FR2474035A2 - Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent - Google Patents
Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent Download PDFInfo
- Publication number
- FR2474035A2 FR2474035A2 FR8000978A FR8000978A FR2474035A2 FR 2474035 A2 FR2474035 A2 FR 2474035A2 FR 8000978 A FR8000978 A FR 8000978A FR 8000978 A FR8000978 A FR 8000978A FR 2474035 A2 FR2474035 A2 FR 2474035A2
- Authority
- FR
- France
- Prior art keywords
- radical
- general formula
- dioxo
- tetrahydro
- alkyl
- 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 198
- 239000000203 mixture Substances 0.000 claims abstract description 80
- 239000002253 acid Substances 0.000 claims abstract description 45
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 229940124587 cephalosporin Drugs 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000003254 radicals Chemical class 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 67
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 65
- 230000002829 reductive effect Effects 0.000 claims description 45
- 125000006239 protecting group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 229930186147 Cephalosporin Natural products 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 230000001681 protective effect Effects 0.000 claims description 20
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 14
- 150000003573 thiols Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000001780 cephalosporins Chemical class 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000002923 oximes Chemical class 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical group 0.000 claims description 8
- 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 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 150000008064 anhydrides 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000007530 organic bases Chemical group 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000004967 formylalkyl group Chemical group 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 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 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 230000002255 enzymatic effect Effects 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 1
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 4
- 241000588724 Escherichia coli Species 0.000 abstract description 3
- 238000000338 in vitro Methods 0.000 abstract description 3
- 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
- 229940092559 enterobacter aerogenes Drugs 0.000 abstract description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 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
- 150000001204 N-oxides Chemical class 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
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 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
- 239000000047 product Substances 0.000 description 123
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 46
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 40
- 229910052753 mercury Inorganic materials 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 29
- 238000002329 infrared spectrum Methods 0.000 description 28
- 125000003277 amino group Chemical group 0.000 description 27
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 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 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 235000019253 formic acid Nutrition 0.000 description 23
- 239000000843 powder Substances 0.000 description 23
- 239000000741 silica gel Substances 0.000 description 23
- 229910002027 silica gel Inorganic materials 0.000 description 23
- 230000008030 elimination Effects 0.000 description 22
- 238000003379 elimination reaction Methods 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 21
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 18
- 238000006722 reduction reaction Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 229910014033 C-OH Inorganic materials 0.000 description 8
- 229910014570 C—OH Inorganic materials 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 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 5
- 0 CCS1(C2CC2)C(C(C2)N*)N2C(*)C(C)C1 Chemical compound CCS1(C2CC2)C(C(C2)N*)N2C(*)C(C)C1 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
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- 238000001816 cooling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 5
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
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- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- OYEHFRMFJLFNSD-UHFFFAOYSA-N 1,2,5,6-tetrahydro-1,2,4-triazine Chemical compound C1CN=CNN1 OYEHFRMFJLFNSD-UHFFFAOYSA-N 0.000 description 3
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
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- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- REPVNSJSTLRQEQ-UHFFFAOYSA-N n,n-dimethylacetamide;n,n-dimethylformamide Chemical compound CN(C)C=O.CN(C)C(C)=O REPVNSJSTLRQEQ-UHFFFAOYSA-N 0.000 description 1
- HYGXISCUUFVGQW-UHFFFAOYSA-N n,n-dimethylformamide;1,4-dioxane Chemical compound CN(C)C=O.C1COCCO1 HYGXISCUUFVGQW-UHFFFAOYSA-N 0.000 description 1
- CZFNISFYDPIDNM-UHFFFAOYSA-N n,n-dimethylformamide;oxolane Chemical compound CN(C)C=O.C1CCOC1 CZFNISFYDPIDNM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000003420 transacetalization reaction Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 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 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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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)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8000978A FR2474035A2 (fr) | 1979-05-23 | 1980-01-17 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| DD22127180A DD151170A5 (de) | 1979-05-23 | 1980-05-21 | Verfahren zur herstellung von neuen 3-thiovinyl-cephalosporinen |
