SU731899A3 - Способ получени -цефалоспориновых сложных эфиров - Google Patents
Способ получени -цефалоспориновых сложных эфиров Download PDFInfo
- Publication number
- SU731899A3 SU731899A3 SU752134779A SU2134779A SU731899A3 SU 731899 A3 SU731899 A3 SU 731899A3 SU 752134779 A SU752134779 A SU 752134779A SU 2134779 A SU2134779 A SU 2134779A SU 731899 A3 SU731899 A3 SU 731899A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- methyl
- solution
- ylthiomethyl
- carboxylic acid
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 3
- -1 alkanoyloxymethyl cephalosporin esters Chemical class 0.000 claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 239000012047 saturated solution Substances 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 2
- RRJHESVQVSRQEX-MRXJRLSOSA-N (6R)-7-[[(2R)-2-formyloxy-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(=O)O[C@@H](C(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)O)C1=O)C1=CC=CC=C1 RRJHESVQVSRQEX-MRXJRLSOSA-N 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229930186147 Cephalosporin Natural products 0.000 abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 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 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
-
- 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/471,528 US3933808A (en) | 1974-05-20 | 1974-05-20 | Cephalosporin esters |
| US471527A US3928333A (en) | 1974-05-20 | 1974-05-20 | Process for the preparation of 3 cephalosporin esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU731899A3 true SU731899A3 (ru) | 1980-04-30 |
Family
ID=27043469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752134779A SU731899A3 (ru) | 1974-05-20 | 1975-05-19 | Способ получени -цефалоспориновых сложных эфиров |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190897B (it) * | 1982-06-29 | 1988-02-24 | Opos Biochimica Srl | Procedimento per la preparazione dell'estere 1-etossicarbonilossietilico dell'acido 6-(d(-)-alfa aminoalfa fenilacetamido)-penicillanico |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
-
1975
- 1975-05-16 YU YU01255/75A patent/YU125575A/xx unknown
- 1975-05-16 CH CH635475A patent/CH601314A5/de not_active IP Right Cessation
- 1975-05-17 PL PL1975180468A patent/PL103490B1/pl unknown
- 1975-05-19 CS CS753481A patent/CS196272B2/cs unknown
- 1975-05-19 SU SU752134779A patent/SU731899A3/ru active
- 1975-05-19 HU HUEI620A patent/HU170561B/hu unknown
- 1975-05-20 DD DD186129A patent/DD120446A5/xx unknown
- 1975-05-20 SE SE7505741A patent/SE421701B/xx unknown
- 1975-05-20 DK DK221875A patent/DK221875A/da unknown
- 1975-05-20 BG BG031234A patent/BG25228A3/xx unknown
- 1975-05-20 ES ES437809A patent/ES437809A1/es not_active Expired
- 1975-05-20 AR AR258878A patent/AR212321A1/es active
- 1975-05-20 BG BG030033A patent/BG25096A3/xx unknown
- 1975-05-20 AT AT381675A patent/AT340589B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH601314A5 (en) | 1978-07-14 |
| HU170561B (enrdf_load_stackoverflow) | 1977-07-28 |
| PL103490B1 (pl) | 1979-06-30 |
| ES437809A1 (es) | 1977-04-01 |
| BG25096A3 (en) | 1978-07-12 |
| AT340589B (de) | 1977-12-27 |
| ATA381675A (de) | 1977-04-15 |
| BG25228A3 (en) | 1978-08-10 |
| DD120446A5 (enrdf_load_stackoverflow) | 1976-06-12 |
| CS196272B2 (en) | 1980-03-31 |
| DK221875A (da) | 1975-11-21 |
| YU125575A (en) | 1982-05-31 |
| SE421701B (sv) | 1982-01-25 |
| AR212321A1 (es) | 1978-06-30 |
| SE7505741L (sv) | 1975-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1093068A (en) | Cephalosporin antibiotics | |
| GB1571683A (en) | Ester derivatives of cefuroxime | |
| US4604457A (en) | 2-substituted cephem derivatives and process for preparing the same | |
| US3963712A (en) | 3-Halo-cephalosporins | |
| SU731899A3 (ru) | Способ получени -цефалоспориновых сложных эфиров | |
| US4147863A (en) | 7-D-(-)-mandelamido-3-(1-methyl-1H-tetrazol-5-yl)vinyl-3-cephem-4-carboxylic acid | |
| DK163584B (da) | 7-amino-3-propenylcephalosporinsyrederivater samt fremgangsmaade til fremstilling deraf | |
| US4888429A (en) | Process for producing allyl aminothiazole acetate intermediates | |
| US3928333A (en) | Process for the preparation of 3 cephalosporin esters | |
| KR890002107B1 (ko) | 세팔로스포린 유도체의 제조방법 | |
| US4451399A (en) | Imidazolecarboxylic acid derivatives | |
| CA1093549A (en) | Cephalosporin antibiotics | |
| US4075219A (en) | Epimerization process | |
| SU543353A3 (ru) | Способ получени производных 7-монохлорацетамидо-3-дезацетоксицефалоспорановой кислоты | |
| JPS60260584A (ja) | セフアロスポリン誘導体 | |
| KR790001175B1 (ko) | 7-아미노 세팔로스포란산 및 그 유도체의 에스테르의 제조방법 | |
| US4046759A (en) | Penicillin esters | |
| JPS59164771A (ja) | 塩素化アゼチジノン誘導体の製造方法 | |
| KR790001503B1 (ko) | △3-세팔로스포린 에스테르의 제조방법 | |
| EP0120094B1 (en) | Azetidinone compounds | |
| US3598832A (en) | 5-esterified hydroxy-thiazolidine-4-carboxylic acid compounds | |
| KR840002142B1 (ko) | 7α-메톡시세팔로스포린 유도체의 제조방법 | |
| KR830001521B1 (ko) | 세팔로스포린 항생물질의 제조 방법 | |
| US4128714A (en) | Process for the preparation of 7-acylamida-3-halo-3-alkyl-cepham-4-carboxylic acids and esters | |
| SU570592A1 (ru) | Способ получени алкиловых эфиров пропаргилового спирта |