NO791687L - Fremgangsmaate for fremstilling av terapeutisk aktive penicillansyre-derivater - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive penicillansyre-derivaterInfo
- Publication number
- NO791687L NO791687L NO791687A NO791687A NO791687L NO 791687 L NO791687 L NO 791687L NO 791687 A NO791687 A NO 791687A NO 791687 A NO791687 A NO 791687A NO 791687 L NO791687 L NO 791687L
- Authority
- NO
- Norway
- Prior art keywords
- group
- stated
- hydrogen atom
- compound
- formula
- Prior art date
Links
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title claims description 136
- 238000000034 method Methods 0.000 title claims description 108
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000001225 therapeutic effect Effects 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 153
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 114
- -1 acetoxyl group Chemical group 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- 125000006239 protecting group Chemical group 0.000 claims description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002585 base Substances 0.000 claims description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 17
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- GIOUOHDKHHZWIQ-UHFFFAOYSA-N 2-(carbamoylamino)-2-phenylacetic acid Chemical class NC(=O)NC(C(O)=O)C1=CC=CC=C1 GIOUOHDKHHZWIQ-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 230000001476 alcoholic effect Effects 0.000 claims description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000003586 protic polar solvent Substances 0.000 claims description 4
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Chemical class 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims 3
- DWVDJLKWAORTCU-UHFFFAOYSA-N 1,2-dichloroethane;ethyl acetate Chemical compound ClCCCl.CCOC(C)=O DWVDJLKWAORTCU-UHFFFAOYSA-N 0.000 claims 1
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 55
- 239000010410 layer Substances 0.000 description 42
- 238000003756 stirring Methods 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- 238000002329 infrared spectrum Methods 0.000 description 31
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 31
- 239000012044 organic layer Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
- 229960003424 phenylacetic acid Drugs 0.000 description 23
- 239000003279 phenylacetic acid Substances 0.000 description 23
- 238000004587 chromatography analysis Methods 0.000 description 22
- 238000004809 thin layer chromatography Methods 0.000 description 21
- 239000000843 powder Substances 0.000 description 19
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- OKMHHBICYZAXBE-UHFFFAOYSA-N acetic acid;ethanol;ethyl acetate Chemical compound CCO.CC(O)=O.CCOC(C)=O OKMHHBICYZAXBE-UHFFFAOYSA-N 0.000 description 18
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 18
- 238000001816 cooling Methods 0.000 description 15
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 15
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 13
- 238000002211 ultraviolet spectrum Methods 0.000 description 13
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 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 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- KCDXWFVBWDBQIE-UHFFFAOYSA-N (2-acetyloxy-4-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(N)=O)C=C1OC(C)=O KCDXWFVBWDBQIE-UHFFFAOYSA-N 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 229960003311 ampicillin trihydrate Drugs 0.000 description 5
