SE452767B - Forbettrat forfarande for framstellning av 6-/d(-)-alfa-(4-c?711-c?714-alkyl-2,3-dioxo-1-piperazinokarbonylamino) fenylacetamido/ penicillinsyror - Google Patents
Forbettrat forfarande for framstellning av 6-/d(-)-alfa-(4-c?711-c?714-alkyl-2,3-dioxo-1-piperazinokarbonylamino) fenylacetamido/ penicillinsyrorInfo
- Publication number
- SE452767B SE452767B SE8201998A SE8201998A SE452767B SE 452767 B SE452767 B SE 452767B SE 8201998 A SE8201998 A SE 8201998A SE 8201998 A SE8201998 A SE 8201998A SE 452767 B SE452767 B SE 452767B
- Authority
- SE
- Sweden
- Prior art keywords
- weight
- dioxo
- ampicillin
- parts
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- -1 PHENYLACETAMIDO Chemical class 0.000 title description 6
- 229930182555 Penicillin Natural products 0.000 title 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 title 1
- 229940049954 penicillin Drugs 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 66
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound 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 claims description 32
- 239000000203 mixture Substances 0.000 claims description 30
- 229960000723 ampicillin Drugs 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 150000004820 halides Chemical class 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 239000012452 mother liquor Substances 0.000 claims description 5
- 229960003311 ampicillin trihydrate Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 3
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000004684 trihydrates Chemical class 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24875481A | 1981-03-30 | 1981-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8201998L SE8201998L (sv) | 1982-10-01 |
| SE452767B true SE452767B (sv) | 1987-12-14 |
Family
ID=22940531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8201998A SE452767B (sv) | 1981-03-30 | 1982-03-29 | Forbettrat forfarande for framstellning av 6-/d(-)-alfa-(4-c?711-c?714-alkyl-2,3-dioxo-1-piperazinokarbonylamino) fenylacetamido/ penicillinsyror |
Country Status (23)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BG46664A1 (en) * | 1985-08-16 | 1990-02-15 | Druzhestven N Izsledovatelski | Method for preparing of 6- /d (-)- alpha- (4- ethyl- 2, 3- dioxo- 1- piperazine carbonylamino)- phenylacetamido/- penicillanic acid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087424A (en) * | 1974-05-09 | 1978-05-02 | Toyama Chemical Co., Ltd. | Novel penicillins and cephalosporins and process for producing the same |
| IL47168A (en) * | 1974-05-09 | 1979-07-25 | Toyama Chemical Co Ltd | Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same |
| US4112090A (en) * | 1974-05-09 | 1978-09-05 | Toyama Chemical Co., Ltd. | Novel penicillins and cephalosporins and process for producing the same |
-
1982
- 1982-01-28 CA CA000395121A patent/CA1200239A/en not_active Expired
- 1982-01-29 GB GB8202662A patent/GB2095661B/en not_active Expired
- 1982-01-29 AU AU79964/82A patent/AU544896B2/en not_active Expired
- 1982-02-02 ZA ZA82674A patent/ZA82674B/xx unknown
- 1982-02-03 GR GR67199A patent/GR76054B/el unknown
- 1982-02-04 DK DK048282A patent/DK161079C/da active
- 1982-02-08 ES ES509424A patent/ES509424A0/es active Granted
- 1982-02-11 IL IL64981A patent/IL64981A/xx unknown
- 1982-02-17 PH PH26877A patent/PH19765A/en unknown
