SK1012000A3 - Alatrofloxacin parenteral compositions - Google Patents

Alatrofloxacin parenteral compositions Download PDF

Info

Publication number: SK1012000A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; less polar; alatrofloxacin; pharmaceutically acceptable
Prior art date: 1997-08-01

Application number

SK101-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Robert Mark Guinn

John Francis Lambert

Subramanian Sam Guhan

Stanley Walter Walinsky

Original Assignee

Pfizer Prod Inc

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.)

1997-08-01

Filing date

1998-07-23

Publication date

2000-09-12

1998-07-23 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2000-09-12 Publication of SK1012000A3 publication Critical patent/SK1012000A3/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 37
229960000919 alatrofloxacin Drugs 0.000 title description 17
UUZPPAMZDFLUHD-VUJLHGSVSA-N alatrofloxacin Chemical compound C([C@@H]1[C@H]([C@@H]1C1)NC(=O)[C@H](C)NC(=O)[C@@H](N)C)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F UUZPPAMZDFLUHD-VUJLHGSVSA-N 0.000 title 1
239000012535 impurity Substances 0.000 claims abstract description 54
238000000034 method Methods 0.000 claims abstract description 51
150000001875 compounds Chemical class 0.000 claims description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
229920005989 resin Polymers 0.000 claims description 22
239000011347 resin Substances 0.000 claims description 22
230000014759 maintenance of location Effects 0.000 claims description 16
239000007795 chemical reaction product Substances 0.000 claims description 13
208000035143 Bacterial infection Diseases 0.000 claims description 11
208000022362 bacterial infectious disease Diseases 0.000 claims description 11
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
229920005990 polystyrene resin Polymers 0.000 claims description 9
230000002209 hydrophobic effect Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
238000000746 purification Methods 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 5
239000012264 purified product Substances 0.000 claims description 3
CYETUYYEVKNSHZ-LGOOQLFJSA-N chembl1200498 Chemical compound CS(O)(=O)=O.C([C@@H]1[C@H]([C@@H]1C1)NC(=O)[C@H](C)NC(=O)[C@@H](N)C)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F CYETUYYEVKNSHZ-LGOOQLFJSA-N 0.000 abstract description 51
229960003601 alatrofloxacin mesylate Drugs 0.000 abstract description 35
239000000243 solution Substances 0.000 description 35
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
238000004128 high performance liquid chromatography Methods 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
239000008215 water for injection Substances 0.000 description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007787 solid Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
239000002002 slurry Substances 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 7
239000000725 suspension Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
-1 hex-yl Chemical group 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
239000008186 active pharmaceutical agent Substances 0.000 description 5
229940088679 drug related substance Drugs 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
229960000497 trovafloxacin Drugs 0.000 description 5
WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000005259 measurement Methods 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000011179 visual inspection Methods 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
235000019796 monopotassium phosphate Nutrition 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000002245 particle Substances 0.000 description 3
239000013618 particulate matter Substances 0.000 description 3
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
241000124008 Mammalia Species 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000003708 ampul Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229960003405 ciprofloxacin Drugs 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
229940126534 drug product Drugs 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
238000002203 pretreatment Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
BZNDDHWTEVCBAD-BQBZGAKWSA-N (2s)-2-[[(2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OC(C)(C)C BZNDDHWTEVCBAD-BQBZGAKWSA-N 0.000 description 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
GJKOYUNIVIJIEA-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid Chemical compound C12=NC=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F GJKOYUNIVIJIEA-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical compound C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 description 1
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
206010019375 Helicobacter infections Diseases 0.000 description 1
DEFJQIDDEAULHB-IMJSIDKUSA-N L-alanyl-L-alanine Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(O)=O DEFJQIDDEAULHB-IMJSIDKUSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
240000006711 Pistacia vera Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
229960003767 alanine Drugs 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
229910052805 deuterium Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000002510 pyrogen Substances 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229960005021 trovafloxacin mesylate Drugs 0.000 description 1
DYNZICQDCVYXFW-AHZSKCOESA-N trovafloxacin mesylate Chemical compound CS(O)(=O)=O.C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F DYNZICQDCVYXFW-AHZSKCOESA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Oncology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Veterinary Medicine (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK101-2000A 1997-08-01 1998-07-23 Alatrofloxacin parenteral compositions SK1012000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5424697P	1997-08-01	1997-08-01
PCT/IB1998/001122 WO1999006430A1 (fr)	1997-08-01	1998-07-23	Compositions a base d'alatrofloxacine, administrables par voie parenterale

Publications (1)

