DD91497B3 - Verfahren zur herstellung neuer penicilline - Google Patents
Verfahren zur herstellung neuer penicilline Download PDFInfo
- Publication number
- DD91497B3 DD91497B3 DD71155301A DD15530171A DD91497B3 DD 91497 B3 DD91497 B3 DD 91497B3 DD 71155301 A DD71155301 A DD 71155301A DD 15530171 A DD15530171 A DD 15530171A DD 91497 B3 DD91497 B3 DD 91497B3
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- parts
- weight
- sodium
- benzylpenicillin
- acid chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 title 1
- 229930182555 Penicillin Natural products 0.000 claims description 142
- 150000002960 penicillins Chemical class 0.000 claims description 102
- 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 96
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 94
- 229960000723 ampicillin Drugs 0.000 claims description 92
- 241001465754 Metazoa Species 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 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 claims description 19
- 229960003669 carbenicillin Drugs 0.000 claims description 19
- 208000015181 infectious disease Diseases 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 241000588748 Klebsiella Species 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000001802 infusion Methods 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical class 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 125000003609 aryl vinyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 206010061259 Klebsiella infection Diseases 0.000 claims 1
- 208000024233 Klebsiella infectious disease Diseases 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000002778 food additive Substances 0.000 claims 1
- 235000013373 food additive Nutrition 0.000 claims 1
- 208000027096 gram-negative bacterial infections Diseases 0.000 claims 1
- 208000027136 gram-positive bacterial infections Diseases 0.000 claims 1
- 244000144977 poultry Species 0.000 claims 1
- 230000002459 sustained effect Effects 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229940056360 penicillin g Drugs 0.000 description 173
- 229940049954 penicillin Drugs 0.000 description 109
- 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 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 52
- 238000002474 experimental method Methods 0.000 description 50
- 239000011734 sodium Substances 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 229910052708 sodium Inorganic materials 0.000 description 48
- 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 47
- 239000000243 solution Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 235000019371 penicillin G benzathine Nutrition 0.000 description 27
- 241000588724 Escherichia coli Species 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 241000589516 Pseudomonas Species 0.000 description 22
- 241000588769 Proteus <enterobacteria> Species 0.000 description 20
- 159000000000 sodium salts Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000002329 infrared spectrum Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 10
- 238000007920 subcutaneous administration Methods 0.000 description 10
