DE2264163C2 - Substituierte 6,7-Dihydro-1-oxo-1H,5H-benzo[ij]chinolizin-2-carbonsäuren - Google Patents
Substituierte 6,7-Dihydro-1-oxo-1H,5H-benzo[ij]chinolizin-2-carbonsäurenInfo
- Publication number
- DE2264163C2 DE2264163C2 DE2264163A DE2264163A DE2264163C2 DE 2264163 C2 DE2264163 C2 DE 2264163C2 DE 2264163 A DE2264163 A DE 2264163A DE 2264163 A DE2264163 A DE 2264163A DE 2264163 C2 DE2264163 C2 DE 2264163C2
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- oxo
- carboxylic acid
- benzo
- quinolizine
- Prior art date
- 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.)
- Expired
Links
- VQLDRXZBNUFGIY-UHFFFAOYSA-N 42835-54-1 Chemical class C1CCC2=CC=CC3=C2N1C=C(C(=O)O)C3=O VQLDRXZBNUFGIY-UHFFFAOYSA-N 0.000 title 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- 239000000203 mixture Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- IAKNLKLKKBPMHN-UHFFFAOYSA-N 4h-quinolizine-2-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CCN21 IAKNLKLKKBPMHN-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- -1 methylenedioxy Chemical group 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- KASNWJJVSFNDJM-UHFFFAOYSA-N 1-azatricyclo[7.3.1.05,13]trideca-3,5,7,9(13),10-pentaene-3-carboxylic acid Chemical compound C1=CCN2CC(C(=O)O)=CC3=CC=CC1=C32 KASNWJJVSFNDJM-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229920000137 polyphosphoric acid Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000004599 antimicrobial 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
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 3
- NITMOXGVLSIHFJ-UHFFFAOYSA-N 1-oxo-1h,5h-benzo[ij]quinolizine-2-carboxylic acid Chemical compound C1C=CC2=CC=CC3=C2N1C=C(C(=O)O)C3=O NITMOXGVLSIHFJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 229930193140 Neomycin Natural products 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229960004927 neomycin Drugs 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- AGPIPWQAOCXUBW-UHFFFAOYSA-N 1-azatricyclo[7.3.1.05,13]trideca-3,5(13),6,8,10-pentaene Chemical compound C1=CCN2CC=CC3=CC=CC1=C32 AGPIPWQAOCXUBW-UHFFFAOYSA-N 0.000 description 1
- GJHQRNOTCPYQDQ-UHFFFAOYSA-N 1-methoxy-3,4-dihydro-2h-quinoline Chemical compound C1=CC=C2N(OC)CCCC2=C1 GJHQRNOTCPYQDQ-UHFFFAOYSA-N 0.000 description 1
- MAQFVOPRKBHTHQ-UHFFFAOYSA-N 10-amino-6,7-dihydro-5-methyl-1-oxo-benzo[ij]quinolizine-2-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=CC=C3N MAQFVOPRKBHTHQ-UHFFFAOYSA-N 0.000 description 1
- COWCJJUEVSTEBW-UHFFFAOYSA-N 2,2-diethoxy-1,3-dioxane-4,6-dione Chemical compound CCOC1(OCC)OC(=O)CC(=O)O1 COWCJJUEVSTEBW-UHFFFAOYSA-N 0.000 description 1
- XBRNQOFIQPGJDQ-UHFFFAOYSA-N 2,4-dimethyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(C)CC(C)C2=C1 XBRNQOFIQPGJDQ-UHFFFAOYSA-N 0.000 description 1
- IHEQGRQCHGIUQE-UHFFFAOYSA-N 2,6-dimethyl-1,2,3,4-tetrahydroquinoline Chemical compound CC1=CC=C2NC(C)CCC2=C1 IHEQGRQCHGIUQE-UHFFFAOYSA-N 0.000 description 1
- XIFZARBGEUHEHW-UHFFFAOYSA-N 2,7-dimethyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=C(C)C=C2NC(C)CCC2=C1 XIFZARBGEUHEHW-UHFFFAOYSA-N 0.000 description 1
- KBEJREJHQMPXJD-UHFFFAOYSA-N 2-ethyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(CC)CCC2=C1 KBEJREJHQMPXJD-UHFFFAOYSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- KQFZOWUXULRDDS-UHFFFAOYSA-N 4h-quinolizine-1-carboxylic acid Chemical class C1=CC=CN2CC=CC(C(=O)O)=C21 KQFZOWUXULRDDS-UHFFFAOYSA-N 0.000 description 1
- SXQFDQPGSZRWIX-UHFFFAOYSA-N 6,7-dihydro-5-ethyl-1-oxo-1h,5h-benzo[ij]quinolizine-2-carboxylic acid Chemical compound C1CC(CC)N2C=C(C(O)=O)C(=O)C3=C2C1=CC=C3 SXQFDQPGSZRWIX-UHFFFAOYSA-N 0.000 description 1
- LUOIOIZZFAHCEE-UHFFFAOYSA-N 6-fluoro-2-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline Chemical compound N1C(C(F)(F)F)CCC2=CC(F)=CC=C21 LUOIOIZZFAHCEE-UHFFFAOYSA-N 0.000 description 1
- LMZQMBQTJLWVBS-UHFFFAOYSA-N 8,12-dimethyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5(13),6,8-tetraene-3-carboxylic acid Chemical compound C1CC(C)N2C=C(C(O)=O)C(=O)C3=C2C1=C(C)C=C3 LMZQMBQTJLWVBS-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 241001261624 Brevundimonas bacteroides Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194022 Streptococcus sp. Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 208000002925 dental caries Diseases 0.000 description 1
- 230000037123 dental health Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation 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
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D215/04—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
-
- 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21440971A | 1971-12-30 | 1971-12-30 | |
| US303254A US3896131A (en) | 1971-12-30 | 1972-11-02 | Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2264163A1 DE2264163A1 (de) | 1973-07-12 |
| DE2264163C2 true DE2264163C2 (de) | 1983-09-15 |
Family
ID=26908979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264163A Expired DE2264163C2 (de) | 1971-12-30 | 1972-12-29 | Substituierte 6,7-Dihydro-1-oxo-1H,5H-benzo[ij]chinolizin-2-carbonsäuren |
Country Status (15)
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1433151A (en) * | 1973-04-05 | 1976-04-22 | Allen & Hanburys Ltd | Benzo-ij-quinolizines |
| JPS584717B2 (ja) * | 1977-11-15 | 1983-01-27 | 大塚製薬株式会社 | ピリド〔３，２，１−ｊｋ〕カルバゾ−ル誘導体 |
| DE2953973C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1978-04-12 | 1989-02-02 | Otsuka Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp | |
| JPS6019910B2 (ja) * | 1979-10-11 | 1985-05-18 | 大塚製薬株式会社 | ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体及びその製造法 |
| US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
| JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
| US4301289A (en) * | 1980-02-19 | 1981-11-17 | Minnesota Mining And Manufacturing Company | Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid |
| US4301288A (en) * | 1980-02-19 | 1981-11-17 | Minnesota Mining And Manufacturing Company | Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid |
| AU524459B2 (en) * | 1980-02-19 | 1982-09-16 | Sanofi Sante Nutrition Animale | Process and intermediates for 6,7-dihydro-9-fluoro-5-methyl- 1-oxo-1h,5h-benzo(ij) quinolizine-2-carboxylic acid |
| US4301291A (en) * | 1980-02-19 | 1981-11-17 | Minnesota Mining And Manufacturing Company | Intermediates for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)quinolizine-2-carboxylic acid |
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| AT380250B (de) * | 1980-12-18 | 1986-04-25 | Otsuka Pharma Co Ltd | Verfahren zur herstellung benzoheterocyclischer verbindungen |
| US4400386A (en) * | 1981-11-06 | 1983-08-23 | Riker Laboratories, Inc. | Antimicrobial derivatives of 8-amino and 8-aminomethyl benzo(ij)quinolizine |
| US4380543A (en) * | 1981-11-06 | 1983-04-19 | Riker Laboratories, Inc. | Antimicrobial 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids |
| US4404207A (en) * | 1981-11-06 | 1983-09-13 | Riker Laboratories, Inc. | Antimicrobial 8-substituted benzo [IJ]quinolizines |
| US4524148A (en) * | 1981-11-06 | 1985-06-18 | Riker Laboratories, Inc. | Antimicrobial 8,9-dihalobenzo[ij]quinolizine carboxylic acids |
| US4456606A (en) * | 1982-05-10 | 1984-06-26 | Minnesota Mining And Manufacturing Company | Substituted naphtho[ij]quinolizines |
| US4443447A (en) * | 1982-10-25 | 1984-04-17 | Riker Laboratories, Inc. | Phenyl-substituted tricyclic antibacterial agents |
| US4585868A (en) * | 1982-11-12 | 1986-04-29 | Riker Laboratories, Inc. | Precursors of 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid |
| US4472405A (en) | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-5,8-dimethyl-9 fluoro-1-oxo-1H, 5H-benzo (ij) quinolizine-2-carboxylic acid and derivatives |
| US4472406A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
| US4567269A (en) * | 1982-11-12 | 1986-01-28 | Riker Laboratories, Inc. | Intermediates for the preparation of 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids |
| HU191508B (en) * | 1982-12-02 | 1987-02-27 | Alkaloida Vegyeszeti Gyar,Hu | Process for preparing new chloromethyl-quinoline derivatives |
