SK146293A3 - Cefalosporine salts and method of their production - Google Patents

Cefalosporine salts and method of their production Download PDF

Info

Publication number: SK146293A3
Authority: SK; Slovakia
Prior art keywords: salt; cephalosporin; articaine; cefotaxime; water
Prior art date: 1992-12-24

Application number

SK1462-93A

Other languages

English (en)

Slovak (sk)

Inventor

Walter Durckheimer

Dieter Isert

Robert Rippel

Ramazan Rangoonwala

Horst Dornauer

Original Assignee

Hoechst Ag

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.)

1992-12-24

Filing date

1993-12-22

Publication date

1994-12-07

1993-12-22 Application filed by Hoechst Ag filed Critical Hoechst Ag

1994-12-07 Publication of SK146293A3 publication Critical patent/SK146293A3/sk

Links

150000003839 salts Chemical class 0.000 title claims description 72
238000000034 method Methods 0.000 title claims description 6
229940124587 cephalosporin Drugs 0.000 claims abstract description 53
229930186147 Cephalosporin Natural products 0.000 claims abstract description 52
-1 cephalosporin salts Chemical class 0.000 claims abstract description 33
150000001780 cephalosporins Chemical class 0.000 claims abstract description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
229940079593 drug Drugs 0.000 claims abstract 3
229960003831 articaine Drugs 0.000 claims description 43
AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims description 39
229960004261 cefotaxime Drugs 0.000 claims description 21
239000002585 base Substances 0.000 claims description 16
JFPVXVDWJQMJEE-IZRZKJBUSA-N cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CC=CO1 JFPVXVDWJQMJEE-IZRZKJBUSA-N 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
229960001139 cefazolin Drugs 0.000 claims description 10
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 claims description 10
229960001668 cefuroxime Drugs 0.000 claims description 10
NNULBSISHYWZJU-LLKWHZGFSA-N ceftizoxime Chemical compound N([C@@H]1C(N2C(=CCS[C@@H]21)C(O)=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 NNULBSISHYWZJU-LLKWHZGFSA-N 0.000 claims description 9
239000003242 anti bacterial agent Substances 0.000 claims description 8
230000003115 biocidal effect Effects 0.000 claims description 7
VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims description 7
229960001991 ceftizoxime Drugs 0.000 claims description 6
238000007918 intramuscular administration Methods 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
125000002091 cationic group Chemical group 0.000 claims description 5
229960004755 ceftriaxone Drugs 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
QYQDKDWGWDOFFU-IUODEOHRSA-N Cefotiam Chemical compound CN(C)CCN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CC=3N=C(N)SC=3)[C@H]2SC1 QYQDKDWGWDOFFU-IUODEOHRSA-N 0.000 claims description 3
229960001958 cefodizime Drugs 0.000 claims description 3
XDZKBRJLTGRPSS-BGZQYGJUSA-N cefodizime Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(C)=C(CC(O)=O)S1 XDZKBRJLTGRPSS-BGZQYGJUSA-N 0.000 claims description 3
229960001242 cefotiam Drugs 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
MBOSUUFPSTZLRU-MMZRWCAGSA-N (6r,7r)-3-[[4-(2-aminoethylsulfonylamino)-3-hydroxybenzoyl]oxymethyl]-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1COC(=O)C1=CC=C(NS(=O)(=O)CCN)C(O)=C1 MBOSUUFPSTZLRU-MMZRWCAGSA-N 0.000 claims description 2
JWCSIUVGFCSJCK-CAVRMKNVSA-N Disodium Moxalactam Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CO[C@@H]21)C(O)=O)=O)C(=O)C(C(O)=O)C1=CC=C(O)C=C1 JWCSIUVGFCSJCK-CAVRMKNVSA-N 0.000 claims description 2
XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound 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 claims description 2
229960000603 cefalotin Drugs 0.000 claims description 2
229960001817 cefbuperazone Drugs 0.000 claims description 2
SMSRCGPDNDCXFR-CYWZMYCQSA-N cefbuperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]1(OC)C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 SMSRCGPDNDCXFR-CYWZMYCQSA-N 0.000 claims description 2
229960002129 cefixime Drugs 0.000 claims description 2
OKBVVJOGVLARMR-QSWIMTSFSA-N cefixime Chemical compound S1C(N)=NC(C(=N\OCC(O)=O)\C(=O)N[C@@H]2C(N3C(=C(C=C)CS[C@@H]32)C(O)=O)=O)=C1 OKBVVJOGVLARMR-QSWIMTSFSA-N 0.000 claims description 2
229960004682 cefoperazone Drugs 0.000 claims description 2
GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 claims description 2
DZMVCVMFETWNIU-LDYMZIIASA-N ceftezole Chemical compound O=C([C@@H](NC(=O)CN1N=NN=C1)[C@H]1SC2)N1C(C(=O)O)=C2CSC1=NN=CS1 DZMVCVMFETWNIU-LDYMZIIASA-N 0.000 claims description 2
229960004366 ceftezole Drugs 0.000 claims description 2
229960004086 ceftibuten Drugs 0.000 claims description 2
UNJFKXSSGBWRBZ-BJCIPQKHSA-N ceftibuten Chemical compound S1C(N)=NC(C(=C\CC(O)=O)\C(=O)N[C@@H]2C(N3C(=CCS[C@@H]32)C(O)=O)=O)=C1 UNJFKXSSGBWRBZ-BJCIPQKHSA-N 0.000 claims description 2
229960005229 ceftiofur Drugs 0.000 claims description 2
ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 claims description 2