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- NXJZQSRAFBHNLI-UHFFFAOYSA-N 2-oxoimidazolidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNC1=O NXJZQSRAFBHNLI-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- KARPAXFMDRDIJO-UHFFFAOYSA-N n-(dimethylcarbamoyl)-n-methylcarbamoyl chloride Chemical compound CN(C)C(=O)N(C)C(Cl)=O KARPAXFMDRDIJO-UHFFFAOYSA-N 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000588767 Proteus vulgaris Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- BXSOOQONKFBTRI-UHFFFAOYSA-N n-(furan-2-carbonyl)-n-phenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C(=O)C1=CC=CO1 BXSOOQONKFBTRI-UHFFFAOYSA-N 0.000 description 3
- XHLLMVSEBKZODD-UHFFFAOYSA-N n-acetyl-n-methylcarbamoyl chloride Chemical compound CC(=O)N(C)C(Cl)=O XHLLMVSEBKZODD-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940007042 proteus vulgaris Drugs 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003952 β-lactams Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ICIKUUBAHVZOQF-UHFFFAOYSA-N 1-trimethylsilylimidazolidine-2-thione Chemical compound C[Si](C)(C)N1CCNC1=S ICIKUUBAHVZOQF-UHFFFAOYSA-N 0.000 description 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 229960000603 cefalotin Drugs 0.000 description 2
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- RDAXGYOBGYRWRE-UHFFFAOYSA-N n-(2,4-dichlorobenzoyl)-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C(=O)C1=CC=C(Cl)C=C1Cl RDAXGYOBGYRWRE-UHFFFAOYSA-N 0.000 description 2
- QNPSJJUCHULMAV-UHFFFAOYSA-N n-(diethylcarbamoyl)-n-methylcarbamoyl chloride Chemical compound CCN(CC)C(=O)N(C)C(Cl)=O QNPSJJUCHULMAV-UHFFFAOYSA-N 0.000 description 2
- FACAXJVAYJPFCX-UHFFFAOYSA-N n-acetyl-n-ethylcarbamoyl chloride Chemical compound CCN(C(C)=O)C(Cl)=O FACAXJVAYJPFCX-UHFFFAOYSA-N 0.000 description 2
- OMISGTJSZGSFEN-UHFFFAOYSA-N n-acetyl-n-phenylcarbamoyl chloride Chemical compound CC(=O)N(C(Cl)=O)C1=CC=CC=C1 OMISGTJSZGSFEN-UHFFFAOYSA-N 0.000 description 2
- KTJVZEYNPCIDBG-UHFFFAOYSA-N n-benzoyl-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C(=O)C1=CC=CC=C1 KTJVZEYNPCIDBG-UHFFFAOYSA-N 0.000 description 2
- UBZZULFRWFTJDH-UHFFFAOYSA-N n-ethyl-n-(furan-2-carbonyl)carbamoyl chloride Chemical compound CCN(C(Cl)=O)C(=O)C1=CC=CO1 UBZZULFRWFTJDH-UHFFFAOYSA-N 0.000 description 2
- MQYGOJLDJALYFZ-UHFFFAOYSA-N n-formyl-n-methylcarbamoyl chloride Chemical compound O=CN(C)C(Cl)=O MQYGOJLDJALYFZ-UHFFFAOYSA-N 0.000 description 2
- JIQBLONORFFMKH-UHFFFAOYSA-N n-methyl-n-(methylcarbamoyl)carbamoyl chloride Chemical compound CNC(=O)N(C)C(Cl)=O JIQBLONORFFMKH-UHFFFAOYSA-N 0.000 description 2
- TWVKGZMOFYALFE-UHFFFAOYSA-N n-methyl-n-propanoylcarbamoyl chloride Chemical compound CCC(=O)N(C)C(Cl)=O TWVKGZMOFYALFE-UHFFFAOYSA-N 0.000 description 2
- YBSLNCGUOFPXNK-UHFFFAOYSA-N n-phenyl-n-propanoylcarbamoyl chloride Chemical compound CCC(=O)N(C(Cl)=O)C1=CC=CC=C1 YBSLNCGUOFPXNK-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- LWWBRCLMTPXMKC-IMJSIDKUSA-N (4s,5s)-4,5-dimethyl-2-oxoimidazolidine-1-carbonyl chloride Chemical compound C[C@@H]1NC(=O)N(C(Cl)=O)[C@H]1C LWWBRCLMTPXMKC-IMJSIDKUSA-N 0.000 description 1
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- FOYPWTVSNASFEJ-UHFFFAOYSA-N 2-oxo-1,3-diazepane-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCNC1=O FOYPWTVSNASFEJ-UHFFFAOYSA-N 0.000 description 1
