JPS5885892A - 新規な結晶性３−セフエム−４−カルボン酸塩および精製法 - Google Patents
新規な結晶性３−セフエム−４−カルボン酸塩および精製法Info
- Publication number
- JPS5885892A JPS5885892A JP57190677A JP19067782A JPS5885892A JP S5885892 A JPS5885892 A JP S5885892A JP 57190677 A JP57190677 A JP 57190677A JP 19067782 A JP19067782 A JP 19067782A JP S5885892 A JPS5885892 A JP S5885892A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- hydrochloric acid
- mixture
- oxime
- 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
- 238000000746 purification Methods 0.000 title claims description 5
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 75
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- 239000012043 crude product Substances 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 239000012458 free base Substances 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 229930186147 Cephalosporin Natural products 0.000 description 8
- 229940124587 cephalosporin Drugs 0.000 description 8
- 150000001780 cephalosporins Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- -1 cephalosporin salts Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/316,615 US4400503A (en) | 1981-10-30 | 1981-10-30 | Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid |
| US316615 | 1981-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5885892A true JPS5885892A (ja) | 1983-05-23 |
Family
ID=23229825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57190677A Pending JPS5885892A (ja) | 1981-10-30 | 1982-10-28 | 新規な結晶性３−セフエム−４−カルボン酸塩および精製法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4400503A (enExample) |
| EP (1) | EP0078671A3 (enExample) |
| JP (1) | JPS5885892A (enExample) |
| KR (1) | KR840002003A (enExample) |
| CA (1) | CA1182810A (enExample) |
| DK (1) | DK480982A (enExample) |
| GB (1) | GB2108124B (enExample) |
| GR (1) | GR77359B (enExample) |
| HU (1) | HU189186B (enExample) |
| IL (1) | IL67099A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2157254T3 (es) * | 1993-03-12 | 2001-08-16 | Upjohn Co | Ceftiofur (acido libre) cristalino. |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| AU2002368494A1 (en) * | 2002-12-20 | 2004-07-14 | Lupin Limited | A process for the preparation of cefpodoxime proxetil |
| EP4169705B1 (de) | 2021-10-21 | 2025-12-17 | Folien + Druck GmbH | Anfaltbare sektflaschenkapsel |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4298606A (en) * | 1974-12-19 | 1981-11-03 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| US4202893A (en) * | 1976-03-25 | 1980-05-13 | Roussel Uclaf | Alkyloximes of 7-amino-thiazolyl-acetamido-cephalosporanic acids |
| GR63088B (en) * | 1976-04-14 | 1979-08-09 | Takeda Chemical Industries Ltd | Preparation process of novel cephalosporins |
| JPS5579393A (en) * | 1978-12-11 | 1980-06-14 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| SE449996B (sv) * | 1979-10-02 | 1987-06-01 | Glaxo Group Ltd | (6r,7r)-7-/(z)-2-(2-aminotiazol-4-yl)-2-(2-karboxiprop-2-oxiimino)acetamidol/-3-(1-pyridiniummetyl)cef-3-em-4-karboxylat i form av en kristallin bishydroklorid farmaceutisk komposition derav samt anvendning som mellanpr |
| GR78221B (enExample) * | 1980-02-01 | 1984-09-26 | Ciba Geigy Ag |
-
1981
- 1981-10-30 US US06/316,615 patent/US4400503A/en not_active Expired - Fee Related
-
1982
- 1982-10-28 EP EP82305743A patent/EP0078671A3/en not_active Ceased
- 1982-10-28 HU HU823464A patent/HU189186B/hu unknown
- 1982-10-28 IL IL67099A patent/IL67099A/xx unknown
- 1982-10-28 GB GB08230756A patent/GB2108124B/en not_active Expired
- 1982-10-28 CA CA000414379A patent/CA1182810A/en not_active Expired
- 1982-10-28 JP JP57190677A patent/JPS5885892A/ja active Pending
- 1982-10-29 KR KR1019820004885A patent/KR840002003A/ko not_active Ceased
- 1982-10-29 DK DK480982A patent/DK480982A/da not_active Application Discontinuation
- 1982-10-29 GR GR69672A patent/GR77359B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL67099A (en) | 1986-07-31 |
| GB2108124A (en) | 1983-05-11 |
| US4400503A (en) | 1983-08-23 |
| EP0078671A2 (en) | 1983-05-11 |
| GR77359B (enExample) | 1984-09-11 |
| HU189186B (en) | 1986-06-30 |
| DK480982A (da) | 1983-05-01 |
| CA1182810A (en) | 1985-02-19 |
| GB2108124B (en) | 1985-07-10 |
| EP0078671A3 (en) | 1984-08-08 |
| KR840002003A (ko) | 1984-06-11 |
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