HU185890B - Process for preparing 7-amino-3-vinyl-cefem-4-carboxylic acid derivatives - Google Patents
Process for preparing 7-amino-3-vinyl-cefem-4-carboxylic acid derivatives Download PDFInfo
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- HU185890B HU185890B HU801278A HU127880A HU185890B HU 185890 B HU185890 B HU 185890B HU 801278 A HU801278 A HU 801278A HU 127880 A HU127880 A HU 127880A HU 185890 B HU185890 B HU 185890B
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- 238000004519 manufacturing process Methods 0.000 title 1
- -1 t-butoxycarbonyl Chemical group 0.000 claims description 227
- 150000001875 compounds Chemical class 0.000 claims description 111
- 238000000034 method Methods 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 77
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229930186147 Cephalosporin Natural products 0.000 claims description 20
- 229940124587 cephalosporin Drugs 0.000 claims description 20
- 150000001780 cephalosporins Chemical class 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000002252 acyl 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 7
- 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 7
- 125000004453 alkoxycarbonyl 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
- 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 6
- 125000005544 phthalimido group Chemical group 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 3
- FMAWQUQMBDQKII-UHFFFAOYSA-N 1-cyclooctyl-3-methylidenecyclooctane Chemical compound C1C(=C)CCCCCC1C1CCCCCCC1 FMAWQUQMBDQKII-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- BYJZKLHQNGBXQC-GVHYBUMESA-N (6R)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-4-carboxylic acid Chemical class C(=C)C=1C(S[C@H]2N(C=1)C(C2)=O)C(=O)O BYJZKLHQNGBXQC-GVHYBUMESA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 303
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 122
- 239000000243 solution Substances 0.000 description 101
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 42
- 239000000741 silica gel Substances 0.000 description 42
- 229910002027 silica gel Inorganic materials 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 39
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000006260 foam Substances 0.000 description 33
- 239000012153 distilled water Substances 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 27
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 description 24
- 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
- 235000019341 magnesium sulphate Nutrition 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 238000010511 deprotection reaction Methods 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 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 13
- 125000003282 alkyl amino group Chemical group 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 13
- 235000019253 formic acid Nutrition 0.000 description 13
- 238000002329 infrared spectrum Methods 0.000 description 13
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 12
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 125000004442 acylamino group Chemical group 0.000 description 11
- 238000010828 elution Methods 0.000 description 11
- HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 150000003462 sulfoxides Chemical class 0.000 description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004103 aminoalkyl group Chemical group 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 9
- 125000004522 1,3,4-thiadiazol-5-yl group Chemical group S1C=NN=C1* 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 125000005354 acylalkyl group Chemical group 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 125000004663 dialkyl amino group Chemical group 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000005281 alkyl ureido group Chemical group 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 150000001241 acetals Chemical group 0.000 description 5
- 125000004945 acylaminoalkyl group Chemical group 0.000 description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 description 5
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 150000007970 thio esters Chemical class 0.000 description 5
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- RMMVAFURHJFLGC-UHFFFAOYSA-N benzhydryl 3-methyl-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC(C)(C)OC(=O)NC1C(=O)N2C1SCC(C)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 RMMVAFURHJFLGC-UHFFFAOYSA-N 0.000 description 4
- 244000309464 bull Species 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000003544 oxime group Chemical group 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 3
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 description 3
- 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 description 3
- NGFVITQWMVMQGZ-UHFFFAOYSA-N 2-methoxy-1-n,1-n,1-n',1-n'-tetramethylethane-1,1-diamine Chemical compound COCC(N(C)C)N(C)C NGFVITQWMVMQGZ-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- MCKABFQWNSFNJE-UHFFFAOYSA-N 3-methyl-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid Chemical compound OC(=O)C1C(C)=CSC2C(NC(=O)OC(C)(C)C)C(=O)N21 MCKABFQWNSFNJE-UHFFFAOYSA-N 0.000 description 3
- HMSADZWLOXHQBR-UHFFFAOYSA-N 3-methylidene-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid Chemical compound S1CC(=C)C(C(O)=O)N2C(=O)C(NC(=O)OC(C)(C)C)C21 HMSADZWLOXHQBR-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 3
- DBJUEJCZPKMDPA-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O DBJUEJCZPKMDPA-UHFFFAOYSA-N 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000000676 alkoxyimino group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- KUCWXIWCKRWEJM-UHFFFAOYSA-N benzhydryl 3-methyl-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylate Chemical compound CC1=CSC2C(NC(=O)OC(C)(C)C)C(=O)N2C1C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 KUCWXIWCKRWEJM-UHFFFAOYSA-N 0.000 description 3
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- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- FZEVMBJWXHDLDB-UHFFFAOYSA-N 5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)CC21 FZEVMBJWXHDLDB-UHFFFAOYSA-N 0.000 description 1
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- WQERJSFTULWVDH-UHFFFAOYSA-N 7-cyclooctyl-1-methylcyclooctene Chemical compound CC=1CC(CCCCC=1)C1CCCCCCC1 WQERJSFTULWVDH-UHFFFAOYSA-N 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- TXRZLRGNICZOJG-UHFFFAOYSA-N benzhydryl 3-[2-(dimethylamino)ethenyl]-7-(1,3-dioxoisoindol-2-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1C(=O)N2C1SCC(C=CN(C)C)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 TXRZLRGNICZOJG-UHFFFAOYSA-N 0.000 description 1
- NTJPMEWSDPWXIJ-UHFFFAOYSA-N benzhydryl 3-[2-(dimethylamino)ethenyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(C=CN(C)C)=C(C(=O)OC(C=2C=CC=CC=2)C=2C=CC=CC=2)N(C2=O)C1C2NC(=O)CC1=CC=CC=C1 NTJPMEWSDPWXIJ-UHFFFAOYSA-N 0.000 description 1
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- YIEAPKXLEUUUMX-UHFFFAOYSA-N benzhydryl 7-[[2-ethenoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[2-(4-methylphenyl)sulfonyloxyethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC=CC1=C(C(=O)OC(C=2C=CC=CC=2)C=2C=CC=CC=2)N2C(=O)C(NC(=O)C(=NOC=C)C=3N=C(NC(C=4C=CC=CC=4)(C=4C=CC=CC=4)C=4C=CC=CC=4)SC=3)C2SC1 YIEAPKXLEUUUMX-UHFFFAOYSA-N 0.000 description 1
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- ZZOYDSOGJBAESO-UHFFFAOYSA-N benzhydryl 7-[[2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(2-methylsulfanylethenyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C=1SC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C(=NOC)C(=O)NC(C(N12)=O)C1SCC(C=CSC)=C2C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 ZZOYDSOGJBAESO-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940092559 enterobacter aerogenes Drugs 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
- BRMYTCBBZHJALF-UHFFFAOYSA-N methyl 3-methyl-7-[(2-methylpropan-2-yl)oxycarbonylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound COC(=O)C1=C(C)CSC2C(NC(=O)OC(C)(C)C)C(=O)N12 BRMYTCBBZHJALF-UHFFFAOYSA-N 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- OLUBAJAIWWXLMQ-UHFFFAOYSA-N n,n'-dimethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CNC(NC)OC(C)(C)C OLUBAJAIWWXLMQ-UHFFFAOYSA-N 0.000 description 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
- JROJIDFJTHBZBD-UHFFFAOYSA-N n,n-dimethoxypropan-2-amine Chemical compound CON(OC)C(C)C JROJIDFJTHBZBD-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LHMRVAWTCGBZLK-UHFFFAOYSA-N n-trityl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)NC1=NC=CS1 LHMRVAWTCGBZLK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 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
- 239000003208 petroleum Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 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
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7913096A FR2457296A1 (fr) | 1979-05-23 | 1979-05-23 | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185890B true HU185890B (en) | 1985-04-28 |
Family
ID=9225762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU801278A HU185890B (en) | 1979-05-23 | 1980-05-21 | Process for preparing 7-amino-3-vinyl-cefem-4-carboxylic acid derivatives |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4307233A (en]) |
| JP (1) | JPS55154981A (en]) |
| AT (1) | AT369375B (en]) |
| AU (1) | AU534806B2 (en]) |
| BE (1) | BE883416A (en]) |
| CA (1) | CA1144919A (en]) |
| CH (1) | CH645379A5 (en]) |
| CS (1) | CS244405B2 (en]) |
| DD (1) | DD150899A5 (en]) |
| DE (1) | DE3019462A1 (en]) |
| DK (1) | DK222080A (en]) |
| ES (1) | ES491687A0 (en]) |
| FI (1) | FI801641A7 (en]) |
| FR (1) | FR2457296A1 (en]) |
| GB (1) | GB2051062B (en]) |
| GR (1) | GR68426B (en]) |
| HU (1) | HU185890B (en]) |
| IE (1) | IE49814B1 (en]) |
| IL (1) | IL60139A (en]) |
