP Right Cessation
- 1971-03-10 ZA ZA711555A patent/ZA711555B/xx unknown
- 1971-03-10 AT AT207771A patent/AT302528B/de not_active IP Right Cessation
- 1971-03-10 FR FR7108270A patent/FR2084422A5/fr not_active Expired
- 1971-04-19 GB GB1175470A patent/GB1327048A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK127188B (da) | 1973-10-01 |
| NL7103177A (enrdf_load_stackoverflow) | 1971-09-14 |
| GB1327048A (en) | 1973-08-15 |
| CH559754A5 (enrdf_load_stackoverflow) | 1975-03-14 |
| BE764055A (fr) | 1971-08-02 |
| FR2084422A5 (enrdf_load_stackoverflow) | 1971-12-17 |
| AT302528B (de) | 1972-10-25 |
| SE380268B (sv) | 1975-11-03 |
| ZA711555B (en) | 1972-10-25 |
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