NO753818L - - Google Patents
Info
- Publication number
- NO753818L NO753818L NO753818A NO753818A NO753818L NO 753818 L NO753818 L NO 753818L NO 753818 A NO753818 A NO 753818A NO 753818 A NO753818 A NO 753818A NO 753818 L NO753818 L NO 753818L
- Authority
- NO
- Norway
- Prior art keywords
- parts
- weight
- formula
- oxo
- compound
- Prior art date
Links
- -1 carboxy, methoxycarbonyl Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 159000000000 sodium salts Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 229910005965 SO 2 Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 6
- 125000002541 furyl group Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001544 thienyl group Chemical class 0.000 claims description 5
- 125000001485 cycloalkadienyl group Chemical group 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
- 230000003115 biocidal effect Effects 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical compound N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 241000231697 Zelus means Species 0.000 claims 1
- 230000001133 acceleration Effects 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- 229910001868 water Inorganic materials 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 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 49
- 239000011734 sodium Substances 0.000 description 47
- 229910052708 sodium Inorganic materials 0.000 description 46
- 239000000126 substance Substances 0.000 description 45
- 239000005662 Paraffin oil Substances 0.000 description 43
- 229930182555 Penicillin Natural products 0.000 description 43
- 239000000243 solution Substances 0.000 description 43
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
- 229940049954 penicillin Drugs 0.000 description 40
- 238000002329 infrared spectrum Methods 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 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 description 33
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 31
- 239000013543 active substance Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 229960003311 ampicillin trihydrate Drugs 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000003776 cleavage reaction Methods 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 27
- 230000007017 scission Effects 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 26
- 239000000460 chlorine Substances 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 26
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 26
- 150000002960 penicillins Chemical class 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 24
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
- 229930186147 Cephalosporin Natural products 0.000 description 21
- 229940124587 cephalosporin Drugs 0.000 description 21
- 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 19
- 150000001780 cephalosporins Chemical class 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
- 229950004030 cefaloglycin Drugs 0.000 description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 16
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 14
- 239000005051 trimethylchlorosilane Substances 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 239000002585 base Substances 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- 235000010288 sodium nitrite Nutrition 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 12
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 241000894006 Bacteria Species 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229940056360 penicillin g Drugs 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 150000003952 β-lactams Chemical class 0.000 description 9
- KURFSUDYQUKEJZ-SBMYYUOMSA-N (6r,7r)-3-(acetyloxymethyl)-7-[[(2r)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;dihydrate Chemical compound O.O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 KURFSUDYQUKEJZ-SBMYYUOMSA-N 0.000 description 8
- VRIKLWVRINZPSR-UHFFFAOYSA-N 1-aminoimidazolidin-2-one;hydrochloride Chemical compound Cl.NN1CCNC1=O VRIKLWVRINZPSR-UHFFFAOYSA-N 0.000 description 8
- 229960004920 amoxicillin trihydrate Drugs 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 230000020477 pH reduction Effects 0.000 description 8
- 239000000825 pharmaceutical preparation Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 6
- 229960002457 epicillin Drugs 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 241000588769 Proteus <enterobacteria> Species 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- DHIVBEZCBBHIPZ-UHFFFAOYSA-N 1-aminoimidazolidin-2-one Chemical compound NN1CCNC1=O DHIVBEZCBBHIPZ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000003513 alkali Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000589968 Borrelia Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