- AFQRORBLVJQAMT-UHFFFAOYSA-N 2-oxo-1,3-diazinane-1-carbonyl chloride Chemical compound ClC(=O)N1CCCNC1=O AFQRORBLVJQAMT-UHFFFAOYSA-N 0.000 description 1
- WPWFNAFNXXIJRV-UHFFFAOYSA-N 2-oxo-3h-benzimidazole-1-carbonyl chloride Chemical compound C1=CC=C2NC(=O)N(C(=O)Cl)C2=C1 WPWFNAFNXXIJRV-UHFFFAOYSA-N 0.000 description 1
- WZBYJLYJTYWHJH-UHFFFAOYSA-N 2-sulfanylidene-1,3-diazinane-1-carbonyl chloride Chemical compound ClC(=O)N1CCCNC1=S WZBYJLYJTYWHJH-UHFFFAOYSA-N 0.000 description 1
- RUZNGTORRLNXHV-UHFFFAOYSA-N 2-sulfanylideneimidazolidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNC1=S RUZNGTORRLNXHV-UHFFFAOYSA-N 0.000 description 1
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- GBEXQPPWSNDVIK-UHFFFAOYSA-N n-methyl-n-(phenylcarbamoyl)carbamoyl chloride Chemical compound ClC(=O)N(C)C(=O)NC1=CC=CC=C1 GBEXQPPWSNDVIK-UHFFFAOYSA-N 0.000 description 1
- CEVZUWMBTPPWID-UHFFFAOYSA-N n-methyl-n-(thiophene-2-carbonyl)carbamoyl chloride Chemical compound ClC(=O)N(C)C(=O)C1=CC=CS1 CEVZUWMBTPPWID-UHFFFAOYSA-N 0.000 description 1
- ZZPBWJZYFLDTNC-UHFFFAOYSA-N n-methyl-n-octadecanoylcarbamoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(=O)N(C)C(Cl)=O ZZPBWJZYFLDTNC-UHFFFAOYSA-N 0.000 description 1
- BIAPVKBQBCMFAS-UHFFFAOYSA-N n-methyl-n-prop-2-enoylcarbamoyl chloride Chemical compound ClC(=O)N(C)C(=O)C=C BIAPVKBQBCMFAS-UHFFFAOYSA-N 0.000 description 1
- GRRYSIXDUIAUGY-UHFFFAOYSA-N n-methylcarbamoyl chloride Chemical compound CNC(Cl)=O GRRYSIXDUIAUGY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- FDJABJJEKWDNQO-UHFFFAOYSA-N pentane;propan-2-one Chemical compound CC(C)=O.CCCCC FDJABJJEKWDNQO-UHFFFAOYSA-N 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- YNWGWXZWWGYIKG-UHFFFAOYSA-N propyl N-carbonochloridoyl-N-methylcarbamate Chemical compound C(CC)OC(=O)N(C(=O)Cl)C YNWGWXZWWGYIKG-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2025414A DE2025414C3 (de) | 1970-05-25 | 1970-05-25 | Cyclische Acylureidophenylacetamidopenicillansäuren |
| DE19712104580 DE2104580C3 (de) | 1971-02-01 | 1971-02-01 | Acylureidopenicilline |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD91497A5 DD91497A5 (de) | 1972-07-20 |
| DD91497B3 true DD91497B3 (de) | 1988-01-27 |
Family
ID=25759178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD71155301A DD91497B3 (de) | 1970-05-25 | 1971-05-24 | Verfahren zur herstellung neuer penicilline |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5538357B1 (en, 2012) |
| AR (2) | AR195267A1 (en, 2012) |
| AT (1) | AT307617B (en, 2012) |
| BE (1) | BE767647A (en, 2012) |
| BG (1) | BG23220A3 (en, 2012) |
| CA (1) | CA943128A (en, 2012) |
| CH (1) | CH562249A5 (en, 2012) |
| CS (1) | CS171230B2 (en, 2012) |
| CY (1) | CY829A (en, 2012) |
| DD (1) | DD91497B3 (en, 2012) |
| DK (1) | DK133679C (en, 2012) |
| EG (1) | EG10856A (en, 2012) |
| ES (4) | ES391532A1 (en, 2012) |
| FI (1) | FI54484C (en, 2012) |
| FR (1) | FR2100681B1 (en, 2012) |
| GB (1) | GB1301961A (en, 2012) |
| HU (1) | HU162205B (en, 2012) |
| IE (1) | IE35311B1 (en, 2012) |
| IL (1) | IL36905A (en, 2012) |
| KE (1) | KE2592A (en, 2012) |
| LU (1) | LU63203A1 (en, 2012) |
