SK280156B6 - Cefalosporíny, ktoré majú v polohe 3 propenylový r - Google Patents
Cefalosporíny, ktoré majú v polohe 3 propenylový r Download PDFInfo
- Publication number
- SK280156B6 SK280156B6 SK1830-91A SK183091A SK280156B6 SK 280156 B6 SK280156 B6 SK 280156B6 SK 183091 A SK183091 A SK 183091A SK 280156 B6 SK280156 B6 SK 280156B6
- Authority
- SK
- Slovakia
- Prior art keywords
- amino
- oxo
- acetyl
- formula
- carboxy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 38
- 229930186147 Cephalosporin Natural products 0.000 title claims abstract description 22
- 229940124587 cephalosporin Drugs 0.000 title claims abstract description 22
- 150000001780 cephalosporins Chemical class 0.000 title claims abstract description 22
- 239000003814 drug Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000543 intermediate Substances 0.000 title claims abstract description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 title description 3
- -1 amine organic base Chemical class 0.000 claims abstract description 585
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 22
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 22
- 239000011777 magnesium Substances 0.000 claims abstract description 22
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 20
- 125000004185 ester group Chemical group 0.000 claims abstract description 16
- 125000002252 acyl group Chemical group 0.000 claims abstract description 10
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 10
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 160
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 135
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 121
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 39
- 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 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 150000007513 acids Chemical class 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 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
- 239000011630 iodine Substances 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 6
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 5
- FIPLAFRCDDWERW-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]pyridine Chemical compound N1=CC=C2SC=NC2=C1 FIPLAFRCDDWERW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000006000 trichloroethyl group Chemical group 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- CDZHZLQKNAKKEC-UHFFFAOYSA-N [bis(hydroxymethylamino)methylamino]methanol Chemical compound OCNC(NCO)NCO CDZHZLQKNAKKEC-UHFFFAOYSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 3
- 229960004919 procaine Drugs 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005633 phthalidyl group Chemical group 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- 125000005425 toluyl group Chemical group 0.000 claims description 2
- UKFAWRZYFYOXEG-UHFFFAOYSA-N 5,6-dimethoxy-3H-isobenzofuran-1-one Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2 UKFAWRZYFYOXEG-UHFFFAOYSA-N 0.000 claims 2
- 125000003431 oxalo group Chemical group 0.000 claims 2
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 claims 1
- 241000282941 Rangifer tarandus Species 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 172
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 110
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 35
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 33
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 26
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
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- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 150000002496 iodine Chemical class 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 14
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 13
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- 229940125670 thienopyridine Drugs 0.000 description 11
- 239000002175 thienopyridine Substances 0.000 description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 235000009518 sodium iodide Nutrition 0.000 description 7
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 7
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- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- RNSPSDZVVQVBFG-UHFFFAOYSA-N I.C1=CC=[NH+]C=C1.[O-]C(=O)C(F)(F)F Chemical compound I.C1=CC=[NH+]C=C1.[O-]C(=O)C(F)(F)F RNSPSDZVVQVBFG-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 6
- 150000003952 β-lactams Chemical class 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- VAKOWVVVSGPEFK-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydroiodide Chemical compound I.OC(=O)C(F)(F)F VAKOWVVVSGPEFK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 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
- 239000002689 soil Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- LAFJKASCBXMWEU-UHFFFAOYSA-N thieno[2,3-c]pyridin-6-ium iodide Chemical compound [I-].S1C=CC=2C1=C[NH+]=CC=2 LAFJKASCBXMWEU-UHFFFAOYSA-N 0.000 description 1
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
- XVLLZOGDFPZANY-UHFFFAOYSA-N thieno[3,2-b]pyridin-4-ium iodide Chemical compound [I-].S1C=CC2=[NH+]C=CC=C21 XVLLZOGDFPZANY-UHFFFAOYSA-N 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl 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
- 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9007491A FR2663332B1 (fr) | 1990-06-15 | 1990-06-15 | Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK280156B6 true SK280156B6 (sk) | 1999-09-10 |
Family
ID=9397653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1830-91A SK280156B6 (sk) | 1990-06-15 | 1991-06-14 | Cefalosporíny, ktoré majú v polohe 3 propenylový r |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5416080A (cs) |
| EP (1) | EP0462009B1 (cs) |
| JP (1) | JP3080692B2 (cs) |
| KR (1) | KR960009266B1 (cs) |
| AT (1) | ATE172733T1 (cs) |
| CA (1) | CA2044700A1 (cs) |
| CZ (1) | CZ282244B6 (cs) |
| DE (1) | DE69130410T2 (cs) |
| DK (1) | DK0462009T3 (cs) |
| ES (1) | ES2124698T3 (cs) |
| FR (1) | FR2663332B1 (cs) |
| HU (1) | HUT58101A (cs) |
| IE (1) | IE912032A1 (cs) |
| IL (3) | IL114629A (cs) |
| NZ (1) | NZ238577A (cs) |
| PT (1) | PT97971B (cs) |
| RU (1) | RU2078085C1 (cs) |
| SK (1) | SK280156B6 (cs) |
| UA (1) | UA26431A (cs) |
| ZA (1) | ZA914457B (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5397779A (en) * | 1990-06-15 | 1995-03-14 | Roussel-Uclaf | Cephalosporins |
| EP0551034B1 (fr) * | 1991-12-12 | 2000-09-20 | Hoechst Marion Roussel | Céphalosporines antibiotiques comportant en position 7 un radical benzyloxyimino substitué |
| US5587372A (en) * | 1991-12-12 | 1996-12-24 | Roussel Uclaf | Cephalosporins |
| FR2699177A1 (fr) * | 1992-12-11 | 1994-06-17 | Roussel Uclaf | Nouvelles céphalosporines comportant en position 7 un radical oxyimino substitué, leur procédé et intermédiaires de préparation et leur application comme médicaments. |
| EP0628562A1 (fr) * | 1993-06-10 | 1994-12-14 | Roussel Uclaf | Céphalosporines comportant en position 7 un radical oxymino substitué, leurs intermédiaires, leurs procédé de préparation et leur application comme médicaments |
| KR100257130B1 (ko) * | 1993-09-11 | 2000-05-15 | 성재갑 | 신규 세팔로스포린계 항생제 및 이의 제조방법 |
| US7427680B2 (en) * | 2001-01-12 | 2008-09-23 | The Regents Of The University Of California | Fluorogenic substrates for BETA-lactamase gene expression |
| KR0164458B1 (ko) * | 1995-04-04 | 1999-01-15 | 김은영 | 암모니오세팔로스포린 계열 항생제 및 그의 제조방법 |
| FR2737893B1 (fr) * | 1995-08-16 | 1997-09-12 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 7, un radical benzyloxyimino substitue, leur procede et intermediaires de preparation, leur application comme medicaments |
| US5872249A (en) * | 1995-09-01 | 1999-02-16 | Korea Institute Of Science And Technology | 3-ammoniopropenyl cephalosporin compounds as antibacterial agents and process for preparing the same |
| GB0215293D0 (en) | 2002-07-03 | 2002-08-14 | Rega Foundation | Viral inhibitors |
| US7214825B2 (en) * | 2003-10-17 | 2007-05-08 | Honeywell International Inc. | O-(3-chloropropenyl) hydroxylamine free base |
| PL1706403T3 (pl) | 2003-12-22 | 2012-07-31 | K U Leuven Res & Development | Związki imidazo[4,5-c]pirydynowe i sposoby leczenia przeciwwirusowego |
| DE602005013580D1 (de) | 2004-12-21 | 2009-05-07 | Leuven K U Res & Dev | Imidazoä4,5-cüpyridinverbindung und verfahren zur antiviralen behandlung |