| JPS59137482A (ja) * | 1983-01-26 | 1984-08-07 | Otsuka Pharmaceut Co Ltd | ピロロ〔３，２，１，−ｉｊ〕キノリン−５−カルボン酸誘導体 |
| US4568750A (en) * | 1983-03-17 | 1986-02-04 | Riker Laboratories, Inc. | Precursors of 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu |
| US4472407A (en) * | 1983-03-17 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu |
| CA1302413C (en) * | 1986-01-22 | 1992-06-02 | Bruce E. Williams | Process for 6,7-dihydro-5,8-dimethyl-9-fluoro-1-oxo- 1h,5h-benzo[ij]quinolizine-2-carboxylic acid |
| FR2595206B1 (fr) * | 1986-03-04 | 1988-06-24 | Riker Laboratories Inc | Suspensions aqueuses contenant au moins un compose choisi parmi les acides 6,7-dihydro-benzoquinolizine-carboxyliques, et leurs applications pour le traitement des vegetaux |
| FR2644784B1 (fr) * | 1989-03-24 | 1994-04-15 | 3M Sante Laboratoires | Solutions de sels basiques de derives de l'acide 6,7-dihydro-benzoquinolizine-carboxylique pour leur utilisation dans le traitement des semences de vegetaux et semences ainsi traitees |
| HUP9601361A3 (en) * | 1996-05-21 | 1999-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing optically active compounds |
| HUP9601362A3 (en) * | 1996-05-21 | 1999-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing optically active compounds |
| EP1993547B1 (en) * | 2006-03-07 | 2012-08-22 | Wockhardt Limited | Prodrugs of benzoquinolizine-2-carboxylic acid |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172811A (en) * | 1965-03-09 | Quinolone proteus infection treatment | ||
| FR1505313A (fr) * | 1962-04-09 | 1967-12-15 | Norwich Pharma Co | Esters d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation |
| US3524858A (en) * | 1967-05-18 | 1970-08-18 | Warner Lambert Pharmaceutical | 1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid |
| CA942310A (en) * | 1969-07-09 | 1974-02-19 | Mitsuo Nakashita | Preparation of n-substituted 6,7-methylenedioxy-4-quinolone derivatives |
-
0
- BE BE793524D patent/BE793524A/xx not_active IP Right Cessation
-
1972
- 1972-11-02 US US303254A patent/US3896131A/en not_active Expired - Lifetime
- 1972-12-29 GB GB6012272A patent/GB1417129A/en not_active Expired
- 1972-12-29 AR AR245946A patent/AR197106A1/es active
- 1972-12-29 DE DE2264163A patent/DE2264163C2/de not_active Expired
- 1972-12-29 DK DK654372AA patent/DK137331B/da unknown
- 1972-12-29 CH CH1900672A patent/CH582176A5/xx not_active IP Right Cessation
- 1972-12-29 FR FR7246988A patent/FR2166196B1/fr not_active Expired
- 1972-12-29 CA CA160,262A patent/CA999584A/en not_active Expired
- 1972-12-29 SU SU1872002A patent/SU521842A3/ru active
- 1972-12-29 IL IL41211A patent/IL41211A/xx unknown
- 1972-12-29 IE IE1801/72A patent/IE37050B1/xx unknown
- 1972-12-29 NL NLAANVRAGE7217862,A patent/NL176564C/xx not_active IP Right Cessation
- 1972-12-29 SE SE7217142A patent/SE406323B/sv unknown
- 1972-12-29 AU AU50591/72A patent/AU459880B2/en not_active Expired
-
1974
- 1974-04-19 SU SU2056283A patent/SU522183A1/ru active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| NL176564B (nl) | 1984-12-03 |
| IL41211A0 (en) | 1973-02-28 |
| CH582176A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-11-30 |
| AU459880B2 (en) | 1975-03-21 |
| CA999584A (en) | 1976-11-09 |
| SU521842A3 (ru) | 1976-07-15 |
| FR2166196B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-02 |
| US3896131A (en) | 1975-07-22 |
| GB1417129A (en) | 1975-12-10 |
| SU522183A1 (ru) | 1976-07-25 |
| SE406323B (sv) | 1979-02-05 |
| FR2166196A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-08-10 |
| DK137331C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-07-24 |
| IE37050B1 (en) | 1977-04-27 |
| DE2264163A1 (de) | 1973-07-12 |
| DK137331B (da) | 1978-02-20 |
| AR197106A1 (es) | 1974-03-15 |
| AU5059172A (en) | 1974-07-04 |
| NL176564C (nl) | 1985-05-01 |
| IE37050L (en) | 1973-06-30 |
| BE793524A (fr) | 1973-06-29 |
| IL41211A (en) | 1975-10-15 |
| NL7217862A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-03 |
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Legal Events
| Date | Code | Title | Description |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |