GB1591990A - 7-acylamino-3-(sulfomethylheterocyclicthiomethyl)-3-cephem-4-carboxylic acids - Google Patents
7-acylamino-3-(sulfomethylheterocyclicthiomethyl)-3-cephem-4-carboxylic acids Download PDFInfo
- Publication number
- GB1591990A GB1591990A GB39119/77A GB3911977A GB1591990A GB 1591990 A GB1591990 A GB 1591990A GB 39119/77 A GB39119/77 A GB 39119/77A GB 3911977 A GB3911977 A GB 3911977A GB 1591990 A GB1591990 A GB 1591990A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cephem
- compound
- sulfomethyl
- formula
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 241000894006 Bacteria Species 0.000 claims abstract description 4
- -1 3 - (5 - sulfomethyl - 1,3,4 - thiadiazol - 2 - ylthiomethyl) - 3 - cephem - 4 carboxylic acid disodium salt Chemical compound 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
- DBXDIUXRJBZXKM-UHFFFAOYSA-N 1h-1,2,4-triazol-5-ylmethanesulfonic acid Chemical compound OS(=O)(=O)CC=1N=CNN=1 DBXDIUXRJBZXKM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- RJOJGLJGELUUPZ-QHDYGNBISA-N (6R)-8-oxo-3-[[5-(sulfomethyl)-1,3,4-thiadiazol-2-yl]sulfanylmethyl]-7-(3,3,3-trifluoropropanethioylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound FC(F)(F)CC(=S)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)CS(=O)(=O)O)C(=O)O)C1=O RJOJGLJGELUUPZ-QHDYGNBISA-N 0.000 claims description 3
- 229910006069 SO3H Inorganic materials 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005494 pyridonyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 238000010255 intramuscular injection Methods 0.000 claims description 2
- 239000007927 intramuscular injection Substances 0.000 claims description 2
- 238000010253 intravenous injection Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- HVUWUQSOEGFNLR-UHFFFAOYSA-N (4-sulfanylthiadiazol-5-yl)methanesulfonic acid Chemical compound S(=O)(=O)(O)CC1=C(N=NS1)S HVUWUQSOEGFNLR-UHFFFAOYSA-N 0.000 abstract 1
- SHNBSVALOBVNKY-UHFFFAOYSA-N (5-sulfanylidene-1,2-dihydrotriazol-4-yl)methanesulfonic acid Chemical compound S(=O)(=O)(O)CC1=C(N=NN1)S SHNBSVALOBVNKY-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229920001429 chelating resin Polymers 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229930186147 Cephalosporin Natural products 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229940124587 cephalosporin Drugs 0.000 description 5
- 150000001780 cephalosporins Chemical class 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- CWJQWLSNKNWCDJ-UHFFFAOYSA-N (2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)methanesulfonic acid Chemical class OS(=O)(=O)CC1=NN=C(S)S1 CWJQWLSNKNWCDJ-UHFFFAOYSA-N 0.000 description 4
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- XCEKTLGBUFKLQB-UHFFFAOYSA-N (5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)methanesulfonic acid Chemical compound OS(=O)(=O)CC1=NNC(S)=N1 XCEKTLGBUFKLQB-UHFFFAOYSA-N 0.000 description 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 2
- 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 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FJRXGBBVWWBHMW-UHFFFAOYSA-N O.O.O.O.[Na].[Na] Chemical compound O.O.O.O.[Na].[Na] FJRXGBBVWWBHMW-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 1
- XHSYLFQTCDHFJK-UHFFFAOYSA-N 2-(chloromethyl)-5-[(4-methoxyphenyl)methylsulfanyl]-1,3,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1CSC1=NN=C(CCl)S1 XHSYLFQTCDHFJK-UHFFFAOYSA-N 0.000 description 1
- GRWKNBPOGBTZMN-UHFFFAOYSA-N 2-benzyl-3-phenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1CC(N)(CN)CC1=CC=CC=C1 GRWKNBPOGBTZMN-UHFFFAOYSA-N 0.000 description 1
- VZFVKQUUOJAIOH-UHFFFAOYSA-N 4-(chloromethyl)thiadiazole Chemical compound ClCC1=CSN=N1 VZFVKQUUOJAIOH-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- WDAQENWVZAETQD-SWEFTRPJSA-L [Na+].[Na+].S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NC(=NN2)CS(=O)(=O)[O-])C(=O)[O-])C1=O Chemical compound [Na+].[Na+].S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CSC2=NC(=NN2)CS(=O)(=O)[O-])C(=O)[O-])C1=O WDAQENWVZAETQD-SWEFTRPJSA-L 0.000 description 1
- ICALPKJJVKJBSS-SWEFTRPJSA-L [Na+].[Na+].S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)CS(=O)(=O)[O-])C(=O)[O-])C1=O Chemical compound [Na+].[Na+].S1C(=CC=C1)CC(=O)NC1[C@@H]2N(C(=C(CS2)CSC=2SC(=NN=2)CS(=O)(=O)[O-])C(=O)[O-])C1=O ICALPKJJVKJBSS-SWEFTRPJSA-L 0.000 description 1