- 241000589902 Leptospira Species 0.000 description 3
- 241000588653 Neisseria Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 241000589886 Treponema Species 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
- SWVIYBHDYSLFNV-UHFFFAOYSA-N 1-(3h-furan-2-ylideneamino)imidazolidin-2-one Chemical compound O=C1NCCN1N=C1OC=CC1 SWVIYBHDYSLFNV-UHFFFAOYSA-N 0.000 description 2
- FZNSBUVCFHSAMS-UHFFFAOYSA-N 1-[(5-bromo-3h-furan-2-ylidene)amino]imidazolidin-2-one Chemical compound O1C(Br)=CCC1=NN1C(=O)NCC1 FZNSBUVCFHSAMS-UHFFFAOYSA-N 0.000 description 2
- OSXNAVXUMPHLTE-UHFFFAOYSA-N 1-[(5-methyl-3h-furan-2-ylidene)amino]imidazolidin-2-one Chemical compound O1C(C)=CCC1=NN1C(=O)NCC1 OSXNAVXUMPHLTE-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- 241000607534 Aeromonas Species 0.000 description 2
- 241000607528 Aeromonas hydrophila Species 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- FNEDHAVUXWEPMP-UHFFFAOYSA-M sodium;2-methylhexanoate Chemical compound [Na+].CCCCC(C)C([O-])=O FNEDHAVUXWEPMP-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229940118696 vibrio cholerae Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742456307 DE2456307A1 (de) | 1974-11-28 | 1974-11-28 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE19752512998 DE2512998A1 (de) | 1975-03-25 | 1975-03-25 | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE19752525541 DE2525541C2 (de) | 1975-06-07 | 1975-06-07 | β-Lactam-Antibiotica, Verfahren zu ihrer Herstellung sowie sie enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753818L true NO753818L (cs) | 1976-05-31 |
Family
ID=27186174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753818A NO753818L (cs) | 1974-11-28 | 1975-11-14 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4147693A (cs) |
| JP (2) | JPS5182286A (cs) |
| AR (1) | AR210103A1 (cs) |
| AT (1) | AT342196B (cs) |
| AU (1) | AU499337B2 (cs) |
| CA (1) | CA1064020A (cs) |
| CH (1) | CH623326A5 (cs) |
| DD (1) | DD124736A5 (cs) |
| DK (1) | DK535675A (cs) |
| ES (1) | ES443008A1 (cs) |
| FI (1) | FI66004C (cs) |
| FR (1) | FR2292471A1 (cs) |
| GB (1) | GB1486349A (cs) |
| HK (1) | HK19678A (cs) |
| IE (1) | IE43813B1 (cs) |
| IL (1) | IL48538A (cs) |
| LU (1) | LU73873A1 (cs) |
| NL (1) | NL7513746A (cs) |
| NO (1) | NO753818L (cs) |
| NZ (1) | NZ179347A (cs) |
| RO (1) | RO68146A (cs) |
| SE (1) | SE434513B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061861A (en) * | 1976-06-21 | 1977-12-06 | Eli Lilly And Company | 7-[α-(2,3-DIHYDRO-2-OXO-1H-benzimidazol-1-ylcarbonyl-amino)arylacetamido]cephalosporins |
| JPS5326143A (en) * | 1976-08-24 | 1978-03-10 | Oki Electric Ind Co Ltd | Coupling method for op tical fiber |
| JPS5331690A (en) * | 1976-09-01 | 1978-03-25 | Shionogi & Co Ltd | Oxadithiacephalosporins |
| GB1584400A (en) * | 1976-12-24 | 1981-02-11 | Bayer Ag | (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins |
| DE2732283A1 (de) * | 1977-07-16 | 1979-01-25 | Bayer Ag | Beta-lactam-verbindungen |
| JPS5616489A (en) * | 1979-07-20 | 1981-02-17 | Ajinomoto Co Inc | Imidazolecarboxylic acid derivative |
| US4386199A (en) * | 1980-01-03 | 1983-05-31 | E. R. Squibb & Sons, Inc. | Cephalosporins having an imino substituted piperazindioncarbonylamino acyl sidechain |
| US4436904A (en) * | 1981-02-14 | 1984-03-13 | Kanto Ishi Pharmaceutical Co., Ltd. | Cephalosporins |
| GB8318846D0 (en) * | 1983-07-12 | 1983-08-10 | Fujisawa Pharmaceutical Co | Prophylactic/therapeutic agent against fish diseases |
| CN103360321B (zh) * | 2012-04-05 | 2016-09-21 | 北京勤邦生物技术有限公司 | 呋喃妥因代谢物半抗原及其制备方法和应用 |
| CN111995663B (zh) * | 2020-09-02 | 2023-07-28 | 重庆大学 | 一种含有N-氨基咪唑烷-2-酮结构的Ang-（1-7）多肽类似物 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3939149A (en) * | 1970-05-25 | 1976-02-17 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| CH571524A5 (cs) * | 1970-05-25 | 1976-01-15 | Bayer Ag | |
| US3974140A (en) * | 1970-05-25 | 1976-08-10 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| CH562249A5 (cs) * | 1970-05-25 | 1975-05-30 | Bayer Ag | |
| US3980792A (en) * | 1970-05-25 | 1976-09-14 | Bayer Aktiengesellschaft | Ureidoacetamido-penicillins |
| US3732332A (en) * | 1970-10-16 | 1973-05-08 | Allied Chem | Production of low molecular weight polyanhydrides and epoxy compositions derived therefrom |
| NL175419C (nl) * | 1971-10-23 | 1984-11-01 | Bayer Ag | Werkwijze ter bereiding of vervaardiging van antibiotisch werkzame farmaceutische preparaten, alsmede werkwijze ter bereiding van antibiotisch werkzame alfa-gesubstitueerde 6-(alfa-(3-acylureido)acetylamino) penicillanzuurderivaten. |
