ES459645A1 - Un procedimiento para reducir un sulfoxido de cefalosporina. - Google Patents
Un procedimiento para reducir un sulfoxido de cefalosporina.Info
- Publication number
- ES459645A1 ES459645A1 ES459645A ES459645A ES459645A1 ES 459645 A1 ES459645 A1 ES 459645A1 ES 459645 A ES459645 A ES 459645A ES 459645 A ES459645 A ES 459645A ES 459645 A1 ES459645 A1 ES 459645A1
- Authority
- ES
- Spain
- Prior art keywords
- reduction process
- cephalosporin
- cephalosporin sulfoxides
- phenoxyacetamido
- cephem
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 cephalosporin sulfoxides Chemical class 0.000 title abstract 4
- 229930186147 Cephalosporin Natural products 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 238000011946 reduction process Methods 0.000 title 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 abstract 2
- YSJGVKHCAVGBIT-AVKWCDSFSA-N (4-nitrophenyl)methyl (6r)-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 YSJGVKHCAVGBIT-AVKWCDSFSA-N 0.000 abstract 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001262 acyl bromides Chemical class 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 150000008301 phosphite esters Chemical class 0.000 abstract 1
- 239000002516 radical scavenger Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Los sulfóxidos de cefalosporina son intermediarios ampliamente utilizados en la síntesis de antibióticos de cefalosporina. Por ejemplo, los sulfóxidos de cefalosporina son útiles en el procedimiento global para convertir los compuestos de 3-metil-3-cefem(desacetoxicefalosporinas) a compuestos antibióticos de metil-3-cefem-3-sustituídos. Esta funcionalización de los compuestos de 3-metil-cefem procede a través de la isomerización del 3-metil-3-cefem a 3-metil-2-cefem, la funcionalización del grupo 3-metilo activado del compuesto 2-cefem, por ejemplo, con bromo, seguido por oxidación del compuesto metil-2-cefem-3-sustituído al sulfóxido. La oxidación al sulfóxido provoca la isomerización del producto 2-cefem- a 3-cefem.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/694,516 US4044002A (en) | 1976-06-09 | 1976-06-09 | Reduction process for cephalosporin sulfoxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES459645A1 true ES459645A1 (es) | 1978-12-01 |
Family
ID=24789147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES459645A Expired ES459645A1 (es) | 1976-06-09 | 1977-06-08 | Un procedimiento para reducir un sulfoxido de cefalosporina. |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US4044002A (es) |
| JP (1) | JPS52151193A (es) |
| AR (1) | AR216074A1 (es) |
| AT (1) | AT349636B (es) |
| AU (1) | AU513323B2 (es) |
| BE (1) | BE855348A (es) |
| BG (1) | BG31648A3 (es) |
| CA (1) | CA1075229A (es) |
| CH (1) | CH637656A5 (es) |
| CS (1) | CS200515B2 (es) |
| DD (1) | DD131022A5 (es) |
| DE (1) | DE2725712C2 (es) |
| DK (1) | DK253377A (es) |
| ES (1) | ES459645A1 (es) |
| FR (1) | FR2354333A1 (es) |
| GB (1) | GB1583169A (es) |
| GR (1) | GR68937B (es) |
| HU (1) | HU176446B (es) |
| IE (1) | IE44738B1 (es) |
| IL (1) | IL51906A (es) |
| MX (1) | MX4497E (es) |
| NL (1) | NL188471C (es) |
| NZ (1) | NZ183900A (es) |
| PH (1) | PH16896A (es) |
| PL (1) | PL110528B1 (es) |
| PT (1) | PT66529B (es) |
| SE (1) | SE438336B (es) |
| SU (1) | SU913943A3 (es) |
| YU (1) | YU140377A (es) |
| ZA (1) | ZA772335B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443598A (en) * | 1977-02-15 | 1984-04-17 | Shionogi & Co., Ltd. | 1-Oxadethiacepham compounds |
