MD247C2 - Method of preparation of hydrated crystalline form of natrium salt of 3-acetaoxymethyl-7-(2-(2-amino-4 thiazolyl)-2-methoxyiminoacetamylou-cef-3em-4-carbonic acid, sin-isomer - Google Patents
Method of preparation of hydrated crystalline form of natrium salt of 3-acetaoxymethyl-7-(2-(2-amino-4 thiazolyl)-2-methoxyiminoacetamylou-cef-3em-4-carbonic acid, sin-isomerInfo
- Publication number
- MD247C2 MD247C2 MD94-0275A MD940275A MD247C2 MD 247 C2 MD247 C2 MD 247C2 MD 940275 A MD940275 A MD 940275A MD 247 C2 MD247 C2 MD 247C2
- Authority
- MD
- Moldova
- Prior art keywords
- cef
- amino
- crystalline form
- carbonic acid
- natrium
- Prior art date
Links
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 abstract 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
-
- 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
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Method of preparation of hydrated crystalline form of natrium salt of 3-acetaoxymethyl-7-[2-(2-amino-4 thiazolyl) -2-methoxyiminoacetamylo]-cef-3em-4-carbonic acid of formula 1.The purpose of invention is the obtaining of new cefalosporinic antibiotic in the new crystalline form with increased stability.The method foresees the treatment of 3-acetoxymethyl-7[2-2(amino-4-tiazolyl)-2-methoxyiminoacetamido] cef-3-em-4-carbonic acid, sin-isomer or its hydrate, ethanolic solvate or mixture of hydrate and ethanolic or formic solvate, by salt of natrium, selected from group, including acetate, diethylacetate and 2-ethylgexanoat of natrium in the solvent medium, selected from group, including methanol, water ethanol, water acetone and water isopropanol.The final product is separated by crystallization, at the necessity with addition of solvent, selected from group, including ethanol, the latter, containing 0,5-1- weight % of water, acetone and isopropanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7725142A FR2400519A1 (en) | 1977-08-17 | 1977-08-17 | CRYSTALLINE FORM OF SODIUM SALT OF AN OXIMIN DERIVATIVE OF 7-AMINO-THIAZOLYL ACETAMIDO CEPHALOSPORANIC, ITS PREPARATION PROCESS AND ITS APPLICATION AS A MEDICINAL PRODUCT |
| SU782645701A SU799666A3 (en) | 1977-08-17 | 1978-08-09 | Method of preparing hydrated crystalline form of sodium salt of 3-acetoxymethyl-7-/2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido/ceph-3-em-4-carboxyl acid, sin-isomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD247B1 MD247B1 (en) | 1995-07-31 |
| MD247C2 true MD247C2 (en) | 1995-12-31 |
Family
ID=9194564
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MD94-0267A MD225C2 (en) | 1977-08-17 | 1994-09-08 | Method of hydrated crystalline form of natrium salt 3-acetoxymethyl-7o2-(2-amino-4-triazolyl)-2-methoxyiminoacetamidou cef-3-em-4-carbonic acid, sin isomer preparation |
| MD94-0275A MD247C2 (en) | 1977-08-17 | 1994-09-08 | Method of preparation of hydrated crystalline form of natrium salt of 3-acetaoxymethyl-7-(2-(2-amino-4 thiazolyl)-2-methoxyiminoacetamylou-cef-3em-4-carbonic acid, sin-isomer |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MD94-0267A MD225C2 (en) | 1977-08-17 | 1994-09-08 | Method of hydrated crystalline form of natrium salt 3-acetoxymethyl-7o2-(2-amino-4-triazolyl)-2-methoxyiminoacetamidou cef-3-em-4-carbonic acid, sin isomer preparation |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US4224371A (en) |
| EP (1) | EP0001024B1 (en) |
| JP (1) | JPS5441890A (en) |
