NZ250823A - Quinolone and naphthyridone carboxylic acid derivatives, medicaments, preparation and pharmaceutical compositions thereof - Google Patents
Quinolone and naphthyridone carboxylic acid derivatives, medicaments, preparation and pharmaceutical compositions thereofInfo
- Publication number
- NZ250823A NZ250823A NZ250823A NZ25082394A NZ250823A NZ 250823 A NZ250823 A NZ 250823A NZ 250823 A NZ250823 A NZ 250823A NZ 25082394 A NZ25082394 A NZ 25082394A NZ 250823 A NZ250823 A NZ 250823A
- Authority
- NZ
- New Zealand
- Prior art keywords
- formula
- straight
- chain
- carbon atoms
- triazol
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims abstract description 11
- -1 naphthyridone carboxylic acid derivatives Chemical class 0.000 title claims description 82
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- 239000002904 solvent Substances 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 150000002431 hydrogen Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000004677 hydrates Chemical class 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000006193 alkinyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 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 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical group [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 156
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- 238000002844 melting Methods 0.000 description 82
- 230000008018 melting Effects 0.000 description 82
- 239000000203 mixture Substances 0.000 description 82
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 48
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- 239000000047 product Substances 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- 238000004440 column chromatography Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000012043 crude product Substances 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000005457 ice water Substances 0.000 description 16
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 14
- 241000700605 Viruses Species 0.000 description 12
- KQKDPROKNKSZOD-UHFFFAOYSA-N ethyl 3-ethoxy-2-(2,4,5-trifluorobenzoyl)prop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC(F)=C(F)C=C1F KQKDPROKNKSZOD-UHFFFAOYSA-N 0.000 description 12
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- HUPWURLXXFQEKJ-UHFFFAOYSA-N 3-(triazol-1-ylmethyl)aniline Chemical compound NC1=CC=CC(CN2N=NC=C2)=C1 HUPWURLXXFQEKJ-UHFFFAOYSA-N 0.000 description 8
- HXNDOWXVGWVDCY-UHFFFAOYSA-N 3-(triazol-2-ylmethyl)aniline Chemical compound NC1=CC=CC(CN2N=CC=N2)=C1 HXNDOWXVGWVDCY-UHFFFAOYSA-N 0.000 description 8
- 241000725303 Human immunodeficiency virus Species 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000011321 prophylaxis Methods 0.000 description 5
- AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- OGSMQKCMSLRGIU-UHFFFAOYSA-N 2-(triazol-1-ylmethyl)aniline Chemical compound NC1=CC=CC=C1CN1N=NC=C1 OGSMQKCMSLRGIU-UHFFFAOYSA-N 0.000 description 4
- 208000030507 AIDS Diseases 0.000 description 4
- 206010001513 AIDS related complex Diseases 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 241001494479 Pecora Species 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- 238000007112 amidation reaction Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 239000011698 potassium fluoride Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 description 3
- XCRWSJGCCFNKLD-UHFFFAOYSA-N 1-[(2-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC=C1CN1N=NC=C1 XCRWSJGCCFNKLD-UHFFFAOYSA-N 0.000 description 3