- BMMTZTCBDAYWHC-UHFFFAOYSA-N [methoxy(phenyl)methyl] N-aminocarbamodithioate Chemical compound C(NN)(=S)SC(C1=CC=CC=C1)OC BMMTZTCBDAYWHC-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
- 229960003866 cefaloridine Drugs 0.000 description 1
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical group N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 1
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 1
- 229960001139 cefazolin Drugs 0.000 description 1
- 229940106164 cephalexin Drugs 0.000 description 1
- AVGYWQBCYZHHPN-CYJZLJNKSA-N cephalexin monohydrate Chemical compound O.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 AVGYWQBCYZHHPN-CYJZLJNKSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- NHPLGHZNJZUXAD-UHFFFAOYSA-N ethoxycarbonylcarbamodithioic acid Chemical compound CCOC(=O)NC(S)=S NHPLGHZNJZUXAD-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- SFQGQKHLJGXJSN-UHFFFAOYSA-M potassium;2-ethoxy-2-oxoethanesulfonate Chemical compound [K+].CCOC(=O)CS([O-])(=O)=O SFQGQKHLJGXJSN-UHFFFAOYSA-M 0.000 description 1
- JMZMKZVNSCMZND-UHFFFAOYSA-M potassium;2-hydrazinyl-2-oxoethanesulfonate Chemical compound [K+].NNC(=O)CS([O-])(=O)=O JMZMKZVNSCMZND-UHFFFAOYSA-M 0.000 description 1
- IXQYZUOOHQWOQL-UHFFFAOYSA-N potassium;methanol;methanolate Chemical compound [K+].OC.[O-]C IXQYZUOOHQWOQL-UHFFFAOYSA-N 0.000 description 1
- ODMABOBKUUZKJB-UHFFFAOYSA-M potassium;n-aminocarbamodithioate Chemical compound [K+].NNC([S-])=S ODMABOBKUUZKJB-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 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
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- POFFTUZDJSLARO-UHFFFAOYSA-M sodium;(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)methanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC1=NC(=S)NN1 POFFTUZDJSLARO-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/726,377 US4083975A (en) | 1976-09-24 | 1976-09-24 | 7-Acylamino-3-(3-sulfomethyl-1,2,4-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acids |
| US05/726,378 US4079134A (en) | 1976-09-24 | 1976-09-24 | 7-Acylamino-3-(5-sulfomethyl-1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1591990A true GB1591990A (en) | 1981-07-01 |
Family
ID=27111308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39119/77A Expired GB1591990A (en) | 1976-09-24 | 1977-09-20 | 7-acylamino-3-(sulfomethylheterocyclicthiomethyl)-3-cephem-4-carboxylic acids |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5340796A (enrdf_load_stackoverflow) |
| CH (1) | CH633557A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2742726A1 (enrdf_load_stackoverflow) |
| DK (1) | DK417777A (enrdf_load_stackoverflow) |
| FR (2) | FR2365571A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1591990A (enrdf_load_stackoverflow) |
| IE (1) | IE45686B1 (enrdf_load_stackoverflow) |
| LU (1) | LU78164A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7710439A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6140291A (ja) * | 1984-07-31 | 1986-02-26 | Shionogi & Co Ltd | ヒドロキシアルキルチオセフアロスポリン |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1201621A (en) * | 1967-05-18 | 1970-08-12 | Agfa Gevaert Nv | Process for stabilizing developed photographic images |
-
1977
- 1977-09-16 FR FR7727983A patent/FR2365571A1/fr active Granted
- 1977-09-19 JP JP11391877A patent/JPS5340796A/ja active Granted
- 1977-09-19 IE IE1912/77A patent/IE45686B1/en unknown
- 1977-09-20 GB GB39119/77A patent/GB1591990A/en not_active Expired
- 1977-09-21 DK DK417777A patent/DK417777A/da not_active Application Discontinuation
- 1977-09-22 DE DE19772742726 patent/DE2742726A1/de not_active Ceased
- 1977-09-22 LU LU78164A patent/LU78164A1/xx unknown
- 1977-09-23 NL NL7710439A patent/NL7710439A/xx not_active Application Discontinuation
- 1977-09-23 CH CH1166877A patent/CH633557A5/de not_active IP Right Cessation
-
1978
- 1978-10-03 FR FR7828261A patent/FR2392014A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2365571B1 (enrdf_load_stackoverflow) | 1983-02-25 |
| FR2392014A1 (fr) | 1978-12-22 |
| JPS6156237B2 (enrdf_load_stackoverflow) | 1986-12-01 |
| LU78164A1 (enrdf_load_stackoverflow) | 1978-01-24 |
| FR2365571A1 (fr) | 1978-04-21 |
| NL7710439A (nl) | 1978-03-29 |
| JPS5340796A (en) | 1978-04-13 |
| CH633557A5 (en) | 1982-12-15 |
| IE45686B1 (en) | 1982-10-20 |
| DE2742726A1 (de) | 1978-03-30 |
| IE45686L (en) | 1978-03-24 |
| DK417777A (da) | 1978-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |