SE7614678L - METHOD OF PREPARING NEW OXIMIDE DERIVATIVES OF 7-AMINOTIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID DERIVATIVES - Google Patents
METHOD OF PREPARING NEW OXIMIDE DERIVATIVES OF 7-AMINOTIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID DERIVATIVESInfo
- Publication number
- SE7614678L SE7614678L SE7614678A SE7614678A SE7614678L SE 7614678 L SE7614678 L SE 7614678L SE 7614678 A SE7614678 A SE 7614678A SE 7614678 A SE7614678 A SE 7614678A SE 7614678 L SE7614678 L SE 7614678L
- Authority
- SE
- Sweden
- Prior art keywords
- derivatives
- acid
- aminotiazolyl
- oximide
- acetamido
- Prior art date
Links
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical class O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- 208000035473 Communicable disease Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- -1 chloracetyl groups Chemical group 0.000 abstract 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
-
- 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The compounds correspond to the formula: <IMAGE> in which R'c represents hydrogen or a C1-C4 alkyl, alkenyl or alkynyl. They are prepared by reacting the 7-aminocephalosporanic acid first with the syn isomer of a 2-(2-Rd-amino-4-thiazolyl)-2-(R'd-oxyimino)acetic acid or of a functional derivative of this acid; Rd and R'd represent groups which can be removed by acid hydrolysis or by hydrogenolysis, or chloroacetyl groups, it being possible for R'd to additionally represent a C1-C4 alkyl, alkenyl or alkynyl. An acid hydrolysis or a hydrogenolysis is then carried out or, in the case of chloracetyl groups, a treatment with thiourea. The compounds and their salts of the carboxylic group have a good antibiotic activity and can be used for the treatment of various infectious diseases.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7601834A FR2346014A1 (en) | 1976-01-23 | 1976-01-23 | Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity |
| FR7617743A FR2361893A2 (en) | 1976-01-23 | 1976-06-11 | Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity |
| FR7625051A FR2361894A2 (en) | 1976-01-23 | 1976-08-18 | Amino-thiazolyl-hydroxyimino-acetamido-cephalosporanic acids - with antibacterial activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7614678L true SE7614678L (en) | 1977-07-24 |
| SE440655B SE440655B (en) | 1985-08-12 |
Family
ID=27250574
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7614678A SE440655B (en) | 1976-01-23 | 1976-12-29 | SET TO MAKE NEW OXIME DERIVATIVES OF 7-AMINO-THIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID |
| SE8204893A SE455307B (en) | 1976-01-23 | 1982-08-26 | 2-AMINO-4-THIAZOLYL-OXIIMINO-ETHYAC ACID DERIVATIVES FOR USE AS AN INTERMEDIATE TO THE SIMILAR CEPHALOSPORINE DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8204893A SE455307B (en) | 1976-01-23 | 1982-08-26 | 2-AMINO-4-THIAZOLYL-OXIIMINO-ETHYAC ACID DERIVATIVES FOR USE AS AN INTERMEDIATE TO THE SIMILAR CEPHALOSPORINE DERIVATIVES AND PROCEDURES FOR PREPARING THEREOF |
Country Status (31)
| Country | Link |
|---|---|
| JP (3) | JPS52102293A (en) |
| AR (1) | AR231985A1 (en) |
| AT (2) | AT355205B (en) |
| AU (1) | AU511680B2 (en) |
| BE (1) | BE850662A (en) |
| CA (1) | CA1319682C (en) |
| CH (1) | CH622264A5 (en) |
| CY (1) | CY1123A (en) |
| DD (2) | DD132869A5 (en) |
| DE (3) | DE2702501C2 (en) |
| DK (1) | DK161082C (en) |
| ES (2) | ES455089A1 (en) |
| GB (2) | GB1580623A (en) |
| GE (1) | GEP19970783B (en) |
| GR (1) | GR70302B (en) |
| HK (1) | HK50381A (en) |
| HU (1) | HU173110B (en) |
| IE (1) | IE45015B1 (en) |
| IL (2) | IL51192A (en) |
| IT (1) | IT1104601B (en) |
| KE (1) | KE3365A (en) |
| LU (1) | LU76624A1 (en) |
| MX (1) | MX4407E (en) |
| MY (1) | MY8500417A (en) |
| NL (1) | NL7700706A (en) |
| NZ (1) | NZ183150A (en) |
| PL (1) | PL122698B1 (en) |
