RU2077533C1 - Производные хинолонкарбоновой кислоты, смесь их изомеров или отдельные изомеры, их фармацевтически приемлемые гидраты и соли, способ их получения - Google Patents

Производные хинолонкарбоновой кислоты, смесь их изомеров или отдельные изомеры, их фармацевтически приемлемые гидраты и соли, способ их получения Download PDF

Info

Publication number: RU2077533C1
Authority: RU; Russia
Prior art keywords: hydrogen; methyl; oxo; dihydro; cyclopropyl
Prior art date: 1991-07-19

Application number

SU925052410A

Other languages

English (en)

Russian (ru)

Inventor

Петерсен Уве

Химмлер Томас

Шенке Томас

Кребс Андреас

Грохе Клаус

Бремм Клаус-Дитер

Метцгер Карл-Георг

Эндерманн Райнер

Цейлер Ханс-Йоахим

Original Assignee

Байер Аг

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.)

1991-07-19

Filing date

1992-07-17

Publication date

1997-04-20

1992-07-17 Application filed by Байер Аг filed Critical Байер Аг

1997-04-20 Application granted granted Critical

1997-04-20 Publication of RU2077533C1 publication Critical patent/RU2077533C1/ru

Links

150000003839 salts Chemical class 0.000 title claims description 43
239000000203 mixture Substances 0.000 title claims description 38
150000004677 hydrates Chemical class 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 13
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 title claims description 4
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 112
239000001257 hydrogen Substances 0.000 claims description 112
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
-1 C 1 C 3 alkoxy Chemical group 0.000 claims description 62
150000002431 hydrogen Chemical class 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
125000004432 carbon atom Chemical group C* 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical group 0.000 claims description 25
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 22
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
239000003513 alkali Substances 0.000 claims description 13
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 11
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 11
150000001342 alkaline earth metals Chemical class 0.000 claims description 11
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 11
229910052709 silver Inorganic materials 0.000 claims description 11
239000004332 silver Substances 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
230000000844 anti-bacterial effect Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 4
125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
IHAHRAVLBSKOJU-UHFFFAOYSA-N 1-cyclopropyl-8-ethynyl-6-fluoro-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C2CN(C)CC2CN1C(C=1C#C)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2C1CC1 IHAHRAVLBSKOJU-UHFFFAOYSA-N 0.000 claims description 2
JUUFAIMQBKXVDD-UHFFFAOYSA-N 1-cyclopropyl-8-ethynyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C#C JUUFAIMQBKXVDD-UHFFFAOYSA-N 0.000 claims description 2
JDMSDXWOUURESP-UHFFFAOYSA-N 8-bromo-1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Br)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F JDMSDXWOUURESP-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
YASFOLXBUALGIY-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-8-(3-methylbut-3-en-1-ynyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C#CC(C)=C YASFOLXBUALGIY-UHFFFAOYSA-N 0.000 claims 1
WFBBRNHULOHRAB-UHFFFAOYSA-N 7-(3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl)-1-cyclopropyl-8-ethynyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#C)C(N3CC4OCCNC4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 WFBBRNHULOHRAB-UHFFFAOYSA-N 0.000 claims 1
WDSURWOQULPLDT-UHFFFAOYSA-N 7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-8-ethynyl-6-fluoro-4-oxoquinoline-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(C)(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C#C WDSURWOQULPLDT-UHFFFAOYSA-N 0.000 claims 1
CRXDQVGHZMLPQC-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-ethynyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1C#C CRXDQVGHZMLPQC-UHFFFAOYSA-N 0.000 claims 1
LFOZXTXYMDLZAO-KPZWWZAWSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-8-ethynyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#C)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 LFOZXTXYMDLZAO-KPZWWZAWSA-N 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
239000002994 raw material Substances 0.000 claims 1
230000003993 interaction Effects 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 6
239000000126 substance Substances 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000005160 1H NMR spectroscopy Methods 0.000 description 22
239000000047 product Substances 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
0 *OC(NC=CC=C)=O Chemical compound *OC(NC=CC=C)=O 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000007787 solid Substances 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
OUVMXIYIIMVFQS-UHFFFAOYSA-N 1-cyclopropyl-8-ethynyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#C)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OUVMXIYIIMVFQS-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
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 6
150000002148 esters Chemical class 0.000 description 6
