CA2073993A1 - 8-vinyl- and 8-ethinyl-quinolone-carboxylic acids - Google Patents

8-vinyl- and 8-ethinyl-quinolone-carboxylic acids

Info

Publication number: CA2073993A1
Authority: CA; Canada
Prior art keywords: methyl; represents hydrogen; salts; oxo; dihydro
Prior art date: 1991-07-19
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002073993A

Other languages

English (en)

French (fr)

Inventor

Uwe Petersen

Thomas Himmler

Thomas Schenke

Andreas Krebs

Klaus Grohe

Klaus-Dieter Bremm

Karl-Georg Metzger

Rainer Endermann

Hans-Joachim Zeiler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Individual

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

1992-07-16

Publication date

1993-01-20

1992-07-16 Application filed by Individual filed Critical Individual

1993-01-20 Publication of CA2073993A1 publication Critical patent/CA2073993A1/en

Status Abandoned legal-status Critical Current

Links

239000002253 acid Substances 0.000 claims abstract description 31
238000000034 method Methods 0.000 claims abstract description 19
230000008569 process Effects 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 103
239000001257 hydrogen Substances 0.000 claims description 103
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
-1 (5-methyl-2-oxo-1,3-dioxol-4-yl)-methyl Chemical group 0.000 claims description 66
150000002431 hydrogen Chemical class 0.000 claims description 58
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
150000001875 compounds Chemical class 0.000 claims description 40
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
239000000460 chlorine Chemical group 0.000 claims description 15
229910052783 alkali metal Inorganic materials 0.000 claims description 14
239000011737 fluorine Chemical group 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
150000004677 hydrates Chemical class 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 11
150000003378 silver Chemical class 0.000 claims description 11
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 10
125000000217 alkyl group Chemical group 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000004663 dialkyl amino group Chemical group 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 4
SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000005188 oxoalkyl group Chemical group 0.000 claims description 3
125000006656 (C2-C4) alkenyl group Chemical class 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
WNHMKPKMWPJOMW-KPZWWZAWSA-N 7-[(4as,7as)-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-8-ethenyl-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 WNHMKPKMWPJOMW-KPZWWZAWSA-N 0.000 claims description 2
JIPURIIUYIXSCB-UHFFFAOYSA-N 8-bromo-1-ethyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(Br)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 JIPURIIUYIXSCB-UHFFFAOYSA-N 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical class 0.000 claims description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 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
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
229940060037 fluorine Drugs 0.000 claims 8
235000019000 fluorine Nutrition 0.000 claims 8
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
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 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 4
239000003242 anti bacterial agent Substances 0.000 abstract description 4
239000003674 animal food additive Substances 0.000 abstract description 2
238000002844 melting Methods 0.000 description 50
230000008018 melting Effects 0.000 description 50
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 49
239000000203 mixture Substances 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
229910001868 water Inorganic materials 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 34
238000000354 decomposition reaction Methods 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
125000000896 monocarboxylic acid group Chemical group 0.000 description 22
239000000047 product Substances 0.000 description 22
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
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 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000005481 NMR spectroscopy Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000012299 nitrogen atmosphere Substances 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000001117 sulphuric acid Chemical class 0.000 description 8
235000011149 sulphuric acid Nutrition 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
238000001819 mass spectrum Methods 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
241000894006 Bacteria Species 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000006193 alkinyl group Chemical group 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
239000003054 catalyst Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
229920001817 Agar Polymers 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
238000005698 Diels-Alder reaction Methods 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
238000005859 coupling reaction Methods 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
150000004678 hydrides Chemical class 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
244000005700 microbiome Species 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