| PT (1) | PT66099B (en) |
| SE (2) | SE440655B (en) |
| SU (1) | SU822754A3 (en) |
| YU (3) | YU41060B (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2408613A2 (en) * | 1977-07-19 | 1979-06-08 | Roussel Uclaf | NEW OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICINAL PRODUCTS |
| GB1576625A (en) * | 1976-04-12 | 1980-10-08 | Fujisawa Pharmaceutical Co | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
| DK162391C (en) * | 1976-04-12 | 1992-03-09 | Fujisawa Pharmaceutical Co | ANALOGY PROCEDURE FOR PREPARING SYN-ISOMERS OF 3,7-DISUBSTITUTED 3-CEPHEM-4-CARBOXYLIC ACID COMPOUNDS |
| DE2715385A1 (en) * | 1976-04-14 | 1977-11-10 | Takeda Chemical Industries Ltd | CEPHALOSPORIN DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THEM |
| ZA781502B (en) * | 1977-03-14 | 1979-09-26 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and processes for preparation thereof |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| DE2714880A1 (en) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | CEPHEMDER DERIVATIVES AND PROCESS FOR THEIR PRODUCTION |
| FR2400519A1 (en) * | 1977-08-17 | 1979-03-16 | Roussel Uclaf | CRYSTALLINE FORM OF SODIUM SALT OF AN OXIMIN DERIVATIVE OF 7-AMINO-THIAZOLYL ACETAMIDO CEPHALOSPORANIC, ITS PREPARATION PROCESS AND ITS APPLICATION AS A MEDICINAL PRODUCT |
| JPS5444695A (en) * | 1977-09-13 | 1979-04-09 | Fujisawa Pharmaceut Co Ltd | 3,7-disubstituted-3-cephem-4-carboxylic acid and its salt and their preparation |
| FR2410655A1 (en) * | 1977-12-05 | 1979-06-29 | Roussel Uclaf | NEW OXIMES DERIVED FROM 3-SUBSTITUTE 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC, THEIR METHOD OF PREPARATION AND THEIR APPLICATION AS MEDICINAL PRODUCTS |
| JPS5498795A (en) * | 1978-01-13 | 1979-08-03 | Takeda Chem Ind Ltd | Cephalosporin derivative and its preparation |
| FR2387235A1 (en) * | 1978-01-23 | 1978-11-10 | Fujisawa Pharmaceutical Co | PROCESS FOR THE PREPARATION OF COMPOUNDS OF 3,7-DISUBSTITUE-3-CEPHEM-4-CARBOXYLIC ACID AND NEW PRODUCTS THUS OBTAINED, HAVING A STRONG ANTIBACTERIAL ACTIVITY |
| FR2432521A1 (en) * | 1978-03-31 | 1980-02-29 | Roussel Uclaf | NOVEL O-SUBSTITUTED OXIMES DERIVED FROM 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC ACID, THEIR PREPARATION PROCESS AND THEIR USE AS MEDICAMENTS |
| SE445350B (en) * | 1978-04-14 | 1986-06-16 | Roussel Uclaf | OXIMO DERIVATIVES OF 3-AZIDOMETHYL-7-AMINO-THIAZOLYL-ACETAMIDO-CEPHALOSPORANIC ACID AND ITS USE AS ANTIBIOTICS |
| US4284631A (en) * | 1978-07-31 | 1981-08-18 | Fujisawa Pharmaceutical Co., Ltd. | 7-Substituted cephem compounds and pharmaceutical antibacterial compositions containing them |
| FR2448543A1 (en) * | 1979-02-09 | 1980-09-05 | Roussel Uclaf | NOVEL OXIMES O-SUBSTITUTED BY A RADICAL COMPRISING A QUATERNARY AMMONIUM AND DERIVATIVES OF 7-AMINO THIAZOLYL ACETAMIDO CEPHALOSPORANIC, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
| FR2461713A1 (en) * | 1979-07-19 | 1981-02-06 | Roussel Uclaf | SUBSTITUTED ALKYLOXIMIC NEWS DERIVED FROM 7- (2-AMINO 4-THIAZOLYL) ACETAMIDO CEPHALOSPORANIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS MEDICAMENTS |
| FR2461712A1 (en) * | 1979-07-23 | 1981-02-06 | Hoechst Ag | 2-Oximino-acylamino cephem cpds. prodn. - by acylating 7-amino-cephem cpds. with complexes of 2-syn-oximino-acyl halide(s) and N,N-di:substd. amide(s) |
| JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
| FR2506307A1 (en) * | 1981-05-22 | 1982-11-26 | Roussel Uclaf | 7-thiazolyl-acetamido-cephalosporin oxime derivs. - useful as broad spectrum antibacterials and disinfectants (BE 1.10.79) |
| JPS57163386A (en) * | 1981-08-13 | 1982-10-07 | Takeda Chem Ind Ltd | Cephalosporin derivative and its production |
| EP0238060B1 (en) | 1986-03-19 | 1992-01-08 | Banyu Pharmaceutical Co., Ltd. | Cephalosporin derivatives, processes for their preparation and antibacterial agents |