MBIVSPDDSIIZOQ-UHFFFAOYSA-N ethyl 8-bromo-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Br)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 MBIVSPDDSIIZOQ-UHFFFAOYSA-N 0.000 description 6
125000004494 ethyl ester group Chemical group 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
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 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
244000005700 microbiome Species 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000008272 agar Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229960003237 betaine Drugs 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
NRKAHECMMVDYGU-UHFFFAOYSA-N n-methyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CNC1C=CCC2CNCC12 NRKAHECMMVDYGU-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
JGOIIPRSFZFFHG-UHFFFAOYSA-N trimethyl(2-tributylstannylethynyl)silane Chemical group CCCC[Sn](CCCC)(CCCC)C#C[Si](C)(C)C JGOIIPRSFZFFHG-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ZIVHBTPWYSNTBP-UHFFFAOYSA-N 1-cyclopropyl-8-ethenyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C=C)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ZIVHBTPWYSNTBP-UHFFFAOYSA-N 0.000 description 3
DTRLPBIKMIQFEJ-UHFFFAOYSA-N 1-trimethylsilylpyrrole-2,5-dione Chemical compound C[Si](C)(C)N1C(=O)C=CC1=O DTRLPBIKMIQFEJ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000005698 Diels-Alder reaction Methods 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
ZESBQVDNKGGIIJ-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7-difluoro-4-oxo-8-(2-trimethylsilylethynyl)quinoline-3-carboxylate Chemical compound C12=C(C#C[Si](C)(C)C)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 ZESBQVDNKGGIIJ-UHFFFAOYSA-N 0.000 description 3
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PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
101150003085 Pdcl gene Proteins 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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239000004098 Tetracycline Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229940126575 aminoglycoside Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
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150000001649 bromium compounds Chemical class 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000001332 colony forming effect Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
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238000011037 discontinuous sequential dilution Methods 0.000 description 1
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239000008298 dragée Substances 0.000 description 1
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BDBFPPPWXPXQKV-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-4-oxo-8-(2-trimethylsilylethynyl)quinoline-3-carboxylate Chemical compound C12=C(C#C[Si](C)(C)C)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F BDBFPPPWXPXQKV-UHFFFAOYSA-N 0.000 description 1
UCHJWSNOVHXTKU-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F UCHJWSNOVHXTKU-UHFFFAOYSA-N 0.000 description 1
MIQSCPWQRWROKA-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7-difluoro-8-(3-methylbut-3-en-1-ynyl)-4-oxoquinoline-3-carboxylate Chemical compound C12=C(C#CC(C)=C)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 MIQSCPWQRWROKA-UHFFFAOYSA-N 0.000 description 1
SCAUCCWHWDTGFM-UHFFFAOYSA-N ethyl 1-ethyl-6,7-difluoro-4-oxo-8-(2-trimethylsilylethynyl)quinoline-3-carboxylate Chemical compound FC1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1C#C[Si](C)(C)C SCAUCCWHWDTGFM-UHFFFAOYSA-N 0.000 description 1
BCKAYYQQKILFDS-UHFFFAOYSA-N ethyl 2-(3-bromo-2,4,5-trifluorobenzoyl)-3-(ethylamino)prop-2-enoate Chemical compound CCNC=C(C(=O)OCC)C(=O)C1=CC(F)=C(F)C(Br)=C1F BCKAYYQQKILFDS-UHFFFAOYSA-N 0.000 description 1
WJGFKSJXLDSFFC-UHFFFAOYSA-N ethyl 8-bromo-1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Br)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F WJGFKSJXLDSFFC-UHFFFAOYSA-N 0.000 description 1
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GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical class IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
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239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
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230000020477 pH reduction Effects 0.000 description 1
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UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
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230000000284 resting effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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238000005245 sintering Methods 0.000 description 1
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239000011775 sodium fluoride Substances 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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DIQWSFWWYVRXRO-UHFFFAOYSA-N tert-butyl n-(3-methylpyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1(C)CCNC1 DIQWSFWWYVRXRO-UHFFFAOYSA-N 0.000 description 1
XUKALTRSOXMVKA-UHFFFAOYSA-N tert-butyl n-penta-1,3-dienylcarbamate Chemical compound CC=CC=CNC(=O)OC(C)(C)C XUKALTRSOXMVKA-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
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DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Images

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Indole Compounds (AREA)
Peptides Or Proteins (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Paints Or Removers (AREA)
Pyridine Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SU925052410A 1991-07-19 1992-07-17 Производные хинолонкарбоновой кислоты, смесь их изомеров или отдельные изомеры, их фармацевтически приемлемые гидраты и соли, способ их получения RU2077533C1 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP4123918.0		1991-07-19
DE4123918A DE4123918A1 (de)	1991-07-19	1991-07-19	8-vinyl- und 8-ethinyl-chinoloncarbonsaeuren

Publications (1)

Publication Number	Publication Date
RU2077533C1 true RU2077533C1 (ru)	1997-04-20

Family

ID=6436512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU925052410A RU2077533C1 (ru)	1991-07-19	1992-07-17	Производные хинолонкарбоновой кислоты, смесь их изомеров или отдельные изомеры, их фармацевтически приемлемые гидраты и соли, способ их получения

Country Status (22)

Country	Link
EP (1)	EP0523512B1 (2)
JP (1)	JP3174405B2 (2)
KR (1)	KR100240608B1 (2)
AT (1)	ATE147733T1 (2)
AU (1)	AU658901B2 (2)
CA (1)	CA2073993A1 (2)
CZ (1)	CZ282037B6 (2)
DE (2)	DE4123918A1 (2)
DK (1)	DK0523512T3 (2)
ES (1)	ES2097835T3 (2)
FI (1)	FI103043B (2)
GR (1)	GR3022305T3 (2)
HU (1)	HU219910B (2)
IE (1)	IE80557B1 (2)
IL (1)	IL102520A (2)
MX (1)	MX9204110A (2)
NO (1)	NO302886B1 (2)
PL (1)	PL171910B1 (2)
RU (1)	RU2077533C1 (2)
SK (1)	SK219192A3 (2)
TW (1)	TW201309B (2)
ZA (1)	ZA925351B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2757741C1 (ru) *	2021-03-01	2021-10-21	Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН)	Производное ципрофлоксацина, обладающее антибактериальной активностью в отношении антибиотикоустойчивых штаммов микроорганизмов

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4121214A1 (de) *	1991-06-27	1993-01-14	Bayer Ag	7-azaisoindolinyl-chinolon- und -naphthyridoncarbonsaeure-derivate
DE4230804A1 (de) *	1992-09-15	1994-03-17	Bayer Ag	7-Isoindolinyl-chinolon- und -naphthyridon-Derivate
DE4303657A1 (de) *	1993-02-09	1994-08-11	Bayer Ag	Neue Chinolon- und Naphthyridoncarbonsäurederivate
KR950018003A (ko) *	1993-12-09	1995-07-22	스미스클라인 비참 피엘씨	신규한 퀴놀론 유도체 및 그의 제조 방법
DE4418510A1 (de) *	1994-05-27	1995-11-30	Bayer Ag	1,9-überbrückte Thiazolol[3,4-a]chinolinderivate
DE4425659A1 (de) *	1994-07-20	1996-01-25	Bayer Ag	Neue N1-diverse 6-Fluor-8-difluormethoxy substituierte Chinoloncarbonsäuren
DE4427530A1 (de) *	1994-08-04	1996-02-08	Bayer Ag	Chinolon- und Naphthyridoncarbonsäure-Derivate
EP0882049B1 (de) *	1996-02-23	2002-11-20	Bayer Ag	Gegebenenfalls substituierte 8-cyan-1-cyclopropyl-7-(2,8-diazabicyclo- 4.3.0]-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren und ihre derivate
ES2224235T3 (es) *	1996-04-19	2005-03-01	Wakunaga Pharmaceutical Co., Ltd.	Nuevos derivados del acido piridonacarboxilico o sus sales y agentes antibacterianos que contienen los mismos como ingredientes activos.
WO1998024781A1 (en) *	1996-12-04	1998-06-11	Daiichi Pharmaceutical Co., Ltd.	Substituted aminomethylpyrrolidine derivatives
ES2321042T3 (es)	1997-09-15	2009-06-01	THE PROCTER & GAMBLE COMPANY	Quinolonas antimicrobianas, composiciones y usos de las mismas.
SG144936A1 (en)	2003-09-10	2008-08-28	Kyorin Seiyaku Kk	7-(4-substituted-3-cyclopropylaminomethyl-1- pyrrolidinyl)quinolonecarboxylic acid derivative
US7563805B2 (en)	2005-05-19	2009-07-21	Daiichi Pharmaceutical Co., Ltd.	Tri-, tetra-substituted-3-aminopyrrolidine derivative
RU2420524C2 (ru) *	2005-05-19	2011-06-10	Дайити Санкио Компани, Лимитед	Производные три- или тетра-замещенного-3-аминопирролидина
JP5073497B2 (ja) *	2005-09-28	2012-11-14	第一三共株式会社	テトラ置換−５−アザスピロ［２．４］へプタン誘導体の製法およびその光学活性中間体
PL2001862T3 (pl)	2006-03-28	2011-09-30	Warner Chilcott Co Llc	Jabłczany oraz odmiany polimorficzne kwasu (3S,5S)-7-[3-amino-5-metylo-piperydynylo]-1-cyklopropylo-1,4-dihydro-8-metoksy-4-okso-3-chinolinokarboksylowego
WO2007110835A2 (en)	2006-03-28	2007-10-04	The Procter & Gamble Company	A coupling process for preparing quinolone intermediates
CA2688008A1 (en)	2007-05-24	2008-11-27	Kyorin Pharmaceutical Co., Ltd.	Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position
JP7403472B2 (ja)	2018-05-09	2023-12-22	バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング	新規キノリン誘導体

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4123536A (en) *	1977-12-14	1978-10-31	Warner-Lambert Company	Dialkyl ({[3-(alkoxycarbonyl)-1,4-dihydro-4-oxo-8-quinolinyl]amino}methylene)propanedioates
DE3705621C2 (de) *	1986-02-25	1997-01-09	Otsuka Pharma Co Ltd	Heterocyclisch substituierte Chinoloncarbonsäurederivate
JPS62215572A (ja) *	1986-03-17	1987-09-22	Kyorin Pharmaceut Co Ltd	キノロンカルボン酸誘導体
US5047538A (en) *	1990-04-12	1991-09-10	Warner-Lambert Company	Quinolinecarboxylic acid antibacterial agents

1991
- 1991-07-19 DE DE4123918A patent/DE4123918A1/de not_active Withdrawn
1992
- 1992-06-26 TW TW081105031A patent/TW201309B/zh active
- 1992-07-03 NO NO922639A patent/NO302886B1/no not_active IP Right Cessation
- 1992-07-06 EP EP92111454A patent/EP0523512B1/de not_active Expired - Lifetime
- 1992-07-06 DE DE59207880T patent/DE59207880D1/de not_active Expired - Fee Related
- 1992-07-06 AT AT92111454T patent/ATE147733T1/de not_active IP Right Cessation
- 1992-07-06 DK DK92111454.2T patent/DK0523512T3/da active
- 1992-07-06 ES ES92111454T patent/ES2097835T3/es not_active Expired - Lifetime
- 1992-07-13 CZ CS922191A patent/CZ282037B6/cs not_active IP Right Cessation
- 1992-07-13 SK SK2191-92A patent/SK219192A3/sk unknown
- 1992-07-14 MX MX9204110A patent/MX9204110A/es not_active IP Right Cessation
- 1992-07-14 AU AU19663/92A patent/AU658901B2/en not_active Ceased
- 1992-07-16 FI FI923268A patent/FI103043B/fi active IP Right Grant
- 1992-07-16 IL IL102520A patent/IL102520A/xx not_active IP Right Cessation
- 1992-07-16 CA CA002073993A patent/CA2073993A1/en not_active Abandoned
- 1992-07-17 ZA ZA925351A patent/ZA925351B/xx unknown
- 1992-07-17 IE IE922348A patent/IE80557B1/en not_active IP Right Cessation
- 1992-07-17 HU HU9202349A patent/HU219910B/hu not_active IP Right Cessation
- 1992-07-17 RU SU925052410A patent/RU2077533C1/ru active
- 1992-07-17 PL PL92295331A patent/PL171910B1/pl unknown
- 1992-07-17 JP JP21245092A patent/JP3174405B2/ja not_active Expired - Fee Related
- 1992-07-18 KR KR1019920012826A patent/KR100240608B1/ko not_active Expired - Fee Related
1997
- 1997-01-16 GR GR970400065T patent/GR3022305T3/el unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Европейский патент N 0230881, кл. A 61 K 31/495, 1987. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2757741C1 (ru) *	2021-03-01	2021-10-21	Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН)	Производное ципрофлоксацина, обладающее антибактериальной активностью в отношении антибиотикоустойчивых штаммов микроорганизмов

Also Published As

Publication number	Publication date
EP0523512A1 (de)	1993-01-20
HUT61741A (en)	1993-03-01
FI103043B1 (fi)	1999-04-15
KR100240608B1 (ko)	2000-03-02
JPH05262738A (ja)	1993-10-12
SK279221B6 (sk)	1998-08-05
DE59207880D1 (de)	1997-02-27
DK0523512T3 (da)	1997-06-30
CZ219192A3 (en)	1993-02-17
EP0523512B1 (de)	1997-01-15
CA2073993A1 (en)	1993-01-20
NO922639L (no)	1993-01-20
FI103043B (fi)	1999-04-15
IE80557B1 (en)	1998-09-23
KR930002320A (ko)	1993-02-22
PL295331A1 (en)	1993-07-12
ZA925351B (en)	1993-04-28
FI923268L (fi)	1993-01-20
ATE147733T1 (de)	1997-02-15
AU1966392A (en)	1993-01-21
ES2097835T3 (es)	1997-04-16
JP3174405B2 (ja)	2001-06-11
CZ282037B6 (cs)	1997-04-16
TW201309B (2)	1993-03-01
AU658901B2 (en)	1995-05-04
MX9204110A (es)	1993-08-01
FI923268A0 (fi)	1992-07-16
NO302886B1 (no)	1998-05-04
HU219910B (hu)	2001-09-28
IL102520A (en)	1997-07-13
GR3022305T3 (en)	1997-04-30
SK219192A3 (en)	1998-08-05
PL171910B1 (pl)	1997-06-30
DE4123918A1 (de)	1993-01-21
IE922348A1 (en)	1993-01-27
HU9202349D0 (en)	1992-10-28
NO922639D0 (no)	1992-07-03
IL102520A0 (en)	1993-01-14

Publication	Publication Date	Title
RU2114832C1 (ru)	1998-07-10	Производные хинолон- и нафтиридон-карбоновой кислоты в виде смеси изомеров или отдельных изомеров, их соли
FI103043B (fi)	1999-04-15	Menetelmä uusien, terapeuttisesti käyttökelpoisten 8-vinyyli- ja 8-ety nyylikinolonikarboksyylihappojohdannaisten valmistamiseksi sekä menete lmässä käyttökelpoiset välituotteet
RU2056411C1 (ru)	1996-03-20	Производные хинолон- или нафтиридонкарбоновой кислоты или их гидраты, или соли, способ их получения и антимикробная композиция
HU222348B1 (hu)	2003-06-28	7-Izoindolinil-kinolon- és naftiridonszármazékok, előállításukra szolgáló eljárások, köztitermékek és ezeket tartalmazó gyógyszerkészítmények
US4840954A (en)	1989-06-20	6,7-disubstituted 1-cycloproply-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids
US5468742A (en)	1995-11-21	8-vinyl- and 9-ethinyl-quinolone-carboxylic acids
AU689189B2 (en)	1998-03-26	5-vinyl- and 5-ethinyl-quinolone- carboxylic acids
US5545642A (en)	1996-08-13	Derivatives of 1-(2-fluorocyclopropyl)-quinolonecarboxylic acid and 1-(2-fluorocyclopropyl)-naphthridonecarboxylic acid
HRP950469A2 (en)	1997-08-31	Quinoline- and naphthyridone carboxylic acid derivatives
NZ239717A (en)	1992-02-25	Fluorinated alkyl benzoic acids and esters and their preparation

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Publications (1)

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ID=6436512

Family Applications (1)

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Cited By (1)

Families Citing this family (19)

Family Cites Families (4)

Non-Patent Citations (1)

Cited By (1)

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