NL8002107A - Werkwijze voor de bereiding van de pivaloxymethylester van 6-beta-amidinopenicillaanzuren. - Google Patents
Werkwijze voor de bereiding van de pivaloxymethylester van 6-beta-amidinopenicillaanzuren. Download PDFInfo
- Publication number
- NL8002107A NL8002107A NL8002107A NL8002107A NL8002107A NL 8002107 A NL8002107 A NL 8002107A NL 8002107 A NL8002107 A NL 8002107A NL 8002107 A NL8002107 A NL 8002107A NL 8002107 A NL8002107 A NL 8002107A
- Authority
- NL
- Netherlands
- Prior art keywords
- ester
- pivaloxymethyl
- compound
- preparing
- beta
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 10
- 150000007513 acids Chemical class 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 claims 2
- 229940118662 aluminum carbonate Drugs 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- -1 hexahydro-1H-azepin-1-yl Chemical group 0.000 description 5
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 4
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NPGNOVNWUSPMDP-UTEPHESZSA-N chembl1650818 Chemical compound N(/[C@H]1[C@@H]2N(C1=O)[C@H](C(S2)(C)C)C(=O)OCOC(=O)C(C)(C)C)=C\N1CCCCCC1 NPGNOVNWUSPMDP-UTEPHESZSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229960004212 pivmecillinam Drugs 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 1
- 241000894006 Bacteria Species 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
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 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 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
- 229940106164 cephalexin Drugs 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 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 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 150000003952 β-lactams 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2186279 | 1979-04-13 | ||
| IT21862/79A IT1119739B (it) | 1979-04-13 | 1979-04-13 | Metodo per la produzione di esteri di derivati dell'acido 6-b-amidino-penicillanico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8002107A true NL8002107A (nl) | 1980-10-15 |
Family
ID=11187898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8002107A NL8002107A (nl) | 1979-04-13 | 1980-04-10 | Werkwijze voor de bereiding van de pivaloxymethylester van 6-beta-amidinopenicillaanzuren. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS55147288A (ja) |
| BE (1) | BE882556A (ja) |
| DE (1) | DE3012666A1 (ja) |
| DK (1) | DK154980A (ja) |
| ES (1) | ES490521A0 (ja) |
| FR (1) | FR2453863A1 (ja) |
| GB (1) | GB2047689A (ja) |
| IT (1) | IT1119739B (ja) |
| NL (1) | NL8002107A (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573603A (zh) * | 2022-03-07 | 2022-06-03 | 南京美智德合成材料有限公司 | 一种一锅合成匹美西林的工艺 |
-
1979
- 1979-04-13 IT IT21862/79A patent/IT1119739B/it active
-
1980
- 1980-03-19 GB GB8009291A patent/GB2047689A/en not_active Withdrawn
- 1980-03-28 FR FR8006992A patent/FR2453863A1/fr not_active Withdrawn
- 1980-03-31 BE BE0/200056A patent/BE882556A/fr unknown
- 1980-04-01 DE DE19803012666 patent/DE3012666A1/de not_active Withdrawn
- 1980-04-01 JP JP4125580A patent/JPS55147288A/ja active Pending
- 1980-04-10 DK DK154980A patent/DK154980A/da not_active IP Right Cessation
- 1980-04-10 NL NL8002107A patent/NL8002107A/nl not_active Application Discontinuation
- 1980-04-12 ES ES490521A patent/ES490521A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2453863A1 (fr) | 1980-11-07 |
| IT1119739B (it) | 1986-03-10 |
| ES8102573A1 (es) | 1981-02-16 |
| GB2047689A (en) | 1980-12-03 |
| BE882556A (fr) | 1980-07-16 |
| IT7921862A0 (it) | 1979-04-13 |
| ES490521A0 (es) | 1981-02-16 |
| DE3012666A1 (de) | 1980-11-27 |
| DK154980A (da) | 1980-10-14 |
| JPS55147288A (en) | 1980-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3543236B1 (en) | Method for preparing avibactam intermediate | |
| NL8002107A (nl) | Werkwijze voor de bereiding van de pivaloxymethylester van 6-beta-amidinopenicillaanzuren. | |
| US3658802A (en) | Cephalosporine derivatives and process | |
| JPS6031838B2 (ja) | ２−アルコキシ−セフアロスポリンの製法 | |
| US6803467B2 (en) | Intermediates for the production of quinolone carboxylic acid derivatives | |
| EP1214321B1 (en) | Process for production of naphthyridine-3-carboxylic acid derivatives | |
| KAMETANI et al. | The Deblocking of Cephalosporin Benzhydryl Esters with Formic Acid | |
| FI86183B (fi) | Foerfarande foer framstaellning av 7-amino-3-alkoximetyl-3-cefem-4-karboxylsyraderivat. | |
| AP670A (en) | Diclavulanate salt with a diamino ether and process of preparation. | |
| KR0122131B1 (ko) | 5-원자 질소 함유 이종원자 방향족 화합물의 제조방법 | |
| CN114014858A (zh) | 多取代中氮茚衍生物的制备方法 | |
| Rigo et al. | Studies on pyrrolidinones. Synthesis of N‐acylpyroglutamic acids having bactericide and fungicide properties | |
| EP0023045B1 (en) | Imidazolecarboxylic acid derivatives of penicillins and cephalosporins | |
| FI66617C (fi) | Foerfarande foer framstaellning av 6-aminopenicillansyra 7-aminocefalosporansyra och dess derivat i 3-staeaeningen | |
| GB2040934A (en) | Vindesine synthesis | |
| Wasserman et al. | The chemistry of vicinal tricarbonyls. Formation of carbazole derivatives. | |
| Kemp et al. | Penicillin N-cyanosulphilmines; cyanamide/iodobenzene diacetate, a convenient cyanonitrene reagent for N-cyano sulphilmines, sulphoximines, phosphinimines and aziridines | |
| JPS60202891A (ja) | デスアセチル‐７‐アミノセフアロスポラニツクアシツドから３‐エステルメチルセフアロスポリン類を製造する解媒方法 | |
| JPH02229196A (ja) | セファロスポリン誘導体およびそれらの製法 | |
| US3868364A (en) | Improved process for producing penicillin compound | |
| JPH01186854A (ja) | ２−置換オキシイミノ−３−オキソ酪酸の製造法 | |
| CA1052771A (en) | METHOD OF PRODUCING 6-.beta.-AMIDINOPENICILLANIC ACID DERIVATIVES | |
| GB2047243A (en) | Preparing derivatives of 6 - amidino - penicillanic acid | |
| FI78703B (fi) | Nya vinylkefalosporin c-derivat, foerfarande foer deras framstaellning och deras anvaendning vid framstaellning av aminokefalosporiner. | |
| JP2735297B2 (ja) | 中間体の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |