FR2506307A1 - Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation - Google Patents
Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation Download PDFInfo
- Publication number
- FR2506307A1 FR2506307A1 FR8110238A FR8110238A FR2506307A1 FR 2506307 A1 FR2506307 A1 FR 2506307A1 FR 8110238 A FR8110238 A FR 8110238A FR 8110238 A FR8110238 A FR 8110238A FR 2506307 A1 FR2506307 A1 FR 2506307A1
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
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- 238000003756 stirring Methods 0.000 description 34
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
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- BLSRNVDCHVKXSO-UHFFFAOYSA-M sodium;2-ethylbutanoate Chemical compound [Na+].CCC(CC)C([O-])=O BLSRNVDCHVKXSO-UHFFFAOYSA-M 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- YIHJHCFUGYYAKW-UHFFFAOYSA-O triethylazanium;azide Chemical compound [N-]=[N+]=[N-].CC[NH+](CC)CC YIHJHCFUGYYAKW-UHFFFAOYSA-O 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8110238A FR2506307A1 (fr) | 1981-05-22 | 1981-05-22 | Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8110238A FR2506307A1 (fr) | 1981-05-22 | 1981-05-22 | Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2506307A1 true FR2506307A1 (fr) | 1982-11-26 |
| FR2506307B1 FR2506307B1 (enExample) | 1984-03-23 |
Family
ID=9258794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8110238A Granted FR2506307A1 (fr) | 1981-05-22 | 1981-05-22 | Nouveaux derives substitues de l'acide 2-(2-amino 4-thiazolyl) 2-hydroxyimino acetique et leur procede de preparation |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2506307A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656166A (en) * | 1983-05-27 | 1987-04-07 | Sanofi | Antibiotic compounds derived from cephalosporins, process for their production and pharmaceutical compositions |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2702501A1 (de) * | 1976-01-23 | 1977-07-28 | Roussel Uclaf | Neue oxime der 7-aminothiazolylacetamidocephalosporansaeure, herstellungsverfahren und pharmazeutische zusammensetzungen |
| FR2348219A1 (fr) * | 1976-04-12 | 1977-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation d'isomeres syn de composes d'acides 3,7-cephem-4-carboxyliques 3,7-disubstitues et nouveaux produits ainsi obtenus, a activite antibacterienne |
| FR2383951A1 (fr) * | 1977-03-14 | 1978-10-13 | Fujisawa Pharmaceutical Co | Procede de preparation d'acides 7-substitue-3-cephem (ou cepham)-4-carboxyliques, de leurs sels et de leurs bioprecurseurs, et nouveaux produits ainsi obtenus, a activite antimicrobienne |
| FR2384782A1 (fr) * | 1977-03-25 | 1978-10-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-acetoxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
-
1981
- 1981-05-22 FR FR8110238A patent/FR2506307A1/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2702501A1 (de) * | 1976-01-23 | 1977-07-28 | Roussel Uclaf | Neue oxime der 7-aminothiazolylacetamidocephalosporansaeure, herstellungsverfahren und pharmazeutische zusammensetzungen |
| FR2348219A1 (fr) * | 1976-04-12 | 1977-11-10 | Fujisawa Pharmaceutical Co | Procede de preparation d'isomeres syn de composes d'acides 3,7-cephem-4-carboxyliques 3,7-disubstitues et nouveaux produits ainsi obtenus, a activite antibacterienne |
| FR2383951A1 (fr) * | 1977-03-14 | 1978-10-13 | Fujisawa Pharmaceutical Co | Procede de preparation d'acides 7-substitue-3-cephem (ou cepham)-4-carboxyliques, de leurs sels et de leurs bioprecurseurs, et nouveaux produits ainsi obtenus, a activite antimicrobienne |
| FR2384782A1 (fr) * | 1977-03-25 | 1978-10-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-acetoxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656166A (en) * | 1983-05-27 | 1987-04-07 | Sanofi | Antibiotic compounds derived from cephalosporins, process for their production and pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2506307B1 (enExample) | 1984-03-23 |
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