- 1982-02-22 JP JP57026170A patent/JPS57165391A/ja active Granted
- 1982-03-01 NZ NZ199869A patent/NZ199869A/en unknown
- 1982-03-09 AT AT0093082A patent/AT381706B/de not_active IP Right Cessation
- 1982-03-09 DE DE19823208506 patent/DE3208506A1/de active Granted
- 1982-03-10 IT IT47962/82A patent/IT1148130B/it active
- 1982-03-17 FR FR8204497A patent/FR2502623A1/fr active Granted
- 1982-03-18 PL PL23550882A patent/PL235508A1/xx unknown
- 1982-03-22 BE BE0/207631A patent/BE892586A/fr not_active IP Right Cessation
- 1982-03-24 LU LU84036A patent/LU84036A1/de unknown
- 1982-03-26 CH CH1898/82A patent/CH654309A5/de not_active IP Right Cessation
- 1982-03-29 SE SE8201998A patent/SE452767B/sv not_active IP Right Cessation
- 1982-03-29 IE IE746/82A patent/IE52907B1/en not_active IP Right Cessation
- 1982-03-29 NL NL192453D patent/NL192453A/xx not_active IP Right Cessation
- 1982-03-29 NL NL8201301A patent/NL192453C/nl not_active IP Right Cessation
-
1990
- 1990-03-29 HK HK235/90A patent/HK23590A/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0019345B1 (en) | Process for the preparation of a (d-alpha-amino-(p-hydroxyphenyl)-acetamido) group containing cephalosporanic acid derivatives | |
| US7071329B2 (en) | Process for preparing cephalosporins with salified intermediate | |
| CN104356146A (zh) | 一种头孢替安盐酸盐的制备方法 | |
| DK143563B (da) | Fremgangsmaade til fremstilling af penicilliner eller salte deraf | |
| CN103319503A (zh) | 一种头孢地尼的制备方法 | |
| KR100491587B1 (ko) | 트리아진 화합물의 제조 방법 | |
| JP2609039B2 (ja) | セフトリアキソンの新規製造法 | |
| SE452767B (sv) | Forbettrat forfarande for framstellning av 6-/d(-)-alfa-(4-c?711-c?714-alkyl-2,3-dioxo-1-piperazinokarbonylamino) fenylacetamido/ penicillinsyror | |
| JPH069647A (ja) | 新規なセファロスポリン中間体 | |
| CA1236089A (en) | Ceftazidime | |
| SE445554B (sv) | Trimetylsilylestrar eller andra letthydrolyserande estrar av 7-trimetylsilyloxikarbonylaminodecefalosporinsyra samt forfarande for framstellning derav | |
| US4610822A (en) | Process for preparing 6-[D(-)-α-(4-C1 -C4)-alkyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetamido]penicillanic acids | |
| EP0088183B1 (en) | Thiazole derivatives and their use in the manufacture of beta lactam antibiotics | |
| US4237280A (en) | Intermediate for cephalosporin type compound | |
| KR850000611B1 (ko) | 6-[d(-)-알파-(4-c₁~c₄)알킬-2,3-디옥소-1-피페라지노 카르보닐아미노)페닐아세트아미도] 페니실란산 제조방법 | |
| EP0341991A2 (en) | Method for recovery of antibiotics from mother liquors and novel pharmaceutically-acceptable salts thereof | |
| KR100432425B1 (ko) | 세펨 유도체 또는 그 염의 신규한 제조방법 | |
| EP0203400B1 (en) | Preparation of 4(5)-hydroxymethyl-5(4)-methylimidazole | |
| IL30640A (en) | Process for the preparation of 5-chloro-uracils-3,6-yeasts | |
| KR870000724B1 (ko) | 세팔로스포린 유도체의 제조방법 | |
| HU199815B (en) | Process for producing 3-isopropylbenzo-2-thia-1,3-diazinone-/4/2,2-dioxide | |
| CN116554205A (zh) | 7β-二卤乙酰氨基-3-(1-甲基-1H-四氮唑-5-基硫甲基)-3-头孢烯-4-羧酸或其盐的合成方法 | |
| HU190394B (en) | Process for producing 7-amino- and 7-phtalimido-3-methyl-3-cepheme-compounds | |
| DK152503B (da) | Fremgangsmaade til fremstilling af cephalosporansyrederivater indeholdende en d-alfa-amino-(p-hydroxyphenyl)acetamidogruppe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8201998-5 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8201998-5 Format of ref document f/p: F |