CXHKZHZLDMQGFF-ZSDSSEDPSA-N cefuzonam Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=CN=NS1 CXHKZHZLDMQGFF-ZSDSSEDPSA-N 0.000 claims description 2
229950000807 cefuzonam Drugs 0.000 claims description 2
239000013256 coordination polymer Substances 0.000 claims description 2
229960002878 flomoxef Drugs 0.000 claims description 2
UHRBTBZOWWGKMK-DOMZBBRYSA-N flomoxef Chemical compound O([C@@H]1[C@@](C(N1C=1C(O)=O)=O)(NC(=O)CSC(F)F)OC)CC=1CSC1=NN=NN1CCO UHRBTBZOWWGKMK-DOMZBBRYSA-N 0.000 claims description 2
229960000433 latamoxef Drugs 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
150000003577 thiophenes Chemical class 0.000 claims description 2
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 claims 1
XSPUSVIQHBDITA-KXDGEKGBSA-N (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CN1N=NC(C)=N1 XSPUSVIQHBDITA-KXDGEKGBSA-N 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 claims 1
HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products 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 claims 1
229960003012 cefamandole Drugs 0.000 claims 1
OLVCFLKTBJRLHI-AXAPSJFSSA-N cefamandole Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)[C@H](O)C=3C=CC=CC=3)[C@H]2SC1 OLVCFLKTBJRLHI-AXAPSJFSSA-N 0.000 claims 1
229960002682 cefoxitin Drugs 0.000 claims 1
229950000679 cefteram Drugs 0.000 claims 1
HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
150000001450 anions Chemical class 0.000 abstract description 7
230000000844 anti-bacterial effect Effects 0.000 abstract description 4
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
125000003545 alkoxy group Chemical group 0.000 abstract description 2
230000015572 biosynthetic process Effects 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
229910052736 halogen Chemical group 0.000 abstract 1
150000002367 halogens Chemical group 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
238000000354 decomposition reaction Methods 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
239000013078 crystal Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
QTGIAADRBBLJGA-UHFFFAOYSA-N Articaine Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC QTGIAADRBBLJGA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
229960002727 cefotaxime sodium Drugs 0.000 description 9
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 9
239000012452 mother liquor Substances 0.000 description 9
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000001816 cooling Methods 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
239000000203 mixture Substances 0.000 description 7
QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
229940088710 antibiotic agent Drugs 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229960002279 articaine hydrochloride Drugs 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
235000002906 tartaric acid Nutrition 0.000 description 4
239000011975 tartaric acid Substances 0.000 description 4
JFPVXVDWJQMJEE-QMTHXVAHSA-N Cefuroxime Chemical compound N([C@@H]1C(N2C(=C(COC(N)=O)CS[C@@H]21)C(O)=O)=O)C(=O)C(=NOC)C1=CC=CO1 JFPVXVDWJQMJEE-QMTHXVAHSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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GPRBEKHLDVQUJE-VINNURBNSA-N cefotaxime Chemical compound N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 GPRBEKHLDVQUJE-VINNURBNSA-N 0.000 description 3
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229940046284 zinacef Drugs 0.000 description 3
RJCSCBNYSOVYEY-UHFFFAOYSA-N 2-(propylamino)propanamide Chemical compound CCCNC(C)C(N)=O RJCSCBNYSOVYEY-UHFFFAOYSA-N 0.000 description 2
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
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239000005662 Paraffin oil Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001413 alkali metal ion Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical class [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
ADLFUPFRVXCDMO-LIGXYSTNSA-M ceftizoxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=CCS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 ADLFUPFRVXCDMO-LIGXYSTNSA-M 0.000 description 1
229960000636 ceftizoxime sodium Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004590 computer program Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
FDRNWTJTHBSPMW-BBJOQENWSA-L disodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-1-oxidoethylidene]amino]-3-[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C FDRNWTJTHBSPMW-BBJOQENWSA-L 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
GDWDBGSWGNEMGJ-UHFFFAOYSA-N hydron;methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate;chloride Chemical compound Cl.CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC GDWDBGSWGNEMGJ-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229940081561 rocephin Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
KTAVBOYXMBQFGR-MAODNAKNSA-J tetrasodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-1-oxidoethylidene]amino]-3-[(2-methyl-5,6-dioxo-1h-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C KTAVBOYXMBQFGR-MAODNAKNSA-J 0.000 description 1
238000005406 washing Methods 0.000 description 1

