FI66387B - Foerfarande foer framstaellning av hydroxi-alfa-aminobensyl-penicillin - Google Patents
Foerfarande foer framstaellning av hydroxi-alfa-aminobensyl-penicillin Download PDFInfo
- Publication number
- FI66387B FI66387B FI773935A FI773935A FI66387B FI 66387 B FI66387 B FI 66387B FI 773935 A FI773935 A FI 773935A FI 773935 A FI773935 A FI 773935A FI 66387 B FI66387 B FI 66387B
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- formula
- ethyl
- reacting
- alpha
- Prior art date
Links
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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (4)
1. Ett nytt förfarande för framställning av hydroxi-alfa-amino-bensylpenicillin, vilket omfattar stegen: (a) man skyddar aminogruppen i D(-)-p-hydroxi-C-fenylglycin som enamin genom omsättande av nämnda glycinderivat med etyl- eller metylacetylacetat och natrium- eller kaliumhydroxid, (b) man bildar motsvarande blandade anhydrid genom omsättande av den i steget (a) erhAllna produkten med syraklorid och/eller alkylklorformiat, (c) man omsätter nämnda blandade anhydrid med en lösning av 6-aminopenicillansyra i form av trietylaminsalt eller trimetylsily-lester, och (d) man isolerar antibiotikum genom hydrolysering frAn den i det föregaende steget erhillna mellanprodukten, känneteck-n a t därav, att man omsätter D-(-)-p-hydroxi-C-fenylglycin, som innehAller en som enamin skyddad aminogrupp, med N-trialkylsilyl-2-oxazoldinon för skyddande av hydroxylgruppen i fenol och därefter med trietylaminhydroklorid, varvid man erhäller en förening med formeIn (I) /-V /°2Η5 R2 ^ * Si0 \ O )—CH-COOH . —C2H5 (I) R2 ^2Η5 H-C T> V 0R1 väri är metyl eller etyl och R2 är C^_^-alkyl, varvid man i steget (b) erhAller en blandad anhydrid med formeln (II) 14 66387 Rj O O R2^> S10-^^C-Rp (II) *2 H3C--V^Nh V 0R1 väri och Rj har ovan angivna betydelse och Rq är en alkoxigrupp med en lig molekylvikt eller en alkylgrupp med 4-9 kolatomer, och frin vilken förening man i steget (c) framställer en mellanprodukt med formeln (III), kwswf·V R2 ' ! v>9: 0R1 _c> "V-i^V™3 |! \
8 Qr -N- COO-R3 I (III)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES459494A ES459494A1 (es) | 1977-06-04 | 1977-06-04 | Procedimiento de preparacion de hidrox-alfa-aminobencilpeni-cilina. |
| ES459494 | 1977-06-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773935A FI773935A (fi) | 1978-12-05 |
| FI66387B true FI66387B (fi) | 1984-06-29 |
| FI66387C FI66387C (fi) | 1984-10-10 |
Family
ID=8473946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773935A FI66387C (fi) | 1977-06-04 | 1977-12-27 | Foerfarande foer framstaellning av hydroxi-alfa-aminobensyl-penicillin |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4193918A (sv) |
| JP (1) | JPS543091A (sv) |
| AT (1) | AT360648B (sv) |
| AU (1) | AU519197B2 (sv) |
| BE (1) | BE867414A (sv) |
| CA (1) | CA1100484A (sv) |
| CH (1) | CH635591A5 (sv) |
| DE (1) | DE2822876A1 (sv) |
| DK (1) | DK248978A (sv) |
| ES (1) | ES459494A1 (sv) |
| FI (1) | FI66387C (sv) |
| FR (1) | FR2392997A1 (sv) |
| GB (1) | GB1604166A (sv) |
| IL (1) | IL53553A (sv) |
| NL (1) | NL7800700A (sv) |