- IZVYBOAHMLOLBO-UHFFFAOYSA-N 1-[(3-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC(CN2N=NC=C2)=C1 IZVYBOAHMLOLBO-UHFFFAOYSA-N 0.000 description 3
- GSBFMKAAXPOQKT-UHFFFAOYSA-N 2-[(2-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC=C1CN1N=CC=N1 GSBFMKAAXPOQKT-UHFFFAOYSA-N 0.000 description 3
- MWIDSSMQUXHYIW-UHFFFAOYSA-N 2-[(3-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC(CN2N=CC=N2)=C1 MWIDSSMQUXHYIW-UHFFFAOYSA-N 0.000 description 3
- RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 3
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 3
- ZGLQVRIVLWGDNA-UHFFFAOYSA-N 4-(1,2,4-triazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1N=CN=C1 ZGLQVRIVLWGDNA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000283707 Capra Species 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives 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
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 235000003270 potassium fluoride Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XQFGVGNRDPFKFJ-UHFFFAOYSA-N 1,2,3,5,6,7-hexahydropyrrolo[1,2-b]pyridazine Chemical compound N1CCC=C2CCCN21 XQFGVGNRDPFKFJ-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- MPUHOVAVZQKRAW-UHFFFAOYSA-N 2-[(4-nitrophenyl)methyl]triazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1N=CC=N1 MPUHOVAVZQKRAW-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CUSKJWJUMHRIHA-UHFFFAOYSA-N 4-(triazol-1-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1N=NC=C1 CUSKJWJUMHRIHA-UHFFFAOYSA-N 0.000 description 2
- NJRZJZTXQXDDMV-UHFFFAOYSA-N 4-(triazol-2-ylmethyl)aniline Chemical compound C1=CC(N)=CC=C1CN1N=CC=N1 NJRZJZTXQXDDMV-UHFFFAOYSA-N 0.000 description 2
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 2
- XOSOJIXGFRWWKZ-UHFFFAOYSA-N 6,7-difluoro-4-oxo-1-[4-(triazol-1-ylmethyl)phenyl]quinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C(C=C1)=CC=C1CN1C=CN=N1 XOSOJIXGFRWWKZ-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000283073 Equus caballus Species 0.000 description 2
- 241000713800 Feline immunodeficiency virus Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- WMZQQNWJWLRTND-UHFFFAOYSA-N ethyl 6,7-difluoro-1-[4-(imidazol-1-ylmethyl)phenyl]-4-oxoquinoline-3-carboxylate Chemical compound FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)CN1C=NC=C1)C(=O)OCC)=O WMZQQNWJWLRTND-UHFFFAOYSA-N 0.000 description 1
- SUGCDQSBUOPPEW-UHFFFAOYSA-N ethyl 6,7-difluoro-4-oxo-1-[2-(1,2,4-triazol-1-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound FC=1C=C2C(C(=CN(C2=CC1F)C1=C(C=CC=C1)CN1N=CN=C1)C(=O)OCC)=O SUGCDQSBUOPPEW-UHFFFAOYSA-N 0.000 description 1
- RBBDZJLPJPWVOE-UHFFFAOYSA-N ethyl 6,7-difluoro-4-oxo-1-[2-(triazol-2-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)F)C1=C(C=CC=C1)CN1N=CC=N1 RBBDZJLPJPWVOE-UHFFFAOYSA-N 0.000 description 1
- WGOUHCNDOUNGEA-UHFFFAOYSA-N ethyl 6,7-difluoro-4-oxo-1-[3-(triazol-2-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)F)C1=CC(=CC=C1)CN1N=CC=N1 WGOUHCNDOUNGEA-UHFFFAOYSA-N 0.000 description 1
- XAAFYXWFCRBDFO-UHFFFAOYSA-N ethyl 6,7-difluoro-4-oxo-1-[4-(1,2,4-triazol-1-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)F)C1=CC=C(C=C1)CN1N=CN=C1 XAAFYXWFCRBDFO-UHFFFAOYSA-N 0.000 description 1
- KIXSQMVCMWZQIO-UHFFFAOYSA-N ethyl 6,7-difluoro-4-oxo-1-[4-(triazol-2-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)F)C1=CC=C(C=C1)CN1N=CC=N1 KIXSQMVCMWZQIO-UHFFFAOYSA-N 0.000 description 1
- ZQOOXDJMPNXCLK-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-[2-(1,2,4-triazol-1-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N1CCN(CC1)C1=CC=CC=C1)C1=C(C=CC=C1)CN1N=CN=C1 ZQOOXDJMPNXCLK-UHFFFAOYSA-N 0.000 description 1
