YU46213B - PROCESS FOR PREPARATION 7- / 2- (5-Amino-1,2,4-Thiadiazol-3-yl) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL / -3-cephem-4-carboxylate - Google Patents
PROCESS FOR PREPARATION 7- / 2- (5-Amino-1,2,4-Thiadiazol-3-yl) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL / -3-cephem-4-carboxylateInfo
- Publication number
- YU46213B YU46213B YU118987A YU118987A YU46213B YU 46213 B YU46213 B YU 46213B YU 118987 A YU118987 A YU 118987A YU 118987 A YU118987 A YU 118987A YU 46213 B YU46213 B YU 46213B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- hydrogen
- amino
- group
- defined above
- Prior art date
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
POSTUPAK ZA DOBIJANJE 7-/2-(5-AMINO-1,2,4-TIADIAZOL-3-IL)-2-(SUPSTITUISANI)IMINOACETAMIDO/-3 -/3-(KVATERNERNI AMONIO)-1-PROPEN-1-IL/-3-CEFEM-4-KARBOKSILATA formule: u kojoj je R1 vodonik ili amino-zaštitna grupa kao što je tricil; R2 je vodonik, C1-4alkil, C3-6cikloalkil, C3-6cikloalkenil ili grupa formule: gde je R3 vodonik, C1-4 alkil ili karboksi, X je halogen, OH ili C1-4alkoksi i R4 i R5 su svaki nezavisno vodonik, metil ili etil ili R4 i R5, zajedno sa ugljenikovim atomom za koji su vezani, grade C3-5 cikloalkilidenski prsten; i je kvaternerna amonio grupa, i njihovih netoksičnih farmaceutski prihvatljivih soli i estara koji hidrolizuju pod fiziološkim uslovima, naznačen time, što obuhvata reakciju jedinjenja formule: sa kiselinom formule: ili sa njenim aktiviranim derivatom, kao što je hlorid, pri čemu je kao što je definisano gore, R2 ima značenja kao što je definisano gor za R2, ili predstavlja grupu formule: gde su X, R4 i R5 kao što je definisano gore, B1 je karboksi-zaštitna grupa kao što je benzhidril ili t-butil i B2 je vodonik ili amino-zaštitna grupa kao što je tricil, u smeši vode i orgnaskog rastvarača kao što je aceton ili dimetilformamid i na temperaturi od -10 do +50 C, poželjno od +10 C do sobne temperature; što se, po potrebi, vrši uklanjanjem zaštitnih grupa reakcijom sa kiselinom kao što je HCl, i što se dobijeni proizvod formule (I), po potrebi, prevodi u svoju netoksičnu far-maceutski prihvatljivu so ili estar koji hidrolizuje pod fiziološkim uslovima. Prijava sadrži još 2 patentna zahteva.PROCESS FOR PREPARATION 7- / 2- (5-AMINO-1,2,4-THIADIAZOL-3-YL) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL--3-CEPHEM-4-CARBOXYLATE of the formula: wherein R 1 is hydrogen or an amino-protecting group such as tricyl; R 2 is hydrogen, C 1-4 alkyl, C 3-6 cycloalkyl, C 3-6 cycloalkenyl or a group of the formula: wherein R 3 is hydrogen, C 1-4 alkyl or carboxy, X is halogen, OH or C 1-4 alkoxy and R 4 and R 5 are each independently hydrogen, methyl or ethyl or R4 and R5, together with the carbon atom to which they are attached, form a C3-5 cycloalkylidene ring; and is a quaternary ammonio group, and their non-toxic pharmaceutically acceptable salts and esters which hydrolyze under physiological conditions, comprising reacting a compound of formula: with an acid of formula: or with an activated derivative thereof, such as chloride, wherein such as as defined above, R 2 has the meaning as defined above for R 2, or represents a group of the formula: wherein X, R 4 and R 5 are as defined above, B 1 is a carboxy-protecting group such as benzhydryl