JPS6052718B2 - 抗菌剤 - Google Patents

抗菌剤

Info

Publication number: JPS6052718B2
Authority: JP; Japan
Prior art keywords: sulfonic acid; sodium; acid; compound according; formula
Prior art date: 1975-01-30
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

Application number

JP51119513A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5246094A (en

Inventor

アーサーカプランマーレン

ジエイゴツトステインウイリアム

ピーターグラナテツクアルフオンス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Co

Original Assignee

Bristol Myers Co

Priority date (The priority date 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 date listed.)

1975-01-30

Filing date

1976-10-06

Publication date

1985-11-20

1976-01-30 Priority claimed from US05/653,999 external-priority patent/US4026888A/en

1976-02-02 Priority claimed from US05/654,314 external-priority patent/US4061862A/en

1976-10-06 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1977-04-12 Publication of JPS5246094A publication Critical patent/JPS5246094A/ja

1985-11-20 Publication of JPS6052718B2 publication Critical patent/JPS6052718B2/ja

Status Expired legal-status Critical Current

Links

239000003242 anti bacterial agent Substances 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims description 152
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 144
-1 hydroxy, methyl Chemical group 0.000 claims description 142
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 120
229910001868 water Inorganic materials 0.000 claims description 105
239000011734 sodium Substances 0.000 claims description 94
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 claims description 93
229910052708 sodium Inorganic materials 0.000 claims description 93
239000000203 mixture Substances 0.000 claims description 86
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 58
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 56
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 51
239000000047 product Substances 0.000 claims description 51
229910052700 potassium Inorganic materials 0.000 claims description 50
239000011591 potassium Substances 0.000 claims description 50
229930186147 Cephalosporin Natural products 0.000 claims description 48
229940124587 cephalosporin Drugs 0.000 claims description 48
238000000034 method Methods 0.000 claims description 48
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 47
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
150000001780 cephalosporins Chemical class 0.000 claims description 47
239000001257 hydrogen Substances 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 44
150000001299 aldehydes Chemical class 0.000 claims description 43
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 42
239000007787 solid Substances 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 37
150000002431 hydrogen Chemical group 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 34
239000000126 substance Substances 0.000 claims description 30
238000001914 filtration Methods 0.000 claims description 29
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 28
230000002378 acidificating effect Effects 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
125000000623 heterocyclic group Chemical group 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 24
239000011541 reaction mixture Substances 0.000 claims description 24
125000001931 aliphatic group Chemical group 0.000 claims description 23
229910052783 alkali metal Inorganic materials 0.000 claims description 23
239000007795 chemical reaction product Substances 0.000 claims description 21
239000012453 solvate Substances 0.000 claims description 21
239000007858 starting material Substances 0.000 claims description 20
239000000725 suspension Substances 0.000 claims description 20
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 18
239000002585 base Substances 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 13
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
239000002244 precipitate Substances 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
150000007524 organic acids Chemical class 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
239000007859 condensation product Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 8
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 6
GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 claims description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
239000007900 aqueous suspension Substances 0.000 claims description 6
159000000001 potassium salts Chemical class 0.000 claims description 6
125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 5
238000001556 precipitation Methods 0.000 claims description 5
URIMPWMBVPNFDM-UHFFFAOYSA-N 5-formylfuran-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)O1 URIMPWMBVPNFDM-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 3
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 claims description 3
LBOUHDMYVURTMA-AATRIKPKSA-N (e)-3-(4-formylphenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(C=O)C=C1 LBOUHDMYVURTMA-AATRIKPKSA-N 0.000 claims description 2
UTCFOFWMEPQCSR-UHFFFAOYSA-N 5-formylsalicylic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1O UTCFOFWMEPQCSR-UHFFFAOYSA-N 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 claims description 2
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 36
OPUAWDUYWRUIIL-UHFFFAOYSA-N methanedisulfonic acid Chemical compound OS(=O)(=O)CS(O)(=O)=O OPUAWDUYWRUIIL-UHFFFAOYSA-N 0.000 claims 21
229940098779 methanesulfonic acid Drugs 0.000 claims 18
125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 3
238000009472 formulation Methods 0.000 claims 2
125000002541 furyl group Chemical group 0.000 claims 2
NTFDWLVIYLPSPK-MRVPVSSYSA-N (6R)-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound N1N=NC=C1SCC=1CS[C@H]2N(C=1C(=O)O)C(C2)=O NTFDWLVIYLPSPK-MRVPVSSYSA-N 0.000 claims 1
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
235000014113 dietary fatty acids Nutrition 0.000 claims 1
239000000194 fatty acid Substances 0.000 claims 1
229930195729 fatty acid Natural products 0.000 claims 1
150000004665 fatty acids Chemical class 0.000 claims 1
239000000243 solution Substances 0.000 description 110
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 59
239000007788 liquid Substances 0.000 description 56
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
238000003756 stirring Methods 0.000 description 36
239000004471 Glycine Substances 0.000 description 35
229960002449 glycine Drugs 0.000 description 35
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
238000004458 analytical method Methods 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000013078 crystal Substances 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 14
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
238000010992 reflux Methods 0.000 description 13
239000002002 slurry Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 10
238000002329 infrared spectrum Methods 0.000 description 10
239000000463 material Substances 0.000 description 10
239000008363 phosphate buffer Substances 0.000 description 10
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
238000001816 cooling Methods 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
241000894006 Bacteria Species 0.000 description 8
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
238000005259 measurement Methods 0.000 description 8
210000002966 serum Anatomy 0.000 description 8
238000012360 testing method Methods 0.000 description 8
241000699666 Mus <mouse, genus> Species 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
239000012467 final product Substances 0.000 description 7
238000004811 liquid chromatography Methods 0.000 description 7
239000012071 phase Substances 0.000 description 7
KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000002245 particle Substances 0.000 description 6
235000011007 phosphoric acid Nutrition 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
150000004683 dihydrates Chemical class 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
238000007911 parenteral administration Methods 0.000 description 5
239000000843 powder Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000005406 washing Methods 0.000 description 5
150000003952 β-lactams Chemical class 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
FHICNDDORUKGPD-UHFFFAOYSA-N 2-azaniumyl-2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound COC1=CC(C(N)C(O)=O)=CC=C1O FHICNDDORUKGPD-UHFFFAOYSA-N 0.000 description 4
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
229920002134 Carboxymethyl cellulose Polymers 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000012535 impurity Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
239000002510 pyrogen Substances 0.000 description 4
ZTJAVDOZUQPVAV-UHFFFAOYSA-M sodium;5-formylfuran-2-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=O)O1 ZTJAVDOZUQPVAV-UHFFFAOYSA-M 0.000 description 4
239000012265 solid product Substances 0.000 description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
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 3
125000002015 acyclic group Chemical group 0.000 description 3
238000007605 air drying Methods 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
BTJRKNUKPQBLAL-UHFFFAOYSA-N hydron;4-methylmorpholine;chloride Chemical compound Cl.CN1CCOCC1 BTJRKNUKPQBLAL-UHFFFAOYSA-N 0.000 description 3
238000010253 intravenous injection Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
239000002207 metabolite Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 3
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Classifications

- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/58—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with a nitrogen atom, which is a member of a hetero ring, attached in position 7

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP51119513A 1975-01-30 1976-10-06 抗菌剤 Expired JPS6052718B2 (ja)

Applications Claiming Priority (10)

Application Number	Priority Date	Filing Date	Title
US62000575A	1975-10-06	1975-10-06
US620005		1975-10-06
US62230675A	1975-10-10	1975-10-10
US622306		1975-10-14
US64031775A	1975-12-12	1975-12-12
US640317		1975-12-12
US05/653,999 US4026888A (en)	1975-10-10	1976-01-30	Certain derivatives of particular 3-thiolated cephalosporins
US05/654,314 US4061862A (en)	1975-10-06	1976-02-02	Derivatives of 7-(cyclized)phenylglycyl-3-triazolo-thio methyl cephalosporin
US653999		1984-09-24
US654314		1996-05-28

Publications (2)

Publication Number	Publication Date
JPS5246094A JPS5246094A (en)	1977-04-12
JPS6052718B2 true JPS6052718B2 (ja)	1985-11-20

Family

ID=27542000

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51119513A Expired JPS6052718B2 (ja)	1975-01-30	1976-10-06	抗菌剤

Country Status (17)

Country	Link
JP (1)	JPS6052718B2 (fr)
AU (1)	AU511344B2 (fr)
BE (1)	BE846890A (fr)
CA (1)	CA1113927A (fr)
CH (1)	CH629500A5 (fr)
CY (1)	CY1121A (fr)
DE (1)	DE2645144C2 (fr)
DK (2)	DK158673C (fr)
FR (1)	FR2326926A1 (fr)
GB (1)	GB1521419A (fr)
HK (1)	HK41281A (fr)
IE (1)	IE43666B1 (fr)
KE (1)	KE3154A (fr)
LU (1)	LU75935A1 (fr)
NL (1)	NL189670C (fr)
SE (1)	SE434952B (fr)
YU (1)	YU40287B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54112892A (en) *	1978-02-23	1979-09-04	Shionogi & Co Ltd	Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acid
JPS54115354A (en) *	1978-02-27	1979-09-07	Chugai Pharmaceut Co Ltd	Biphenylylglycine derivative
JP7013048B2 (ja) *	2018-03-02	2022-01-31	国立大学法人大阪大学	タンパク質及び／又はペプチド修飾用分子

