SU525431A3 - Способ получени кристаллического пивалоилоксиметилового эфира ампициллина - Google Patents
Способ получени кристаллического пивалоилоксиметилового эфира ампициллинаInfo
- Publication number
- SU525431A3 SU525431A3 SU1963763A SU1963763A SU525431A3 SU 525431 A3 SU525431 A3 SU 525431A3 SU 1963763 A SU1963763 A SU 1963763A SU 1963763 A SU1963763 A SU 1963763A SU 525431 A3 SU525431 A3 SU 525431A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- water
- pivampicillin
- crystalline
- solution
- pivaloyloxymethyl ester
- Prior art date
Links
- 229960003342 pivampicillin Drugs 0.000 title description 13
- ZEMIJUDPLILVNQ-ZXFNITATSA-N pivampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 ZEMIJUDPLILVNQ-ZXFNITATSA-N 0.000 title description 13
- 239000013078 crystal Substances 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- DQECFVGMGBQCPA-GLCLSGQWSA-N 2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydron;chloride Chemical compound Cl.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 DQECFVGMGBQCPA-GLCLSGQWSA-N 0.000 description 4
- 229960004632 pivampicillin hydrochloride Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000013405 beer Nutrition 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- -1 pivaloyloxymethyl ester Chemical class 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 239000002585 base Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000011440 grout Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4631772A GB1413516A (en) | 1972-10-06 | 1972-10-06 | Crystalline pivaloyloxymethal d - -alpha- aminobenzylpenicillinate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU525431A3 true SU525431A3 (ru) | 1976-08-15 |
Family
ID=10440753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1963763A SU525431A3 (ru) | 1972-10-06 | 1973-10-05 | Способ получени кристаллического пивалоилоксиметилового эфира ампициллина |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US3956279A (enExample) |
| JP (1) | JPS5243884B2 (enExample) |
| AR (1) | AR201671A1 (enExample) |
| AT (1) | AT331394B (enExample) |
| AU (1) | AU474646B2 (enExample) |
| BE (1) | BE805717A (enExample) |
| CA (1) | CA1000270A (enExample) |
| CH (1) | CH593982A5 (enExample) |
| CS (1) | CS179991B2 (enExample) |
| DD (1) | DD107050A5 (enExample) |
| DE (1) | DE2349971C3 (enExample) |
| DK (1) | DK131034B (enExample) |
| ES (1) | ES419148A1 (enExample) |
| FI (1) | FI59412C (enExample) |
| FR (1) | FR2201873B1 (enExample) |
| GB (1) | GB1413516A (enExample) |
| HU (1) | HU165706B (enExample) |
| IE (1) | IE38819B1 (enExample) |
| IL (1) | IL43235A (enExample) |
| IT (1) | IT1055540B (enExample) |
| LU (1) | LU68565A1 (enExample) |
| NL (1) | NL7313532A (enExample) |
| NO (1) | NO148849C (enExample) |
| PH (1) | PH12040A (enExample) |
| PL (1) | PL94275B1 (enExample) |
| SE (1) | SE410735B (enExample) |
| SU (1) | SU525431A3 (enExample) |
| YU (1) | YU39580B (enExample) |
| ZA (1) | ZA737270B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS541891U (enExample) * | 1977-06-08 | 1979-01-08 | ||
| 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 |
| 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 |
| RU2167162C1 (ru) * | 2000-02-28 | 2001-05-20 | Савельев Евгений Александрович | Способ получения гидроиодида диэтиламиноэтилового эфира бензилпенициллина |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1241844A (en) * | 1968-08-23 | 1971-08-04 | Beecham Group Ltd | Penicillins |
| US3697507A (en) * | 1968-09-26 | 1972-10-10 | Leo Pharm Prod Ltd | Esters of {60 -aminobenzylpenicillin |
| NL7204264A (enExample) * | 1971-04-02 | 1972-10-04 |
