NL8203482A - Cefalosporine-chinolinium-betainen. - Google Patents

Cefalosporine-chinolinium-betainen. Download PDF

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Publication number: NL8203482A
Authority: NL; Netherlands
Prior art keywords: group; formula; amino; alkyl; substituted
Prior art date: 1981-09-08

Application number

NL8203482A

Other languages

English (en)

Dutch (nl)

Original Assignee

Lilly Co Eli

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.)

1981-09-08

Filing date

1982-09-07

Publication date

1983-04-05

1982-09-07 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1983-04-05 Publication of NL8203482A publication Critical patent/NL8203482A/nl

Links

-1 amino, hydroxyl Chemical group 0.000 claims description 117
150000001875 compounds Chemical class 0.000 claims description 72
150000003839 salts Chemical class 0.000 claims description 23
230000003115 biocidal effect Effects 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229940124587 cephalosporin Drugs 0.000 claims description 18
239000003242 anti bacterial agent Substances 0.000 claims description 17
229930186147 Cephalosporin Natural products 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 11
150000001780 cephalosporins Chemical class 0.000 claims description 11
150000002431 hydrogen Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000006239 protecting group Chemical group 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
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 description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical group [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000002837 carbocyclic group Chemical group 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 29
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 26
239000002253 acid Substances 0.000 description 25
238000000034 method Methods 0.000 description 25
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
238000002360 preparation method Methods 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
229940088710 antibiotic agent Drugs 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
230000010933 acylation Effects 0.000 description 13
238000005917 acylation reaction Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
MSPCIZMDDUQPGJ-UHFFFAOYSA-N N-methyl-N-(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)N(C)C(=O)C(F)(F)F MSPCIZMDDUQPGJ-UHFFFAOYSA-N 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
239000000203 mixture Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
150000003248 quinolines Chemical class 0.000 description 9
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000005947 deacylation reaction Methods 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
244000005700 microbiome Species 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000006884 silylation reaction Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
230000002441 reversible effect Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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 3
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
208000035473 Communicable disease Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 3
HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
230000001717 pathogenic effect Effects 0.000 description 3
239000012264 purified product Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 description 2
YIFZKLFTSGGGQW-UHFFFAOYSA-N 5-(trifluoromethyl)quinoline Chemical compound C1=CC=C2C(C(F)(F)F)=CC=CC2=N1 YIFZKLFTSGGGQW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
230000006181 N-acylation Effects 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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150000001450 anions Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
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230000000694 effects Effects 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
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UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
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LEWDKQKVAFOMPI-UHFFFAOYSA-N quinoline-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=NC2=C1 LEWDKQKVAFOMPI-UHFFFAOYSA-N 0.000 description 2
