YU46151B - 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 - Google Patents
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-carboxylateInfo
- Publication number
- YU46151B YU46151B YU60085A YU60085A YU46151B YU 46151 B YU46151 B YU 46151B YU 60085 A YU60085 A YU 60085A YU 60085 A YU60085 A YU 60085A YU 46151 B YU46151 B YU 46151B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- hydrogen
- amino
- group
- protecting group
- 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
opšte 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, C1-4alkil ili karboksi, X je halogen, hidroksi ili C1-4alkoksi, i R4 i R5 su svaki nezavisno vodonik, metil ili etil, ili R4 i R5, uzeti zajedno sa ugljenikovim atomom za koji su vezani, grade cikloalkilidenski prsten sa 3-5 ugljenikovih atoma; i kvaternerna amino grupa; i njihovih netoksičnih farmaceutski prihvatljivih soli i estara koji hidrolizuju pod fiziološkim uslovima, naznačen ti me, što obuhvata reakciju jedinjenja formule: u kojoj je R2 isto kao 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, B2 je vodonik ili amino- zaštitna grupa kao što je tricil, Z je hloro, bromo ili jodo i m ima vrednost 0 ili 1, u rastvaraču kao što je etil acetat, dimetilsulfoksid, acetonitril ili metilehn hlorid, na temperaturi od oko -5 C do sobne temperature, sa tercijarnim aminom formule: Q N nakon čega se, ukoliko m ima vrednost 1, vrši redukcija sulfoksida pa se dobijeni zaštićeni intermedijer tretira kiselinom, kao što je mravlja kiselina, da bi se uklonile zaštitne grupe i dobio željeni proizvod; i što se, po potrebi, proizvod formule (I) prevodi u svoju netoksičnu farmaceutski prihvatljvu so ili estar koji hidrolizuje pod fiziološkim uslovima. Prijava sadrži još 2 zahteva.a general 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, hydroxy or C 1-4 alkoxy, and R 4 and R 5 are each independently hydrogen, methyl or ethyl, or R4 and R5, taken together with the carbon atom to which they are attached, form a cycloalkylidene ring of 3-5 carbon atoms; and a quaternary amino group; and their non-toxic pharmaceutically acceptable salts and esters which hydrolyze under physiological conditions, comprising reacting a compound of formula: wherein R 2 is the same as R 2, or represents a group of the formula: wherein X, R 4 and R 5 are as defined above, B1 is a carboxy-protecting group such as benzhydryl or t-butyl, B2 is hydrogen or an amino-protecting group such as tricyl, Z is chloro, bromo or iodo having a value of 0 or 1, in a solvent such as ethyl acetate, dimethylsulfoxide, acetonitrile or methylene chloride, at a temperature of about -5 C to room temperature, with a tertiary amine of formula: QN after which, if m has a value of 1, the sulfoxide is reduced and the resulting protected intermediate is treated with an acid such as formic acid , to remove the protecting groups and obtain the desired product; and optionally converting the product of formula (I) into its non-toxic pharmaceutically acceptable salt or ester which hydrolyzes under physiological conditions. The application contains 2 more requests.
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59794184A | 1984-04-09 | 1984-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU60085A YU60085A (en) | 1987-12-31 |
| YU46151B true YU46151B (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 After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
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) | DD236735A5 (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 |
| ATE114657T1 (en) * | 1985-12-26 | 1994-12-15 | Eisai Co Ltd | CEPHALOSPORIN 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 |
| CA1339738C (en) * | 1988-03-16 | 1998-03-17 | Takashi Kamiya | Process for the preparation of cephem derivatives and entermediates 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 |
| EP0723966A4 (en) * | 1994-08-16 | 1997-01-29 | Meiji Seika Co | Novel cephem derivative |
| KR100414336B1 (en) | 1998-06-22 | 2004-01-07 | 바실리어 파마슈티카 아게 | Propenyl cephalosporin derivatives |
| EP1666483B1 (en) | 2003-09-09 | 2011-08-17 | Nippon Chemical Industrial Company Limited | Process 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 DD DD85274832A patent/DD236735A5/en unknown
- 1985-04-03 DD DD85287524A patent/DD249024A5/en unknown
- 1985-04-03 DK DK155985A patent/DK155985A/en not_active Application Discontinuation
- 1985-04-03 SE SE8501680A patent/SE466205B/en not_active IP Right Cessation
- 1985-04-03 DE DE19853512225 patent/DE3512225A1/en active Granted
- 1985-04-04 PT PT80246A patent/PT80246B/en unknown
- 1985-04-04 AU AU40862/85A patent/AU580990B2/en not_active Expired
- 1985-04-04 CH CH1498/85A patent/CH669197A5/en not_active IP Right Cessation
- 1985-04-04 FI FI851379A patent/FI84830C/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 IE IE86685A patent/IE58408B1/en not_active IP Right Cessation
- 1985-04-04 NL NL8501002A patent/NL192925C/en not_active IP Right Cessation
- 1985-04-05 FR FR8505281A patent/FR2563832B1/en not_active Expired
- 1985-04-05 AT AT0103985A patent/AT388735B/en not_active IP Right Cessation
- 1985-04-05 IT IT20267/85A patent/IT1190353B/en active
- 1985-04-05 IL IL74826A patent/IL74826A/en not_active IP Right Cessation
- 1985-04-05 LU LU85840A patent/LU85840A1/en unknown
- 1985-04-08 ES ES542013A patent/ES8607318A1/en not_active Expired
- 1985-04-08 GR GR850883A patent/GR850883B/el not_active IP Right Cessation
- 1985-04-08 RU SU853878102A patent/RU2056425C1/en active
- 1985-04-09 BE BE0/214810A patent/BE902148A/en not_active IP Right Cessation
- 1985-04-09 JP JP60075233A patent/JPS615084A/en active Granted
- 1985-04-09 KR KR1019850002383A patent/KR870002166B1/en not_active Expired
- 1985-04-09 YU YU60085A patent/YU46151B/en unknown
- 1985-04-09 HU HU851299A patent/HU193750B/en unknown
- 1985-04-09 HU HU87151A patent/HU204277B/en unknown
- 1985-11-12 JP JP60252138A patent/JPS61143390A/en active Granted
- 1985-11-12 JP JP60252140A patent/JPS61143387A/en active Granted
- 1985-11-12 JP JP60252139A patent/JPS61143391A/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 SU864018257A patent/SU1375140A3/en active
- 1986-02-06 SU SU864019975A patent/SU1487814A3/en active
- 1986-02-06 SU SU864023036A patent/SU1367858A3/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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