| BE790441A (fr) * | 1971-10-23 | 1973-04-24 | Bayer Ag | Nouvelles penicillines, leur procede de preparation et medicament les contenant |
| US3974142A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
| US3983105A (en) * | 1971-10-23 | 1976-09-28 | Bayer Aktiengesellschaft | Penicillins |
| US3974141A (en) * | 1971-10-23 | 1976-08-10 | Bayer Aktiengesellschaft | Penicillins |
| US3978056A (en) * | 1971-10-23 | 1976-08-31 | Bayer Aktiengesellschaft | Penicillins |
| US3972870A (en) * | 1971-10-23 | 1976-08-03 | Bayer Aktiengesellschaft | Penicillins |
| DE2354219A1 (de) * | 1973-10-30 | 1975-05-07 | Bayer Ag | Beta-lactam-antibiotica, ein verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1975
- 1975-10-28 GB GB44296/75A patent/GB1486349A/en not_active Expired
- 1975-11-13 US US05/631,515 patent/US4147693A/en not_active Expired - Lifetime
- 1975-11-14 NO NO753818A patent/NO753818L/no unknown
- 1975-11-18 CA CA239,913A patent/CA1064020A/en not_active Expired
- 1975-11-24 CH CH1523375A patent/CH623326A5/de not_active IP Right Cessation
- 1975-11-25 IL IL48538A patent/IL48538A/xx unknown
- 1975-11-25 NZ NZ179347A patent/NZ179347A/xx unknown
- 1975-11-25 NL NL7513746A patent/NL7513746A/xx not_active Application Discontinuation
- 1975-11-26 RO RO7584030A patent/RO68146A/ro unknown
- 1975-11-26 JP JP50140877A patent/JPS5182286A/ja active Granted
- 1975-11-26 DD DD189709A patent/DD124736A5/xx unknown
- 1975-11-26 LU LU73873A patent/LU73873A1/xx unknown
- 1975-11-26 FI FI753333A patent/FI66004C/fi not_active IP Right Cessation
- 1975-11-26 ES ES443008A patent/ES443008A1/es not_active Expired
- 1975-11-26 JP JP50140878A patent/JPS6043332B2/ja not_active Expired
- 1975-11-27 DK DK535675A patent/DK535675A/da not_active Application Discontinuation
- 1975-11-27 SE SE7513378A patent/SE434513B/xx unknown
- 1975-11-27 IE IE2588/75A patent/IE43813B1/en unknown
- 1975-11-28 FR FR7536543A patent/FR2292471A1/fr active Granted
- 1975-11-28 AT AT907275A patent/AT342196B/de not_active IP Right Cessation
- 1975-11-28 AU AU87085/75A patent/AU499337B2/en not_active Expired
- 1975-11-28 AR AR261391A patent/AR210103A1/es active
-
1978
- 1978-04-13 HK HK196/78A patent/HK19678A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4147693A (en) | 1979-04-03 |
| CA1064020A (en) | 1979-10-09 |
| IL48538A (en) | 1979-07-25 |
| SE434513B (sv) | 1984-07-30 |
| AT342196B (de) | 1978-03-28 |
| IE43813L (en) | 1976-05-28 |
| AU8708575A (en) | 1977-06-02 |
| FR2292471A1 (fr) | 1976-06-25 |
| IL48538A0 (en) | 1976-01-30 |
| IE43813B1 (en) | 1981-06-03 |
| NZ179347A (en) | 1978-04-28 |
| FI66004B (fi) | 1984-04-30 |
| ES443008A1 (es) | 1977-05-01 |
| FI66004C (fi) | 1984-08-10 |
| JPS5182286A (en) | 1976-07-19 |
| JPS5176438A (cs) | 1976-07-02 |
| RO68146A (ro) | 1980-04-15 |
| FI753333A (cs) | 1976-05-29 |
| DD124736A5 (cs) | 1977-03-09 |
| GB1486349A (en) | 1977-09-21 |
| DK535675A (da) | 1976-05-29 |
| JPS6114151B2 (cs) | 1986-04-17 |
| NL7513746A (nl) | 1976-06-01 |
| SE7513378L (sv) | 1976-05-31 |
| LU73873A1 (cs) | 1976-09-06 |
| ATA907275A (de) | 1977-07-15 |
| AU499337B2 (en) | 1979-04-12 |
| HK19678A (en) | 1978-04-20 |
| JPS6043332B2 (ja) | 1985-09-27 |
| CH623326A5 (cs) | 1981-05-29 |
| FR2292471B1 (cs) | 1981-12-31 |
| AR210103A1 (es) | 1977-06-30 |
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| NO753818L (cs) | ||
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| NO750351L (cs) | ||
| CA1040622A (en) | Penicillins and cephalosporins and their production | |
| US4235774A (en) | Penicillin derivatives | |
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| US4039673A (en) | Penicillins and cephalosporins and their production | |
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| DE2456307A1 (de) | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| US4208412A (en) | β-Lactam antibiotics | |
| US4294827A (en) | Antibacterial and growth promoting β-lactam antibiotics carrying an -ylidene-2-pyrrolidinon-1-yl radical | |
| KR810000186B1 (ko) | β-락탐 항생물질의 제조방법 | |
| US4081539A (en) | Penicillins and cephalosporins and their production | |
| US4071683A (en) | Oxoimidazolidinylthiocarbonyl derivatives of ceph-3-em-4-carboxylic acids | |
| JPS5852996B2 (ja) | β−ラクタム及び抗バクテリア剤 | |
| CA1084906A (en) | Cephalosporins, processes for their preparation and their use as medicaments | |
| DE2658718A1 (de) | Methoxy-beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2528078A1 (de) | Beta-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2525541A1 (de) | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2512998A1 (de) | Beta-lactam-antibiotica, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE2658906A1 (de) | Beta-lactam-antibiotika, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |