SU566525A3 - Способ получени производных цефалоспорина или их солей с металлами или азотсодержащими основани ми - Google Patents
Способ получени производных цефалоспорина или их солей с металлами или азотсодержащими основани миInfo
- Publication number
- SU566525A3 SU566525A3 SU7402077414A SU2077414A SU566525A3 SU 566525 A3 SU566525 A3 SU 566525A3 SU 7402077414 A SU7402077414 A SU 7402077414A SU 2077414 A SU2077414 A SU 2077414A SU 566525 A3 SU566525 A3 SU 566525A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyl
- reduced pressure
- dihydro
- under reduced
- acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 229910052751 metal Inorganic materials 0.000 title claims description 4
- 239000002184 metal Substances 0.000 title claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000002739 metals Chemical class 0.000 title claims description 3
- HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000001914 filtration Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- -1 oxathiin-3-yl Chemical group 0.000 claims description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- 241000534944 Thia Species 0.000 claims description 8
- 239000006229 carbon black Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 7
- 235000011152 sodium sulphate Nutrition 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 claims description 2
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 2
- 229930186147 Cephalosporin Natural products 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229940124587 cephalosporin Drugs 0.000 claims description 2
- 150000001780 cephalosporins Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- YBKGERLDRMINOV-UHFFFAOYSA-N oxathiine Chemical compound O1SC=CC=C1 YBKGERLDRMINOV-UHFFFAOYSA-N 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 description 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
- 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 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- FLVUYLNVCUGFGX-UHFFFAOYSA-N 2,3-dihydro-1,4-dithiine Chemical compound C1CSC=CS1 FLVUYLNVCUGFGX-UHFFFAOYSA-N 0.000 description 2
- PSORZDDANGBQTD-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acid Chemical compound OC(=O)CC1=CSCCS1 PSORZDDANGBQTD-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- QYEBUKAVBUDNME-UHFFFAOYSA-N ethyl 2-(2,3-dihydro-1,4-dithiin-5-yl)acetate Chemical compound CCOC(=O)CC1=CSCCS1 QYEBUKAVBUDNME-UHFFFAOYSA-N 0.000 description 2
- JXRVBUYYAPUWOY-UHFFFAOYSA-N ethyl 2-(2,3-dihydro-1,4-oxathiin-6-yl)acetate Chemical compound CCOC(=O)CC1=CSCCO1 JXRVBUYYAPUWOY-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical compound S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 description 1
- CPRVXMQHLPTWLY-UHFFFAOYSA-N 1,4-oxathiine Chemical compound O1C=CSC=C1 CPRVXMQHLPTWLY-UHFFFAOYSA-N 0.000 description 1
- JCAIBTLLMPPCQU-UHFFFAOYSA-N 2,3-dihydro-1,4-oxathiine Chemical compound C1CSC=CO1 JCAIBTLLMPPCQU-UHFFFAOYSA-N 0.000 description 1
- VGGIEUBFOMMVIK-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-oxathiin-5-yl)acetic acid Chemical compound OC(=O)CC1=COCCS1 VGGIEUBFOMMVIK-UHFFFAOYSA-N 0.000 description 1
- VNJOEUSYAMPBAK-UHFFFAOYSA-N 2-methylbenzenesulfonic acid;hydrate Chemical compound O.CC1=CC=CC=C1S(O)(=O)=O VNJOEUSYAMPBAK-UHFFFAOYSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 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 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- HYODXKJMSFJXSP-UHFFFAOYSA-N acetyl 2-bromoacetate Chemical compound CC(=O)OC(=O)CBr HYODXKJMSFJXSP-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- HUMHYXGDUOGHTG-HEZXSMHISA-N alpha-D-GalpNAc-(1->3)-[alpha-L-Fucp-(1->2)]-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](O)[C@@H](CO)OC1O HUMHYXGDUOGHTG-HEZXSMHISA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DGZBBJYRLCXFIW-UHFFFAOYSA-N ethyl 2-(2,3-dihydro-1,4-oxathiin-5-yl)acetate Chemical compound CCOC(=O)CC1=COCCS1 DGZBBJYRLCXFIW-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- PLXKEUBOZXHXGA-UHFFFAOYSA-N formyl propanoate Chemical compound CCC(=O)OC=O PLXKEUBOZXHXGA-UHFFFAOYSA-N 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- JBJAQFNXULUGCG-UHFFFAOYSA-N methyl 3-bromo-4-oxobutanoate Chemical compound COC(=O)CC(Br)C=O JBJAQFNXULUGCG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7340431A FR2250517A1 (en) | 1973-11-14 | 1973-11-14 | Dihydro-dithiinyl-and-oxathiinyl-methyl cephalosporins - with broad-spectrum antibacterial activity |
| FR7414436A FR2268525A1 (en) | 1974-04-25 | 1974-04-25 | Dihydro-dithiinyl-and-oxathiinyl-methyl cephalosporins - with broad-spectrum antibacterial activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU566525A3 true SU566525A3 (ru) | 1977-07-25 |
Family
ID=26218022
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402077414A SU566525A3 (ru) | 1973-11-14 | 1974-11-13 | Способ получени производных цефалоспорина или их солей с металлами или азотсодержащими основани ми |
| SU7502190958A SU576947A3 (ru) | 1973-11-14 | 1975-11-20 | Способ получени производных цефалоспорина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502190958A SU576947A3 (ru) | 1973-11-14 | 1975-11-20 | Способ получени производных цефалоспорина или их солей |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4007176A (enExample) |
| JP (1) | JPS5082090A (enExample) |
| AR (2) | AR205728A1 (enExample) |
| AT (1) | AT335608B (enExample) |
| CA (1) | CA1026745A (enExample) |
| CH (2) | CH608499A5 (enExample) |
| DE (1) | DE2454109A1 (enExample) |
| DK (1) | DK590774A (enExample) |
| ES (1) | ES431943A1 (enExample) |
| FI (1) | FI330074A7 (enExample) |
| GB (1) | GB1430908A (enExample) |
| HU (1) | HU168853B (enExample) |
| IE (1) | IE40206B1 (enExample) |
| IL (1) | IL46040A (enExample) |
| NL (1) | NL7414486A (enExample) |
| NO (1) | NO744081L (enExample) |
| SE (1) | SE7414263L (enExample) |
| SU (2) | SU566525A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2338045A1 (fr) * | 1976-01-19 | 1977-08-12 | Rhone Poulenc Ind | Nouveaux derives de la cephalosporine, leur preparation et les compositions qui les contiennent |
| NL7714319A (nl) * | 1976-12-27 | 1978-06-29 | Fujisawa Pharmaceutical Co | Cefalosporineverbindingen en werkwijzen om deze te bereiden. |
| JPS53103493A (en) * | 1977-02-18 | 1978-09-08 | Takeda Chem Ind Ltd | Cephalosporin derivatives and process for their preparation |
| DE2824559C2 (de) * | 1977-06-10 | 1985-01-10 | Yamanouchi Pharmaceutical Co., Ltd., Tokio / Tokyo | 7α-Methoxy-7β-(4-substituierte-methylen-1,3-dithietan-2-yl)-carboxamido-3-Δ↑3↑-cephem-4-carbonsäuren, Verfahren zu deren Herstellung sowie ihre Verwendung |
| US4172941A (en) * | 1978-05-12 | 1979-10-30 | Richardson-Merrell Inc. | 7-[2-[ω-(1,3-Dithiolan-2-imino)substituted]-acetylamino]cephalosporanic acid derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH527215A (de) * | 1967-04-15 | 1972-08-31 | Fujisawa Pharmaceutical Co | Verfahren zur Herstellung von 3,7-disubstituierten Cephalosporinderivaten |
| US3692779A (en) * | 1970-08-12 | 1972-09-19 | Bristol Myers Co | 7-{8 n-(substituted-imidoyl)aminoacetamide{9 cephalosporanic acids and derivatives thereof |
| US3886151A (en) * | 1974-03-18 | 1975-05-27 | American Home Prod | 7-{8 2-(Heteroazinylthio)acetamido{9 {0 cephalosporanic acid derivatives |
-
1974
- 1974-01-01 AR AR256515A patent/AR205728A1/es active
- 1974-11-06 NL NL7414486A patent/NL7414486A/xx not_active Application Discontinuation
- 1974-11-11 HU HURO809A patent/HU168853B/hu unknown
- 1974-11-12 IL IL46040A patent/IL46040A/en unknown
- 1974-11-12 JP JP49129663A patent/JPS5082090A/ja active Pending
- 1974-11-12 IE IE2325/74A patent/IE40206B1/xx unknown
- 1974-11-12 GB GB4897874A patent/GB1430908A/en not_active Expired
- 1974-11-12 US US05/523,007 patent/US4007176A/en not_active Expired - Lifetime
- 1974-11-13 DK DK590774A patent/DK590774A/da unknown
- 1974-11-13 SU SU7402077414A patent/SU566525A3/ru active
- 1974-11-13 CA CA213,621A patent/CA1026745A/en not_active Expired
- 1974-11-13 NO NO744081A patent/NO744081L/no unknown
- 1974-11-13 CH CH1515974A patent/CH608499A5/xx not_active IP Right Cessation
- 1974-11-13 SE SE7414263A patent/SE7414263L/xx unknown
- 1974-11-13 CH CH778377A patent/CH602762A5/xx not_active IP Right Cessation
- 1974-11-14 FI FI3300/74A patent/FI330074A7/fi unknown
- 1974-11-14 DE DE19742454109 patent/DE2454109A1/de active Pending
- 1974-11-14 AT AT914274A patent/AT335608B/de not_active IP Right Cessation
- 1974-11-14 ES ES431943A patent/ES431943A1/es not_active Expired
-
1975
- 1975-01-01 AR AR259958A patent/AR205398A1/es active
- 1975-11-20 SU SU7502190958A patent/SU576947A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| IL46040A0 (en) | 1975-02-10 |
| AR205728A1 (es) | 1976-05-31 |
| GB1430908A (en) | 1976-04-07 |
| AU7528474A (en) | 1976-05-13 |
| CH602762A5 (enExample) | 1978-07-31 |
| DK590774A (enExample) | 1975-07-14 |
| IL46040A (en) | 1977-12-30 |
| NO744081L (enExample) | 1975-06-09 |
| SU576947A3 (ru) | 1977-10-15 |
| CA1026745A (en) | 1978-02-21 |
| ATA914274A (de) | 1976-07-15 |
| AR205398A1 (es) | 1976-04-30 |
| IE40206L (en) | 1975-05-14 |
| AT335608B (de) | 1977-03-25 |
| DE2454109A1 (de) | 1975-05-15 |
| US4007176A (en) | 1977-02-08 |
| NL7414486A (nl) | 1975-05-16 |
| HU168853B (enExample) | 1976-07-28 |
| SE7414263L (enExample) | 1975-05-15 |
| JPS5082090A (enExample) | 1975-07-03 |
| FI330074A7 (enExample) | 1975-05-15 |
| CH608499A5 (enExample) | 1979-01-15 |
| IE40206B1 (en) | 1979-04-11 |
| ES431943A1 (es) | 1977-01-16 |
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