| TW200637559A (en) * | 2005-03-29 | 2006-11-01 | Shionogi & Co | 3-propenylcefem derivative |
| TWI360549B (en) | 2006-07-07 | 2012-03-21 | Gilead Sciences Inc | Novel pyridazine compound and use thereof |
| UA99466C2 (en) | 2007-07-06 | 2012-08-27 | Гилиад Сайенсиз, Инк. | Crystalline pyridazine compound |
| CN115260213A (zh) * | 2022-05-27 | 2022-11-01 | 山东普洛得邦医药有限公司 | 一种头孢地尼的合成方法 |
| CN114805394A (zh) * | 2022-05-27 | 2022-07-29 | 山东普洛得邦医药有限公司 | 一种头孢克肟的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
| CA1276929C (en) * | 1984-04-09 | 1990-11-27 | Masahisa Oka | Cephalosporin antibacterial agents |
| US4840945A (en) * | 1985-04-01 | 1989-06-20 | Mochida Pharmaceutical Co., Ltd. | Cephalosporin derivatives |
| ATE114657T1 (de) * | 1985-12-26 | 1994-12-15 | Eisai Co Ltd | Cephalosporin-verbindungen. |
| GB8623211D0 (en) * | 1986-09-26 | 1986-10-29 | Glaxo Group Ltd | Chemical compounds |
| IL84128A (en) * | 1986-10-13 | 1992-12-01 | Eisai Co Ltd | 3-propenylcephem derivatives, their preparation and pharmaceutical compositions containing them |
| FR2622585B1 (fr) * | 1987-11-03 | 1991-04-19 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
| DE68928174T2 (de) * | 1988-03-16 | 1997-12-18 | Eisai Co Ltd | Verfahren zur Herstellung von Cephemderivaten |
| US5373001A (en) * | 1990-06-15 | 1994-12-13 | Roussel Uclaf | Cephalosporins |
-
1990
- 1990-06-15 FR FR9007491A patent/FR2663332B1/fr not_active Expired - Fee Related
-
1991
- 1991-05-31 IL IL114629A patent/IL114629A/xx active IP Right Grant
- 1991-05-31 IL IL9831891A patent/IL98318A/en active IP Right Grant
- 1991-06-11 ZA ZA914457A patent/ZA914457B/xx unknown
- 1991-06-13 EP EP91401570A patent/EP0462009B1/fr not_active Expired - Lifetime
- 1991-06-13 DE DE69130410T patent/DE69130410T2/de not_active Expired - Fee Related
- 1991-06-13 ES ES91401570T patent/ES2124698T3/es not_active Expired - Lifetime
- 1991-06-13 DK DK91401570T patent/DK0462009T3/da active
- 1991-06-13 JP JP03167421A patent/JP3080692B2/ja not_active Expired - Fee Related
- 1991-06-13 AT AT91401570T patent/ATE172733T1/de not_active IP Right Cessation
- 1991-06-14 KR KR1019910010030A patent/KR960009266B1/ko not_active IP Right Cessation
- 1991-06-14 HU HU911985A patent/HUT58101A/hu unknown
- 1991-06-14 UA UA5052193A patent/UA26431A/uk unknown
- 1991-06-14 CZ CS911830A patent/CZ282244B6/cs unknown
- 1991-06-14 IE IE203291A patent/IE912032A1/en not_active IP Right Cessation
- 1991-06-14 SK SK1830-91A patent/SK280156B6/sk unknown
- 1991-06-14 PT PT97971A patent/PT97971B/pt not_active IP Right Cessation
- 1991-06-14 CA CA002044700A patent/CA2044700A1/fr not_active Abandoned
- 1991-06-17 NZ NZ238577A patent/NZ238577A/en unknown
-
1992
- 1992-08-03 RU SU925052193A patent/RU2078085C1/ru active
-
1993
- 1993-06-21 US US08/080,572 patent/US5416080A/en not_active Expired - Fee Related
-
1995
- 1995-07-17 IL IL11462995A patent/IL114629A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT58101A (en) | 1992-01-28 |
| US5416080A (en) | 1995-05-16 |
| DK0462009T3 (da) | 1999-07-05 |
| HU911985D0 (en) | 1991-12-30 |
| JPH04230289A (ja) | 1992-08-19 |
| RU2078085C1 (ru) | 1997-04-27 |
| IL114629A (en) | 1997-06-10 |
| NZ238577A (en) | 1992-04-28 |
| JP3080692B2 (ja) | 2000-08-28 |
| CZ282244B6 (cs) | 1997-06-11 |
| PT97971A (pt) | 1992-03-31 |
| KR960009266B1 (ko) | 1996-07-16 |
| FR2663332B1 (fr) | 1997-11-07 |
| IL98318A (en) | 1996-01-31 |
| EP0462009A1 (fr) | 1991-12-18 |
| DE69130410T2 (de) | 1999-04-22 |
| IE912032A1 (en) | 1991-12-18 |
| AU643289B2 (en) | 1993-11-11 |
| CS183091A3 (en) | 1992-10-14 |
| AU7837091A (en) | 1991-12-19 |
| KR920000766A (ko) | 1992-01-29 |
| EP0462009B1 (fr) | 1998-10-28 |
| UA26431A (uk) | 1999-08-30 |
| ES2124698T3 (es) | 1999-02-16 |
| ATE172733T1 (de) | 1998-11-15 |
| CA2044700A1 (fr) | 1991-12-16 |
| PT97971B (pt) | 1998-11-30 |
| IL114629A0 (en) | 1995-11-27 |
| DE69130410D1 (de) | 1998-12-03 |
| ZA914457B (en) | 1992-08-26 |
| IL98318A0 (en) | 1992-06-21 |
| FR2663332A1 (fr) | 1991-12-20 |
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