or t-butyl and B2 is hydrogen or an amino-protecting group such as tricyl, in a mixture of water and an organic solvent such as acetone or dimethylformamide and at a temperature of -10 to +50 C, preferably from +10 C to room temperature; which is optionally carried out by deprotection by reaction with an acid such as HCl, and the resulting product of formula (I) is optionally converted into its non-toxic pharmaceutically acceptable salt or ester which hydrolyzes under physiological conditions. The application contains 2 more patent claims.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU118987A YU46213B (en) | 1984-04-09 | 1987-06-25 | PROCESS FOR PREPARATION 7- / 2- (5-Amino-1,2,4-Thiadiazol-3-yl) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL / -3-cephem-4-carboxylate |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59794184A | 1984-04-09 | 1984-04-09 | |
| YU60085A YU46151B (en) | 1984-04-09 | 1985-04-09 | PROCESS FOR OBTAINING 7- / 2- (5-AMINO-1,2,4-THIADIAZOL-3-YL) -2- (SUBSTITUTED) IMINOACETAMIDO / 3- / 3- (QUATERNARY AMMONIO) -1-PROPEN-1-YL / -3-cephem-4-carboxylate |
| YU118987A YU46213B (en) | 1984-04-09 | 1987-06-25 | PROCESS FOR PREPARATION 7- / 2- (5-Amino-1,2,4-Thiadiazol-3-yl) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL / -3-cephem-4-carboxylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU118987A YU118987A (en) | 1988-10-31 |
| YU46213B true YU46213B (en) | 1993-05-28 |
Family
ID=24393575
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU60085A YU46151B (en) | 1984-04-09 | 1985-04-09 | PROCESS FOR OBTAINING 7- / 2- (5-AMINO-1,2,4-THIADIAZOL-3-YL) -2- (SUBSTITUTED) IMINOACETAMIDO / 3- / 3- (QUATERNARY AMMONIO) -1-PROPEN-1-YL / -3-cephem-4-carboxylate |
| YU118987A YU46213B (en) | 1984-04-09 | 1987-06-25 | PROCESS FOR PREPARATION 7- / 2- (5-Amino-1,2,4-Thiadiazol-3-yl) -2- (SUBSTITUTED) IMINOACETAMIDO / -3- / 3- (QUATERNARY AMMONIO) -1-PROPENE-1- IL / -3-cephem-4-carboxylate |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU60085A YU46151B (en) | 1984-04-09 | 1985-04-09 | PROCESS FOR OBTAINING 7- / 2- (5-AMINO-1,2,4-THIADIAZOL-3-YL) -2- (SUBSTITUTED) IMINOACETAMIDO / 3- / 3- (QUATERNARY AMMONIO) -1-PROPEN-1-YL / -3-cephem-4-carboxylate |
Country Status (31)
| Country | Link |
|---|---|
| JP (4) | JPS615084A (en) |
| KR (1) | KR870002166B1 (en) |
| AR (1) | AR244694A1 (en) |
| AT (1) | AT388735B (en) |
| AU (2) | AU580990B2 (en) |
| BE (1) | BE902148A (en) |
| CA (3) | CA1276929C (en) |
| CH (1) | CH669197A5 (en) |
| DD (3) | DD249024A5 (en) |
| DE (1) | DE3512225A1 (en) |
| DK (1) | DK155985A (en) |
| ES (4) | ES8607318A1 (en) |
| FI (1) | FI84830C (en) |
| FR (1) | FR2563832B1 (en) |
| GB (3) | GB2157293B (en) |
| GR (1) | GR850883B (en) |
| HU (2) | HU193750B (en) |
| IE (2) | IE58408B1 (en) |
| IL (1) | IL74826A (en) |
| IT (1) | IT1190353B (en) |
| LU (1) | LU85840A1 (en) |
| MY (1) | MY101940A (en) |
| NL (1) | NL192925C (en) |
| NZ (1) | NZ211659A (en) |
| OA (1) | OA07985A (en) |
| PT (1) | PT80246B (en) |
| RU (1) | RU2056425C1 (en) |
| SE (4) | SE466205B (en) |
| SU (4) | SU1436882A3 (en) |
| YU (2) | YU46151B (en) |
| ZA (1) | ZA852236B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145186A (en) * | 1984-12-20 | 1986-07-02 | Meiji Seika Kaisha Ltd | Novel cephem compound and preparation thereof |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| DE3650157T2 (en) * | 1985-12-26 | 1995-05-04 | Eisai Co Ltd | CEPHALOSPORINE COMPOUNDS. |
| AU614723B2 (en) * | 1986-10-13 | 1991-09-12 | Eisai Co. Ltd. | 3-propenylcephem derivative |
| IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
| JPH085897B2 (en) * | 1986-11-06 | 1996-01-24 | エーザイ株式会社 | 3-propenyl cephem derivative |
| FR2622585B1 (en) * | 1987-11-03 | 1991-04-19 | Roussel Uclaf | NOVEL CEPHALOSPORINS COMPRISING IN POSITION 3 A SUBSTITUTED VINYL RADICAL, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS, THE COMPOSITIONS CONTAINING THEM AND THE NEW INTERMEDIATES OBTAINED |
| CN1022837C (en) * | 1988-03-16 | 1993-11-24 | 卫材株式会社 | Process for preparation of cephem derivatives and intermediates therefor |
| JPH0699449B2 (en) * | 1988-03-16 | 1994-12-07 | エーザイ株式会社 | Synthetic intermediate of cephem derivative |
| FR2655042B1 (en) * | 1989-11-29 | 1994-01-21 | Adir Cie | NOVEL SUBSTITUTED BENZOTHIAZOLINONES, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2663332B1 (en) * | 1990-06-15 | 1997-11-07 | Roussel Uclaf | NOVEL CEPHALOSPORINS COMPRISING IN POSITION 3 A RADICAL PROPENYL SUBSTITUTED BY A QUATERNARY AMMONIUM, THEIR PREPARATION PROCESS, THEIR APPLICATION AS MEDICAMENTS, THE COMPOSITIONS CONTAINING THEM AND THE NEW INTERMEDIATES OBTAINED. |
| US5126336A (en) * | 1990-08-23 | 1992-06-30 | Bristol-Myers Squibb Company | Antibiotic c-3 catechol-substituted cephalosporin compounds, compositions and method of use thereof |
| AT396108B (en) * | 1991-08-21 | 1993-06-25 | Biochemie Gmbh | NEW PROCESS AND NEW INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF 7-AMINOCEPHALOSPORANIC ACID DERIVATIVES |
| JPH0741484A (en) * | 1993-07-29 | 1995-02-10 | Katayama Seiyakushiyo:Kk | Cephem compound and antimicrobial agent |
| US5661144A (en) * | 1994-08-16 | 1997-08-26 | Meiji Seika Kabushiki Kaisha | Cephem derivatives with 3-substituted bis heterocycles |
| ID28433A (en) | 1998-06-22 | 2001-05-24 | Hoffmann La Roche | PROPENIL SEFALOSPORIN DEPOSITS |
| JP4658806B2 (en) | 2003-09-09 | 2011-03-23 | 日本化学工業株式会社 | Method for producing 3-chloromethyl-3-cephem derivative |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1342241A (en) * | 1970-01-23 | 1974-01-03 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4390534A (en) * | 1978-12-29 | 1983-06-28 | Fujisawa Pharmaceutical Co., Ltd. | Cephem and cepham compounds |
| EP0025017A1 (en) * | 1979-08-28 | 1981-03-11 | Ciba-Geigy Ag | Polyazathia compounds, process for their preparation, pharmaceutical preparations containing such compounds and use of the latter |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| GR75644B (en) * | 1980-06-18 | 1984-08-02 | Fujisawa Pharmaceutical Co | |
| GR78245B (en) * | 1980-09-12 | 1984-09-26 | Ciba Geigy Ag | |
| US4521413A (en) * | 1981-09-14 | 1985-06-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
-
1985
- 1985-02-14 CA CA000474260A patent/CA1276929C/en not_active Expired - Lifetime
- 1985-03-25 ZA ZA852236A patent/ZA852236B/en unknown
- 1985-04-02 NZ NZ211659A patent/NZ211659A/en unknown
- 1985-04-02 AR AR85299945A patent/AR244694A1/en active
- 1985-04-03 SE SE8501680A patent/SE466205B/en not_active IP Right Cessation
- 1985-04-03 DD DD85287524A patent/DD249024A5/en unknown
- 1985-04-03 DD DD85274832A patent/DD236735A5/en unknown
- 1985-04-03 DE DE19853512225 patent/DE3512225A1/en active Granted
- 1985-04-03 DK DK155985A patent/DK155985A/en not_active Application Discontinuation
- 1985-04-04 CH CH1498/85A patent/CH669197A5/en not_active IP Right Cessation
- 1985-04-04 IE IE86685A patent/IE58408B1/en not_active IP Right Cessation
- 1985-04-04 GB GB08508846A patent/GB2157293B/en not_active Expired
- 1985-04-04 OA OA58561A patent/OA07985A/en unknown
- 1985-04-04 NL NL8501002A patent/NL192925C/en not_active IP Right Cessation
- 1985-04-04 PT PT80246A patent/PT80246B/en unknown
- 1985-04-04 FI FI851379A patent/FI84830C/en not_active IP Right Cessation
- 1985-04-04 AU AU40862/85A patent/AU580990B2/en not_active Expired
- 1985-04-05 IL IL74826A patent/IL74826A/en not_active IP Right Cessation
- 1985-04-05 IT IT20267/85A patent/IT1190353B/en active
- 1985-04-05 FR FR8505281A patent/FR2563832B1/en not_active Expired
- 1985-04-05 LU LU85840A patent/LU85840A1/en unknown
- 1985-04-05 AT AT0103985A patent/AT388735B/en not_active IP Right Cessation
- 1985-04-08 GR GR850883A patent/GR850883B/el not_active IP Right Cessation
- 1985-04-08 RU SU853878102A patent/RU2056425C1/en active
- 1985-04-08 ES ES542013A patent/ES8607318A1/en not_active Expired
- 1985-04-09 HU HU851299A patent/HU193750B/en unknown
- 1985-04-09 JP JP60075233A patent/JPS615084A/en active Granted
- 1985-04-09 YU YU60085A patent/YU46151B/en unknown
- 1985-04-09 HU HU87151A patent/HU204277B/en unknown
- 1985-04-09 BE BE0/214810A patent/BE902148A/en not_active IP Right Cessation
- 1985-04-09 KR KR1019850002383A patent/KR870002166B1/en not_active IP Right Cessation
- 1985-11-12 JP JP60252139A patent/JPS61143391A/en active Granted
- 1985-11-12 JP JP60252140A patent/JPS61143387A/en active Granted
- 1985-11-12 JP JP60252138A patent/JPS61143390A/en active Granted
-
1986
- 1986-01-31 ES ES551550A patent/ES8706155A1/en not_active Expired
- 1986-01-31 ES ES551551A patent/ES8706694A1/en not_active Expired
- 1986-02-06 SU SU864020682A patent/SU1436882A3/en active
- 1986-02-06 SU SU864023036A patent/SU1367858A3/en active
- 1986-02-06 SU SU864019975A patent/SU1487814A3/en active
- 1986-02-06 SU SU864018257A patent/SU1375140A3/en active
- 1986-03-03 DD DD86287525A patent/DD251752A5/en unknown
- 1986-09-10 ES ES557060A patent/ES8800949A1/en not_active Expired
-
1987
- 1987-06-25 YU YU118987A patent/YU46213B/en unknown
- 1987-09-10 GB GB08721346A patent/GB2194789B/en not_active Expired
- 1987-09-10 GB GB08721347A patent/GB2194790B/en not_active Expired
- 1987-10-01 MY MYPI87002761A patent/MY101940A/en unknown
-
1988
- 1988-11-11 AU AU25041/88A patent/AU610278B2/en not_active Expired
-
1989
- 1989-04-04 IE IE121089A patent/IE58403B1/en not_active IP Right Cessation
- 1989-04-06 SE SE8901224A patent/SE470259B/en not_active IP Right Cessation
- 1989-04-06 SE SE8901225A patent/SE505256C2/en not_active IP Right Cessation
- 1989-04-06 SE SE8901226A patent/SE470260B/en not_active IP Right Cessation
-
1991
- 1991-08-12 CA CA000616143A patent/CA1340638C/en not_active Expired - Fee Related
- 1991-08-21 CA CA000616144A patent/CA1340672C/en not_active Expired - Fee Related
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