1976
- 1976-09-30 AU AU18245/76A patent/AU511344B2/en not_active Expired
- 1976-10-01 BE BE171201A patent/BE846890A/fr not_active IP Right Cessation
- 1976-10-04 YU YU2431/76A patent/YU40287B/xx unknown
- 1976-10-04 SE SE7610989A patent/SE434952B/xx not_active IP Right Cessation
- 1976-10-04 LU LU75935A patent/LU75935A1/xx unknown
- 1976-10-04 DK DK446576A patent/DK158673C/da not_active IP Right Cessation
- 1976-10-04 FR FR7629825A patent/FR2326926A1/fr active Granted
- 1976-10-05 CA CA262,753A patent/CA1113927A/fr not_active Expired
- 1976-10-05 CH CH1259376A patent/CH629500A5/de not_active IP Right Cessation
- 1976-10-05 IE IE2192/76A patent/IE43666B1/en not_active IP Right Cessation
- 1976-10-05 CY CY1121A patent/CY1121A/xx unknown
- 1976-10-05 GB GB41293/76A patent/GB1521419A/en not_active Expired
- 1976-10-06 JP JP51119513A patent/JPS6052718B2/ja not_active Expired
- 1976-10-06 DE DE2645144A patent/DE2645144C2/de not_active Expired
- 1976-10-06 NL NLAANVRAGE7611026,A patent/NL189670C/xx not_active IP Right Cessation
1981
- 1981-08-20 HK HK412/81A patent/HK41281A/xx unknown
- 1981-08-25 KE KE3154A patent/KE3154A/xx unknown
1988
- 1988-04-12 DK DK200488A patent/DK164225C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK158673C (da)	1991-01-14
IE43666L (en)	1977-04-06
DK200488D0 (da)	1988-04-12
DK164225B (da)	1992-05-25
HK41281A (en)	1981-08-28
DE2645144C2 (de)	1986-11-27
NL189670B (nl)	1993-01-18
YU40287B (en)	1985-12-31
YU243176A (en)	1982-06-30
BE846890A (fr)	1977-04-01
DK164225C (da)	1992-10-19
KE3154A (en)	1981-09-18
DE2645144A1 (de)	1977-04-14
CA1113927A (fr)	1981-12-08
CY1121A (en)	1981-12-04
DK200488A (da)	1988-04-12
DK446576A (da)	1977-04-07
FR2326926B1 (fr)	1980-07-11
SE434952B (sv)	1984-08-27
GB1521419A (en)	1978-08-16
NL7611026A (nl)	1977-04-12
JPS5246094A (en)	1977-04-12
CH629500A5 (en)	1982-04-30
IE43666B1 (en)	1981-04-22
SE7610989L (sv)	1977-04-07
FR2326926A1 (fr)	1977-05-06
AU1824576A (en)	1978-04-06
AU511344B2 (en)	1980-08-14
NL189670C (nl)	1993-06-16
LU75935A1 (fr)	1977-05-25
DK158673B (da)	1990-07-02

Publication	Publication Date	Title
CH634578A5 (de)	1983-02-15	Verfahren zur herstellung von neuen cephalosporinderivaten.
JPS62174018A (ja)	1987-07-30	細菌性感染症治療剤
JPS5919959B2 (ja)	1984-05-09	トリフルオルメチルニルカプトアセトアミドセフアロスポリン類の製法
US3579501A (en)	1971-05-18	6-(alpha-(3 - guanyl - 1 - ureido)phenyl- or thienyl-acetamido)penicillanic acids
JPS58501377A (ja)	1983-08-18	抗炎症性置換１，２，４−トリアゾロ〔４，３−ｂ〕−１，２，４−トリアジン類
JPS6052718B2 (ja)	1985-11-20	抗菌剤
US3634418A (en)	1972-01-11	3 - azidomethyl - 7-(alpha-aminophenyl(or thienyl)acetamido)ceph - 3 -em-4-oic acids
US4091213A (en)	1978-05-23	7-Cyclizedamino-3-heterothiomethyl cephalosporin derivatives
US3382241A (en)	1968-05-07	Certain orally active cephalosporin antibiotics
JPH085863B2 (ja)	1996-01-24	１４−アニソイルアコニンおよびそれを有効成分とする新規な鎮痛・抗炎症剤
JPS6123197B2 (fr)	1986-06-04
US4026888A (en)	1977-05-31	Certain derivatives of particular 3-thiolated cephalosporins
AU672056B2 (en)	1996-09-19	Cephalosporin salts and process for the preparation thereof
US4061862A (en)	1977-12-06	Derivatives of 7-(cyclized)phenylglycyl-3-triazolo-thio methyl cephalosporin
KR920003902B1 (ko)	1992-05-18	페니실린 유도체의 수화물 및 그 제조방법
US4064345A (en)	1977-12-20	Cephalosporins derivatives 7-cyclized α-amino-3-heterothio
JPH0324477B2 (fr)	1991-04-03
JPS6126548B2 (fr)	1986-06-20
JP2000514832A (ja)	2000-11-07	抗菌性の置換７−アシルアミノ−３−（メチルヒドラゾノ）メチルセファロスポリンおよび中間体
KR880000691B1 (ko)	1988-04-23	세팔렉신의 수용성 유도체의 제조 방법
US4058609A (en)	1977-11-15	7-Dithioacetamido cephalosporins
US4035381A (en)	1977-07-12	Antibacterial agents
US3459749A (en)	1969-08-05	Orally effective cephalosporin antibiotic
US4101657A (en)	1978-07-18	Cephamycins as antibacterial agents
KR840001286B1 (ko)	1984-09-07	2-이미다졸린 유도체류의 제조방법