HRP931517A2 - Cefalosporin salts and a process for the preparation thereof - Google Patents

Cefalosporin salts and a process for the preparation thereof Download PDF

Info

Publication number: HRP931517A2
Authority: HR; Croatia
Prior art keywords: cephalosporin; salt; articaine; salt according; cefotaxime
Prior art date: 1992-12-24

Application number

HR931517A

Other languages

English (en)

Croatian (hr)

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

1993-12-23

Publication date

1994-12-31

1993-12-23 Application filed by Hoechst Ag filed Critical Hoechst Ag

1994-12-31 Publication of HRP931517A2 publication Critical patent/HRP931517A2/hr

Links

150000003839 salts Chemical class 0.000 title claims description 39
238000000034 method Methods 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 3
229940124587 cephalosporin Drugs 0.000 claims description 46
229930186147 Cephalosporin Natural products 0.000 claims description 45
-1 Cephalosporin salt Chemical class 0.000 claims description 35
QTGIAADRBBLJGA-UHFFFAOYSA-N Articaine Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC QTGIAADRBBLJGA-UHFFFAOYSA-N 0.000 claims description 29
150000001780 cephalosporins Chemical class 0.000 claims description 25
229960003831 articaine Drugs 0.000 claims description 23
239000002585 base Substances 0.000 claims description 20
229960004261 cefotaxime Drugs 0.000 claims description 12
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 11
238000004519 manufacturing process Methods 0.000 claims description 11
229960001668 cefuroxime Drugs 0.000 claims description 7
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 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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 6
229960004755 ceftriaxone Drugs 0.000 claims description 6
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 6
150000001875 compounds Chemical class 0.000 claims description 6
238000007918 intramuscular administration Methods 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
230000003115 biocidal effect Effects 0.000 claims description 5
125000002091 cationic group Chemical group 0.000 claims description 5
229960001139 cefazolin Drugs 0.000 claims description 5
229960001991 ceftizoxime Drugs 0.000 claims description 5
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 5
238000000926 separation method Methods 0.000 claims description 5
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 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
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 3
239000003814 drug Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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 description 2
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 2
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 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
229960000603 cefalotin Drugs 0.000 claims description 2
229960003012 cefamandole Drugs 0.000 claims description 2
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 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
229950006550 cefdaloxime Drugs 0.000 claims description 2
HOGISBSFFHDTRM-GHXIOONMSA-N cefdaloxime Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC)C(O)=O)C(=O)C(=N/O)\C1=CSC(N)=N1 HOGISBSFFHDTRM-GHXIOONMSA-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
229960003791 cefmenoxime Drugs 0.000 claims description 2
HJJDBAOLQAWBMH-YCRCPZNHSA-N cefmenoxime 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=NN=NN1C HJJDBAOLQAWBMH-YCRCPZNHSA-N 0.000 claims description 2
229960002025 cefminox Drugs 0.000 claims description 2
JSDXOWVAHXDYCU-VXSYNFHWSA-N cefminox Chemical compound S([C@@H]1[C@@](C(N1C=1C(O)=O)=O)(NC(=O)CSC[C@@H](N)C(O)=O)OC)CC=1CSC1=NN=NN1C JSDXOWVAHXDYCU-VXSYNFHWSA-N 0.000 claims description 2
229960004489 cefonicid Drugs 0.000 claims description 2
DYAIAHUQIPBDIP-AXAPSJFSSA-N cefonicid Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](O)C=2C=CC=CC=2)CC=1CSC1=NN=NN1CS(O)(=O)=O DYAIAHUQIPBDIP-AXAPSJFSSA-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
SRZNHPXWXCNNDU-RHBCBLIFSA-N cefotetan Chemical compound N([C@]1(OC)C(N2C(=C(CSC=3N(N=NN=3)C)CS[C@@H]21)C(O)=O)=O)C(=O)C1SC(=C(C(N)=O)C(O)=O)S1 SRZNHPXWXCNNDU-RHBCBLIFSA-N 0.000 claims description 2
229960005495 cefotetan Drugs 0.000 claims description 2
229960001242 cefotiam Drugs 0.000 claims description 2
229960002682 cefoxitin Drugs 0.000 claims description 2
LNZMRLHZGOBKAN-KAWPREARSA-N cefpimizole Chemical compound N1=CNC(C(=O)N[C@@H](C(=O)N[C@@H]2C(N3C(=C(C[N+]=4C=CC(CCS(O)(=O)=O)=CC=4)CS[C@@H]32)C([O-])=O)=O)C=2C=CC=CC=2)=C1C(=O)O LNZMRLHZGOBKAN-KAWPREARSA-N 0.000 claims description 2
229950004036 cefpimizole Drugs 0.000 claims description 2
229960005446 cefpiramide Drugs 0.000 claims description 2
PWAUCHMQEXVFJR-PMAPCBKXSA-N cefpiramide Chemical compound C1=NC(C)=CC(O)=C1C(=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 PWAUCHMQEXVFJR-PMAPCBKXSA-N 0.000 claims description 2
229960000484 ceftazidime Drugs 0.000 claims description 2
NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 claims description 2
229950000679 cefteram Drugs 0.000 claims description 2
229960004366 ceftezole Drugs 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
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
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims description 2