| HUT53892A (en) * | 1989-04-07 | 1990-12-28 | Technologishen Kom Za Promy Mi | Process for producing synaminothiazolyl and synaminooxazolyl derivatives |
| CN112457271A (en) * | 2020-11-18 | 2021-03-09 | 河北合佳医药科技集团股份有限公司 | Continuous flow synthesis method of aminothiazoly loximate intermediate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| GB1536281A (en) * | 1975-06-09 | 1978-12-20 | Takeda Chemical Industries Ltd | Cephem compounds |
| DK154939C (en) | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | METHOD OF ANALOGUE FOR THE PREPARATION OF THIAZOLYLACETAMIDO-CEPHEM COMPOUNDS OR PHARMACEUTICAL ACCEPTABLE SALTS OR ESTERS THEREOF |
| DE2760123C2 (en) | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporanic acids, their preparation and pharmaceutical compositions containing them |
| JPS6011713B2 (en) | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | Cephalosporin derivatives and their production method |
-
1976
- 1976-12-29 SE SE7614678A patent/SE440655B/en not_active IP Right Cessation
- 1976-12-31 IL IL51192A patent/IL51192A/en unknown
-
1977
- 1977-01-15 ES ES455089A patent/ES455089A1/en not_active Expired
- 1977-01-18 SU SU772439818A patent/SU822754A3/en active
- 1977-01-19 AR AR266241A patent/AR231985A1/en active
- 1977-01-19 YU YU137/77A patent/YU41060B/en unknown
- 1977-01-20 MX MX775372U patent/MX4407E/en unknown
- 1977-01-20 IT IT47727/77A patent/IT1104601B/en active Protection Beyond IP Right Term
- 1977-01-21 CH CH78777A patent/CH622264A5/en not_active IP Right Cessation
- 1977-01-21 GB GB15561/79A patent/GB1580623A/en not_active Expired
- 1977-01-21 LU LU76624A patent/LU76624A1/xx unknown
- 1977-01-21 GB GB2640/77A patent/GB1580621A/en not_active Expired
- 1977-01-21 PT PT66099A patent/PT66099B/en unknown
- 1977-01-21 DE DE2702501A patent/DE2702501C2/en not_active Expired
- 1977-01-21 DD DD7700200629A patent/DD132869A5/en unknown
- 1977-01-21 HU HU77RO909A patent/HU173110B/en unknown
- 1977-01-21 DE DE2759895A patent/DE2759895C2/en not_active Expired
- 1977-01-21 NZ NZ183150A patent/NZ183150A/en unknown
- 1977-01-21 CA CA000270375A patent/CA1319682C/en not_active Expired - Lifetime
- 1977-01-21 DK DK023677A patent/DK161082C/en active
- 1977-01-21 DD DD7700197036A patent/DD128594A5/en unknown
- 1977-01-21 BE BE174311A patent/BE850662A/en not_active IP Right Cessation
- 1977-01-21 CY CY1123A patent/CY1123A/en unknown
- 1977-01-21 JP JP504977A patent/JPS52102293A/en active Granted
- 1977-01-21 DE DE2760287A patent/DE2760287C2/de not_active Expired
- 1977-01-22 GR GR52630A patent/GR70302B/el unknown
- 1977-01-22 PL PL1977195504A patent/PL122698B1/en unknown
- 1977-01-24 AU AU21579/77A patent/AU511680B2/en not_active Expired
- 1977-01-24 AT AT41277A patent/AT355205B/en not_active IP Right Cessation
- 1977-01-24 NL NL7700706A patent/NL7700706A/en not_active Application Discontinuation
- 1977-01-24 IE IE148/77A patent/IE45015B1/en not_active IP Right Cessation
-
1978
- 1978-02-01 ES ES466539A patent/ES466539A1/en not_active Expired
-
1979
- 1979-03-20 AT AT0209479A patent/AT373592B/en not_active IP Right Cessation
- 1979-05-31 IL IL57445A patent/IL57445A0/en not_active IP Right Cessation
-
1981
- 1981-10-22 HK HK503/81A patent/HK50381A/en unknown
-
1982
- 1982-08-26 SE SE8204893A patent/SE455307B/en not_active IP Right Cessation
-
1983
- 1983-01-04 YU YU11/83A patent/YU43143B/en unknown
- 1983-01-04 YU YU00012/83A patent/YU1283A/en unknown
-
1984
- 1984-01-11 KE KE3365A patent/KE3365A/en unknown
-
1985
- 1985-12-30 MY MY417/85A patent/MY8500417A/en unknown
-
1990
- 1990-04-19 JP JP2101872A patent/JPH03204868A/en active Pending
-
1993
- 1993-01-20 JP JP5023427A patent/JPH05247013A/en active Pending
- 1993-09-09 GE GEAP19931537A patent/GEP19970783B/en unknown
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