SU566843A1 - Способ получени производных 6- -амидинопенициллановой кислоты - Google Patents
Способ получени производных 6- -амидинопенициллановой кислотыInfo
- Publication number
- SU566843A1 SU566843A1 SU7502092903A SU2092903A SU566843A1 SU 566843 A1 SU566843 A1 SU 566843A1 SU 7502092903 A SU7502092903 A SU 7502092903A SU 2092903 A SU2092903 A SU 2092903A SU 566843 A1 SU566843 A1 SU 566843A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ester
- penicillanic acid
- amidino
- preparing derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 10
- -1 amidine penicillins Chemical class 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 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 7
- 239000013078 crystal Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 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 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 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)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU7502092903A SU566843A1 (ru) | 1975-01-06 | 1975-01-06 | Способ получени производных 6- -амидинопенициллановой кислоты |
| CA230,488A CA1052771A (en) | 1975-01-06 | 1975-06-30 | METHOD OF PRODUCING 6-.beta.-AMIDINOPENICILLANIC ACID DERIVATIVES |
| GB27639/75A GB1482388A (en) | 1975-01-06 | 1975-07-01 | Method of producing 6-beta-amidinopenicillanic acid derivatives |
| DE19752530299 DE2530299A1 (de) | 1975-01-06 | 1975-07-07 | Verfahren zur herstellung von 6- beta-amidinopenicillansaeure-derivaten |
| JP50083616A JPS5210287A (en) | 1975-01-06 | 1975-07-09 | Novel production of 66betaaamzinopenicillanic acid derivative |
| CH968675A CH612974A5 (en) | 1975-01-06 | 1975-07-24 | Process for the preparation of 6 beta -aminomethyleneaminopenicillanic acid derivatives |
| FR7530540A FR2296638A1 (fr) | 1975-01-06 | 1975-10-06 | Procede de preparation de derives de l'acide 6-b-amidinopenicillanique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU7502092903A SU566843A1 (ru) | 1975-01-06 | 1975-01-06 | Способ получени производных 6- -амидинопенициллановой кислоты |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU566843A1 true SU566843A1 (ru) | 1977-07-30 |
Family
ID=20606315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502092903A SU566843A1 (ru) | 1975-01-06 | 1975-01-06 | Способ получени производных 6- -амидинопенициллановой кислоты |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5210287A (enExample) |
| CA (1) | CA1052771A (enExample) |
| CH (1) | CH612974A5 (enExample) |
| DE (1) | DE2530299A1 (enExample) |
| FR (1) | FR2296638A1 (enExample) |
| GB (1) | GB1482388A (enExample) |
| SU (1) | SU566843A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77362A1 (enExample) * | 1977-05-17 | 1979-01-19 | ||
| 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 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758782A (fr) * | 1969-11-11 | 1971-05-10 | Leo Pharm Prod Ltd | Nouveaux derives d'acide 6-amidino penicillanique leur procede de preparation et leurs applications comme antibiotiques |
| GB1427139A (en) * | 1972-03-13 | 1976-03-10 | Astra Laekemedel Ab | Penicillins |
| GB1417099A (en) * | 1973-02-02 | 1975-12-10 | Leo Pharm Prod Ltd | Method for the production of derivatives of 6-aminopenicillanic acid |
-
1975
- 1975-01-06 SU SU7502092903A patent/SU566843A1/ru active
- 1975-06-30 CA CA230,488A patent/CA1052771A/en not_active Expired
- 1975-07-01 GB GB27639/75A patent/GB1482388A/en not_active Expired
- 1975-07-07 DE DE19752530299 patent/DE2530299A1/de active Pending
- 1975-07-09 JP JP50083616A patent/JPS5210287A/ja active Granted
- 1975-07-24 CH CH968675A patent/CH612974A5/xx not_active IP Right Cessation
- 1975-10-06 FR FR7530540A patent/FR2296638A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5210287A (en) | 1977-01-26 |
| CA1052771A (en) | 1979-04-17 |
| FR2296638B1 (enExample) | 1978-04-07 |
| DE2530299A1 (de) | 1976-07-08 |
| FR2296638A1 (fr) | 1976-07-30 |
| JPS5417756B2 (enExample) | 1979-07-02 |
| GB1482388A (en) | 1977-08-10 |
| CH612974A5 (en) | 1979-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU508193A3 (ru) | Способ получени -(метоксиметил-фурилметил)-6,7-бензоморфанов или-морфинанов | |
| Charette et al. | A new method for the conversion of secondary and tertiary amides to bridged orthoesters | |
| SU450400A3 (ru) | Способ получени аминофениламидина или его соли | |
| SU566843A1 (ru) | Способ получени производных 6- -амидинопенициллановой кислоты | |
| SU546280A3 (ru) | Способ получени 2-(3-) 4-дифенилметил-1-пиперазинил (-пропил)- -триазоло (1,5- ) пиридина или его дигидрохлорида | |
| US3247213A (en) | Heterocyclic nitrogen compounds | |
| US3870718A (en) | 2-imidazolidine substituted quinoxaline-1,4-dioxides and intermediates therefor | |
| US2772280A (en) | Synthesis of 4-amino-3-isoxazolidone and its derivatives | |
| NO137999B (no) | Analogifremgangsm}te ved fremstilling av terapeutisk aktive oxofurylestere av 6-(alfa-aminofenylacetamido)-penicillansyre | |
| SU501673A3 (ru) | Способ получени производных 2-(5-нитро-2-фурил)-тиено(2,3- ) пиримидина | |
| US3655673A (en) | Process for the preparation of oxazolidinone derivatives | |
| OKAWARA et al. | Facile Formation of 1, 3-Disubstituted 2, 3, 5, 6-Tetrahydro-2-thioxopyrimidin-4 (1H)-ones and 2-N, 3-Disubstituted 2, 3, 5, 6-Tetrahyro-2-imino-1, 3-thiazin-4-ones from Thioureas and β-Haloacyl Halides | |
| SU618045A3 (ru) | Способ получени производных тиено (2,3-с) пиридина или их солей | |
| US2857386A (en) | Iso reserpic and iso deserpidic acids, salts and esters | |
| US3459764A (en) | Preparation of nitroimidazole carbamates | |
| SU503523A3 (ru) | Способ получени -(гетероарилметил)- -дезокси-нормофинов или -норкодеинов | |
| US2821531A (en) | Preparation of 3-acyl-6-substituted delta6-desoxymorphine | |
| US3939167A (en) | 3-(2-Methylthio-2-tertiary aminoacetyl)-5-phenylisoxazoles | |
| US2903464A (en) | Quaternary ammonium compounds | |
| US2694067A (en) | delta 6-desoxymorphine compounds and processes of preparing the same | |
| US2189809A (en) | Alkyl esters of hydrohalides of methyl-hydrasteine and processes for producing the same | |
| US3878198A (en) | {62 -Ketoacyl derivatives of 6-aminopenicillanic acid and process thereof | |
| US2654743A (en) | Delta-piperidinobutyl diphenylacetate salt of penicillin | |
| SU511011A3 (ru) | Способ получени производных пенициллина | |
| SU430545A1 (ru) | Способ получения сложных эфиров 6-дезокси-5-окситетрац,иклина |