Publication Number	Publication Date
SK1012000A3 true SK1012000A3 (en)	2000-09-12

Family

ID=21989735

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK101-2000A SK1012000A3 (en)	1997-08-01	1998-07-23	Alatrofloxacin parenteral compositions

Country Status (40)

Country	Link
US (1)	US6194429B1 (fr)
EP (1)	EP1000086B1 (fr)
JP (1)	JP3463928B2 (fr)
KR (1)	KR20010022495A (fr)
CN (1)	CN1265671A (fr)
AP (1)	AP1031A (fr)
AR (1)	AR015417A1 (fr)
AT (1)	ATE259827T1 (fr)
AU (1)	AU734863B2 (fr)
BG (1)	BG104105A (fr)
BR (1)	BR9811580A (fr)
CA (1)	CA2296466C (fr)
CO (1)	CO4970688A1 (fr)
DE (1)	DE69821767T2 (fr)
DK (1)	DK1000086T3 (fr)
DZ (1)	DZ2576A1 (fr)
EA (1)	EA002120B1 (fr)
ES (1)	ES2214716T3 (fr)
GT (1)	GT199800112A (fr)
HN (1)	HN1998000106A (fr)
HR (1)	HRP980417B1 (fr)
HU (1)	HUP0004793A3 (fr)
ID (1)	ID24374A (fr)
IL (1)	IL134156A0 (fr)
IS (1)	IS5339A (fr)
MA (1)	MA24626A1 (fr)
NO (1)	NO20000485L (fr)
NZ (1)	NZ502249A (fr)
OA (1)	OA11281A (fr)
PA (1)	PA8456701A1 (fr)
PE (1)	PE103799A1 (fr)
PL (1)	PL338477A1 (fr)
PT (1)	PT1000086E (fr)
SK (1)	SK1012000A3 (fr)
TN (1)	TNSN98146A1 (fr)
TW (1)	TW538043B (fr)
UY (1)	UY25113A1 (fr)
WO (1)	WO1999006430A1 (fr)
YU (1)	YU2500A (fr)
ZA (1)	ZA986874B (fr)

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EP1575951B1 (fr)	2002-12-06	2014-06-25	Debiopharm International SA	Composes heterocycliques, procedes de production de ceux-ci et utilisation de ceux-ci dans un traitement
WO2004082586A2 (fr)	2003-03-17	2004-09-30	Affinium Pharmaceuticals, Inc.	Compositions comportant plusieurs agents antibiotiques, et leurs procedes de mise en oeuvre
CA2467321A1 (fr) *	2004-05-14	2005-11-14	Paul J. Santerre	Agents de couplage polymeres et polymeres ayant une activite pharmaceutique produits a partir de ceux-ci
US8450307B2 (en)	2004-06-04	2013-05-28	Affinium Pharmaceuticals, Inc.	Therapeutic agents, and methods of making and using the same
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EP2687533B1 (fr)	2006-07-20	2017-07-19	Debiopharm International SA	Dérivés d'acrylamide en tant qu'inhibiteurs de FAB I
WO2008098374A1 (fr) *	2007-02-16	2008-08-21	Affinium Pharmaceuticals, Inc.	Sels, promédicaments et polymorphes d'inhibiteurs de fab 1
KR101720885B1 (ko)	2012-06-19	2017-03-28	데비오팜 인터네셔날 에스 에이	(e)-n-메틸-n-((3-메틸벤조푸란-2-일)메틸)-3-(7-옥소-5,6,7,8-테트라히드로-1,8-나프티리딘-3-일)아크릴아미드의전구약물 유도체
RU2716164C2 (ru) *	2014-04-25	2020-03-06	Наурекс, Инк.	Стабильные композиции нейроактивных пептидов
RS61312B1 (sr)	2016-02-26	2021-02-26	Debiopharm Int Sa	Lek za lečenje infekcija dijabetskog stopala
CA3087898A1 (fr)	2018-02-02	2019-08-08	Ripple Therapeutics Corporation	Formulations de verre comprenant des dimeres steroidiens et utilisations associees
WO2020154815A1 (fr)	2019-02-01	2020-08-06	Ripple Therapeutics Corporation	Formes cristallines de dimères de dexaméthasone et leurs utilisations
MY203711A (en)	2019-02-14	2024-07-15	Debiopharm Int Sa	Afabicin formulation, method for making the same and uses thereof
JP7418475B2 (ja)	2019-06-14	2024-01-19	デバイオファームインターナショナルエス．エー．	バイオフィルムが関与する細菌感染症を治療するための医薬及びその使用
US12509469B2 (en)	2019-08-07	2025-12-30	Ripple Therapeutics Corporation	Compositions and methods for the treatment of pain and dependence disorders
JP2023524494A (ja)	2020-05-01	2023-06-12	リップルセラピューティクスコーポレーション	眼障害を処置するためのヘテロ二量体組成物と方法

