FR2499995A1 - Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. - Google Patents
Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. Download PDFInfo
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- FR2499995A1 FR2499995A1 FR8106736A FR8106736A FR2499995A1 FR 2499995 A1 FR2499995 A1 FR 2499995A1 FR 8106736 A FR8106736 A FR 8106736A FR 8106736 A FR8106736 A FR 8106736A FR 2499995 A1 FR2499995 A1 FR 2499995A1
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- 241000894006 Bacteria Species 0.000 title abstract description 7
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 239000002253 acid Substances 0.000 claims abstract description 76
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 150000002148 esters Chemical class 0.000 claims abstract description 23
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000011777 magnesium Substances 0.000 claims abstract description 15
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 11
- 125000002252 acyl group Chemical group 0.000 claims abstract description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 8
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- -1 alkyl radical Chemical class 0.000 claims description 393
- 238000000034 method Methods 0.000 claims description 37
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 34
- 150000003254 radicals Chemical class 0.000 claims description 32
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000006239 protecting group Chemical group 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 125000004185 ester group Chemical group 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 150000007513 acids Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 150000008064 anhydrides Chemical class 0.000 claims description 11
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 235000005985 organic acids Nutrition 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
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- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 230000032050 esterification Effects 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 150000003462 sulfoxides Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 241000588748 Klebsiella Species 0.000 abstract description 25
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract description 22
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- 241000295644 Staphylococcaceae Species 0.000 abstract description 5
- 208000015181 infectious disease Diseases 0.000 abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- 241000699670 Mus sp. Species 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
- 201000004813 Bronchopneumonia Diseases 0.000 abstract description 2
- 229930182555 Penicillin Natural products 0.000 abstract description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract description 2
- 206010040047 Sepsis Diseases 0.000 abstract description 2
- 238000001727 in vivo Methods 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229940049954 penicillin Drugs 0.000 abstract description 2
- 230000000699 topical effect Effects 0.000 abstract description 2
- 241000193738 Bacillus anthracis Species 0.000 abstract 1
- 241000192125 Firmicutes Species 0.000 abstract 1
- 206010052428 Wound Diseases 0.000 abstract 1
- 208000027418 Wounds and injury Diseases 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000002685 pulmonary effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 234
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 181
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 136
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 106
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 100
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 96
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 84
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
- 239000000203 mixture Substances 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 67
- 230000002829 reductive effect Effects 0.000 description 61
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 59
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 51
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- 241000588722 Escherichia Species 0.000 description 46
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 45
- 238000002211 ultraviolet spectrum Methods 0.000 description 45
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 235000019253 formic acid Nutrition 0.000 description 42
- 239000012043 crude product Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- 241000191940 Staphylococcus Species 0.000 description 36
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 29
- 239000012074 organic phase Substances 0.000 description 29
- 239000011780 sodium chloride Substances 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
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- 239000007864 aqueous solution Substances 0.000 description 26
- 241000194017 Streptococcus Species 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000004098 Tetracycline Substances 0.000 description 23
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- 150000003522 tetracyclines Chemical class 0.000 description 23
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 21
- 229930182566 Gentamicin Natural products 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- 235000011167 hydrochloric acid Nutrition 0.000 description 20
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 239000012298 atmosphere Substances 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 15
- 229960002518 gentamicin Drugs 0.000 description 15
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 14
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 13
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- 239000002198 insoluble material Substances 0.000 description 11
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 11
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- 239000002904 solvent Substances 0.000 description 11
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
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- 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 description 6
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- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
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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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP81400224A EP0034536B1 (fr) | 1980-02-18 | 1981-02-13 | Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl 7-amino thiazolylacétamido céphalosporanique, leur préparation, leur application comme médicaments et les compositions les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2499995A1 true FR2499995A1 (fr) | 1982-08-20 |
| FR2499995B1 FR2499995B1 (en, 2012) | 1985-01-18 |
Family
ID=8188499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8106736A Granted FR2499995A1 (fr) | 1981-02-13 | 1981-04-03 | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkylthiomethyl 7-amino thiazolylacetamido cephalosporanique, leur preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2499995A1 (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043334A (en) * | 1984-11-02 | 1991-08-27 | Glaxo Group Limited | Cephalosporin antibiotics |
| WO2007083017A2 (fr) | 2006-01-23 | 2007-07-26 | Aventis Pharma S.A. | Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| US8188078B2 (en) | 2007-10-19 | 2012-05-29 | Sanofi-Aventis | 6-aryl/heteroalkyloxy benzothiazole and benzimidazole derivatives, method for preparing same, application thereof as drugs, pharmaceutical compositions and novel use in particular as C-MET inhibitors |
| US8546393B2 (en) | 2007-08-09 | 2013-10-01 | Sanofi | 6-triazolopyridazine sulfanyl benzothiazole derivatives as MET inhibitors |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2119074A1 (en, 2012) * | 1970-12-24 | 1972-08-04 | Takeda Chemical Industries Ltd | |
| FR2137899A1 (en, 2012) * | 1971-05-14 | 1972-12-29 | Glaxo Lab Ltd | |
| FR2348218A1 (fr) * | 1976-04-14 | 1977-11-10 | Takeda Chemical Industries Ltd | Nouveaux derives cephalosporines ayant un nouveau groupe 7-acyle et leur procede de fabrication |
| FR2379540A1 (fr) * | 1977-02-08 | 1978-09-01 | Toyama Chemical Co Ltd | Nouveau procede de preparation d'un acide 7-(substitue)-amino-3-thiomethyl substitue cephem carboxylique |
| FR2476087A1 (fr) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
-
1981
- 1981-04-03 FR FR8106736A patent/FR2499995A1/fr active Granted
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2119074A1 (en, 2012) * | 1970-12-24 | 1972-08-04 | Takeda Chemical Industries Ltd | |
| FR2137899A1 (en, 2012) * | 1971-05-14 | 1972-12-29 | Glaxo Lab Ltd | |
| FR2348218A1 (fr) * | 1976-04-14 | 1977-11-10 | Takeda Chemical Industries Ltd | Nouveaux derives cephalosporines ayant un nouveau groupe 7-acyle et leur procede de fabrication |
| FR2379540A1 (fr) * | 1977-02-08 | 1978-09-01 | Toyama Chemical Co Ltd | Nouveau procede de preparation d'un acide 7-(substitue)-amino-3-thiomethyl substitue cephem carboxylique |
| FR2476087A1 (fr) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| EP0034536B1 (fr) * | 1980-02-18 | 1984-12-27 | Roussel-Uclaf | Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl 7-amino thiazolylacétamido céphalosporanique, leur préparation, leur application comme médicaments et les compositions les renfermant |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5043334A (en) * | 1984-11-02 | 1991-08-27 | Glaxo Group Limited | Cephalosporin antibiotics |
| WO2007083017A2 (fr) | 2006-01-23 | 2007-07-26 | Aventis Pharma S.A. | Nouveaux derives d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| US7935819B2 (en) | 2006-01-23 | 2011-05-03 | Aventis Pharma S.A. | Cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors |
| US8546393B2 (en) | 2007-08-09 | 2013-10-01 | Sanofi | 6-triazolopyridazine sulfanyl benzothiazole derivatives as MET inhibitors |
| US9115134B2 (en) | 2007-08-09 | 2015-08-25 | Sanofi | 6-triazolopyridazine sulfanyl benzothiazole derivatives as MET inhibitors |
| US9321777B2 (en) | 2007-08-09 | 2016-04-26 | Sanofi | 6-triazolopyridazine sulfanyl benzothiazole derivatives as MET inhibitors |
| US8188078B2 (en) | 2007-10-19 | 2012-05-29 | Sanofi-Aventis | 6-aryl/heteroalkyloxy benzothiazole and benzimidazole derivatives, method for preparing same, application thereof as drugs, pharmaceutical compositions and novel use in particular as C-MET inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2499995B1 (en, 2012) | 1985-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CA | Change of address | ||
| CD | Change of name or company name | ||
| TP | Transmission of property |