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- UNCACEGCFURZQB-UHFFFAOYSA-N (2-acetyloxy-4-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(Cl)=O)C=C1OC(C)=O UNCACEGCFURZQB-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- 229920002307 Dextran Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- NVOKNDLZPHTWQO-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbonisocyanatidoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(=O)N=C=O)=CC(OC(C)=O)=C1OC(C)=O NVOKNDLZPHTWQO-UHFFFAOYSA-N 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MHDYEKBSPRGXKV-UHFFFAOYSA-N [2-acetyloxy-4-(methylcarbamoyl)phenyl] acetate Chemical compound CNC(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 MHDYEKBSPRGXKV-UHFFFAOYSA-N 0.000 description 3
- NNFFSHMEYWJGHP-UHFFFAOYSA-N [2-acetyloxy-4-[carbonochloridoyl(methyl)carbamoyl]phenyl] acetate Chemical compound ClC(=O)N(C)C(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 NNFFSHMEYWJGHP-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000010640 amide synthesis reaction Methods 0.000 description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 3
- 229960003669 carbenicillin Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 150000002960 penicillins Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 3
- SBGXXBVOLADOOR-UHFFFAOYSA-N (2-acetyloxy-3-carbonisocyanatidoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(=O)N=C=O)=C1OC(C)=O SBGXXBVOLADOOR-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RMIJYCIGXVCHAF-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;n,n-diethylethanamine;n,n-dimethylformamide Chemical compound CN(C)C=O.CCN(CC)CC.OCCN(CCO)CCO RMIJYCIGXVCHAF-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- WOGOVLDRNCSMCN-UHFFFAOYSA-N [2-acetyloxy-4-[carbonochloridoyl(ethyl)carbamoyl]phenyl] acetate Chemical compound CCN(C(Cl)=O)C(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 WOGOVLDRNCSMCN-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000019371 penicillin G benzathine Nutrition 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- AHBNUYOASRDREM-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(N)=O)=CC(OC(C)=O)=C1OC(C)=O AHBNUYOASRDREM-UHFFFAOYSA-N 0.000 description 1
- RVJVBYRLRQOHCL-UHFFFAOYSA-N (2,3-diacetyloxy-5-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC(C(Cl)=O)=CC(OC(C)=O)=C1OC(C)=O RVJVBYRLRQOHCL-UHFFFAOYSA-N 0.000 description 1
- LLGJUWCBCMAZRK-UHFFFAOYSA-N (2-acetyloxy-3-carbamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(N)=O)=C1OC(C)=O LLGJUWCBCMAZRK-UHFFFAOYSA-N 0.000 description 1
- JWIRVWSAMLMXIV-UHFFFAOYSA-N (2-acetyloxy-3-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(C(Cl)=O)=C1OC(C)=O JWIRVWSAMLMXIV-UHFFFAOYSA-N 0.000 description 1
- GIDRESFLRLUCAE-UHFFFAOYSA-N (2-acetyloxy-4-carbonisocyanatidoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C(=O)N=C=O)C=C1OC(C)=O GIDRESFLRLUCAE-UHFFFAOYSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical class C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BFJSMSPRRMOLIE-UHFFFAOYSA-N [2,3-diacetyloxy-5-(methylcarbamoyl)phenyl] acetate Chemical compound CNC(=O)C1=CC(OC(C)=O)=C(OC(C)=O)C(OC(C)=O)=C1 BFJSMSPRRMOLIE-UHFFFAOYSA-N 0.000 description 1
- KBJOLWXNZKTYBV-UHFFFAOYSA-N [2,3-diacetyloxy-5-[carbonochloridoyl(methyl)carbamoyl]phenyl] acetate Chemical compound ClC(=O)N(C)C(=O)C1=CC(OC(C)=O)=C(OC(C)=O)C(OC(C)=O)=C1 KBJOLWXNZKTYBV-UHFFFAOYSA-N 0.000 description 1
- CLXGFJDXCVPBHR-UHFFFAOYSA-N [2-acetyloxy-4-(ethylcarbamoyl)phenyl] acetate Chemical compound CCNC(=O)C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 CLXGFJDXCVPBHR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6216478A JPS54154782A (en) | 1978-05-26 | 1978-05-26 | Penicillin derivative and its salt |