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1998
- 1998-07-10 HN HN1998000106A patent/HN1998000106A/es unknown
- 1998-07-23 DE DE1998621767 patent/DE69821767T2/de not_active Expired - Fee Related
- 1998-07-23 AT AT98932444T patent/ATE259827T1/de not_active IP Right Cessation
- 1998-07-23 US US09/403,886 patent/US6194429B1/en not_active Expired - Fee Related
- 1998-07-23 ID IDW20000200A patent/ID24374A/id unknown
- 1998-07-23 ES ES98932444T patent/ES2214716T3/es not_active Expired - Lifetime
- 1998-07-23 KR KR1020007001081A patent/KR20010022495A/ko not_active Ceased
- 1998-07-23 IL IL13415698A patent/IL134156A0/xx unknown
- 1998-07-23 WO PCT/IB1998/001122 patent/WO1999006430A1/fr not_active Ceased
- 1998-07-23 NZ NZ502249A patent/NZ502249A/en unknown
- 1998-07-23 HU HU0004793A patent/HUP0004793A3/hu unknown
- 1998-07-23 EA EA200000086A patent/EA002120B1/ru not_active IP Right Cessation
- 1998-07-23 SK SK101-2000A patent/SK1012000A3/sk unknown
- 1998-07-23 PT PT98932444T patent/PT1000086E/pt unknown
- 1998-07-23 AU AU82368/98A patent/AU734863B2/en not_active Ceased
- 1998-07-23 JP JP2000505185A patent/JP3463928B2/ja not_active Expired - Fee Related
- 1998-07-23 EP EP98932444A patent/EP1000086B1/fr not_active Expired - Lifetime
- 1998-07-23 CN CN98807829A patent/CN1265671A/zh active Pending
- 1998-07-23 YU YU2500A patent/YU2500A/sh unknown
- 1998-07-23 CA CA002296466A patent/CA2296466C/fr not_active Expired - Fee Related
- 1998-07-23 PL PL98338477A patent/PL338477A1/xx not_active Application Discontinuation
- 1998-07-23 BR BR9811580-4A patent/BR9811580A/pt not_active Application Discontinuation
- 1998-07-23 DK DK98932444T patent/DK1000086T3/da active
- 1998-07-24 PE PE1998000667A patent/PE103799A1/es not_active Application Discontinuation
- 1998-07-24 GT GT199800112A patent/GT199800112A/es unknown
- 1998-07-27 TW TW087112260A patent/TW538043B/zh not_active IP Right Cessation
- 1998-07-28 HR HR980417A patent/HRP980417B1/xx not_active IP Right Cessation
- 1998-07-28 UY UY25113A patent/UY25113A1/es unknown
- 1998-07-29 DZ DZ980186A patent/DZ2576A1/fr active
- 1998-07-30 AP APAP/P/1998/001310A patent/AP1031A/en active
- 1998-07-31 CO CO98043890A patent/CO4970688A1/es unknown
- 1998-07-31 MA MA25198A patent/MA24626A1/fr unknown
- 1998-07-31 AR ARP980103814A patent/AR015417A1/es unknown
- 1998-07-31 TN TNTNSN98146A patent/TNSN98146A1/fr unknown
- 1998-07-31 ZA ZA9806874A patent/ZA986874B/xx unknown
- 1998-08-03 PA PA19988456701A patent/PA8456701A1/es unknown
2000
- 2000-01-14 IS IS5339A patent/IS5339A/is unknown
- 2000-01-25 BG BG104105A patent/BG104105A/bg unknown
- 2000-01-26 OA OA1200000019A patent/OA11281A/en unknown
- 2000-01-31 NO NO20000485A patent/NO20000485L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
JP2001512133A (ja)	2001-08-21
PE103799A1 (es)	1999-10-25
HUP0004793A2 (hu)	2001-04-28
DE69821767T2 (de)	2005-01-13
PL338477A1 (en)	2000-11-06
TW538043B (en)	2003-06-21
KR20010022495A (ko)	2001-03-15
NO20000485L (no)	2000-03-27
TNSN98146A1 (fr)	2005-03-15
CA2296466A1 (fr)	1999-02-11
PT1000086E (pt)	2004-05-31
AU8236898A (en)	1999-02-22
IL134156A0 (en)	2001-04-30
NZ502249A (en)	2001-11-30
EP1000086A1 (fr)	2000-05-17
DE69821767D1 (de)	2004-03-25
BG104105A (bg)	2000-08-31
CA2296466C (fr)	2003-04-15
IS5339A (is)	2000-01-14
JP3463928B2 (ja)	2003-11-05
GT199800112A (es)	2000-01-15
DK1000086T3 (da)	2004-05-17
ID24374A (id)	2000-07-13
HN1998000106A (es)	1999-01-08
WO1999006430A1 (fr)	1999-02-11
AU734863B2 (en)	2001-06-21
MA24626A1 (fr)	1999-04-01
CN1265671A (zh)	2000-09-06
YU2500A (sh)	2002-09-19
AP1031A (en)	2001-12-21
HRP980417A2 (en)	1999-08-31
EA002120B1 (ru)	2001-12-24
AR015417A1 (es)	2001-05-02
US6194429B1 (en)	2001-02-27
UY25113A1 (es)	2000-12-29
NO20000485D0 (no)	2000-01-31
CO4970688A1 (es)	2000-11-07
HRP980417B1 (en)	2002-10-31
ZA986874B (en)	2000-01-31
AP9801310A0 (en)	1998-09-30
HUP0004793A3 (en)	2001-10-29
ATE259827T1 (de)	2004-03-15
EP1000086B1 (fr)	2004-02-18
ES2214716T3 (es)	2004-09-16
EA200000086A1 (ru)	2000-08-28
BR9811580A (pt)	2000-08-22
PA8456701A1 (es)	2000-05-24
OA11281A (en)	2002-11-19
DZ2576A1 (fr)	2003-02-22

Publication	Publication Date	Title
SK1012000A3 (en)	2000-09-12	Alatrofloxacin parenteral compositions
IE882363L (en)	1989-02-21	Quinolone and naphthyridine antibacterial agents containing an alpha-amino acid in the side chain of the 7-substituent
WO2012038975A2 (fr)	2012-03-29	Procédé de préparation de maléate de (3ars,12brs)-5-chloro-2-méthyl- 2,3,3a,12b-tétrahydro-1h-dibenzo[2,3:6,7]oxépino[4,5-c]pyrrole et composition pharmaceutique le contenant
RS50919B (sr)	2010-08-31	Derivati merkaptoacetilamida, postupak za njihovo pripremanje i njihova upotreba
OA10293A (en)	1997-09-19	Novel crystal form of anhydrous 7-(Ä1alpha, 5alpha, 6alphaÜ-6-amino-3-azabicyclo Ä3.1.0Ü hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4- dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid methanesulfonic acid salt
EP0516861A1 (fr)	1992-12-09	Derive d'acide pyridonecarboxylique
CA3174145A1 (fr)	2022-11-10	Composes puissants de liaison a l'asgpr permettant la degradation d'immunoglobulines et d'autres proteines
MXPA00001142A (en)	2001-05-07	Alatrofloxacin parenteral compositions
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EP0847400B1 (fr)	2001-11-14	Polymorphes du promedicament 6-n-(l-ala-l-ala)-trovafloxacine
HK1027361A (en)	2001-01-12	Alatrofloxacin parenteral compositions
CZ2000224A3 (cs)	2000-11-15	Alatrofloxacinové paranterální kompozice
EP0930297B1 (fr)	2003-04-23	Un procédé de préparation de naphthyridones et intermédiaires
JPS62267228A (ja)	1987-11-19	抗菌剤
CN118459472A (zh)	2024-08-09	一种异喹啉生物碱类化合物及其制备方法和应用
WO2023134730A1 (fr)	2023-07-20	Composé antiviral amide
WO2000042041A1 (fr)	2000-07-20	Composes a base d'esters de carbapenem
JP2004504322A (ja)	2004-02-12	（４ｒ，５ｓ，６ｓ）−３−（（（２ｒ，３ｒ）−２−（（（（ｓ）−２−アミノ−３−メチル−１−オキソブチル）メチル）テトラヒドロ−３−フラニル）チオ）−６−（（ｒ）−１−ヒドロキシエチル）−４−メチル−７−オキソ−１−アザビシクロ（３．２．０）ヘプタ−２−エン−２−カルボン酸の改良された製造
EP0989119A1 (fr)	2000-03-29	Procede et intermediaires destines a la preparation de sels d'acide trovafloxacincarboxylique
KR20100098439A (ko)	2010-09-06	β-락탐 화합물의 안정형 결정
JP2002029972A (ja)	2002-01-29	カルバペネムエステル化合物を含有する抗菌剤