| IT (1) | IT1140974B (en]) |
| LU (1) | LU82477A1 (en]) |
| NL (1) | NL8003023A (en]) |
| NO (1) | NO801502L (en]) |
| NZ (1) | NZ193799A (en]) |
| PH (1) | PH15946A (en]) |
| PL (1) | PL126481B1 (en]) |
| PT (1) | PT71276A (en]) |
| SE (1) | SE451072B (en]) |
| SU (1) | SU1031409A3 (en]) |
| YU (1) | YU136880A (en]) |
| ZA (1) | ZA803038B (en]) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES485938A1 (es) * | 1978-11-15 | 1980-07-01 | Glaxo Group Ltd | Un procedimiento para la preparacion de antibioticos de ce- falosporina |
| FR2494275A2 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouveaux derives de vinyl-3 cephalosporines et leur preparation |
| FR2494279A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouvelles oxacephalosporines, leur preparation et les medicaments qui les contiennent |
| FR2494280A1 (fr) * | 1980-11-20 | 1982-05-21 | Rhone Poulenc Ind | Nouveaux derives de la cephalosporine et leur preparation |
| FR2505334A1 (fr) * | 1981-05-11 | 1982-11-12 | Rhone Poulenc Sante | Nouvelles oxacephalosporines et leur preparation |
| FR2511372A1 (fr) * | 1981-08-17 | 1983-02-18 | Rhone Poulenc Sante | Nouveaux derives de la cephalosporine et leur preparation |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
| US4560749A (en) * | 1983-11-18 | 1985-12-24 | Eli Lilly And Company | Cephem-3-imidates and 3-amidines |
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4874856A (en) * | 1985-06-24 | 1989-10-17 | Bristol-Myers Company | 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof |
| WO1987006232A1 (en) * | 1986-04-14 | 1987-10-22 | Banyu Pharmaceutical Co., Ltd. | 1-carboxy-1-vyniloxyiminoaminothiazole cephalosporing derivatives and process for their preparation |
| EP0841339B1 (en) | 1996-11-06 | 2007-02-21 | Basilea Pharmaceutica AG | Vinylpyrrolidinon cephalosporin derivatives |
| US8883772B2 (en) * | 2007-10-09 | 2014-11-11 | Sopharmia, Inc. | Broad spectrum beta-lactamase inhibitors |
| EP2968352B1 (en) | 2013-03-12 | 2018-09-26 | Gladius Pharmaceuticals Corporation | Derivatized 3-styryl-cephalosporins |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065620A (en) * | 1971-06-14 | 1977-12-27 | Eli Lilly And Company | 3-(Substituted) vinyl cephalosporins |
| GB1463077A (en) * | 1973-04-19 | 1977-02-02 | Glaxo Lab Ltd | 7-substituted-ethyl-cephalosporin derivatives |
| SE7416195L (sv) * | 1973-12-21 | 1975-09-22 | Glaxo Lab Ltd | Forfarande for framstellning av cefalosporiner. |
| US4144393A (en) * | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group |
| JPS5129492A (en) * | 1974-09-04 | 1976-03-12 | Sankyo Co | Sefuarosuhorinjudotai no seiho |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| JPS5253890A (en) * | 1975-10-14 | 1977-04-30 | Syntex Inc | Production of cephalosporin type compound |
| PT71652B (en) * | 1979-08-15 | 1982-01-21 | Merck & Co Inc | Process for preparing allysulfoxide enzyme inhibitor |
-
1979
- 1979-05-23 FR FR7913096A patent/FR2457296A1/fr active Granted
-
1980
- 1980-05-21 ES ES491687A patent/ES491687A0/es active Granted
- 1980-05-21 AU AU58595/80A patent/AU534806B2/en not_active Ceased
- 1980-05-21 HU HU801278A patent/HU185890B/hu unknown
- 1980-05-21 PL PL1980224391A patent/PL126481B1/pl unknown
- 1980-05-21 LU LU82477A patent/LU82477A1/fr unknown
- 1980-05-21 GR GR62015A patent/GR68426B/el unknown
- 1980-05-21 CH CH398980A patent/CH645379A5/fr not_active IP Right Cessation
- 1980-05-21 ZA ZA00803038A patent/ZA803038B/xx unknown
- 1980-05-21 YU YU01368/80A patent/YU136880A/xx unknown
- 1980-05-21 FI FI801641A patent/FI801641A7/fi not_active Application Discontinuation
- 1980-05-21 DD DD80221272A patent/DD150899A5/de unknown
- 1980-05-21 NZ NZ193799A patent/NZ193799A/xx unknown
- 1980-05-21 NO NO801502A patent/NO801502L/no unknown
- 1980-05-21 AT AT0270980A patent/AT369375B/de active
- 1980-05-21 IT IT22243/80A patent/IT1140974B/it active
- 1980-05-21 IE IE1062/80A patent/IE49814B1/en unknown
- 1980-05-21 PT PT71276A patent/PT71276A/pt unknown
- 1980-05-21 US US06/152,085 patent/US4307233A/en not_active Expired - Lifetime
- 1980-05-21 DK DK222080A patent/DK222080A/da not_active Application Discontinuation
- 1980-05-21 DE DE19803019462 patent/DE3019462A1/de not_active Ceased
- 1980-05-21 SE SE8003821A patent/SE451072B/sv not_active IP Right Cessation
- 1980-05-21 CA CA000352324A patent/CA1144919A/fr not_active Expired
- 1980-05-21 GB GB8016727A patent/GB2051062B/en not_active Expired
- 1980-05-21 BE BE0/200707A patent/BE883416A/fr not_active IP Right Cessation
- 1980-05-21 CS CS803543A patent/CS244405B2/cs unknown
- 1980-05-21 SU SU802926697A patent/SU1031409A3/ru active
- 1980-05-22 PH PH24056A patent/PH15946A/en unknown
- 1980-05-22 IL IL60139A patent/IL60139A/xx unknown
- 1980-05-23 JP JP6800980A patent/JPS55154981A/ja active Granted
- 1980-05-23 NL NL8003023A patent/NL8003023A/nl not_active Application Discontinuation
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