CA1065855A - Virtually solvent-free crystal form of the sodium salt of cephacetril - Google Patents
Virtually solvent-free crystal form of the sodium salt of cephacetrilInfo
- Publication number
- CA1065855A CA1065855A CA267,272A CA267272A CA1065855A CA 1065855 A CA1065855 A CA 1065855A CA 267272 A CA267272 A CA 267272A CA 1065855 A CA1065855 A CA 1065855A
- Authority
- CA
- Canada
- Prior art keywords
- cephacetril
- sodium salt
- solution
- aqueous
- ethanol
- 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.)
- Expired
Links
- 159000000000 sodium salts Chemical class 0.000 title claims abstract description 42
- RRYMAQUWDLIUPV-BXKDBHETSA-N cefacetrile Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-BXKDBHETSA-N 0.000 title claims abstract description 38
- 229960003972 cefacetrile Drugs 0.000 title claims abstract description 37
- 239000013078 crystal Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 238000001228 spectrum Methods 0.000 claims description 9
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 235000017281 sodium acetate Nutrition 0.000 claims description 8
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 claims description 6
- 229940087562 sodium acetate trihydrate Drugs 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000004048 modification Effects 0.000 description 37
- 238000012986 modification Methods 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960005419 nitrogen Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 238000005056 compaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- RRYMAQUWDLIUPV-FFFFSGIJSA-N (6r)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CC#N)[C@@H]12 RRYMAQUWDLIUPV-FFFFSGIJSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 206010014666 Endocarditis bacterial Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010027202 Meningitis bacterial Diseases 0.000 description 1
- -1 acetronitrile Chemical compound 0.000 description 1
- 208000009361 bacterial endocarditis Diseases 0.000 description 1
- 201000009904 bacterial meningitis Diseases 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000007119 infective endocarditis Diseases 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- AYRVGWHSXIMRAB-UHFFFAOYSA-M sodium acetate trihydrate Chemical compound O.O.O.[Na+].CC([O-])=O AYRVGWHSXIMRAB-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000004684 trihydrates 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/28—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by an aliphatic carboxylic acid, which is substituted by hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1597475 | 1975-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065855A true CA1065855A (en) | 1979-11-06 |
Family
ID=4413483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,272A Expired CA1065855A (en) | 1975-12-09 | 1976-12-07 | Virtually solvent-free crystal form of the sodium salt of cephacetril |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4061853A (en, 2012) |
| JP (1) | JPS5270012A (en, 2012) |
| AR (1) | AR210185A1 (en, 2012) |
| AT (1) | AT348676B (en, 2012) |
| AU (1) | AU503493B2 (en, 2012) |
| BE (1) | BE849160A (en, 2012) |
| BG (1) | BG24818A3 (en, 2012) |
| CA (1) | CA1065855A (en, 2012) |
| CS (1) | CS188297B2 (en, 2012) |
| DD (1) | DD127277A5 (en, 2012) |
| DE (1) | DE2655130C3 (en, 2012) |
| DK (1) | DK550276A (en, 2012) |
| EG (1) | EG12407A (en, 2012) |
| ES (1) | ES454023A1 (en, 2012) |
| FI (1) | FI763504A7 (en, 2012) |
| FR (1) | FR2334685A1 (en, 2012) |
| GB (1) | GB1561060A (en, 2012) |
| GR (1) | GR73008B (en, 2012) |
| HU (1) | HU176213B (en, 2012) |
| IE (1) | IE44319B1 (en, 2012) |
| IL (1) | IL51067A (en, 2012) |
| NL (1) | NL7613712A (en, 2012) |
| NO (1) | NO764182L (en, 2012) |
| NZ (1) | NZ182832A (en, 2012) |
| OA (1) | OA05502A (en, 2012) |
| PH (1) | PH11990A (en, 2012) |
| PL (1) | PL104763B1 (en, 2012) |
| PT (1) | PT65932B (en, 2012) |
| RO (1) | RO70871A (en, 2012) |
| SE (1) | SE7613802L (en, 2012) |
| SU (1) | SU657750A3 (en, 2012) |
| YU (1) | YU297976A (en, 2012) |
| ZA (1) | ZA767330B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4132848A (en) * | 1977-11-03 | 1979-01-02 | Eli Lilly And Company | Method of preparing a rapidly dissolving powder of crystalline cephalothin sodium for parenteral administration |
| IT1214587B (it) * | 1986-12-23 | 1990-01-18 | Giovanni Bonfanti | Metodo per la produzione diprodotti cristallini puri. |
| JP3266395B2 (ja) * | 1993-11-24 | 2002-03-18 | 富士写真フイルム株式会社 | 有機薬品の晶析方法 |
| USRE43932E1 (en) | 1997-07-18 | 2013-01-15 | Novartis Ag | Crystal modification of a N-phenyl-2-pyrimidineamine derivative, processes for its manufacture and its use |
| CO4940418A1 (es) * | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH480365A (de) * | 1965-01-18 | 1969-10-31 | Ciba Geigy | Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure |
-
1976
- 1976-11-01 US US05/737,376 patent/US4061853A/en not_active Expired - Lifetime
- 1976-11-17 RO RO7688475A patent/RO70871A/ro unknown
- 1976-11-27 EG EG76735A patent/EG12407A/xx active
- 1976-11-29 AR AR265653A patent/AR210185A1/es active
- 1976-12-03 OA OA56003A patent/OA05502A/xx unknown
- 1976-12-04 DE DE2655130A patent/DE2655130C3/de not_active Expired
- 1976-12-06 PH PH19205A patent/PH11990A/en unknown
- 1976-12-06 PT PT65932A patent/PT65932B/pt unknown
- 1976-12-07 DD DD196175A patent/DD127277A5/xx unknown
- 1976-12-07 SU SU762426141A patent/SU657750A3/ru active
- 1976-12-07 AT AT904776A patent/AT348676B/de not_active IP Right Cessation
- 1976-12-07 GB GB50970/76A patent/GB1561060A/en not_active Expired
- 1976-12-07 BG BG034852A patent/BG24818A3/xx unknown
- 1976-12-07 FI FI763504A patent/FI763504A7/fi not_active Application Discontinuation
- 1976-12-07 CA CA267,272A patent/CA1065855A/en not_active Expired
- 1976-12-07 FR FR7636781A patent/FR2334685A1/fr active Granted
- 1976-12-07 GR GR52337A patent/GR73008B/el unknown
- 1976-12-07 ES ES454023A patent/ES454023A1/es not_active Expired
- 1976-12-07 HU HU76CI1701A patent/HU176213B/hu unknown
- 1976-12-08 ZA ZA767330A patent/ZA767330B/xx unknown
- 1976-12-08 SE SE7613802A patent/SE7613802L/ not_active Application Discontinuation
- 1976-12-08 IL IL7651067A patent/IL51067A/xx unknown
- 1976-12-08 YU YU02979/76A patent/YU297976A/xx unknown
- 1976-12-08 BE BE173041A patent/BE849160A/xx unknown
- 1976-12-08 NZ NZ182832A patent/NZ182832A/xx unknown
- 1976-12-08 NO NO764182A patent/NO764182L/no unknown
- 1976-12-08 PL PL1976194233A patent/PL104763B1/pl unknown
- 1976-12-08 DK DK550276A patent/DK550276A/da unknown
- 1976-12-08 AU AU20364/76A patent/AU503493B2/en not_active Expired
- 1976-12-08 CS CS768023A patent/CS188297B2/cs unknown
- 1976-12-08 IE IE2684/76A patent/IE44319B1/en unknown
- 1976-12-09 JP JP51147183A patent/JPS5270012A/ja active Granted
- 1976-12-09 NL NL7613712A patent/NL7613712A/xx not_active Application Discontinuation
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