-
1972
- 1972-10-06 GB GB4631772A patent/GB1413516A/en not_active Expired
-
1973
- 1973-09-11 IE IE1618/73A patent/IE38819B1/xx unknown
- 1973-09-12 ZA ZA737270A patent/ZA737270B/xx unknown
- 1973-09-14 IL IL43235A patent/IL43235A/en unknown
- 1973-09-17 YU YU2450/73A patent/YU39580B/xx unknown
- 1973-09-21 AT AT813273A patent/AT331394B/de not_active IP Right Cessation
- 1973-09-21 CA CA181,627A patent/CA1000270A/en not_active Expired
- 1973-09-21 AU AU60581/73A patent/AU474646B2/en not_active Expired
- 1973-09-21 US US05/399,736 patent/US3956279A/en not_active Expired - Lifetime
- 1973-09-24 PH PH15042A patent/PH12040A/en unknown
- 1973-09-27 CH CH1385573A patent/CH593982A5/xx not_active IP Right Cessation
- 1973-09-28 ES ES419148A patent/ES419148A1/es not_active Expired
- 1973-10-02 NL NL7313532A patent/NL7313532A/xx active Search and Examination
- 1973-10-03 FI FI3079/73A patent/FI59412C/fi active
- 1973-10-04 DK DK538573AA patent/DK131034B/da not_active IP Right Cessation
- 1973-10-04 DE DE2349971A patent/DE2349971C3/de not_active Expired
- 1973-10-05 SE SE7313611A patent/SE410735B/xx unknown
- 1973-10-05 AR AR250387A patent/AR201671A1/es active
- 1973-10-05 BE BE136385A patent/BE805717A/xx not_active IP Right Cessation
- 1973-10-05 SU SU1963763A patent/SU525431A3/ru active
- 1973-10-05 IT IT69943/73A patent/IT1055540B/it active
- 1973-10-05 CS CS7300006882A patent/CS179991B2/cs unknown
- 1973-10-05 JP JP48111579A patent/JPS5243884B2/ja not_active Expired
- 1973-10-05 LU LU68565A patent/LU68565A1/xx unknown
- 1973-10-05 DD DD173901A patent/DD107050A5/xx unknown
- 1973-10-05 FR FR7335729A patent/FR2201873B1/fr not_active Expired
- 1973-10-05 HU HULE724A patent/HU165706B/hu unknown
- 1973-10-05 NO NO3884/73A patent/NO148849C/no unknown
- 1973-10-06 PL PL1973165681A patent/PL94275B1/pl unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH02167286A (ja) | クラバラン酸の塩、その製法及び用途 | |
| JP7240397B2 (ja) | ガドリニウム系イオン性造影剤の中間体の調製方法及びその応用 | |
| SU799666A3 (ru) | Способ получени гидратированной крис-ТАлличЕСКОй фОРМы НАТРиЕВОй СОли 3-АцЕТОКСи-МЕТил-7 2-(2-АМиНО-4-ТиАзОлил)-2-МЕТОКСи-иМиНОАцЕТАМидО цЕф-3-EM-4-КАРбОНОВОй КиС-лОТы,СиН-изОМЕРА | |
| SU525431A3 (ru) | Способ получени кристаллического пивалоилоксиметилового эфира ампициллина | |
| CN105254649B (zh) | 一种盐酸头孢卡品酯的制备方法 | |
| BR112020010618B1 (pt) | Método para preparar acetato de salicilamina | |
| Jacobs et al. | ON NITRO-AND AMINOARYL ARSONIC ACIDS. | |
| JP4658806B2 (ja) | ３−クロロメチル−３−セフェム誘導体の製造方法 | |
| US3983109A (en) | Process for recovering cephalosporin C from A fermentation broth as the N-(p-nitrobenzoyl) derivative | |
| JP2618271B2 (ja) | モノｐ―ニトロベンジルマロネートマグネシウム塩の結晶変態及びその製法 | |
| CN115572227B (zh) | 一种制备卡巴匹林钙的方法 | |
| JP4880332B2 (ja) | 結晶性ｌ−カルノシン亜鉛錯体の製造方法 | |
| US2064817A (en) | Manufacture of salts of diazotized tetrazole derivatives | |
| US3932439A (en) | N-substituted cycloserine compounds, salts thereof, and processes for preparing them | |
| JPH04261189A (ja) | トリフルオロメタンスルホン酸スズの製造法 | |
| PL85039B1 (pl) | Sposób wytwarzania soli sodowej a-ftminobenzylopeiiicylmy | |
| US2668852A (en) | Neutral calcium 4-aminosalicylate hemihydrate and preparation of the same | |
| JPH07101937A (ja) | フェニルアゾピラゾール系化合物の精製方法 | |
| Chattaway et al. | XLIX.—The reduction of o-nitrophenyl iso diazomethanes | |
| US2839583A (en) | Process for the preparation of | |
| US3711490A (en) | Method for preparing 2,3-pyridinediol | |
| JPS6165885A (ja) | 新規合成中間体及びその製法 | |
| CN101111498A (zh) | 头孢卡品酯的甲磺酸盐 | |
| US917758A (en) | Calcium salt of dibrombehenic acid. | |
| US667381A (en) | Xanthin homologue and process of making same. |