| IE1061/80A IE50626B1 (en) | 1979-05-23 | 1980-05-21 | Novel 3-thiovinyl-cephalosporins,their preparation,and the compositions containing these compounds |
| US06/152,115 US4307116A (en) | 1979-05-23 | 1980-05-21 | 3-Thiovinyl-cephalosporins |
| DE19803019400 DE3019400A1 (de) | 1979-05-23 | 1980-05-21 | Neue 3-thiovinyl-cephalosporine, verfahren zu deren herstellung und diese enthaltende zusammensetzungen |
| AT542181A AT374480B (de) | 1979-05-23 | 1980-05-21 | Verfahren zur herstellung von neuen 3-thiovinylcephalosporinderivaten |
| ES491686A ES491686A0 (es) | 1979-05-23 | 1980-05-21 | Procedimiento para la obtencion de tiovinil-3 cefalosporinas |
| DK222180A DK222180A (da) | 1979-05-23 | 1980-05-21 | Fremgangsmaade til fremstilling af 3-thiovinylcephalosporiner |
| IT22240/80A IT1148830B (it) | 1979-05-23 | 1980-05-21 | Tiovinil-3 cefalosporine, loro preparazione e composizioni che le contengono |
| 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 |
| YU01367/80A YU136780A (en) | 1979-05-23 | 1980-05-21 | Process for obtaining new 3-thiovinyl-cephalosporins |
| AU58596/80A AU534807B2 (en) | 1979-05-23 | 1980-05-21 | 3-thiovinyl cephalosporins |
| GR62014A GR68074B (enExample) | 1979-05-23 | 1980-05-21 | |
| GB8016728A GB2051788B (en) | 1979-05-23 | 1980-05-21 | 3 - thiovinyl - cephalosporins their preparation and compositions containing them |
| CA000352357A CA1145744A (fr) | 1979-05-23 | 1980-05-21 | Thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent |
| SU802925202A SU1130167A3 (ru) | 1979-05-23 | 1980-05-21 | Способ получени 3-тиовинилцефалоспоринов или их солей с щелочными металлами или их аддитивных солей с азотсодержащими органическими основани ми |
| CH398880A CH645117A5 (fr) | 1979-05-23 | 1980-05-21 | Thiovinyl-3 cephalosporines, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| BE0/200706A BE883415A (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les compositions qui les contiennent |
| PT71275A PT71275A (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines et les compositions qui les contiennent |
| AT270880A AT369378B (de) | 1979-05-23 | 1980-05-21 | Verfahren zur herstellung von neuen 3-thiovinyl-cephalosporinderivaten |
| PL23038080A PL127207B1 (en) | 1979-05-23 | 1980-05-21 | Method of obtaining new 3-thiovinylcephalosporin |
| HU801277A HU184771B (en) | 1979-05-23 | 1980-05-21 | Process for producing new 3-thiovinyl-cepheme-carboxylic acid derivatives |
| NZ193798A NZ193798A (en) | 1979-05-23 | 1980-05-21 | 3-thiovinyl-cephalosporin derivatives and pharmaceutical compositions |
| LU82479A LU82479A1 (fr) | 1979-05-23 | 1980-05-21 | Nouvelles thiovinyl-3 cephalosporines,leur preparation et les compositions qui les contiennent |
| NO801501A NO801501L (no) | 1979-05-23 | 1980-05-21 | Fremgangsmaate for fremstilling av 3-tiovinylcefalosporiner |
| SE8003820A SE8003820L (sv) | 1979-05-23 | 1980-05-21 | Nya 3-tiovinylcefalosporiner, forfaranden for framstellning av desamma och farmaceutiska kompositioner innehallande desamma |
| 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 |
| PH24055A PH15929A (en) | 1979-05-23 | 1980-05-22 | 3-thiovinyl cephalosporin |
| NL8003011A NL8003011A (nl) | 1979-05-23 | 1980-05-23 | 3-thiovinylcefalosporinen, de bereiding daarvan alsmede farmaceutische preparaten die deze verbindingen als actieve component bevatten. |
| SU802991487A SU1114339A3 (ru) | 1979-05-23 | 1980-10-09 | Способ получени 3-тиовинилцефалоспоринов или их солей |
| ES496193A ES496193A0 (es) | 1979-05-23 | 1980-10-23 | Procedimiento para la obtencion de tiovinil-3 cefalosporinas |
| ES496196A ES8107230A1 (es) | 1980-01-17 | 1980-10-23 | Procedimiento para la obtencion de tiovinil-3 cefalosporinas |
| YU58383A YU58383A (en) | 1979-05-23 | 1983-03-10 | Process for obtaining new 3-thiovinyl cephalosporins |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7913095A FR2474504A1 (fr) | 1979-05-23 | 1979-05-23 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| FR7927687A FR2469415A2 (fr) | 1979-05-23 | 1979-11-09 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
| FR8000978A FR2474035A2 (fr) | 1979-05-23 | 1980-01-17 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2474035A2 true FR2474035A2 (fr) | 1981-07-24 |
| FR2474035B2 FR2474035B2 (enExample) | 1983-04-29 |
Family
ID=27250927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8000978A Granted FR2474035A2 (fr) | 1979-05-23 | 1980-01-17 | Nouvelles thiovinyl-3 cephalosporines, leur preparation et les medicaments qui les contiennent |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT369378B (enExample) |
| DD (1) | DD151170A5 (enExample) |
| ES (1) | ES496193A0 (enExample) |
| FR (1) | FR2474035A2 (enExample) |
| PL (1) | PL127207B1 (enExample) |
| SU (2) | SU1130167A3 (enExample) |
| YU (1) | YU58383A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120737809A (zh) * | 2025-08-14 | 2025-10-03 | 鄂尔多斯市神东天隆化工有限责任公司 | 一种低氯复合环保煤炭运输防冻剂的制备方法 |
-
1980
- 1980-01-17 FR FR8000978A patent/FR2474035A2/fr active Granted
- 1980-05-21 PL PL23038080A patent/PL127207B1/pl unknown
- 1980-05-21 DD DD22127180A patent/DD151170A5/de unknown
- 1980-05-21 AT AT270880A patent/AT369378B/de active
- 1980-05-21 SU SU802925202A patent/SU1130167A3/ru active
- 1980-10-09 SU SU802991487A patent/SU1114339A3/ru active
- 1980-10-23 ES ES496193A patent/ES496193A0/es active Granted
-
1983
- 1983-03-10 YU YU58383A patent/YU58383A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN120737809A (zh) * | 2025-08-14 | 2025-10-03 | 鄂尔多斯市神东天隆化工有限责任公司 | 一种低氯复合环保煤炭运输防冻剂的制备方法 |
| CN120737809B (zh) * | 2025-08-14 | 2026-01-30 | 鄂尔多斯市神东天隆化工有限责任公司 | 一种低氯复合环保煤炭运输防冻剂的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| SU1130167A3 (ru) | 1984-12-15 |
| FR2474035B2 (enExample) | 1983-04-29 |
| PL127207B1 (en) | 1983-10-31 |
| AT369378B (de) | 1982-12-27 |
| YU58383A (en) | 1984-02-29 |
| ATA270880A (de) | 1982-05-15 |
| ES8107228A1 (es) | 1981-10-01 |
| SU1114339A3 (ru) | 1984-09-15 |
| ES496193A0 (es) | 1981-10-01 |
| DD151170A5 (de) | 1981-10-08 |
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