| AT (2) | AT366049B (en) |
| AU (1) | AU520898B2 (en) |
| BG (2) | BG33887A3 (en) |
| CA (1) | CA1121343A (en) |
| CS (2) | CS207646B2 (en) |
| DD (1) | DD137588A5 (en) |
| DE (1) | DE2860358D1 (en) |
| DK (2) | DK152213C (en) |
| EG (1) | EG13520A (en) |
| ES (1) | ES472381A1 (en) |
| FI (1) | FI65433C (en) |
| FR (1) | FR2400519A1 (en) |
| GE (2) | GEP19960475B (en) |
| GR (1) | GR73661B (en) |
| HR (1) | HRP931395B1 (en) |
| HU (1) | HU181497B (en) |
| IE (1) | IE47230B1 (en) |
| IL (1) | IL55186A (en) |
| IT (1) | IT1107961B (en) |
| MD (2) | MD225C2 (en) |
| MX (2) | MX5448E (en) |
| NO (1) | NO156168C (en) |
| NZ (1) | NZ188163A (en) |
| OA (1) | OA06016A (en) |
| PL (1) | PL126619B1 (en) |
| PT (1) | PT68431A (en) |
| RO (1) | RO79999A (en) |
| SI (1) | SI7811917A8 (en) |
| SU (2) | SU799666A3 (en) |
| YU (1) | YU42166B (en) |
| ZA (1) | ZA784187B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60120886A (en) * | 1983-12-02 | 1985-06-28 | Takeda Chem Ind Ltd | Crystal of cephemcarboxylic acid sodium salt |
| DE150507T1 (en) * | 1983-12-29 | 1987-02-26 | Mochida Pharmaceutical Co., Ltd., Tokio/Tokyo | CEPHALOSPORINE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS. |
| JPS60142987A (en) * | 1983-12-29 | 1985-07-29 | Mochida Pharmaceut Co Ltd | Cephalosporin derivative |
| US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| US4937330A (en) * | 1985-08-12 | 1990-06-26 | The Upjohn Company | Conversion of cephalosporin hydrohalide salt to alkali metal salt |
| JPS63132893A (en) * | 1986-11-25 | 1988-06-04 | Mochida Pharmaceut Co Ltd | Novel cephalosporin derivative, production thereof and antibacterial agent containing said derivative as active ingredient |
| US4880798A (en) * | 1986-11-25 | 1989-11-14 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| RU2021274C1 (en) | 1991-05-17 | 1994-10-15 | Польска Акадэмия Наук Институт Хэмии Органичнэй | Process for preparing aminothiazolyl cephalosporin derivatives |
| US5318781A (en) * | 1993-04-06 | 1994-06-07 | Hoffmann-La Roche Inc. | Absorption enhancement of antibiotics |
| US5574154A (en) * | 1994-09-29 | 1996-11-12 | Alnejma Bulk Pharmaceutical Co. A.B.P.C. | Process for the preparation of cephalosporanic compounds |
| GB9423459D0 (en) * | 1994-11-21 | 1995-01-11 | Biochemie Gmbh | Silylation process |
| AT402928B (en) * | 1994-12-23 | 1997-09-25 | Biochemie Gmbh | NEW METHOD FOR PRODUCING CEFOTAXIM |
| AU690482B2 (en) * | 1996-03-18 | 1998-04-23 | Ranbaxy Laboratories Limited | Process for producing cephalosporin antibiotics |
| GB9717629D0 (en) * | 1997-08-21 | 1997-10-22 | Johnson Matthey Plc | Removal of residual organic solvents |
| WO2001092254A1 (en) * | 2000-05-30 | 2001-12-06 | Fujisawa Pharmaceutical Co., Ltd. | Method for replacing organic solvents contained in clathrate crystals |
| WO2004063203A1 (en) * | 2003-01-10 | 2004-07-29 | Orchid Chemicals & Pharmaceuticals Ltd | Process for the preparation of cefotaxime sodium |
| CN100361995C (en) * | 2004-10-27 | 2008-01-16 | 山东瑞阳制药有限公司 | One-step preparation process of injection-grade sterile cefotaxime sodium |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970651A (en) * | 1974-01-07 | 1976-07-20 | Bristol-Myers Company | Crystalline cephalosporin derivative |
| US3985747A (en) * | 1974-05-24 | 1976-10-12 | Bristol-Myers Company | Crystalline sesquihydrate of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| DK154939C (en) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | METHOD OF ANALOGUE FOR THE PREPARATION OF THIAZOLYLACETAMIDO-CEPHEM COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS OR ESTERS THEREOF |
