ES2118287T3 - 2-bromo- y 2-nitroxi derivados de 3-bromo- y 3,3-dibromo-4-oxo-azetidines, procedimiento para la preparacion de los mismos y su utilizacion. - Google Patents
2-bromo- y 2-nitroxi derivados de 3-bromo- y 3,3-dibromo-4-oxo-azetidines, procedimiento para la preparacion de los mismos y su utilizacion.Info
- Publication number
- ES2118287T3 ES2118287T3 ES94110387T ES94110387T ES2118287T3 ES 2118287 T3 ES2118287 T3 ES 2118287T3 ES 94110387 T ES94110387 T ES 94110387T ES 94110387 T ES94110387 T ES 94110387T ES 2118287 T3 ES2118287 T3 ES 2118287T3
- Authority
- ES
- Spain
- Prior art keywords
- bromo
- dibromo
- oxo
- nitroxy
- derivatives
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 abstract 2
- FMNUBORQHLJREC-UHFFFAOYSA-N (3,3-dibromo-4-oxoazetidin-2-yl) nitrate Chemical compound [O-][N+](=O)OC1NC(=O)C1(Br)Br FMNUBORQHLJREC-UHFFFAOYSA-N 0.000 abstract 1
- VVLJZVLXDNESKI-UHFFFAOYSA-N 3,3,4-tribromoazetidin-2-one Chemical compound BrC1NC(=O)C1(Br)Br VVLJZVLXDNESKI-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 229910001961 silver nitrate Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003952 β-lactams Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
DE ACUERDO CON LA INVENCION LOS DERIVADOS DE 2-BROMO 2NITROXIDO DE 3-BROMO AN HACIENDO REACCIONAR DERIVADOS DE 1,1-DIOXIDOS DE ACIDO FENILICILANICO PROTEGIDO CON UN REACTANTE DBN (1,5-DIAZABICICLO/3.4.0/NON-5-ENO) Y POSTERIORMENTE LA SAL DE DBN OBTENIDA DEL ACIDO SULFINICO O EL ACIDO SULFINICO AISLADO SE TRATA CON CLORURO DE TIONILO, Y DESPUES DE ELIMINAR EL CLORURO DE TIONILO MEDIANTE EVAPORACION, EL RESIDUO OBTENIDO SE HACE PASAR A TRAVES DE UNA COLUMNA DE GEL DE SILICE CON CLORURO DE METILENO O ALGUN OTRO SOLVENTE COMO ELUYENTE O EL RESIDUO OBTENIDO SE DISUELVE EN TETRAHIDROFURAN O ALGUN OTRO SOLVENTE ADECUADO Y SE TRATA CON AMONIO DE TETRABUTIL, BROMURO Y POSTERIORMENTE AL TRATAMIENTO SE AISLA UN DERIVADO DE 2-BROMO, 3BROMO O 2-BROMO-3,3-DIBROMO-4-OXO-ACETIDINA, DICHO DERIVADO PUEDE SER EXPUESTO A UNA REACCION CON NITRATO DE PLATA EN 2-PROPANOL Y, DESPUES DEL TRATAMIENTO DE LA MEZCLA DE REACCION, SE AISLAN DERIVADOS DE 2NITROXI-, 3-BROMO- O 2-NITROXIDO-3,3-DIBROMO-4-OXO-ACETIDINA. LAS SUSTANCIAS OBTENIDAS SON UTILES COMO PRODUCTOS INTERMEDIOS EN LA SINTESIS DE ANALOGOS DEL BETA-LACTAM O COMO COMPONENTES EN FORMULACIONES QUE TENGAN UNA ACCION ANTIBACTERIANA, INHIBITORIA, ANTITUMORAL O ANTAGONICA.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR931047A HRP931047B1 (en) | 1993-07-09 | 1993-07-09 | 2-bromo- and 2-nitroxy derivatives of 3-bromo- and 3,3-dibromo-4-oxo-azetidines, processes for the preparation thereof and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2118287T3 true ES2118287T3 (es) | 1998-09-16 |
Family
ID=10945991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES94110387T Expired - Lifetime ES2118287T3 (es) | 1993-07-09 | 1994-07-04 | 2-bromo- y 2-nitroxi derivados de 3-bromo- y 3,3-dibromo-4-oxo-azetidines, procedimiento para la preparacion de los mismos y su utilizacion. |
Country Status (16)
| Country | Link |
|---|---|
| US (4) | US5670638A (es) |
| EP (1) | EP0633247B1 (es) |
| JP (1) | JPH07149716A (es) |
| CN (1) | CN1100719A (es) |
| AT (1) | ATE166644T1 (es) |
| BG (1) | BG61645B1 (es) |
| CA (1) | CA2127677C (es) |
| CZ (1) | CZ286810B6 (es) |
| DE (1) | DE69410539T2 (es) |
| ES (1) | ES2118287T3 (es) |
| HR (1) | HRP931047B1 (es) |
| HU (1) | HUT68298A (es) |
| PL (1) | PL178949B1 (es) |
| RU (1) | RU2134685C1 (es) |
| SI (1) | SI0633247T1 (es) |
| SK (1) | SK79194A3 (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK13897A3 (en) | 1996-02-06 | 1998-05-06 | Pliva Pharm & Chem Works | 3-bromo- and 3,3-dibromo-4-oxo-1-azetidines, method for preparation thereof and their use |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS607635B2 (ja) * | 1976-04-27 | 1985-02-26 | 塩野義製薬株式会社 | オキサゾリジン化合物 |
| DE3169939D1 (en) * | 1980-02-28 | 1985-05-23 | Schering Corp | 2-penem compounds, pharmaceutical compositions containing them and methods for their preparation |
| WO1982001705A1 (en) * | 1980-11-13 | 1982-05-27 | Takeda Chemical Industries Ltd | 4-substituted-2-oxoazetidine derivatives and process for their preparation |
| JPH03271297A (ja) * | 1990-03-22 | 1991-12-03 | Sankyo Co Ltd | 白金複核錯体 |
| US5075439A (en) * | 1990-08-17 | 1991-12-24 | Pfizer Inc. | Processes for (3S,4R)-3-[1(R)-t-butyl-dimethylsilyloxy)-ethyl]-4-[1-oxo-3-thiolanylthio(thiocarbonyl)thio]azetidin-2-ones and intermediates therefor |
| US5250525A (en) * | 1991-02-12 | 1993-10-05 | Pliva Handels Gmbh | 4-oxo-azetidine-2-sulfonic acids and their salts, processes for the preparation thereof and their use |
-
1993
- 1993-07-09 HR HR931047A patent/HRP931047B1/xx not_active IP Right Cessation
-
1994
- 1994-06-30 SK SK791-94A patent/SK79194A3/sk unknown
- 1994-07-04 SI SI9430165T patent/SI0633247T1/xx unknown
- 1994-07-04 DE DE69410539T patent/DE69410539T2/de not_active Expired - Fee Related
- 1994-07-04 AT AT94110387T patent/ATE166644T1/de not_active IP Right Cessation
- 1994-07-04 ES ES94110387T patent/ES2118287T3/es not_active Expired - Lifetime
- 1994-07-04 EP EP94110387A patent/EP0633247B1/en not_active Expired - Lifetime
- 1994-07-06 JP JP6154546A patent/JPH07149716A/ja active Pending
- 1994-07-07 CZ CZ19941647A patent/CZ286810B6/cs not_active IP Right Cessation
- 1994-07-08 HU HU9402053A patent/HUT68298A/hu unknown
- 1994-07-08 CN CN94108240A patent/CN1100719A/zh active Pending
- 1994-07-08 RU RU94026293A patent/RU2134685C1/ru active
- 1994-07-08 PL PL94304191A patent/PL178949B1/pl unknown
- 1994-07-08 BG BG98895A patent/BG61645B1/bg unknown
- 1994-07-08 CA CA002127677A patent/CA2127677C/en not_active Expired - Fee Related
- 1994-07-08 US US08/272,206 patent/US5670638A/en not_active Expired - Fee Related
-
1995
- 1995-07-10 US US08/500,001 patent/US5637581A/en not_active Expired - Fee Related
-
1996
- 1996-03-27 US US08/624,919 patent/US5847119A/en not_active Expired - Fee Related
-
1997
- 1997-09-10 US US08/926,449 patent/US5892036A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| RU94026293A (ru) | 1996-05-27 |
| SK79194A3 (en) | 1995-04-12 |
| CZ164794A3 (en) | 1995-07-12 |
| CZ286810B6 (en) | 2000-07-12 |
| EP0633247A1 (en) | 1995-01-11 |
| US5670638A (en) | 1997-09-23 |
| US5847119A (en) | 1998-12-08 |
| SI0633247T1 (en) | 1998-10-31 |
| BG98895A (bg) | 1995-05-31 |
| PL178949B1 (pl) | 2000-07-31 |
| US5637581A (en) | 1997-06-10 |
| ATE166644T1 (de) | 1998-06-15 |
| US5892036A (en) | 1999-04-06 |
| EP0633247B1 (en) | 1998-05-27 |
| HUT68298A (en) | 1995-06-28 |
| DE69410539T2 (de) | 1998-11-26 |
| JPH07149716A (ja) | 1995-06-13 |
| DE69410539D1 (de) | 1998-07-02 |
| BG61645B1 (bg) | 1998-02-27 |
| CA2127677C (en) | 2000-02-08 |
| HU9402053D0 (en) | 1994-09-28 |
| HRP931047A2 (en) | 1997-04-30 |
| PL304191A1 (en) | 1995-01-23 |
| RU2134685C1 (ru) | 1999-08-20 |
| CN1100719A (zh) | 1995-03-29 |
| HRP931047B1 (en) | 2000-02-29 |
| CA2127677A1 (en) | 1995-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG2A | Definitive protection |
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