238000004448 titration Methods 0.000 description 2
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125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
102100027324 2-hydroxyacyl-CoA lyase 1 Human genes 0.000 description 1
SNOUUOAHKFPCAK-UHFFFAOYSA-N 2-hydroxyimino-2-(1H-pyrazol-5-yl)acetic acid Chemical compound ON=C(C(O)=O)C1=CC=NN1 SNOUUOAHKFPCAK-UHFFFAOYSA-N 0.000 description 1
PBZUAIHRZUBBAJ-UHFFFAOYSA-N 2-hydroxyiminoacetic acid Chemical compound ON=CC(O)=O PBZUAIHRZUBBAJ-UHFFFAOYSA-N 0.000 description 1
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RIVWMKJAARUHDW-UHFFFAOYSA-N 3-ethylquinoline-6-carbonitrile Chemical group C1=CC(C#N)=CC2=CC(CC)=CN=C21 RIVWMKJAARUHDW-UHFFFAOYSA-N 0.000 description 1
LEKRLCOTKUTART-UHFFFAOYSA-N 3-ethylquinoline-6-carboxamide Chemical compound C1=CC(C(N)=O)=CC2=CC(CC)=CN=C21 LEKRLCOTKUTART-UHFFFAOYSA-N 0.000 description 1
BMFXRNKKJGBMEH-UHFFFAOYSA-N 3-hydroxyquinoline-5-carbonitrile Chemical compound C1=CC=C(C#N)C2=CC(O)=CN=C21 BMFXRNKKJGBMEH-UHFFFAOYSA-N 0.000 description 1
LRIOBKKSONRPSN-UHFFFAOYSA-N 3-methoxyquinolin-5-amine Chemical compound C1=CC=C(N)C2=CC(OC)=CN=C21 LRIOBKKSONRPSN-UHFFFAOYSA-N 0.000 description 1
AQCRFDKOKZGTDE-UHFFFAOYSA-N 3-methoxyquinoline Chemical compound C1=CC=CC2=CC(OC)=CN=C21 AQCRFDKOKZGTDE-UHFFFAOYSA-N 0.000 description 1
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241000588914 Enterobacter Species 0.000 description 1
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238000006460 hydrolysis reaction Methods 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
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239000007924 injection Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
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229910052740 iodine Chemical group 0.000 description 1
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238000002156 mixing Methods 0.000 description 1
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FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 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
150000003140 primary amides Chemical class 0.000 description 1
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FLGKQMOTLCGOQH-UHFFFAOYSA-N quinolin-3-ylmethanol Chemical compound C1=CC=CC2=CC(CO)=CN=C21 FLGKQMOTLCGOQH-UHFFFAOYSA-N 0.000 description 1
XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 description 1
OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
RZAUIOKDXQWSQE-UHFFFAOYSA-N quinolin-7-amine Chemical compound C1=CC=NC2=CC(N)=CC=C21 RZAUIOKDXQWSQE-UHFFFAOYSA-N 0.000 description 1
XCRPPAPDRUBKRJ-UHFFFAOYSA-N quinolin-7-ol Chemical compound C1=CC=NC2=CC(O)=CC=C21 XCRPPAPDRUBKRJ-UHFFFAOYSA-N 0.000 description 1
KDYVCOSVYOSHOL-UHFFFAOYSA-N quinolin-7-ylmethanamine Natural products C1=CC=NC2=CC(C)=CC=C21 KDYVCOSVYOSHOL-UHFFFAOYSA-N 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-O quinolin-8-yloxidanium Chemical compound C1=C[NH+]=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-O 0.000 description 1
RYGIHSLRMNXWCN-UHFFFAOYSA-N quinoline-3-carbaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CN=C21 RYGIHSLRMNXWCN-UHFFFAOYSA-N 0.000 description 1
QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical group C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 description 1
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
UJRYDUDEJGXDNA-UHFFFAOYSA-N quinoline-4-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=NC2=C1 UJRYDUDEJGXDNA-UHFFFAOYSA-N 0.000 description 1
CKKBFRWSTPFAHR-UHFFFAOYSA-N quinoline-5-carbonitrile Chemical group C1=CC=C2C(C#N)=CC=CC2=N1 CKKBFRWSTPFAHR-UHFFFAOYSA-N 0.000 description 1
LZHJFZLHEGJWAU-UHFFFAOYSA-N quinoline-5-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=N1 LZHJFZLHEGJWAU-UHFFFAOYSA-N 0.000 description 1
KVGSJGNWRDPVKA-UHFFFAOYSA-N quinoline-5-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=N1 KVGSJGNWRDPVKA-UHFFFAOYSA-N 0.000 description 1
VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000005389 trialkylsiloxy group Chemical group 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
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Classifications

- 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
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
- 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

Landscapes

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

NL8203482A 1981-09-08 1982-09-07 Cefalosporine-chinolinium-betainen. NL8203482A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/300,131 US4396620A (en)	1981-09-08	1981-09-08	Cephalosporin quinolinium betaines
US30013181		1981-09-08

Publications (1)

Publication Number	Publication Date
NL8203482A true NL8203482A (nl)	1983-04-05

Family

ID=23157840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8203482A NL8203482A (nl)	1981-09-08	1982-09-07	Cefalosporine-chinolinium-betainen.

Country Status (11)

Country	Link
US (1)	US4396620A (fr)
JP (1)	JPS5857387A (fr)
AU (1)	AU550341B2 (fr)
BE (1)	BE894334A (fr)
DE (1)	DE3233376A1 (fr)
FR (1)	FR2512449B1 (fr)
GB (1)	GB2105335B (fr)
IL (1)	IL66811A0 (fr)
IT (1)	IT1158050B (fr)
NL (1)	NL8203482A (fr)
ZA (1)	ZA826540B (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1582884A (en) *	1977-05-19	1981-01-14	Beecham Group Ltd	Clavulanic acid derivatives their preparation and use
ZA804670B (en) *	1979-08-03	1981-07-29	Beecham Group Ltd	Derivatives of clavulanic acid, a process for their preparation and their use
EP0053893B1 (fr) *	1980-12-09	1985-03-20	Beecham Group Plc	Dérivés de l'acide clavulanique, leur préparation et leur application
US4562182A (en) *	1980-12-23	1985-12-31	Beecham Group P.L.C.	Compounds containing beta-lactams
DE3207840A1 (de) *	1982-03-04	1983-09-15	Hoechst Ag, 6230 Frankfurt	"cephalosporinderivate und verfahren zu ihrer herstellung"
DE3247614A1 (de) *	1982-12-23	1984-07-05	Hoechst Ag, 6230 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
DE3316798A1 (de) *	1983-05-07	1984-11-08	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von cephemverbindungen
DE3316797A1 (de) *	1983-05-07	1984-11-08	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von cephemverbindungen
EP0137442A3 (fr) *	1983-10-08	1986-01-15	Hoechst Aktiengesellschaft	Dérivés de céphalosporine et procédé pour leur préparation
GB8401093D0 (en) *	1984-01-16	1984-02-15	Fujisawa Pharmaceutical Co	Cephem compounds
DE3419012A1 (de) *	1984-05-22	1985-11-28	Bayer Ag, 5090 Leverkusen	Ss-lactamantibiotika, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel oder wachstumsfoerderer in der tieraufzucht oder als antioxidantien
ATE121746T1 (de) *	1984-11-23	1995-05-15	Biochemie Gmbh	Verfahren zur herstellung bissilylierter 3- iodmethylcephalosporinderivaten.
ES8704943A1 (es) *	1984-12-27	1987-04-16	Banyu Pharma Co Ltd	Un procedimiento para la fabricacion de derivados de cefalosporina.
ATE89826T1 (de) *	1985-03-01	1993-06-15	Takeda Chemical Industries Ltd	Antibakterielle verbindungen, ihre herstellung und verwendung.
US4703118A (en) *	1985-04-08	1987-10-27	Eli Lilly And Company	Synthesis of 3-iodomethyl cephalosporins
US4749522A (en) *	1985-10-31	1988-06-07	Angio-Medical Corporation	Supercritical fluid extraction of animal derived materials
US4814328A (en) *	1986-03-19	1989-03-21	Banyu Pharmaceutical Co., Ltd.	Cephalosporin derivatives, and antibacterial agents
US5147871A (en) *	1986-07-03	1992-09-15	Hoffmann La-Roche, Inc.	Anti-bacterial cephalosporin compounds
NZ227470A (en) *	1987-12-28	1991-06-25	Hoffmann La Roche	Acyl derivatives of substituted cephem compounds; pharmaceutical compositions and methods for preparation and treatment
US5019571A (en) *	1988-01-25	1991-05-28	Eli Lilly And Company	1-carbacephalosporin antibiotics
DE3910421A1 (de) *	1989-03-31	1990-10-04	Hoechst Ag	Polare cephalosporinderivate und verfahren zu ihrer herstellung
US5159077A (en) *	1989-07-21	1992-10-27	Hoffmann-La Roche Inc.	Penam antibacterial compounds
US5162523A (en) *	1989-07-21	1992-11-10	Hoffmann-La Roche Inc.	Cephalosporin antibacterial compounds
FR2873695A1 (fr) *	2004-07-30	2006-02-03	Palumed Sa	Molecules hybrides qa ou q est une aminoquinoleine et a est un antibiotique ou un inhibiteur de resistance), leur synthese et leurs utilisations en tant qu'agent antibacterien

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE786271A (fr) *	1971-07-17	1973-01-15	Takeda Chemical Industries Ltd	Cephalosporines
US4160830A (en) *	1971-07-17	1979-07-10	Takeda Chemical Industries, Ltd.	Cephalosporins
DK154939C (da) *	1974-12-19	1989-06-12	Takeda Chemical Industries Ltd	Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
DE2760123C2 (de) *	1976-01-23	1986-04-30	Roussel-Uclaf, Paris	7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
DE2760484C2 (fr) *	1976-04-14	1992-12-03	Takeda Chemical Industries, Ltd., Osaka, Jp
JPS6011713B2 (ja) *	1976-09-08	1985-03-27	武田薬品工業株式会社	セフアロスポリン誘導体およびその製造法
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
JPS609719B2 (ja) *	1977-08-06	1985-03-12	武田薬品工業株式会社	セフアロスポリン誘導体およびその製造法
FR2410655A1 (fr) *	1977-12-05	1979-06-29	Roussel Uclaf	Nouvelles oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments

1981
- 1981-09-08 US US06/300,131 patent/US4396620A/en not_active Expired - Fee Related
1982
- 1982-09-07 NL NL8203482A patent/NL8203482A/nl not_active Application Discontinuation
- 1982-09-07 IT IT23152/82A patent/IT1158050B/it active
- 1982-09-07 FR FR8215171A patent/FR2512449B1/fr not_active Expired
- 1982-09-07 GB GB08225404A patent/GB2105335B/en not_active Expired
- 1982-09-07 BE BE6/47714A patent/BE894334A/fr not_active IP Right Cessation
- 1982-09-07 AU AU88090/82A patent/AU550341B2/en not_active Expired - Fee Related
- 1982-09-07 ZA ZA826540A patent/ZA826540B/xx unknown
- 1982-09-08 DE DE19823233376 patent/DE3233376A1/de not_active Withdrawn
- 1982-09-08 JP JP57157973A patent/JPS5857387A/ja active Pending
- 1982-09-16 IL IL66811A patent/IL66811A0/xx unknown

Also Published As

Publication number	Publication date
GB2105335B (en)	1985-05-15
IT1158050B (it)	1987-02-18
DE3233376A1 (de)	1983-03-24
AU550341B2 (en)	1986-03-20
GB2105335A (en)	1983-03-23
IL66811A0 (en)	1982-12-31
IT8223152A0 (it)	1982-09-07
JPS5857387A (ja)	1983-04-05
BE894334A (fr)	1983-03-07
FR2512449B1 (fr)	1986-04-18
ZA826540B (en)	1984-04-25
FR2512449A1 (fr)	1983-03-11
AU8809082A (en)	1983-03-17
US4396620A (en)	1983-08-02

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-05-04	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8203482A (nl)	1983-04-05	Cefalosporine-chinolinium-betainen.
US4396619A (en)	1983-08-02	Cephalosporin betaines
US4402955A (en)	1983-09-06	Dioximino cephalosporin antibiotics
JPH05502884A (ja)	1993-05-20	新規３―置換セフェム化合物及びその製造方法
CA1225390A (fr)	1987-08-11	Cephalosporines 3-bicyclopyridinium-methyliques
US4785090A (en)	1988-11-15	Cephalosporin derivatives
US4692443A (en)	1987-09-08	3-bicyclicpyridinium-methyl cephalosporins
EP0074268A2 (fr)	1983-03-16	Dérivés de céphalosporines thiéno- et furopyridinium substitués
DE3854684T2 (de)	1996-03-28	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate.
US5202315A (en)	1993-04-13	Cephalosporin compounds
US4501739A (en)	1985-02-26	Thieno and furopyridinium-substituted cephalosporins
US4748172A (en)	1988-05-31	3-bicyclicpyridinium-methyl cephalosporins
IE54050B1 (en)	1989-05-24	Pyrazinium substituted cephalosporins
US4382932A (en)	1983-05-10	Isoquinolinium substituted cephalosporins
US4577014A (en)	1986-03-18	Thieno and furopyridinium-substituted cephalosporins
CS248714B2 (en)	1987-02-12	Production method of new 7-(2 syn-oxomino-(5 amino-1,2,4-thiadiazol-3-y)cefeme derivatives
US4450270A (en)	1984-05-22	Dioximino cephalosporin antibiotics
US4382931A (en)	1983-05-10	3'-Substituted quinolinium cephalosporins
JPS5857390A (ja)	1983-04-05	チエノ−およびフロ−ピリジニウム置換セフアロスポリン誘導体
EP0193858B1 (fr)	1991-11-27	Dérivés de 1-oxa-1-déthia-céphalosporine et agent antibactérien les contenant
JPS62158282A (ja)	1987-07-14	１−カルバセフアロスポリン抗生物質
KR920002848B1 (ko)	1992-04-06	신규한 세팔로스포린 화합물과 그의 제조방법
KR0154901B1 (ko)	1998-11-16	신규 세팔로스포린계 항생제(v)
JPH04266889A (ja)	1992-09-22	抗生物質ｃ−３カテコ−ル−置換セファロスボリン化合物、組成物およびその使用法
US4857521A (en)	1989-08-15	Trialkylsilyl pyridinium cephalosporin antibiotics