MX3329E - Procedimiento para la preparacion de cefalosporinas - Google Patents
Procedimiento para la preparacion de cefalosporinasInfo
- Publication number
- MX3329E MX3329E MX000139U MX13976U MX3329E MX 3329 E MX3329 E MX 3329E MX 000139 U MX000139 U MX 000139U MX 13976 U MX13976 U MX 13976U MX 3329 E MX3329 E MX 3329E
- Authority
- MX
- Mexico
- Prior art keywords
- metal
- lithium
- compound
- thiophenate
- cefem
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 title 1
- 229910052751 metal Inorganic materials 0.000 abstract 5
- 239000002184 metal Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 229910052744 lithium Inorganic materials 0.000 abstract 3
- -1 potassium metal amide Chemical class 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 2
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 abstract 1
- 150000008046 alkali metal hydrides Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- SHZJQHKVVLJYOD-UHFFFAOYSA-N benzhydrylbenzene;potassium Chemical compound [K].C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 SHZJQHKVVLJYOD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 abstract 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 abstract 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical class CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 abstract 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D501/08—Preparation by forming the ring or condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
Abstract
La presente invención se refiere a un procedimiento para la preparación de cefalosporinas, de estructura; (VER FIGURA) caracterizados porque se hacen reaccionar, independientemente o en mezcla, compuestos de estructura: (VER FIGURA) en un disolvente apropiado a una temperatura comprendida entre -100°C y +120°C con una base fuerte para obtener por último un compuesto de la fórmula I, o sea una mezcla de delta2 y delta3 cefem-derivados de la que, por medios conocidos se separan los delta3 cefem-derivados; las bases fuertes utilizadas para convertir los intermediarios de las fórmulas II o III en el compuesto I deseado se eligen de la clase constituída por alcoholato o tioalcoholato metálico; un fenato o tiofenato metálico con uno o más substituyentes de la clase constituída por alcoholato o tioalcolato metálico; un fenato o tiofenato metálico con uno o más substituyentes en el anillo aromático; una amida metálica tal como la amida metálica de litio, sodio o potasio de las di-isopropil-amidas,diciclohaxilamidas isopropil-ciclohexil-amidas; un compuesto organo metálico como el fenil-litio, alquil-litio, trifenilmetano lítico, sódico o potásico un hexametildisilazano de litio, un hidruro de metal alcalino o una base conjugada de sulfóxido de dialquilo; el disolvente utilizado para convertir los intermediarios de la fórmula II o III en el compuesto I deseado es tetrahidrofurano, éter dietílico, dimetilformamida, sulfóxido de dimetilo, diglima o hexametilfosforoso triamida.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1424175A GB1472864A (en) | 1975-04-05 | 1975-04-05 | Method of preparing cephalosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX3329E true MX3329E (es) | 1980-09-29 |
Family
ID=10037590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX000139U MX3329E (es) | 1975-04-05 | 1976-04-02 | Procedimiento para la preparacion de cefalosporinas |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4035362A (es) |
| JP (1) | JPS51122089A (es) |
| AT (1) | AT342200B (es) |
| AU (1) | AU499604B2 (es) |
| BE (1) | BE840329A (es) |
| CA (1) | CA1060433A (es) |
| CH (1) | CH608810A5 (es) |
| DE (1) | DE2613641C2 (es) |
| DK (1) | DK160776A (es) |
| ES (1) | ES446673A1 (es) |
| FR (1) | FR2306207A1 (es) |
| GB (1) | GB1472864A (es) |
| MX (1) | MX3329E (es) |
| NL (1) | NL172544C (es) |
| NO (1) | NO150883C (es) |
| SE (1) | SE428691B (es) |
| YU (1) | YU82976A (es) |
| ZA (1) | ZA761993B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0065488B1 (de) * | 1981-05-19 | 1985-08-14 | Ciba-Geigy Ag | Verfahren zur Herstellung von 4-Thio-azetidinon-Verbindungen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR6915080D0 (pt) * | 1969-06-12 | 1973-03-08 | Lilly Co Eli | Processo para a preparacao de um produto rearranjado de penicilina |
| BE787618A (fr) * | 1971-08-17 | 1973-02-16 | Gist Brocades Nv | Procede pour preparer des composes heterocycliques |
| US3962277A (en) * | 1973-02-09 | 1976-06-08 | Gist-Brocades N.V. | Acetidine derivatives |
| GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
| GB1472866A (en) * | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
-
1975
- 1975-04-05 GB GB1424175A patent/GB1472864A/en not_active Expired
-
1976
- 1976-03-29 NL NLAANVRAGE7603264,A patent/NL172544C/xx not_active IP Right Cessation
- 1976-03-31 FR FR7609284A patent/FR2306207A1/fr active Granted
- 1976-03-31 US US05/672,527 patent/US4035362A/en not_active Expired - Lifetime
- 1976-03-31 DE DE2613641A patent/DE2613641C2/de not_active Expired
- 1976-03-31 YU YU00829/76A patent/YU82976A/xx unknown
- 1976-04-01 AU AU12568/76A patent/AU499604B2/en not_active Expired
- 1976-04-02 AT AT238176A patent/AT342200B/de not_active IP Right Cessation
- 1976-04-02 ZA ZA761993A patent/ZA761993B/xx unknown
- 1976-04-02 DK DK160776A patent/DK160776A/da not_active IP Right Cessation
- 1976-04-02 MX MX000139U patent/MX3329E/es unknown
- 1976-04-02 SE SE7603960A patent/SE428691B/xx unknown
- 1976-04-02 NO NO761141A patent/NO150883C/no unknown
- 1976-04-02 CH CH764166A patent/CH608810A5/xx not_active IP Right Cessation
- 1976-04-02 BE BE165799A patent/BE840329A/xx not_active IP Right Cessation
- 1976-04-03 ES ES446673A patent/ES446673A1/es not_active Expired
- 1976-04-03 JP JP51036722A patent/JPS51122089A/ja active Pending
- 1976-04-05 CA CA249,604A patent/CA1060433A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO150883B (no) | 1984-09-24 |
| ATA238176A (de) | 1977-07-15 |
| YU82976A (en) | 1982-06-30 |
| DE2613641C2 (de) | 1982-12-23 |
| SE7603960L (sv) | 1976-10-06 |
| ZA761993B (en) | 1977-03-30 |
| SE428691B (sv) | 1983-07-18 |
| GB1472864A (en) | 1977-05-11 |
| AU499604B2 (en) | 1979-04-26 |
| AT342200B (de) | 1978-03-28 |
| DK160776A (da) | 1976-10-06 |
| FR2306207B1 (es) | 1979-04-20 |
| AU1256876A (en) | 1977-10-06 |
| JPS51122089A (en) | 1976-10-25 |
| NO761141L (es) | 1976-10-06 |
| CA1060433A (en) | 1979-08-14 |
| BE840329A (fr) | 1976-10-04 |
| FR2306207A1 (fr) | 1976-10-29 |
| US4035362A (en) | 1977-07-12 |
| NO150883C (no) | 1985-01-09 |
| NL172544C (nl) | 1983-09-16 |
| NL172544B (nl) | 1983-04-18 |
| ES446673A1 (es) | 1977-06-01 |
| NL7603264A (nl) | 1976-10-07 |
| CH608810A5 (es) | 1979-01-31 |
| DE2613641A1 (de) | 1976-10-21 |
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