| US4006138A (en) * | 1975-04-11 | 1977-02-01 | Eli Lilly And Company | Crystalline form of sodium O-formylcefamandole |
| SE440655B (en) * | 1976-01-23 | 1985-08-12 | Roussel Uclaf | SET TO MAKE NEW OXIME DERIVATIVES OF 7-AMINO-THIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID |
| DE2760123C2 (en) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporanic acids, their preparation and pharmaceutical compositions containing them |
-
1977
- 1977-08-17 FR FR7725142A patent/FR2400519A1/en active Granted
-
1978
- 1978-07-20 IL IL55186A patent/IL55186A/en active IP Right Grant
- 1978-07-22 OA OA56566A patent/OA06016A/en unknown
- 1978-07-24 ZA ZA00784187A patent/ZA784187B/en unknown
- 1978-08-02 DD DD78207090A patent/DD137588A5/en unknown
- 1978-08-03 EP EP78400072A patent/EP0001024B1/en not_active Expired
- 1978-08-03 AT AT0563578A patent/AT366049B/en not_active IP Right Cessation
- 1978-08-03 DE DE7878400072T patent/DE2860358D1/en not_active Expired
- 1978-08-04 ES ES472381A patent/ES472381A1/en not_active Expired
- 1978-08-08 IT IT50648/78A patent/IT1107961B/en active Protection Beyond IP Right Term
- 1978-08-08 CS CS785183A patent/CS207646B2/en unknown
- 1978-08-09 SU SU782645701A patent/SU799666A3/en active
- 1978-08-10 SI SI7811917A patent/SI7811917A8/en unknown
- 1978-08-10 YU YU1917/78A patent/YU42166B/en unknown
- 1978-08-10 US US05/932,437 patent/US4224371A/en not_active Expired - Lifetime
- 1978-08-11 MX MX787309U patent/MX5448E/en unknown
- 1978-08-11 MX MX7926A patent/MX155976A/en unknown
- 1978-08-11 GR GR56985A patent/GR73661B/el unknown
- 1978-08-15 BG BG040671A patent/BG33887A3/en unknown
- 1978-08-15 BG BG042035A patent/BG33888A3/en unknown
- 1978-08-16 FI FI782494A patent/FI65433C/en not_active IP Right Cessation
- 1978-08-16 HU HU78RO993A patent/HU181497B/en unknown
- 1978-08-16 PT PT68431A patent/PT68431A/en unknown
- 1978-08-16 CA CA000309454A patent/CA1121343A/en not_active Expired
- 1978-08-16 AU AU38965/78A patent/AU520898B2/en not_active Expired
- 1978-08-16 NZ NZ188163A patent/NZ188163A/en unknown
- 1978-08-16 DK DK361078A patent/DK152213C/en not_active IP Right Cessation
- 1978-08-16 PL PL1978209080A patent/PL126619B1/en unknown
- 1978-08-16 NO NO782782A patent/NO156168C/en unknown
- 1978-08-16 RO RO78101982A patent/RO79999A/en unknown
- 1978-08-16 EG EG510/78A patent/EG13520A/en active
- 1978-08-17 JP JP9958078A patent/JPS5441890A/en active Granted
- 1978-08-17 IE IE1669/78A patent/IE47230B1/en not_active IP Right Cessation
-
1979
- 1979-06-27 CS CS794439A patent/CS207647B2/en unknown
-
1980
- 1980-01-31 AT AT0052280A patent/AT366050B/en not_active IP Right Cessation
- 1980-03-12 SU SU802891755A patent/SU852175A3/en active
-
1986
- 1986-04-09 DK DK159786A patent/DK163514C/en not_active IP Right Cessation
-
1993
- 1993-07-31 GE GEAP19931371A patent/GEP19960475B/en unknown
- 1993-07-31 GE GEAP19931355A patent/GEP19960476B/en unknown
- 1993-11-11 HR HRP-1917/78A patent/HRP931395B1/en not_active IP Right Cessation
-
1994
- 1994-09-08 MD MD94-0267A patent/MD225C2/en unknown
- 1994-09-08 MD MD94-0275A patent/MD247C2/en unknown
Non-Patent Citations (1)
| Title |
|---|
| Cererea nr. 2439818/23-04, SU, Int. cl. C 07 D 501/60, 1976 * |
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