FR2475545A1 - Nouveaux thioloesters, leur preparation et leur utilisation en synthese - Google Patents
Nouveaux thioloesters, leur preparation et leur utilisation en synthese Download PDFInfo
- Publication number
- FR2475545A1 FR2475545A1 FR8003057A FR8003057A FR2475545A1 FR 2475545 A1 FR2475545 A1 FR 2475545A1 FR 8003057 A FR8003057 A FR 8003057A FR 8003057 A FR8003057 A FR 8003057A FR 2475545 A1 FR2475545 A1 FR 2475545A1
- Authority
- FR
- France
- Prior art keywords
- radical
- alkyl
- general formula
- amino
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 3
- 229940088710 antibiotic agent Drugs 0.000 title abstract 2
- 241000192125 Firmicutes Species 0.000 title 1
- -1 L-2-amino-2-carboxy-ethyl Chemical group 0.000 claims abstract description 218
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 57
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 229940124587 cephalosporin Drugs 0.000 claims abstract description 15
- 150000003254 radicals Chemical class 0.000 claims description 92
- 238000000034 method Methods 0.000 claims description 62
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 230000001681 protective effect Effects 0.000 claims description 15
- 229930186147 Cephalosporin Natural products 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims description 13
- 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 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 150000001780 cephalosporins Chemical class 0.000 claims description 9
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 8
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 6
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 150000007970 thio esters Chemical class 0.000 claims description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 2
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- 125000004967 formylalkyl group Chemical group 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 2
- 125000005544 phthalimido group Chemical group 0.000 claims description 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 claims 2
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 125000001271 cephalosporin group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 abstract description 36
- 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 10
- 229940056360 penicillin g Drugs 0.000 abstract description 5
- 241000588724 Escherichia coli Species 0.000 abstract description 3
- 238000000338 in vitro Methods 0.000 abstract description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 2
- 241000588915 Klebsiella aerogenes Species 0.000 abstract description 2
- 241000588772 Morganella morganii Species 0.000 abstract description 2
- 241000699670 Mus sp. Species 0.000 abstract description 2
- 150000001204 N-oxides Chemical class 0.000 abstract description 2
- 229940092559 enterobacter aerogenes Drugs 0.000 abstract description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 abstract description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 98
- 239000000047 product Substances 0.000 description 79
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 62
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- 238000002329 infrared spectrum Methods 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 239000000843 powder Substances 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 20
- 229910052753 mercury Inorganic materials 0.000 description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 239000002609 medium Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 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 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 235000019253 formic acid Nutrition 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 230000008030 elimination Effects 0.000 description 8
- 238000003379 elimination reaction Methods 0.000 description 8
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229950003476 aminothiazole Drugs 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 3
- OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
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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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (42)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8003057A FR2475545A1 (fr) | 1980-02-12 | 1980-02-12 | Nouveaux thioloesters, leur preparation et leur utilisation en synthese |
| YU01367/80A YU136780A (en) | 1979-05-23 | 1980-05-21 | Process for obtaining new 3-thiovinyl-cephalosporins |
| IT22240/80A IT1148830B (it) | 1979-05-23 | 1980-05-21 | Tiovinil-3 cefalosporine, loro preparazione e composizioni che le contengono |
| AU58596/80A AU534807B2 (en) | 1979-05-23 | 1980-05-21 | 3-thiovinyl cephalosporins |
| LU82479A LU82479A1 (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines,leur preparation et les compositions qui les contiennent |
| GR62014A GR68074B (OSRAM) | 1979-05-23 | 1980-05-21 | |
| US06/152,115 US4307116A (en) | 1979-05-23 | 1980-05-21 | 3-Thiovinyl-cephalosporins |
| GB8016728A GB2051788B (en) | 1979-05-23 | 1980-05-21 | 3 - thiovinyl - cephalosporins their preparation and compositions containing them |
| DE19803019400 DE3019400A1 (de) | 1979-05-23 | 1980-05-21 | Neue 3-thiovinyl-cephalosporine, verfahren zu deren herstellung und diese enthaltende zusammensetzungen |
| ES491686A ES491686A0 (es) | 1979-05-23 | 1980-05-21 | Procedimiento para la obtencion de tiovinil-3 cefalosporinas |
| BE0/200706A BE883415A (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent |
| PL23037980A PL127301B1 (en) | 1980-02-12 | 1980-05-21 | Method of obtaining new 3-thiovinylocephalosporines |