239000013256 coordination polymer Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
150000003577 thiophenes Chemical class 0.000 claims description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
235000002639 sodium chloride Nutrition 0.000 description 44
239000000243 solution Substances 0.000 description 43
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 20
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 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000013078 crystal Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
229960002279 articaine hydrochloride Drugs 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
239000012452 mother liquor Substances 0.000 description 9
229960002727 cefotaxime sodium Drugs 0.000 description 8
238000001816 cooling Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000005457 ice water Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
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
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000004108 freeze drying Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 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
URDOHUPGIOGTKV-JTBFTWTJSA-M Cefuroxime sodium Chemical compound [Na+].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 URDOHUPGIOGTKV-JTBFTWTJSA-M 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [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 3
229960000534 cefuroxime sodium Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000284 extract Substances 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000017550 sodium carbonate Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229940046284 zinacef Drugs 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
WJQWYZIFAQBREB-UHFFFAOYSA-N Cl.CC=1C(=C(SC1)C(=O)OCC)NC(C(C)NCCC)=O Chemical compound Cl.CC=1C(=C(SC1)C(=O)OCC)NC(C(C)NCCC)=O WJQWYZIFAQBREB-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 2
239000001358 L(+)-tartaric acid Substances 0.000 description 2
235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229960003408 cefazolin sodium Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002168 ethanoic acid esters Chemical class 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000047 product Substances 0.000 description 2
VNRUVEZSCGNWDL-UHFFFAOYSA-N propyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate hydrochloride Chemical compound Cl.CC=1C(=C(SC1)C(=O)OCCC)NC(C(C)NCCC)=O VNRUVEZSCGNWDL-UHFFFAOYSA-N 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000008719 thickening Effects 0.000 description 2
QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 2
OLZGWRMESNXXHN-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate Chemical compound OC(=O)C(O)C(O)C(O)=O.CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OC OLZGWRMESNXXHN-UHFFFAOYSA-N 0.000 description 1
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
YCJOLFSBNPBIRE-UHFFFAOYSA-N Cl.CC=1C(=C(SC1)C(=O)OCCCCCCCC)NC(C(C)NCCC)=O Chemical compound Cl.CC=1C(=C(SC1)C(=O)OCCCCCCCC)NC(C(C)NCCC)=O YCJOLFSBNPBIRE-UHFFFAOYSA-N 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
238000002768 Kirby-Bauer method Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FGUPDJCDZLLQSM-UHFFFAOYSA-N N-(2-butyl-4-methylthiophen-3-yl)-2-(propylamino)propanamide Chemical compound C(CCC)C=1SC=C(C=1NC(C(C)NCCC)=O)C FGUPDJCDZLLQSM-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
NKTMOCGRPXOQQS-UHFFFAOYSA-N benzyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate Chemical compound CC1=CSC(C(=O)OCC=2C=CC=CC=2)=C1NC(=O)C(C)NCCC NKTMOCGRPXOQQS-UHFFFAOYSA-N 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
DEJNSXMLZVCRLO-UHFFFAOYSA-N butyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate Chemical compound CCCCOC(=O)C=1SC=C(C)C=1NC(=O)C(C)NCCC DEJNSXMLZVCRLO-UHFFFAOYSA-N 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
150000001768 cations Chemical class 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
UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004590 computer program 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
238000004090 dissolution Methods 0.000 description 1
PAGIBGJDQXJNKV-UHFFFAOYSA-N ethyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OCC PAGIBGJDQXJNKV-UHFFFAOYSA-N 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
238000001914 filtration Methods 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 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
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
DCTDHLFKDIIPGD-UHFFFAOYSA-N methyl 4,5-dimethyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate;hydrochloride Chemical compound Cl.CCCNC(C)C(=O)NC=1C(C)=C(C)SC=1C(=O)OC DCTDHLFKDIIPGD-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 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
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
JOXJWSVTGQYDOC-UHFFFAOYSA-N propyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate Chemical compound CCCNC(C)C(=O)NC=1C(C)=CSC=1C(=O)OCCC JOXJWSVTGQYDOC-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229940081561 rocephin Drugs 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 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
238000002560 therapeutic procedure Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 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)

HR931517A 1992-12-24 1993-12-23 Cefalosporin salts and a process for the preparation thereof HRP931517A2 (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
HRP931517A2 true HRP931517A2 (en)	1994-12-31

Family

ID=6476531

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR931517A HRP931517A2 (en)	1992-12-24	1993-12-23	Cefalosporin salts and a process for the preparation thereof

Country Status (27)

Country	Link
EP (1)	EP0603755A3 (hu)
JP (1)	JPH06247974A (hu)
KR (1)	KR940014406A (hu)
CN (1)	CN1093089A (hu)
AU (1)	AU672056B2 (hu)
BR (1)	BR9305213A (hu)
CA (1)	CA2112196A1 (hu)
CZ (1)	CZ285693A3 (hu)
DE (1)	DE4244069A1 (hu)
EC (1)	ECSP930947A (hu)
FI (1)	FI935797A (hu)
HR (1)	HRP931517A2 (hu)
HU (1)	HUT66141A (hu)
IL (1)	IL108134A0 (hu)
MA (1)	MA23070A1 (hu)
MX (1)	MX9308061A (hu)
NO (1)	NO934791L (hu)
NZ (1)	NZ250547A (hu)
OA (1)	OA09846A (hu)
PL (1)	PL301623A1 (hu)
SI (1)	SI9300685A (hu)
SK (1)	SK146293A3 (hu)
TN (1)	TNSN93138A1 (hu)
TW (1)	TW353662B (hu)
UY (1)	UY23683A1 (hu)
YU (1)	YU80593A (hu)
ZA (1)	ZA939609B (hu)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6881741B2 (en)	2001-06-11	2005-04-19	Virochem Pharma Inc.	Compounds and methods for the treatment or prevention of Flavivirus infections
US8329924B2 (en)	2001-06-11	2012-12-11	Vertex Pharmaceuticals (Canada) Incorporated	Compounds and methods for the treatment or prevention of Flavivirus infections

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 AU AU52667/93A patent/AU672056B2/en not_active Ceased
- 1993-12-22 CA CA002112196A patent/CA2112196A1/en not_active Abandoned
- 1993-12-22 FI FI935797A patent/FI935797A/fi not_active Application Discontinuation
- 1993-12-22 ZA ZA939609A patent/ZA939609B/xx unknown
- 1993-12-22 YU YU80593A patent/YU80593A/sh unknown
- 1993-12-22 IL IL10813493A patent/IL108134A0/xx unknown
- 1993-12-22 JP JP5323921A patent/JPH06247974A/ja active Pending
- 1993-12-22 NZ NZ250547A patent/NZ250547A/en unknown
- 1993-12-22 SK SK1462-93A patent/SK146293A3/sk unknown
- 1993-12-23 BR BR9305213A patent/BR9305213A/pt not_active Application Discontinuation
- 1993-12-23 PL PL93301623A patent/PL301623A1/xx unknown
- 1993-12-23 NO NO934791A patent/NO934791L/no unknown
- 1993-12-23 HR HR931517A patent/HRP931517A2/hr not_active Application Discontinuation
- 1993-12-23 TN TNTNSN93138A patent/TNSN93138A1/fr unknown
- 1993-12-23 CN CN93112787A patent/CN1093089A/zh active Pending
- 1993-12-23 HU HU9303747A patent/HUT66141A/hu unknown
- 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
CZ285693A3 (en)	1994-07-13
NO934791D0 (no)	1993-12-23
JPH06247974A (ja)	1994-09-06
HU9303747D0 (en)	1994-04-28
AU5266793A (en)	1994-07-07
ECSP930947A (es)	1994-11-16
NZ250547A (en)	1995-08-28
FI935797A0 (fi)	1993-12-22
TW353662B (en)	1999-03-01
BR9305213A (pt)	1994-07-26
ZA939609B (en)	1994-08-11
NO934791L (no)	1994-06-27
HUT66141A (en)	1994-09-28
CN1093089A (zh)	1994-10-05
OA09846A (fr)	1994-08-15
AU672056B2 (en)	1996-09-19
PL301623A1 (en)	1994-06-27
SK146293A3 (en)	1994-12-07
TNSN93138A1 (fr)	1994-03-17
DE4244069A1 (de)	1994-06-30
MX9308061A (es)	1994-06-30
KR940014406A (ko)	1994-07-18
EP0603755A2 (de)	1994-06-29
CA2112196A1 (en)	1994-06-25
UY23683A1 (es)	1993-12-17
EP0603755A3 (en)	1994-09-28
IL108134A0 (en)	1994-04-12
FI935797A (fi)	1994-06-25
YU80593A (sh)	1996-10-09
SI9300685A (en)	1994-06-30
MA23070A1 (fr)	1994-07-01

Publication	Publication Date	Title
RU2125571C1 (ru)	1999-01-27	СОЛЬ 7-([1α,5α,6α]-6-АМИНО-3-АЗАБИЦИКЛО [3.1.0] ГЕКС-3-ИЛ)-6-ФТОР-1-(2,4-ДИФТОРФЕНИЛ)-1,4- ДИГИДРО-4-ОКСО-1,8-НАФТИРИДИН-3-КАРБОНОВОЙ И МЕТАНСУЛЬФОНОВОЙ КИСЛОТ И СПОСОБ ЕЕ ПОЛУЧЕНИЯ
KR101978364B1 (ko)	2019-05-14	알킬카바모일 나프탈렌일옥시 옥테노일 하이드록시아마이드 또는 그 유도체의 약학적으로 허용 가능한 염 및 그 제조방법
DK166211B (da)	1993-03-22	Krystalliseret cephem-syreadditionssalt, dets fremstilling og anvendelse
DD262658A5 (de)	1988-12-07	Verfahren zur herstellung von oxidiazolylalkylpurin-derivaten
JPH0428269B2 (hu)	1992-05-13
CS207646B2 (en)	1981-08-31	Method of making the crystallic hydrated form of the sodium salt of the oximine derivative of the 7-aminothiazolylacetamidocephalosporan acid
HRP931517A2 (en)	1994-12-31	Cefalosporin salts and a process for the preparation thereof
CS195746B2 (en)	1980-02-29	Process for preparing crystalline methanolate of natrium salt of cephamandole
HRP20010920A2 (en)	2003-02-28	Polymorphs of crystalline (2-benzhydryl-1-azabicyclo[2,2,2]oct-3-yl)-(5-isopropyl-2-methoxybenzyl)-ammoniumchloride as nk-1 receptor antagonists
AU704115B2 (en)	1999-04-15	Zwitterionic forms of trovafloxacin
JP2511083B2 (ja)	1996-06-26	［３ｓ（ｚ）］−２−［［［１−（２−アミノ−４−チアゾリル）−２−［［２，２−ジメチル−４−オキソ−１−（スルホオキシ）−３−アゼチジニル］アミノ］−２−オキソエチリデン］アミノ］オキシ］酢酸の結晶塩
KR100696422B1 (ko)	2007-03-20	항생물질로서 사이클릭 아미노구아니딘 치환체를 가진세팔로스포린
JPS588082A (ja)	1983-01-18	置換されたピロロ〔２，１−ｂ〕キナゾリンおよびピリド〔２，１−ｂ〕キナゾリンおよびそれらの製造法
DE2258088A1 (de)	1974-04-18	Optisch aktive isoindolinderivate und verfahren zu ihrer herstellung
DE2217420A1 (de)	1973-10-31	N-thienylmethyl-heterocyclen, deren saeureadditionssalze sowie verfahren zu deren herstellung
CS223895B2 (en)	1983-11-25	Method of making the n-l-allyl-2-pyrolidineylmethyl/-2-methoxy-4-amino-5-methylsulphamoylbenzenamides
AT405180B (de)	1999-06-25	Neue derivate von substituierten 3-cephem-4-carbonsäurederivaten und verfahren zu deren herstellung
JP2577215B2 (ja)	1997-01-29	ベンジルイソキノリン誘導体
SU583749A3 (ru)	1977-12-05	Способ получени производных бициклических карбоновых кислот или их аддативных солей с кислотами
KR100828705B1 (ko)	2008-05-09	리세드론산 나트륨 수화물의 제조방법
PL82724B1 (en)	1975-10-31	N-vinyl-quinolones[gb1282076a]
Arnaiz et al.	1966	N-(2-Chloroethyl)-DL-aspartic Acid and Some Related Amino Acids
JPS6011492A (ja)	1985-01-21	７−（イミダゾ−ル−２−イル）アミノ−３−（１ｈ−１，２，３−トリアゾ−ル−４−イル）−チオメチルセフ−３−エム−４−カルボン酸の結晶状塩基付加塩、その製法及びこの化合物を
CS195747B2 (cs)	1980-02-29	Způsob výroby krystalické bezvodé sodné soli cefamandolu
DE2106500B2 (de)	1979-10-04	deren Salze und Verfahren zu deren Herstellung

Legal Events

Date	Code	Title
1994-12-31	A1OB	Publication of a patent application
1995-06-29	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1997-11-14	OBST	Application withdrawn