SU973024A3 - Способ получени аддитивных солей пивалоилоксиметилового эфира 7 @ -[2-(2-аминотиазол-4-ил) ацетамидо]-3-[1-(2-диметиламиноэтил)-1н-тетразол-5-илтиометил]-3-цефем-4-карбоновой кислоты с сол ной,винной или лимонной кислотой - Google Patents
Способ получени аддитивных солей пивалоилоксиметилового эфира 7 @ -[2-(2-аминотиазол-4-ил) ацетамидо]-3-[1-(2-диметиламиноэтил)-1н-тетразол-5-илтиометил]-3-цефем-4-карбоновой кислоты с сол ной,винной или лимонной кислотой Download PDFInfo
- Publication number
- SU973024A3 SU973024A3 SU802921250A SU2921250A SU973024A3 SU 973024 A3 SU973024 A3 SU 973024A3 SU 802921250 A SU802921250 A SU 802921250A SU 2921250 A SU2921250 A SU 2921250A SU 973024 A3 SU973024 A3 SU 973024A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- tetrazol
- dimethylaminoethyl
- acetamido
- tartaric
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title claims abstract description 14
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000011975 tartaric acid Substances 0.000 title claims abstract description 6
- 235000002906 tartaric acid Nutrition 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 9
- 239000000654 additive Substances 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title claims 2
- -1 cephalosporin salts Chemical class 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 3
- IIEQJSIHKZXTHY-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethoxymethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCOCOC(=O)C(C)(C)C IIEQJSIHKZXTHY-UHFFFAOYSA-N 0.000 claims 1
- 102100035475 Blood vessel epicardial substance Human genes 0.000 claims 1
- 101001094636 Homo sapiens Blood vessel epicardial substance Proteins 0.000 claims 1
- 101000608194 Homo sapiens Pyrin domain-containing protein 1 Proteins 0.000 claims 1
- 101000595404 Homo sapiens Ribonucleases P/MRP protein subunit POP1 Proteins 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract description 5
- NEYLVMUGIIOTQK-SBXXRYSUSA-N (6R)-3-[[1-[2-[[2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-2-(dimethylamino)ethyl]tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound NC=1SC=C(N=1)CC(=O)NC(CN1N=NN=C1SCC=1CS[C@H]2N(C=1C(=O)O)C(C2)=O)N(C)C NEYLVMUGIIOTQK-SBXXRYSUSA-N 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 210000001035 gastrointestinal tract Anatomy 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 13
- 229940125904 compound 1 Drugs 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 230000010287 polarization Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5948179A JPS55151588A (en) | 1979-05-14 | 1979-05-14 | Preparation of cephalosporin salt crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU973024A3 true SU973024A3 (ru) | 1982-11-07 |
Family
ID=13114535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU802921250A SU973024A3 (ru) | 1979-05-14 | 1980-05-14 | Способ получени аддитивных солей пивалоилоксиметилового эфира 7 @ -[2-(2-аминотиазол-4-ил) ацетамидо]-3-[1-(2-диметиламиноэтил)-1н-тетразол-5-илтиометил]-3-цефем-4-карбоновой кислоты с сол ной,винной или лимонной кислотой |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR78221B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-02-01 | 1984-09-26 | Ciba Geigy Ag | |
| US4616008A (en) * | 1984-05-02 | 1986-10-07 | Takeda Chemical Industries, Ltd. | Antibacterial solid composition for oral administration |
| FR2585705B1 (fr) * | 1985-08-05 | 1989-01-13 | Bristol Myers Co | Sels de cephalosporine et compositions injectables |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS603314B2 (ja) * | 1976-08-31 | 1985-01-26 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| US4189479A (en) * | 1977-12-22 | 1980-02-19 | Takeda Chemical Industries, Ltd. | Cephalosporin esters |
-
1979
- 1979-05-14 JP JP5948179A patent/JPS55151588A/ja active Pending
-
1980
- 1980-05-03 GR GR61865A patent/GR68203B/el unknown
- 1980-05-06 US US06/147,053 patent/US4316018A/en not_active Expired - Lifetime
- 1980-05-06 NZ NZ193634A patent/NZ193634A/xx unknown
- 1980-05-12 ES ES491386A patent/ES491386A0/es active Granted
- 1980-05-12 SE SE8003548A patent/SE8003548L/ not_active Application Discontinuation
- 1980-05-13 GB GB8015741A patent/GB2052483A/en not_active Withdrawn
- 1980-05-13 BE BE1/9820A patent/BE883250A/fr unknown
- 1980-05-13 DE DE19803018340 patent/DE3018340A1/de not_active Withdrawn
- 1980-05-13 IT IT22020/80A patent/IT1132053B/it active
- 1980-05-13 DK DK209380A patent/DK209380A/da unknown
- 1980-05-13 NO NO801428A patent/NO801428L/no unknown
- 1980-05-13 NL NL8002758A patent/NL8002758A/nl not_active Application Discontinuation
- 1980-05-14 ZA ZA00802874A patent/ZA802874B/xx unknown
- 1980-05-14 AU AU58380/80A patent/AU5838080A/en not_active Abandoned
- 1980-05-14 FI FI801563A patent/FI801563A7/fi not_active Application Discontinuation
- 1980-05-14 AT AT0259180A patent/AT367427B/de not_active IP Right Cessation
- 1980-05-14 FR FR8010921A patent/FR2456746A1/fr not_active Withdrawn
- 1980-05-14 SU SU802921250A patent/SU973024A3/ru active
- 1980-05-14 PT PT71241A patent/PT71241B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1132053B (it) | 1986-06-25 |
| FR2456746A1 (fr) | 1980-12-12 |
| NZ193634A (en) | 1982-05-25 |
| NL8002758A (nl) | 1980-11-18 |
| ATA259180A (de) | 1981-11-15 |
| FI801563A7 (fi) | 1980-11-15 |
| ES8102132A1 (es) | 1980-12-16 |
| DK209380A (da) | 1980-11-15 |
| JPS55151588A (en) | 1980-11-26 |
| AT367427B (de) | 1982-07-12 |
| GB2052483A (en) | 1981-01-28 |
| DE3018340A1 (de) | 1980-11-27 |
| IT8022020A0 (it) | 1980-05-13 |
| NO801428L (no) | 1980-11-17 |
| ES491386A0 (es) | 1980-12-16 |
| BE883250A (fr) | 1980-11-13 |
| SE8003548L (sv) | 1980-11-15 |
| PT71241A (en) | 1980-06-01 |
| AU5838080A (en) | 1980-11-20 |
| US4316018A (en) | 1982-02-16 |
| GR68203B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-11-10 |
| PT71241B (en) | 1982-06-08 |
| ZA802874B (en) | 1980-12-31 |
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