| NZ (1) | NZ187327A (sv) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5846197A (ja) * | 1981-09-11 | 1983-03-17 | 星光化学工業株式会社 | 石膏ボ−ド用原紙の製造方法 |
| JPS6042386A (ja) * | 1983-08-17 | 1985-03-06 | ユング ジン フア−マシウテイカル インダストリアル カンパニイ リミテツド | ペニシリン誘導体の製造方法 |
| HU221200B1 (en) * | 1990-01-22 | 2002-08-28 | Biochemie Gmbh | Process for producing beta-lactames |
| JP2002535680A (ja) | 1999-01-27 | 2002-10-22 | ファルマシア・アンド・アップジョン・カンパニー | 延長因子ｐ活性モジュレーターのアッセイ方法 |
| CN102408437A (zh) * | 2011-10-21 | 2012-04-11 | 西南交通大学 | 一种阿扑西林的制备方法 |
| CN103772414B (zh) * | 2013-12-31 | 2016-03-09 | 福建省福抗药业股份有限公司 | 一种制备丙二醇头孢曲嗪的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES401263A1 (es) * | 1972-03-28 | 1975-02-16 | Beecham Group Ltd | Un procedimiento para la produccion de alfa - amino-(p-hi- droxibencil) penicilina. |
| ES411867A1 (es) * | 1973-02-21 | 1976-01-01 | Gema Sa | Procedimiento para la preparacion de agentes sililantes. |
| JPS50129589A (sv) * | 1974-03-30 | 1975-10-13 | ||
| GB1494902A (en) * | 1974-05-09 | 1977-12-14 | Glaxo Lab Ltd | Penicillins |
| US3980637A (en) * | 1975-03-17 | 1976-09-14 | Bristol-Myers Company | Production of amoxicillin |
| NL162387C (nl) * | 1977-09-06 | 1980-05-16 | Gist Brocades Nv | Werkwijze voor het bereiden van 6-(d-alpha-amino-p- -hydroxyfenylacetamido)penicillanzuur. |
-
1977
- 1977-06-04 ES ES459494A patent/ES459494A1/es not_active Expired
- 1977-12-07 IL IL53553A patent/IL53553A/xx unknown
- 1977-12-27 FI FI773935A patent/FI66387C/fi not_active IP Right Cessation
-
1978
- 1978-01-19 NL NL7800700A patent/NL7800700A/xx active Search and Examination
- 1978-05-10 GB GB18691/78A patent/GB1604166A/en not_active Expired
- 1978-05-11 CA CA303,095A patent/CA1100484A/en not_active Expired
- 1978-05-11 JP JP5506478A patent/JPS543091A/ja active Pending
- 1978-05-22 NZ NZ187327A patent/NZ187327A/xx unknown
- 1978-05-23 CH CH558178A patent/CH635591A5/fr not_active IP Right Cessation
- 1978-05-24 BE BE187985A patent/BE867414A/xx not_active IP Right Cessation
- 1978-05-26 DE DE19782822876 patent/DE2822876A1/de active Granted
- 1978-05-29 AU AU36597/78A patent/AU519197B2/en not_active Expired
- 1978-06-01 US US05/911,513 patent/US4193918A/en not_active Expired - Lifetime
- 1978-06-02 DK DK248978A patent/DK248978A/da unknown
- 1978-06-02 FR FR7816590A patent/FR2392997A1/fr active Granted
- 1978-06-02 AT AT401978A patent/AT360648B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES459494A1 (es) | 1978-05-01 |
| IL53553A (en) | 1980-12-31 |
| NL7800700A (nl) | 1978-12-06 |
| DK248978A (da) | 1978-12-05 |
| BE867414A (fr) | 1978-09-18 |
| NZ187327A (en) | 1981-05-29 |
| FI66387C (fi) | 1984-10-10 |
| ATA401978A (de) | 1980-06-15 |
| CA1100484A (en) | 1981-05-05 |
| FI773935A (fi) | 1978-12-05 |
| AT360648B (de) | 1981-01-26 |
| FR2392997B1 (sv) | 1981-02-06 |
| AU519197B2 (en) | 1981-11-19 |
| GB1604166A (en) | 1981-12-02 |
| CH635591A5 (fr) | 1983-04-15 |
| JPS543091A (en) | 1979-01-11 |
| DE2822876C2 (sv) | 1988-01-07 |
| US4193918A (en) | 1980-03-18 |
| IL53553A0 (en) | 1978-03-10 |
| FR2392997A1 (fr) | 1978-12-29 |
| AU3659778A (en) | 1979-12-06 |
| DE2822876A1 (de) | 1978-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: ANTIBIOTICOS S.A. |