| GB1557552A (en) * | 1977-02-15 | 1979-12-12 | Shionogi & Co | 1 oxadethiacepham compounds |
| US4533730A (en) * | 1977-02-15 | 1985-08-06 | Shionogi & Co., Ltd. | 1-Oxadethiacepham compounds |
| IE49374B1 (en) * | 1979-02-01 | 1985-09-18 | Lilly Co Eli | Crystalline 3-hydroxycephalosporin solvates |
| US4223133A (en) * | 1979-02-01 | 1980-09-16 | Eli Lilly And Company | Cephalosporin reduction process |
| US4237279A (en) * | 1979-07-27 | 1980-12-02 | Eli Lilly And Company | Crystalline 3-hydroxycephalosporin solvates |
| AU566944B2 (en) * | 1983-10-07 | 1987-11-05 | Gist-Brocades N.V. | Preparation of 3-cephem derivatives |
| GB8424692D0 (en) * | 1984-10-01 | 1984-11-07 | Glaxo Group Ltd | Chemical compounds |
| US5159071A (en) * | 1990-09-06 | 1992-10-27 | Ranbaxy Laboratories Limited | Process for the manufacture of 7-amino-3-exomethylene-3-cepham-4-carboxylic acid ester |
| KR100386906B1 (ko) * | 1996-02-14 | 2003-08-27 | 주식회사 코오롱 | (1)3-할로메틸-3-세펨-4-카르복실레이트 1-옥사이드의신규제조방법 |
| KR100390549B1 (ko) * | 1996-07-22 | 2003-11-17 | 주식회사 코오롱 | 3-할로메틸-3-세펨의 제조방법 |
| KR100390550B1 (ko) * | 1996-08-22 | 2003-11-28 | 주식회사 코오롱 | 3-할로메틸-3-세펨의 제조방법 |
| KR19980073026A (ko) * | 1997-03-11 | 1998-11-05 | 구광시 | 3-할로메틸-3-세펨의 제조 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641014A (en) * | 1968-10-03 | 1972-02-08 | Lilly Co Eli | Reduction of delta**3-cephalosporin sulfoxides |
-
1976
- 1976-06-09 US US05/694,516 patent/US4044002A/en not_active Expired - Lifetime
-
1977
- 1977-04-15 IE IE788/77A patent/IE44738B1/en unknown
- 1977-04-16 GR GR53229A patent/GR68937B/el unknown
- 1977-04-18 ZA ZA00772335A patent/ZA772335B/xx unknown
- 1977-04-19 IL IL51906A patent/IL51906A/xx unknown
- 1977-04-19 NZ NZ183900A patent/NZ183900A/xx unknown
- 1977-04-20 AU AU24447/77A patent/AU513323B2/en not_active Expired
- 1977-04-20 CA CA276,593A patent/CA1075229A/en not_active Expired
- 1977-05-09 PT PT66529A patent/PT66529B/pt unknown
- 1977-05-26 SE SE7706208A patent/SE438336B/xx not_active IP Right Cessation
- 1977-05-31 GB GB23032/77A patent/GB1583169A/en not_active Expired
- 1977-06-03 HU HU77EI743A patent/HU176446B/hu unknown
- 1977-06-03 FR FR7717117A patent/FR2354333A1/fr active Granted
- 1977-06-03 BE BE1008174A patent/BE855348A/xx not_active IP Right Cessation
- 1977-06-03 BG BG036494A patent/BG31648A3/xx unknown
- 1977-06-06 YU YU01403/77A patent/YU140377A/xx unknown
- 1977-06-06 PH PH19849A patent/PH16896A/en unknown
- 1977-06-06 AR AR267956A patent/AR216074A1/es active
- 1977-06-07 AT AT402477A patent/AT349636B/de not_active IP Right Cessation
- 1977-06-07 CH CH702577A patent/CH637656A5/de not_active IP Right Cessation
- 1977-06-07 DE DE2725712A patent/DE2725712C2/de not_active Expired
- 1977-06-08 ES ES459645A patent/ES459645A1/es not_active Expired
- 1977-06-08 CS CS773789A patent/CS200515B2/cs unknown
- 1977-06-08 MX MX775788U patent/MX4497E/es unknown
- 1977-06-08 NL NLAANVRAGE7706326,A patent/NL188471C/xx not_active IP Right Cessation
- 1977-06-08 SU SU772488997A patent/SU913943A3/ru active
- 1977-06-08 PL PL1977198727A patent/PL110528B1/pl unknown
- 1977-06-08 JP JP6837377A patent/JPS52151193A/ja active Granted
- 1977-06-08 DK DK253377A patent/DK253377A/da not_active Application Discontinuation
- 1977-06-09 DD DD7700199390A patent/DD131022A5/xx unknown
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