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
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid

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 And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK1462-93A 1992-12-24 1993-12-22 Cefalosporine salts and method of their production SK146293A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4244069A DE4244069A1 (de)	1992-12-24	1992-12-24	Cephalosporinsalze und Verfahren zu deren Herstellung

Publications (1)

Publication Number	Publication Date
SK146293A3 true SK146293A3 (en)	1994-12-07

Family

ID=6476531

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1462-93A SK146293A3 (en)	1992-12-24	1993-12-22	Cefalosporine salts and method of their production

Country Status (27)

Country	Link
EP (1)	EP0603755A3 (zh)
JP (1)	JPH06247974A (zh)
KR (1)	KR940014406A (zh)
CN (1)	CN1093089A (zh)
AU (1)	AU672056B2 (zh)
BR (1)	BR9305213A (zh)
CA (1)	CA2112196A1 (zh)
CZ (1)	CZ285693A3 (zh)
DE (1)	DE4244069A1 (zh)
EC (1)	ECSP930947A (zh)
FI (1)	FI935797L (zh)
HR (1)	HRP931517A2 (zh)
HU (1)	HUT66141A (zh)
IL (1)	IL108134A0 (zh)
MA (1)	MA23070A1 (zh)
MX (1)	MX9308061A (zh)
NO (1)	NO934791L (zh)
NZ (1)	NZ250547A (zh)
OA (1)	OA09846A (zh)
PL (1)	PL301623A1 (zh)
SI (1)	SI9300685A (zh)
SK (1)	SK146293A3 (zh)
TN (1)	TNSN93138A1 (zh)
TW (1)	TW353662B (zh)
UY (1)	UY23683A1 (zh)
YU (1)	YU80593A (zh)
ZA (1)	ZA939609B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8329924B2 (en)	2001-06-11	2012-12-11	Vertex Pharmaceuticals (Canada) Incorporated	Compounds and methods for the treatment or prevention of Flavivirus infections
SI1401825T1 (sl)	2001-06-11	2010-01-29	Virochem Pharma Inc	Tiofenski derivati kot protivirusna sredstva za flavirusno infekcijo

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1643325B2 (de) *	1967-07-07	1976-05-06	Hoechst Ag, 6000 Frankfurt	3-aminoacylaminothiophene und verfahren zu ihrer herstellung

1992
- 1992-12-24 DE DE4244069A patent/DE4244069A1/de not_active Withdrawn
1993
- 1993-06-28 EC EC1993000947A patent/ECSP930947A/es unknown
- 1993-09-17 TW TW082107623A patent/TW353662B/zh active
- 1993-12-09 UY UY23683A patent/UY23683A1/es unknown
- 1993-12-16 MX MX9308061A patent/MX9308061A/es unknown
- 1993-12-17 EP EP9393120375A patent/EP0603755A3/en not_active Withdrawn
- 1993-12-21 CZ CZ932856A patent/CZ285693A3/cs unknown
- 1993-12-22 SK SK1462-93A patent/SK146293A3/sk unknown
- 1993-12-22 IL IL10813493A patent/IL108134A0/xx unknown
- 1993-12-22 CA CA002112196A patent/CA2112196A1/en not_active Abandoned
- 1993-12-22 ZA ZA939609A patent/ZA939609B/xx unknown
- 1993-12-22 YU YU80593A patent/YU80593A/sh unknown
- 1993-12-22 JP JP5323921A patent/JPH06247974A/ja active Pending
- 1993-12-22 AU AU52667/93A patent/AU672056B2/en not_active Ceased
- 1993-12-22 FI FI935797A patent/FI935797L/fi not_active Application Discontinuation
- 1993-12-22 NZ NZ250547A patent/NZ250547A/en unknown
- 1993-12-23 NO NO934791A patent/NO934791L/no unknown
- 1993-12-23 BR BR9305213A patent/BR9305213A/pt not_active Application Discontinuation
- 1993-12-23 HU HU9303747A patent/HUT66141A/hu unknown
- 1993-12-23 CN CN93112787A patent/CN1093089A/zh active Pending
- 1993-12-23 TN TNTNSN93138A patent/TNSN93138A1/fr unknown
- 1993-12-23 PL PL93301623A patent/PL301623A1/xx unknown
- 1993-12-23 HR HR931517A patent/HRP931517A2/hr not_active Application Discontinuation
- 1993-12-24 SI SI9300685A patent/SI9300685A/sl unknown
- 1993-12-24 MA MA23380A patent/MA23070A1/fr unknown
- 1993-12-24 KR KR1019930029471A patent/KR940014406A/ko not_active Application Discontinuation
- 1993-12-24 OA OA60452A patent/OA09846A/fr unknown

Also Published As

Publication number	Publication date
AU5266793A (en)	1994-07-07
NZ250547A (en)	1995-08-28
IL108134A0 (en)	1994-04-12
EP0603755A3 (en)	1994-09-28
HUT66141A (en)	1994-09-28
DE4244069A1 (de)	1994-06-30
PL301623A1 (en)	1994-06-27
TW353662B (en)	1999-03-01
YU80593A (sh)	1996-10-09
NO934791L (no)	1994-06-27
ZA939609B (en)	1994-08-11
EP0603755A2 (de)	1994-06-29
MX9308061A (es)	1994-06-30
CA2112196A1 (en)	1994-06-25
CN1093089A (zh)	1994-10-05
OA09846A (fr)	1994-08-15
HU9303747D0 (en)	1994-04-28
NO934791D0 (no)	1993-12-23
JPH06247974A (ja)	1994-09-06
BR9305213A (pt)	1994-07-26
AU672056B2 (en)	1996-09-19
FI935797L (fi)	1994-06-25
MA23070A1 (fr)	1994-07-01
CZ285693A3 (en)	1994-07-13
SI9300685A (en)	1994-06-30
ECSP930947A (es)	1994-11-16
FI935797A0 (fi)	1993-12-22
UY23683A1 (es)	1993-12-17
HRP931517A2 (en)	1994-12-31
TNSN93138A1 (fr)	1994-03-17
KR940014406A (ko)	1994-07-18

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MXPA02000033A (es)	2002-07-02	Polimorfos de un diclorhidrato cristalino de azobiciclo (2, 2, 2)oct-3-ilamina y sus composiciones farmaceuticas.
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