230000009467 reduction Effects 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
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 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
UMIZTIYZNFUATK-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydropyrrolo[3,4-b][1,4]oxazine Chemical compound O1CCNC2CNCC21 UMIZTIYZNFUATK-UHFFFAOYSA-N 0.000 description 3
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 description 3
KYINPWAJIVTFBW-UHFFFAOYSA-N 3-methylpyrrolidine Chemical compound CC1CCNC1 KYINPWAJIVTFBW-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 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
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 3
239000007789 gas Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
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 3
229910052757 nitrogen Inorganic materials 0.000 description 3
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
244000052769 pathogen Species 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000011282 treatment Methods 0.000 description 3
QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 description 2
MIMQEVRXLNVDIH-UHFFFAOYSA-N 2,2-dimethyl-n-pyrrolidin-3-ylpropan-1-imine Chemical compound CC(C)(C)C=NC1CCNC1 MIMQEVRXLNVDIH-UHFFFAOYSA-N 0.000 description 2
KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
YCAZALSUJDPQPP-UHFFFAOYSA-N 4-oxo-3h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)C=NC2=C1 YCAZALSUJDPQPP-UHFFFAOYSA-N 0.000 description 2
BNLKJYVQFIOOTE-UHFFFAOYSA-N 5-methyl-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine Chemical compound C1N(C)CCC2CNCC21 BNLKJYVQFIOOTE-UHFFFAOYSA-N 0.000 description 2
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150000001337 aliphatic alkines Chemical class 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
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 description 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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229910017052 cobalt Inorganic materials 0.000 description 1
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244000000058 gram-negative pathogen Species 0.000 description 1
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150000003840 hydrochlorides Chemical class 0.000 description 1
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YMIGDZKZDDAGJE-UHFFFAOYSA-N n,5-dimethylpyrrolidin-3-amine Chemical compound CNC1CNC(C)C1 YMIGDZKZDDAGJE-UHFFFAOYSA-N 0.000 description 1
PPNDPGDWMJJOSY-UHFFFAOYSA-N n,6-dimethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CNC1C=C(C)CC2CNCC12 PPNDPGDWMJJOSY-UHFFFAOYSA-N 0.000 description 1
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JVODWNWKCOVKTO-UHFFFAOYSA-N n-methyl-1-pyrrolidin-3-ylmethanamine Chemical compound CNCC1CCNC1 JVODWNWKCOVKTO-UHFFFAOYSA-N 0.000 description 1
NGZYRKGJWYJGRS-UHFFFAOYSA-N n-methylpyrrolidin-3-amine Chemical compound CNC1CCNC1 NGZYRKGJWYJGRS-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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PKVRJCUKSNFIBN-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 PKVRJCUKSNFIBN-UHFFFAOYSA-N 0.000 description 1
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239000003755 preservative agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 description 1
QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
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229910052703 rhodium Inorganic materials 0.000 description 1
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238000013207 serial dilution Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
238000005245 sintering Methods 0.000 description 1
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235000013024 sodium fluoride Nutrition 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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238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
DKBQOIAVVRJJJL-UHFFFAOYSA-N tert-butyl n-buta-1,3-dienylcarbamate Chemical compound CC(C)(C)OC(=O)NC=CC=C DKBQOIAVVRJJJL-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
UPBMYNLFTYQJDO-UHFFFAOYSA-N tributyl(3-methylbut-3-en-1-ynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#CC(C)=C UPBMYNLFTYQJDO-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 1
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
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
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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)

CA002073993A 1991-07-19 1992-07-16 8-vinyl- and 8-ethinyl-quinolone-carboxylic acids Abandoned CA2073993A1 (en)

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
CA2073993A1 true CA2073993A1 (en)	1993-01-20

Family

ID=6436512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002073993A Abandoned CA2073993A1 (en)	1991-07-19	1992-07-16	8-vinyl- and 8-ethinyl-quinolone-carboxylic acids

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 (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7868021B2 (en)	1997-09-15	2011-01-11	Warner Chilcott Company, Llc	Antimicrobial quinolones, their compositions and uses
US8039485B2 (en)	2006-03-28	2011-10-18	Warner Chilcott Company, Llc	Malate salts, and polymorphs of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
US8158798B2 (en)	2006-03-28	2012-04-17	Taigen Biotechnology Co., Ltd.	Coupling process for preparing quinolone intermediates

Families Citing this family (17)

* 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
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
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
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

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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7868021B2 (en)	1997-09-15	2011-01-11	Warner Chilcott Company, Llc	Antimicrobial quinolones, their compositions and uses
US8039485B2 (en)	2006-03-28	2011-10-18	Warner Chilcott Company, Llc	Malate salts, and polymorphs of (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
US8158798B2 (en)	2006-03-28	2012-04-17	Taigen Biotechnology Co., Ltd.	Coupling process for preparing quinolone intermediates

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
RU2077533C1 (ru)	1997-04-20
DK0523512T3 (da)	1997-06-30
CZ219192A3 (en)	1993-02-17
EP0523512B1 (de)	1997-01-15
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

Legal Events

Date	Code	Title	Description
1999-03-18	EEER	Examination request
2003-05-05	FZDE	Discontinued

Publication	Publication Date	Title
AU658901B2 (en)	1995-05-04	8-vinyl- and 8-ethinyl-quinolone-carboxylic acids
AU650316B2 (en)	1994-06-16	Intermediates for preparing 7-(1-pyrrolidinyl) -3-quinolone- and -naphthyridone- carboxylic acid derivatives
CZ396692A3 (en)	1993-08-11	Quinolonecarboxylic and naphthyridonecarboxylic acids derivatives
CA2012681A1 (en)	1990-09-30	Quinolone derivatives, preparation processes thereof, and antibacterial agents containing the same
RU2114832C1 (ru)	1998-07-10	Производные хинолон- и нафтиридон-карбоновой кислоты в виде смеси изомеров или отдельных изомеров, их соли
JPH05213947A (ja)	1993-08-24	７−アザイソインドリニル−キノロン−及びナフチリドンカルボン酸誘導体
SK190192A3 (en)	1995-08-09	Quinoline carboxylic and naphthyridone carboxylic acid derivatives
AU689189B2 (en)	1998-03-26	5-vinyl- and 5-ethinyl-quinolone- carboxylic acids
US5468742A (en)	1995-11-21	8-vinyl- and 9-ethinyl-quinolone-carboxylic acids
CA2108060A1 (en)	1994-04-13	Quinolonecarboxylic acids
JPH04282384A (ja)	1992-10-07	７−（２，７−ジアザビシクロ〔３．３．０〕オクチル）−３−キノロン及びナフチリドンカルボン酸誘導体
KR100371883B1 (ko)	2003-03-29	퀴놀론-및나프티리돈카르복실산유도체
CA2135548A1 (en)	1995-05-17	Derivatives of 1-(2-fluorocyclopropyl)-quinolonecarboxylic acid and 1-(2-fluorocyclopropyl)-naphthyridonecarboxylic acid
CA2106822A1 (en)	1994-03-26	7-(aminomethyl-oxa-7-aza-bicyclo(3.3.0)oct-7-yl) quinolonecarboxylic and 7-(aminomethyl-oxa- 7-aza-bicyclo(3.3.0)oct-7-yl) naphthyridonecarboxylic acid derivatives
NZ250005A (en)	1995-07-26	4-amino-hexahydroisoindoles as process intermediates
IE19970856A1 (en)	2000-02-23	7-(1-Pyrrolidinyl)-3-quinolone and naphthyridone carboxylic acid derivatives, method for their preparation and for substituted mono- and bicyclic pyrrolidine intermediates, and their antibacterial and feed additive compositions
IE84193B1 (en)	2006-04-19	7-(1-Pyrrolidinyl)-3-quinolone and naphthyridone carboxylic acid derivatives, method for their preparation and for substituted mono- and bicyclic pyrrolidine intermediates, and their antibacterial and feed additive compositions

CA2073993A1 - 8-vinyl- and 8-ethinyl-quinolone-carboxylic acids - Google Patents

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Applications Claiming Priority (2)

Publications (1)

Family

ID=6436512

Family Applications (1)

Country Status (22)

Cited By (3)

Families Citing this family (17)

Family Cites Families (4)

Cited By (3)

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