| NL (1) | NL172660C (en, 2012) |
| NO (1) | NO141164C (en, 2012) |
| PH (1) | PH14794A (en, 2012) |
| RO (2) | RO59157A (en, 2012) |
| SE (1) | SE395896B (en, 2012) |
| SU (1) | SU472507A3 (en, 2012) |
| YU (1) | YU130271A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2354219A1 (de) * | 1973-10-30 | 1975-05-07 | Bayer Ag | Beta-lactam-antibiotica, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4039673A (en) | 1973-10-30 | 1977-08-02 | Bayer Aktiengesellschaft | Penicillins and cephalosporins and their production |
| GB1486349A (en) * | 1974-11-28 | 1977-09-21 | Bayer Ag | Beta-lactam antibiotics process for their preparation and their use as medicaments |
| GB1584400A (en) * | 1976-12-24 | 1981-02-11 | Bayer Ag | (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins |
| DE2658906A1 (de) * | 1976-12-24 | 1978-07-06 | Bayer Ag | Beta-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4229348A (en) * | 1978-05-26 | 1980-10-21 | Chugai Seiyaku Kabushiki Kaisha | Penicillanic acid derivatives |
| JPS5732289A (en) | 1980-08-05 | 1982-02-20 | Chugai Pharmaceut Co Ltd | Alpha-substituted ureidobenzylpenicillin |
-
1971
- 1971-04-23 CH CH599071A patent/CH562249A5/xx not_active IP Right Cessation
- 1971-05-13 BG BG017580A patent/BG23220A3/xx unknown
- 1971-05-19 EG EG209/71A patent/EG10856A/xx active
- 1971-05-19 CS CS3646A patent/CS171230B2/cs unknown
- 1971-05-20 SU SU1661304A patent/SU472507A3/ru active
- 1971-05-21 LU LU63203D patent/LU63203A1/xx unknown
- 1971-05-21 IE IE643/71A patent/IE35311B1/xx unknown
- 1971-05-21 FI FI1401/71A patent/FI54484C/fi active
- 1971-05-24 DK DK251071A patent/DK133679C/da active
- 1971-05-24 IL IL7136905A patent/IL36905A/xx unknown
- 1971-05-24 PH PH12493A patent/PH14794A/en unknown
- 1971-05-24 YU YU01302/71A patent/YU130271A/xx unknown
- 1971-05-24 AR AR235756A patent/AR195267A1/es active
- 1971-05-24 NO NO1945/71A patent/NO141164C/no unknown
- 1971-05-24 SE SE7106667A patent/SE395896B/xx unknown
- 1971-05-24 DD DD71155301A patent/DD91497B3/de unknown
- 1971-05-25 BE BE767647A patent/BE767647A/xx not_active IP Right Cessation
- 1971-05-25 AT AT450471A patent/AT307617B/de not_active IP Right Cessation
- 1971-05-25 HU HUBA2591A patent/HU162205B/hu unknown
- 1971-05-25 CA CA113,784A patent/CA943128A/en not_active Expired
- 1971-05-25 RO RO67014A patent/RO59157A/ro unknown
- 1971-05-25 JP JP3524471A patent/JPS5538357B1/ja active Pending
- 1971-05-25 CY CY829A patent/CY829A/xx unknown
- 1971-05-25 ES ES391532A patent/ES391532A1/es not_active Expired
- 1971-05-25 GB GB1688071A patent/GB1301961A/en not_active Expired
- 1971-05-25 RO RO7100078134A patent/RO62689A/ro unknown
- 1971-05-25 FR FR7118932A patent/FR2100681B1/fr not_active Expired
- 1971-05-25 NL NLAANVRAGE7107175,A patent/NL172660C/xx not_active IP Right Cessation
-
1972
- 1972-05-24 ES ES403124A patent/ES403124A1/es not_active Expired
- 1972-05-24 ES ES403125A patent/ES403125A1/es not_active Expired
- 1972-05-24 ES ES403126A patent/ES403126A1/es not_active Expired
-
1973
- 1973-09-14 AR AR250097A patent/AR195946A1/es active
-
1975
- 1975-12-22 KE KE2592*UA patent/KE2592A/xx unknown
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