| JP7036578A JPS54163590A (en) | 1978-06-13 | 1978-06-13 | Penicilunic acid derivative and salt thereof |
| JP9730978A JPS5524135A (en) | 1978-08-11 | 1978-08-11 | Penicillin derivative and its preparation |
| JP10436278A JPS5531044A (en) | 1978-08-29 | 1978-08-29 | Penicillanic acid derivative and its preparation |
| JP10915778A JPS5536411A (en) | 1978-09-07 | 1978-09-07 | Benzylpenicillin derivative and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791687L true NO791687L (no) | 1979-11-27 |
Family
ID=27523696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791687A NO791687L (no) | 1978-05-26 | 1979-05-22 | Fremgangsmaate for fremstilling av terapeutisk aktive penicillansyre-derivater |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4229348A (hu) |
| AU (1) | AU4689879A (hu) |
| CA (1) | CA1133896A (hu) |
| DD (1) | DD143259A5 (hu) |
| DE (1) | DE2921324C2 (hu) |
| DK (1) | DK179579A (hu) |
| FI (1) | FI791680A (hu) |
| FR (1) | FR2426691A1 (hu) |
| GB (1) | GB2021576B (hu) |
| HU (1) | HU176076B (hu) |
| IL (1) | IL57264A0 (hu) |
| IT (1) | IT1120970B (hu) |
| NL (1) | NL7904112A (hu) |
| NO (1) | NO791687L (hu) |
| PT (1) | PT69665A (hu) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5732289A (en) * | 1980-08-05 | 1982-02-20 | Chugai Pharmaceut Co Ltd | Alpha-substituted ureidobenzylpenicillin |
| DE3372208D1 (en) * | 1982-04-29 | 1987-07-30 | Beecham Group Plc | Beta-lactam antibiotics |
| MXPA05010296A (es) * | 2003-03-26 | 2005-11-17 | Bayer Cropscience Gmbh | Utilizacion de compuestos hidroxilicos aromaticos como antidotos. |
| EP4141110A1 (en) | 2020-04-24 | 2023-03-01 | Obshchestvo S Ogranichennoy Otvetstvennost'yu "Ingenik" | Method for producing particles of bacteriophages of the genus levivirus |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE32700B1 (en) * | 1968-02-03 | 1973-10-31 | Beecham Group Ltd | Penicillins |
| GB1250611A (hu) * | 1968-02-03 | 1971-10-20 | ||
| DE1770620A1 (de) * | 1968-06-12 | 1971-11-11 | Bayer Ag | Neue Penicilline |
| US3479339A (en) * | 1968-06-13 | 1969-11-18 | Bristol Myers Co | 6-(alpha-3 - acylureidophenylacetamido)- and 6-(alpha - 3 - acylureidothienylacetamido)-penicillanic acids |
| US3936442A (en) * | 1970-05-25 | 1976-02-03 | Bayer Aktiengesellschaft | Unreidoacetamido-penicilins |
| CH562249A5 (hu) * | 1970-05-25 | 1975-05-30 | Bayer Ag | |
| US3980792A (en) * | 1970-05-25 | 1976-09-14 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3933795A (en) * | 1970-05-25 | 1976-01-20 | Hans-Bodo Konig | Ureidoacetamido-penicillins |
| US3939149A (en) * | 1970-05-25 | 1976-02-17 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3959258A (en) * | 1970-05-25 | 1976-05-25 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US4016282A (en) * | 1970-05-25 | 1977-04-05 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3978223A (en) * | 1970-05-25 | 1976-08-31 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins for treating bacterial infections |
| US3974140A (en) * | 1970-05-25 | 1976-08-10 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| GB1433131A (en) * | 1972-03-13 | 1976-04-22 | Astra Laekemedel Ab | Penicillins |
| DE2258973A1 (de) * | 1972-12-01 | 1974-06-06 | Bayer Ag | Penicilline, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1979
- 1979-01-23 CA CA320,106A patent/CA1133896A/en not_active Expired
- 1979-01-23 US US06/005,832 patent/US4229348A/en not_active Expired - Lifetime
- 1979-01-25 DD DD79210631A patent/DD143259A5/de unknown
- 1979-01-26 HU HU79CU160A patent/HU176076B/hu unknown
- 1979-05-01 DK DK179579A patent/DK179579A/da unknown
- 1979-05-09 AU AU46898/79A patent/AU4689879A/en not_active Abandoned
- 1979-05-09 GB GB7916058A patent/GB2021576B/en not_active Expired
- 1979-05-14 IL IL57264A patent/IL57264A0/xx unknown
- 1979-05-22 NO NO791687A patent/NO791687L/no unknown
- 1979-05-24 PT PT69665A patent/PT69665A/pt unknown
- 1979-05-24 IT IT68103/79A patent/IT1120970B/it active
- 1979-05-25 FI FI791680A patent/FI791680A/fi not_active Application Discontinuation
- 1979-05-25 DE DE2921324A patent/DE2921324C2/de not_active Expired
- 1979-05-25 FR FR7913332A patent/FR2426691A1/fr active Granted
- 1979-05-25 NL NL7904112BA patent/NL7904112A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DD143259A5 (de) | 1980-08-13 |
| CA1133896A (en) | 1982-10-19 |
| AU4689879A (en) | 1979-11-29 |
| FI791680A (fi) | 1979-11-27 |
| US4229348A (en) | 1980-10-21 |
| DE2921324A1 (de) | 1979-11-29 |
| GB2021576A (en) | 1979-12-05 |
| NL7904112A (nl) | 1979-11-28 |
| HU176076B (en) | 1980-12-28 |
| IL57264A0 (en) | 1979-09-30 |
| DK179579A (da) | 1979-11-27 |
| PT69665A (pt) | 1979-06-01 |
| IT1120970B (it) | 1986-03-26 |
| IT7968103A0 (it) | 1979-05-24 |
| DE2921324C2 (de) | 1983-02-10 |
| FR2426691A1 (fr) | 1979-12-21 |
| GB2021576B (en) | 1982-09-29 |
| FR2426691B1 (hu) | 1982-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2477154A1 (fr) | Bis-esters de methanediol avec des penicillines et le 1,1-dioxyde d'acide penicillanique, leur procede de production et composition pharmaceutique les contenant | |
| CA1319682C (fr) | Procede de preparation de nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique | |
| EP1219596A1 (en) | Salicylamide derivatives | |
| NO153573B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive n-acylamino-alfa-arylacet-amidocefalosporiner. | |
| FI65253B (fi) | Foerfarande foer framstaellning av antibakteriellt verksamma 9-aminodeoxi-clavulansyraderivat | |
| US5081116A (en) | Cephalosporin derivatives | |
| GB1589094A (en) | 7 - - oxyiminoacylaminocephalosporins | |
| NO791687L (no) | Fremgangsmaate for fremstilling av terapeutisk aktive penicillansyre-derivater | |
| CH621125A5 (hu) | ||
| US3951954A (en) | Novel oxofuryl ester derivatives of penicillin and cephalosporin | |
| US4104469A (en) | 7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids | |
| CH626370A5 (en) | Process for the preparation of the syn isomer or of a mixture of syn and anti isomers of 7beta-acylamidoceph-3-em-4-carboxylic acids with antibiotic activity | |
| FR2496666A1 (fr) | Nouveaux derives de cephalosporine et composition pharmaceutique les contenant | |
| US4193918A (en) | Process for the preparation of hydroxy-alpha-amino-benzyl penicillin | |
| FR2466466A1 (fr) | Nouvelles penicillines, utiles notamment comme antibiotiques, et leur procede de preparation | |
| US4178444A (en) | Hydrazono derivatives of cephalosporins | |
| US4179502A (en) | 7[2-Hydroxyiminoacetamido]cephalosporins | |
| US4328224A (en) | Cephalosporin derivatives | |
| US4185015A (en) | Methoxymethyl 6-[D-2,2-dimethyl-4-(4-hydroxyphenyl)-5-oxo-1-imidazolyl]penicillanate | |
| EP1370515A2 (en) | Synthesis of n,n-dimethyl-3-(4-methyl) benzoyl propionamide, a key intermediate of zolpidem | |
| US3985738A (en) | 7-(D-.alpha.-Hydroxy-2-arylacetamido)-3-(tetrazolo-[4,5-b]pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acids | |
| CA2064566A1 (en) | Kynurenic acid derivatives, their preparation and pharmaceutical compositions containing them | |
| KR830000343B1 (ko) | 세팔로스포린 유도체의 제법 | |
| NO761438L (hu) | ||
| CA2233842C (en) | Novel heterocyclic derivatives having indoline, indole or tetrahydroquinoline ring and pharmaceutical use thereof |