| PL1980224389A PL125471B1 (en) | 1979-05-23 | 1980-05-21 | Process for preparing novel 3-thiovinylcephalosporin |
| FI801640A FI801640A7 (fi) | 1979-05-23 | 1980-05-21 | Nya tiovinyl-3 kefalosporiner deras framstaellning och dessa innehaollande kompositioner |
| NZ193798A NZ193798A (en) | 1979-05-23 | 1980-05-21 | 3-thiovinyl-cephalosporin derivatives and pharmaceutical compositions |
| CH398880A CH645117A5 (fr) | 1979-05-23 | 1980-05-21 | Thiovinyl-3 cephalosporines, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| IE1061/80A IE50626B1 (en) | 1979-05-23 | 1980-05-21 | Novel 3-thiovinyl-cephalosporins,their preparation,and the compositions containing these compounds |
| DK222180A DK222180A (da) | 1979-05-23 | 1980-05-21 | Fremgangsmaade til fremstilling af 3-thiovinylcephalosporiner |
| CA000352357A CA1145744A (fr) | 1979-05-23 | 1980-05-21 | Thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent |
| SE8003820A SE8003820L (sv) | 1979-05-23 | 1980-05-21 | Nya 3-tiovinylcefalosporiner, forfaranden for framstellning av desamma och farmaceutiska kompositioner innehallande desamma |
| HU801277A HU184771B (en) | 1979-05-23 | 1980-05-21 | Process for producing new 3-thiovinyl-cepheme-carboxylic acid derivatives |
| PT71275A PT71275A (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines et les compositions qui les contiennent |
| NO801501A NO801501L (no) | 1979-05-23 | 1980-05-21 | Fremgangsmaate for fremstilling av 3-tiovinylcefalosporiner |
| PH24055A PH15929A (en) | 1979-05-23 | 1980-05-22 | 3-thiovinyl cephalosporin |
| IL60138A IL60138A (en) | 1979-05-23 | 1980-05-22 | 7-(-2-aminothiazolyl-2-methoxy-imino acetamido)-3-thiovinyl-cephalosporins,their preparation and compositions containing them |
| NL8003011A NL8003011A (nl) | 1979-05-23 | 1980-05-23 | 3-thiovinylcefalosporinen, de bereiding daarvan alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten. |
| SU802991491A SU1098522A3 (ru) | 1980-02-12 | 1980-10-15 | Способ получени 3-тиовинилцефалоспоринов или их солей |
| ES496194A ES496194A0 (es) | 1980-02-12 | 1980-10-23 | Procedimiento para la obtencion de tiovinil-3 cefalosporinas |
| NL8100539A NL8100539A (nl) | 1980-02-12 | 1981-02-04 | Nieuwe thiolesters, de bereiding daarvan en hun gebruik bij syntheses. |
| CH85681A CH646963A5 (fr) | 1980-02-12 | 1981-02-09 | Thioloesters et procede pour leur preparation. |
| US06/233,109 US4385181A (en) | 1980-02-12 | 1981-02-10 | Thioloesters |
| GB8103963A GB2068957B (en) | 1980-02-12 | 1981-02-10 | Thioloesters and process for their preparation |
| JP1761181A JPS56127375A (en) | 1980-02-12 | 1981-02-10 | Novel thiol esters and manufacture |
| HU81334A HU185627B (en) | 1980-02-12 | 1981-02-11 | Process for producing new thiazolyl-thiolesters |
| SE8100954A SE8100954L (sv) | 1980-02-12 | 1981-02-11 | Nya tioloestrar och forfaranden for framstellning derav |
| BE0/203768A BE887474A (fr) | 1980-02-12 | 1981-02-11 | Nouveaux thioloesters, leur preparation et leur utilisation en synthese |
| CA000370640A CA1187496A (fr) | 1980-02-12 | 1981-02-11 | Thioloesters, leur preparation et leur utilisation en synthese |
| DK58581A DK58581A (da) | 1980-02-12 | 1981-02-11 | Thiolestere deres fremstilling og anvendelse |
| DE3105136A DE3105136A1 (de) | 1980-02-12 | 1981-02-12 | "neue thioloester, ihre herstellung und ihre verwendung zur synthese" |
| IT19703/81A IT1141966B (it) | 1980-02-12 | 1981-02-12 | Tiol-esteri,loro preparazione e lo impiego in sintesi |
| AT542281A AT374481B (de) | 1979-05-23 | 1981-05-21 | Verfahren zur herstellung von neuen 3-thiovinylcephalosporinderivaten |
| YU58483A YU58483A (en) | 1980-02-12 | 1983-03-10 | Process for obtaining new 3-thiovinyl cephalosporins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8003057A FR2475545A1 (fr) | 1980-02-12 | 1980-02-12 | Nouveaux thioloesters, leur preparation et leur utilisation en synthese |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475545A1 true FR2475545A1 (fr) | 1981-08-14 |
| FR2475545B1 FR2475545B1 (OSRAM) | 1983-09-30 |
Family
ID=9238493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8003057A Granted FR2475545A1 (fr) | 1979-05-23 | 1980-02-12 | Nouveaux thioloesters, leur preparation et leur utilisation en synthese |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS56127375A (OSRAM) |
| ES (1) | ES496194A0 (OSRAM) |
| FR (1) | FR2475545A1 (OSRAM) |
| PL (1) | PL127301B1 (OSRAM) |
| SU (1) | SU1098522A3 (OSRAM) |
| YU (1) | YU58483A (OSRAM) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346014A1 (fr) * | 1976-01-23 | 1977-10-28 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| DE2804040A1 (de) * | 1978-01-31 | 1979-08-02 | Hoechst Ag | Verfahren zur herstellung von cephemverbindungen |
-
1980
- 1980-02-12 FR FR8003057A patent/FR2475545A1/fr active Granted
- 1980-05-21 PL PL23037980A patent/PL127301B1/pl unknown
- 1980-10-15 SU SU802991491A patent/SU1098522A3/ru active
- 1980-10-23 ES ES496194A patent/ES496194A0/es active Granted
-
1981
- 1981-02-10 JP JP1761181A patent/JPS56127375A/ja active Pending
-
1983
- 1983-03-10 YU YU58483A patent/YU58483A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2346014A1 (fr) * | 1976-01-23 | 1977-10-28 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| DE2804040A1 (de) * | 1978-01-31 | 1979-08-02 | Hoechst Ag | Verfahren zur herstellung von cephemverbindungen |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/70 * |
Also Published As
| Publication number | Publication date |
|---|---|
| SU1098522A3 (ru) | 1984-06-15 |
| FR2475545B1 (OSRAM) | 1983-09-30 |
| ES8107229A1 (es) | 1981-10-01 |
| PL127301B1 (en) | 1983-10-31 |
| YU58483A (en) | 1984-02-29 |
| JPS56127375A (en) | 1981-10-06 |
| ES496194A0 (es) | 1981-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |