DD144169A5 - Verfahren zur herstellung einer kristallinen form eines cefamandolderivats - Google Patents
Verfahren zur herstellung einer kristallinen form eines cefamandolderivats Download PDFInfo
- Publication number
- DD144169A5 DD144169A5 DD79213398A DD21339879A DD144169A5 DD 144169 A5 DD144169 A5 DD 144169A5 DD 79213398 A DD79213398 A DD 79213398A DD 21339879 A DD21339879 A DD 21339879A DD 144169 A5 DD144169 A5 DD 144169A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- sodium
- suspension
- crystalline
- methyl alcohol
- formylcefamandol
- Prior art date
Links
- OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical class CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 42
- 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 claims abstract description 26
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 26
- 239000011734 sodium Substances 0.000 claims abstract description 26
- 239000000725 suspension Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 229960003012 cefamandole Drugs 0.000 abstract description 7
- 229930186147 Cephalosporin Natural products 0.000 abstract description 2
- 229940124587 cephalosporin Drugs 0.000 abstract description 2
- 150000001780 cephalosporins Chemical class 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 description 11
- -1 formyl ester Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- ICZOIXFFVKYXOM-YCLOEFEOSA-M cefamandole nafate Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)C=3C=CC=CC=3)[C@H]2SC1 ICZOIXFFVKYXOM-YCLOEFEOSA-M 0.000 description 5
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- RRJHESVQVSRQEX-SUYBPPKGSA-N O-formylcefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)C=3C=CC=CC=3)[C@H]2SC1 RRJHESVQVSRQEX-SUYBPPKGSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- OLVCFLKTBJRLHI-ZUZSALNQSA-N (6R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C([C@H](O)C1=CC=CC=C1)(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O OLVCFLKTBJRLHI-ZUZSALNQSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OJMNTWPPFNMOCJ-CFOLLTDRSA-M cefamandole sodium Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OJMNTWPPFNMOCJ-CFOLLTDRSA-M 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 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
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/912,613 US4168376A (en) | 1978-06-05 | 1978-06-05 | Process for crystalline sodium cefamandole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD144169A5 true DD144169A5 (de) | 1980-10-01 |
Family
ID=25432187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79213398A DD144169A5 (de) | 1978-06-05 | 1979-06-05 | Verfahren zur herstellung einer kristallinen form eines cefamandolderivats |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4168376A (cs) |
| EP (1) | EP0007689B1 (cs) |
| JP (1) | JPS54163591A (cs) |
| AR (1) | AR221240A1 (cs) |
| AT (1) | AT364462B (cs) |
| AU (1) | AU525538B2 (cs) |
| BE (1) | BE876532A (cs) |
| BG (1) | BG32858A3 (cs) |
| CA (1) | CA1122974A (cs) |
| CH (1) | CH639098A5 (cs) |
| CS (1) | CS207792B2 (cs) |
| DD (1) | DD144169A5 (cs) |
| DE (1) | DE2963471D1 (cs) |
| DK (1) | DK157759C (cs) |
| EG (1) | EG14096A (cs) |
| ES (1) | ES481295A1 (cs) |
| FI (1) | FI67223C (cs) |
| FR (1) | FR2428043A1 (cs) |
| GB (1) | GB2023588B (cs) |
| GR (1) | GR73835B (cs) |
| HU (1) | HU180455B (cs) |
| IE (1) | IE48572B1 (cs) |
| IL (1) | IL57396A (cs) |
| LU (1) | LU81347A1 (cs) |
| NZ (1) | NZ190548A (cs) |
| PH (1) | PH13643A (cs) |
| PL (1) | PL116636B1 (cs) |
| PT (1) | PT69679A (cs) |
| RO (1) | RO77194A (cs) |
| ZA (1) | ZA792753B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57138959A (en) * | 1981-02-23 | 1982-08-27 | Fuji Xerox Co Ltd | Holding mechanism of electrostatic recording head |
| EP0432297A1 (en) * | 1989-12-13 | 1991-06-19 | Technologitschen Kombinat Sa Promischlena Mikrobiologia | A method for the preparation of the sodium salt of O-formyl cefamandole |
| US5550231A (en) * | 1993-06-15 | 1996-08-27 | Eli Lilly And Company | Loracarbef hydrochloride C1-C3 alcohol solvates and uses thereof |
| CN104530086B (zh) * | 2014-12-16 | 2015-12-09 | 天津大学 | 头孢孟多酯钠化合物的新晶型及其结晶制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
| US4006138A (en) * | 1975-04-11 | 1977-02-01 | Eli Lilly And Company | Crystalline form of sodium O-formylcefamandole |
| US4054738A (en) * | 1975-12-22 | 1977-10-18 | Eli Lilly And Company | Sodium cefamandole crystalline forms |
| JPS5283574A (en) * | 1976-01-01 | 1977-07-12 | Lilly Co Eli | Sephamandol salt crystal containing dioxane |
-
1978
- 1978-06-05 US US05/912,613 patent/US4168376A/en not_active Expired - Lifetime
-
1979
- 1979-05-23 CA CA328,114A patent/CA1122974A/en not_active Expired
- 1979-05-23 AU AU47364/79A patent/AU525538B2/en not_active Ceased
- 1979-05-23 CS CS793541A patent/CS207792B2/cs unknown
- 1979-05-24 FI FI791646A patent/FI67223C/fi not_active IP Right Cessation
- 1979-05-24 JP JP6457179A patent/JPS54163591A/ja active Pending
- 1979-05-24 PH PH22558A patent/PH13643A/en unknown
- 1979-05-24 IL IL57396A patent/IL57396A/xx unknown
- 1979-05-24 RO RO7997628A patent/RO77194A/ro unknown
- 1979-05-25 NZ NZ190548A patent/NZ190548A/xx unknown
- 1979-05-25 BE BE1/9404A patent/BE876532A/xx not_active IP Right Cessation
- 1979-05-28 PT PT69679A patent/PT69679A/pt unknown
- 1979-05-28 FR FR7913465A patent/FR2428043A1/fr active Granted
- 1979-05-28 AR AR276675A patent/AR221240A1/es active
- 1979-05-31 LU LU81347A patent/LU81347A1/xx unknown
- 1979-05-31 CH CH511279A patent/CH639098A5/fr not_active IP Right Cessation
- 1979-06-01 DE DE7979301030T patent/DE2963471D1/de not_active Expired
- 1979-06-01 DK DK231979A patent/DK157759C/da not_active IP Right Cessation
- 1979-06-01 GB GB7919259A patent/GB2023588B/en not_active Expired
- 1979-06-01 AT AT0401479A patent/AT364462B/de not_active IP Right Cessation
- 1979-06-01 EP EP79301030A patent/EP0007689B1/en not_active Expired
- 1979-06-04 HU HU79EI858A patent/HU180455B/hu not_active IP Right Cessation
- 1979-06-04 BG BG043816A patent/BG32858A3/xx unknown
- 1979-06-04 ZA ZA792753A patent/ZA792753B/xx unknown
- 1979-06-04 EG EG341/79A patent/EG14096A/xx active
- 1979-06-04 PL PL1979216089A patent/PL116636B1/pl unknown
- 1979-06-04 GR GR59265A patent/GR73835B/el unknown
- 1979-06-05 ES ES481295A patent/ES481295A1/es not_active Expired
- 1979-06-05 DD DD79213398A patent/DD144169A5/de unknown
- 1979-08-08 IE IE1060/79A patent/IE48572B1/en unknown
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