- UKANBDNCEKKTRW-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-[2-(triazol-2-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound C(C)OC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N1CCN(CC1)C1=CC=CC=C1)C1=C(C=CC=C1)CN1N=CC=N1 UKANBDNCEKKTRW-UHFFFAOYSA-N 0.000 description 1
- HPBOIXWPEKXMQB-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-[3-(triazol-1-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N3CCN(CC3)C4=CC=CC=C4)C5=CC=CC(=C5)CN6C=CN=N6 HPBOIXWPEKXMQB-UHFFFAOYSA-N 0.000 description 1
- OCSHXLMIRFGACP-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-[4-(1,2,4-triazol-1-ylmethyl)phenyl]-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN(C2=NC(=C(C=C2C1=O)F)N3CCN(CC3)C4=CC=CC=C4)C5=CC=C(C=C5)CN6C=NC=N6 OCSHXLMIRFGACP-UHFFFAOYSA-N 0.000 description 1
- WAUGJBPTJUSEFO-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-(4-phenylpiperazin-1-yl)-1-[4-(1,2,4-triazol-1-ylmethyl)phenyl]quinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN(C2=CC(=C(C=C2C1=O)F)N3CCN(CC3)C4=CC=CC=C4)C5=CC=C(C=C5)CN6C=NC=N6 WAUGJBPTJUSEFO-UHFFFAOYSA-N 0.000 description 1
- VWAHIVFKYTYVOT-UHFFFAOYSA-N ethyl 7-chloro-4-oxo-1-[4-(1,2,4-triazol-1-ylmethyl)phenyl]-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN(C2=C(C1=O)C=CC(=N2)Cl)C3=CC=C(C=C3)CN4C=NC=N4 VWAHIVFKYTYVOT-UHFFFAOYSA-N 0.000 description 1
- XWYBYHJIKDFWCE-UHFFFAOYSA-N ethyl 7-chloro-6-fluoro-4-oxo-1-[4-(triazol-1-ylmethyl)phenyl]-1,8-naphthyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN(C2=NC(=C(C=C2C1=O)F)Cl)C3=CC=C(C=C3)CN4C=CN=N4 XWYBYHJIKDFWCE-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000017960 syncytium formation Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BHBIPLOIWQSVID-UHFFFAOYSA-N thiohypofluorous acid Chemical group SF BHBIPLOIWQSVID-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4303657A DE4303657A1 (de) | 1993-02-09 | 1993-02-09 | Neue Chinolon- und Naphthyridoncarbonsäurederivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ250823A true NZ250823A (en) | 1995-04-27 |
Family
ID=6479930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ250823A NZ250823A (en) | 1993-02-09 | 1994-02-04 | Quinolone and naphthyridone carboxylic acid derivatives, medicaments, preparation and pharmaceutical compositions thereof |
Country Status (15)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI9300097B (en) * | 1992-02-27 | 2001-12-31 | Janssen Pharmaceutica Nv | (benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines |
| DE4425648A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Neue 6 und 6,8-substituierte 1-[4-(1H-1,2,4-triazol-l-yl-methyl)phenyl] Chinoloncarbonsäuren |
| DE4425660A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 7-substituierte 1-[4-(1H-1,2,4-triazol-1-yl-methyl)phenyl] substituierte Chinoloncarbonsäuren |
| DE4425650A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Substituierte Triazolylmethylphenylnaphthyridone |
| DE4425659A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Neue N1-diverse 6-Fluor-8-difluormethoxy substituierte Chinoloncarbonsäuren |
| DE4425649A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Neue 1-[4-(Aminomethyl)phenyl] substituierte Chinoloncarbonsäuren |
| DE4425647A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Heterocyclyl-1-phenyl substituierte Chinoloncarbonsäuren |
| US5945431A (en) * | 1996-03-15 | 1999-08-31 | Biochem Therapeutics Incorporated | Cytomegalovirus inhibiting compounds |
| GB9605437D0 (en) * | 1996-03-15 | 1996-05-15 | Iaf Biochem Int | Cytomegalovirus inhibiting compounds |
| US6093737A (en) * | 1996-12-30 | 2000-07-25 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5939439A (en) * | 1996-12-30 | 1999-08-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6127390A (en) * | 1997-10-02 | 2000-10-03 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
| WO1999042106A1 (fr) * | 1998-02-19 | 1999-08-26 | Sankyo Company, Limited | Agent anti-hcmv |
| PE20011349A1 (es) | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
| BR0212864A (pt) | 2001-09-26 | 2004-08-17 | Bayer Pharmaceuticals Corp | Derivados de 1,6-naftiridina como antidiabéticos |
| US7279487B2 (en) * | 2002-01-17 | 2007-10-09 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as HIV integrase inhibitors |
| DE102004035203A1 (de) | 2004-07-21 | 2006-02-16 | Bayer Healthcare Ag | Substituierte Chinolone |
| DE102005030524A1 (de) | 2005-06-30 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone II |
| DE102006005861A1 (de) | 2006-02-09 | 2007-08-23 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone III |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ208470A (en) * | 1983-07-18 | 1988-06-30 | Abbott Lab | 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives and antibacterial compositions containing such |
| EP0470252A4 (en) * | 1989-04-28 | 1992-12-02 | Daiichi Pharmaceutical Co., Ltd. | Anti-hiv drug |
| DE3934082A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Chinoloncarbonsaeurederivate, verfahren zu ihrer herstellung sowie ihre verwendung als antivirale mittel |
| DE4123918A1 (de) * | 1991-07-19 | 1993-01-21 | Bayer Ag | 8-vinyl- und 8-ethinyl-chinoloncarbonsaeuren |
-
1993
- 1993-02-09 DE DE4303657A patent/DE4303657A1/de not_active Withdrawn
-
1994
- 1994-01-12 AU AU53148/94A patent/AU670470B2/en not_active Ceased
- 1994-01-27 ES ES94101223T patent/ES2105362T3/es not_active Expired - Lifetime
- 1994-01-27 AT AT94101223T patent/ATE157088T1/de not_active IP Right Cessation
- 1994-01-27 DE DE59403757T patent/DE59403757D1/de not_active Expired - Fee Related
- 1994-01-27 DK DK94101223.9T patent/DK0612731T3/da active
- 1994-01-27 EP EP94101223A patent/EP0612731B1/de not_active Expired - Lifetime
- 1994-01-28 TW TW083100712A patent/TW248559B/zh active
- 1994-02-04 JP JP6032000A patent/JPH06271570A/ja active Pending
- 1994-02-04 CA CA002115021A patent/CA2115021A1/en not_active Abandoned
- 1994-02-04 NZ NZ250823A patent/NZ250823A/en unknown
- 1994-02-07 IL IL10857194A patent/IL108571A0/xx unknown
- 1994-02-08 ZA ZA94841A patent/ZA94841B/xx unknown
- 1994-02-08 KR KR1019940002423A patent/KR940019702A/ko not_active Withdrawn
- 1994-02-08 HU HU9400352A patent/HUT70044A/hu unknown
-
1997
- 1997-09-10 GR GR970402334T patent/GR3024686T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0612731A1 (de) | 1994-08-31 |
| ATE157088T1 (de) | 1997-09-15 |
| ES2105362T3 (es) | 1997-10-16 |
| HUT70044A (en) | 1995-09-28 |
| DE4303657A1 (de) | 1994-08-11 |
| DK0612731T3 (da) | 1998-03-23 |
| GR3024686T3 (en) | 1997-12-31 |
| AU5314894A (en) | 1994-08-11 |
| JPH06271570A (ja) | 1994-09-27 |
| CA2115021A1 (en) | 1994-08-10 |
| TW248559B (enrdf_load_stackoverflow) | 1995-06-01 |
| AU670470B2 (en) | 1996-07-18 |
| DE59403757D1 (de) | 1997-09-25 |
| EP0612731B1 (de) | 1997-08-20 |
| IL108571A0 (en) | 1994-05-30 |
| ZA94841B (en) | 1994-09-05 |
| HU9400352D0 (en) | 1994-05-30 |
| KR940019702A (ko) | 1994-09-14 |
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