NO874786L - Optisk aktive gyrasehemmere, deres fremstilling og anvendelse som antibiotika. - Google Patents

Optisk aktive gyrasehemmere, deres fremstilling og anvendelse som antibiotika.

Info

Publication number: NO874786L
Authority: NO; Norway
Prior art keywords: optically active; formula; hydrazinium; alkyl; fluorine
Prior art date: 1986-11-18

Application number

NO874786A

Other languages

English (en)

Norwegian (no)

Other versions

NO874786D0 (no

Inventor

Walter Durckheimer

Karl Leube

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.)

1986-11-18

Filing date

1987-11-17

Publication date

1988-05-19

1987-11-17 Application filed by Hoechst Ag filed Critical Hoechst Ag

1987-11-17 Publication of NO874786D0 publication Critical patent/NO874786D0/no

1988-05-19 Publication of NO874786L publication Critical patent/NO874786L/no

Links

239000002271 gyrase inhibitor Substances 0.000 title claims description 8
239000003242 anti bacterial agent Substances 0.000 title description 3
229940088710 antibiotic agent Drugs 0.000 title description 3
238000002360 preparation method Methods 0.000 title description 3
239000000543 intermediate Substances 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 18
OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 claims description 15
GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
238000005576 amination reaction Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
-1 hydroxy, methoxy, ethoxy Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
229960001699 ofloxacin Drugs 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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 9
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 9
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 7
DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000001302 tertiary amino group Chemical group 0.000 claims description 5
208000035143 Bacterial infection Diseases 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
208000022362 bacterial infectious disease Diseases 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
229920006395 saturated elastomer Chemical group 0.000 claims description 4
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
239000000460 chlorine Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
229960002510 mandelic acid Drugs 0.000 claims description 3
238000006894 reductive elimination reaction Methods 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
239000000825 pharmaceutical preparation Substances 0.000 claims 2
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 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000003776 cleavage reaction Methods 0.000 description 14
230000007017 scission Effects 0.000 description 14
239000000243 solution Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 5
239000013543 active substance Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 4
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229960003237 betaine Drugs 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
229960000583 acetic acid Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
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 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
XUJHKPSBHDQIOD-UHFFFAOYSA-N (2-bromo-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)C(Br)C1C2(C)C XUJHKPSBHDQIOD-UHFFFAOYSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 1
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
DEOGHEOMNKHODW-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C(=O)N)CC(=O)O Chemical compound C1(=CC=CC=C1)CCC(C(=O)N)CC(=O)O DEOGHEOMNKHODW-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
NEAPKZHDYMQZCB-UHFFFAOYSA-N N-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]ethyl]-2-oxo-3H-1,3-benzoxazole-6-carboxamide Chemical compound C1CN(CCN1CCNC(=O)C2=CC3=C(C=C2)NC(=O)O3)C4=CN=C(N=C4)NC5CC6=CC=CC=C6C5 NEAPKZHDYMQZCB-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
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 1
229920001615 Tragacanth Polymers 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
CHKQALUEEULCPZ-UHFFFAOYSA-N amino 2,4,6-trimethylbenzenesulfonate Chemical compound CC1=CC(C)=C(S(=O)(=O)ON)C(C)=C1 CHKQALUEEULCPZ-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
229960003405 ciprofloxacin Drugs 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical group CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
229960002549 enoxacin Drugs 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000006419 fluorocyclopropyl group Chemical group 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000007040 multi-step synthesis reaction Methods 0.000 description 1
MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 1
229960000210 nalidixic acid Drugs 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
229960001180 norfloxacin Drugs 0.000 description 1
SJECIYLGISUNRO-UHFFFAOYSA-N o-diphenylphosphorylhydroxylamine Chemical compound C=1C=CC=CC=1P(=O)(ON)C1=CC=CC=C1 SJECIYLGISUNRO-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 1
229960004236 pefloxacin Drugs 0.000 description 1
FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
150000007660 quinolones Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
230000007306 turnover Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
- 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

Landscapes

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

NO874786A 1986-11-18 1987-11-17 Optisk aktive gyrasehemmere, deres fremstilling og anvendelse som antibiotika. NO874786L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863639465 DE3639465A1 (de)	1986-11-18	1986-11-18	Optisch aktive gyrasehemmer, ihre herstellung und verwendung als antibiotika

Publications (2)

Publication Number	Publication Date
NO874786D0 NO874786D0 (no)	1987-11-17
NO874786L true NO874786L (no)	1988-05-19

Family

ID=6314254

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO874786A NO874786L (no)	1986-11-18	1987-11-17	Optisk aktive gyrasehemmere, deres fremstilling og anvendelse som antibiotika.

Country Status (14)

Country	Link
EP (1)	EP0268223A3 (da)
JP (1)	JPS63135372A (da)
KR (1)	KR880006239A (da)
AU (1)	AU602024B2 (da)
DE (1)	DE3639465A1 (da)
DK (1)	DK602987A (da)
FI (1)	FI875055A7 (da)
HU (1)	HU199848B (da)
IE (1)	IE873091L (da)
IL (1)	IL84508A0 (da)
NO (1)	NO874786L (da)
NZ (1)	NZ222571A (da)
PT (1)	PT86153B (da)
ZA (1)	ZA878593B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS63264419A (ja) *	1986-12-19	1988-11-01	Dai Ichi Seiyaku Co Ltd	含水製剤
JPH0228178A (ja) *	1988-04-23	1990-01-30	Toyama Chem Co Ltd	新規なピリドンカルボン酸誘導体およびその塩並びにそれらの製造法
DE3814552A1 (de) *	1988-04-29	1989-11-09	Hoechst Ag	9-oxo-1,9a-10-triaza-9-hydro-anthracen- verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbmittel
US5104868A (en) *	1988-06-21	1992-04-14	Pfizer Inc.	Tricyclic derivatives of 7-substituted-6-fluoro-1,4-dihydroquinol-4-one-3-carboxylic acids and esters
MY104139A (en) *	1988-08-09	1994-02-28	Daiichi Seiyaku Co	Antimicrobial agent for animals
JPH07501835A (ja) *	1992-10-07	1995-02-23	デリバドス・デル・エチロ・ソシエダッド・アノニマ	オフロキサジン，レボフロキサジン及び誘導体の合成に使用されるベンゾキサジンの製造法
ES2055656B1 (es) *	1992-10-07	1995-11-16	Etilo Derivados	Procedimiento para la obtencion de benzoxazinas utiles para sintesis de ofloxacina, levofloxacina y derivados.
WO1994008967A1 (fr) *	1992-10-09	1994-04-28	Chugai Seiyaku Kabushiki Kaisha	Derive de fluoroquinoleine
SE9904108D0 (sv)	1999-11-15	1999-11-15	New Pharma Research Ab	Nya föreningar
JP2008058417A (ja)	2006-08-29	2008-03-13	Brother Ind Ltd	画像形成装置

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4571396A (en) *	1984-04-16	1986-02-18	Warner-Lambert Company	Antibacterial agents
DE3420798A1 (de) *	1984-06-04	1985-12-05	Bayer Ag, 5090 Leverkusen	7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren
US4604401A (en) *	1984-07-20	1986-08-05	Warner-Lambert Company	Antibacterial agents III
FR2574404B1 (fr) *	1984-12-12	1987-04-24	Provesan Sa	Derives 1-substitues de l'acide 6-fluoro-7-(pyrrol-1-yl)-1,4-dihydro-4-oxoquinoleine-3-carboxylique, leur preparation et leur application en tant que medicaments
JPH0635457B2 (ja) *	1985-06-28	1994-05-11	杏林製薬株式会社	ピリドンカルボン酸誘導体およびその製造方法

1986
- 1986-11-18 DE DE19863639465 patent/DE3639465A1/de not_active Withdrawn
1987
- 1987-11-13 EP EP87116760A patent/EP0268223A3/de not_active Withdrawn
- 1987-11-16 FI FI875055A patent/FI875055A7/fi not_active Application Discontinuation
- 1987-11-17 HU HU875098Q patent/HU199848B/hu unknown
- 1987-11-17 AU AU81285/87A patent/AU602024B2/en not_active Ceased
- 1987-11-17 IL IL84508A patent/IL84508A0/xx unknown
- 1987-11-17 NO NO874786A patent/NO874786L/no unknown
- 1987-11-17 DK DK602987A patent/DK602987A/da not_active Application Discontinuation
- 1987-11-17 PT PT86153A patent/PT86153B/pt not_active IP Right Cessation
- 1987-11-17 ZA ZA878593A patent/ZA878593B/xx unknown
- 1987-11-17 IE IE873091A patent/IE873091L/xx unknown
- 1987-11-17 KR KR870012903A patent/KR880006239A/ko not_active Withdrawn
- 1987-11-17 NZ NZ222571A patent/NZ222571A/xx unknown
- 1987-11-17 JP JP62288602A patent/JPS63135372A/ja active Pending

Also Published As

Publication number	Publication date
DE3639465A1 (de)	1988-05-19
IE873091L (en)	1988-05-18
HU199848B (en)	1990-03-28
AU8128587A (en)	1988-05-19
PT86153A (de)	1987-12-01
EP0268223A3 (de)	1990-03-28
DK602987D0 (da)	1987-11-17
IL84508A0 (en)	1988-04-29
ZA878593B (en)	1988-05-09
KR880006239A (ko)	1988-07-22
EP0268223A2 (de)	1988-05-25
DK602987A (da)	1988-05-19
PT86153B (pt)	1990-11-20
NO874786D0 (no)	1987-11-17
FI875055A7 (fi)	1988-05-19
NZ222571A (en)	1989-11-28
AU602024B2 (en)	1990-09-27
FI875055A0 (fi)	1987-11-16
JPS63135372A (ja)	1988-06-07

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KR910006806B1 (ko)	1991-09-02	퀴놀린 유도체의 제조방법
US4429127A (en)	1984-01-31	Quinoline carboxylic acid derivative
NO874786L (no)	1988-05-19	Optisk aktive gyrasehemmere, deres fremstilling og anvendelse som antibiotika.
WO2001085728A2 (en)	2001-11-15	Antibacterial chiral 8-(substituted piperidino)-benzo [i, j] quinolizines, processes, compositions and methods of treatment
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US6608078B2 (en)	2003-08-19	Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment
EP0591027A1 (fr)	1994-04-06	Dérivés de pipéridine, leur préparation et leur application en thérapeutique
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HU204056B (en)	1991-11-28	Process for producing new azetidine derivatives
US5990106A (en)	1999-11-23	Bicyclic amino group-substituted pyridonecarboxylic acid derivatives, esters thereof and salts thereof, and bicyclic amines useful as intermediates thereof
US5106854A (en)	1992-04-21	Quinolinecarboxylic acids
NO752174L (da)	1975-12-22
US5126337A (en)	1992-06-30	Thiazetoquinoline-3-carboxylic acid derivative and a pharmaceutical composition comprising the same
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US11999726B2 (en)	2024-06-04	5-methyl-4-fluoro-thiazol-2-yl compounds
US4946844A (en)	1990-08-07	Optically active benzoquinolizine compounds, process for preparing same, and antibacterial preparation containing same as active ingredient
KR0166179B1 (ko)	1999-01-15	새로운 퀴놀론 카르복실산 유도체 및 그 제조방법
CN110041329B (zh)	2021-08-10	一种甲苯磺酸妥舒沙星一水合物的制备方法
JPS61122273A (ja)	1986-06-10	新規キノロン化合物ならびにその製造法
NO152788B (no)	1985-08-12	Analogifremgangsmaate for fremstilling av terapeutisk aktive piperazinylbenzoheterocykliske forbindelser
JPH0674260B2 (ja)	1994-09-21	キノリン誘導体、そのエステルおよびその塩