CN1097423A - 喹诺酮-及二氮杂萘酮甲酸衍生物 - Google Patents
喹诺酮-及二氮杂萘酮甲酸衍生物 Download PDFInfo
- Publication number
- CN1097423A CN1097423A CN94101078A CN94101078A CN1097423A CN 1097423 A CN1097423 A CN 1097423A CN 94101078 A CN94101078 A CN 94101078A CN 94101078 A CN94101078 A CN 94101078A CN 1097423 A CN1097423 A CN 1097423A
- Authority
- CN
- China
- Prior art keywords
- oxo
- dihydro
- methyl
- cyclopropyl
- represent hydrogen
- 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.)
- Pending
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- 239000002253 acid Substances 0.000 title claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 65
- -1 phthalazone carboxylic acid derivatives Chemical class 0.000 claims description 58
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 241000894006 Bacteria Species 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- ZWDOGGWAZPIAQF-UHFFFAOYSA-N 1-cyclopropyl-7-fluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound C12=C(C(F)(F)F)C(F)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 ZWDOGGWAZPIAQF-UHFFFAOYSA-N 0.000 claims description 4
- SZESLTPCOVTJOL-UHFFFAOYSA-N 1-cyclopropyl-7-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 SZESLTPCOVTJOL-UHFFFAOYSA-N 0.000 claims description 4
- STXGXKMSBSCFDC-UHFFFAOYSA-N 1-cyclopropyl-7-fluoro-8-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound CC1=C(F)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 STXGXKMSBSCFDC-UHFFFAOYSA-N 0.000 claims description 4
- PNDIMNCSIJHBFG-UHFFFAOYSA-N 8-chloro-1-ethyl-7-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(F)C(Cl)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 PNDIMNCSIJHBFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 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 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-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
- 229940079593 drug Drugs 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000002252 acyl group Chemical group 0.000 claims 3
- HJZQMXIVAIMIQA-UHFFFAOYSA-N 1-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C(=O)O)=CN(F)C2=C1 HJZQMXIVAIMIQA-UHFFFAOYSA-N 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZVSZJAGTJUZSJO-UHFFFAOYSA-N FC=1N(C2=CC=CC=C2C(C1C(=O)O)=O)C1=C(C=C(C=C1)F)F Chemical compound FC=1N(C2=CC=CC=C2C(C1C(=O)O)=O)C1=C(C=C(C=C1)F)F ZVSZJAGTJUZSJO-UHFFFAOYSA-N 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 101
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 5
- 239000003674 animal food additive Substances 0.000 abstract description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 150000007660 quinolones Chemical class 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 87
- 230000008018 melting Effects 0.000 description 87
- 239000000047 product Substances 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000243 solution Substances 0.000 description 36
- 238000003756 stirring Methods 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 239000005457 ice water Substances 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 238000000354 decomposition reaction Methods 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000012043 crude product Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 13
- QMNBWOHIZQXHJZ-UHFFFAOYSA-N 2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound NC1C=CCC2CNCC12 QMNBWOHIZQXHJZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- WZLAZGPMHURVPH-UHFFFAOYSA-N 7-methyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CC1C=CC(N)C2CNCC12 WZLAZGPMHURVPH-UHFFFAOYSA-N 0.000 description 11
- 239000012280 lithium aluminium hydride Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 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 6
- 239000007787 solid Substances 0.000 description 6
- PMGVNGKNLMRPNP-UHFFFAOYSA-N 1-cyclopropyl-5,7-difluoro-4-oxo-8-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound C12=C(C(F)(F)F)C(F)=CC(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 PMGVNGKNLMRPNP-UHFFFAOYSA-N 0.000 description 5
- PCJAYPISTMMNOD-UHFFFAOYSA-N 1-cyclopropyl-7,8-difluoro-4-oxo-5-(trifluoromethyl)quinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=CC(C(F)(F)F)=C2C(=O)C(C(=O)O)=CN1C1CC1 PCJAYPISTMMNOD-UHFFFAOYSA-N 0.000 description 5
- CYVZKNGTMLEZJV-UHFFFAOYSA-N 8-chloro-1-(2,4-difluorophenyl)-7-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F CYVZKNGTMLEZJV-UHFFFAOYSA-N 0.000 description 5
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 4
- NGLDWMSYOVCBJM-DTWKUNHWSA-N 7,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=CC=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F NGLDWMSYOVCBJM-DTWKUNHWSA-N 0.000 description 4
- UCMALGPOKGHHBC-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-7-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 UCMALGPOKGHHBC-UHFFFAOYSA-N 0.000 description 4
- RGAXBLUMQQIVDG-RKDXNWHRSA-N 8-chloro-7-fluoro-1-[(1r,2r)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@H]1F RGAXBLUMQQIVDG-RKDXNWHRSA-N 0.000 description 4
- RGAXBLUMQQIVDG-DTWKUNHWSA-N 8-chloro-7-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F RGAXBLUMQQIVDG-DTWKUNHWSA-N 0.000 description 4
- 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
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
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- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
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- RURDTLWJWHPJGF-UHFFFAOYSA-N ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=C(F)C(Cl)=C1F RURDTLWJWHPJGF-UHFFFAOYSA-N 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
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- 230000002829 reductive effect Effects 0.000 description 4
- DFGOAOUXPTZDHD-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=CC=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F DFGOAOUXPTZDHD-UHFFFAOYSA-N 0.000 description 3
- WXWWWVVJPQQHPP-UHFFFAOYSA-N 1-cyclopropyl-5,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=CC(F)=C2C(=O)C(C(=O)O)=CN1C1CC1 WXWWWVVJPQQHPP-UHFFFAOYSA-N 0.000 description 3
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- AOUDSRSOXFMPNL-UHFFFAOYSA-N ethyl 7-chloro-1-cyclopropyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=NC(Cl)=CC=C2C(=O)C(C(=O)OCC)=CN1C1CC1 AOUDSRSOXFMPNL-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- SFIBLXYGWQPAOY-UHFFFAOYSA-N n,7-dimethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CNC1C=CC(C)C2CNCC12 SFIBLXYGWQPAOY-UHFFFAOYSA-N 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 3
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- XONQGZXKUAYDLP-UHFFFAOYSA-N ethyl 1-ethyl-7,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound FC1=CC=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1F XONQGZXKUAYDLP-UHFFFAOYSA-N 0.000 description 1
- WLDNTAIBAORFKK-UHFFFAOYSA-N ethyl 2-(2,4-difluorobenzoyl)-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=C(F)C=C1F WLDNTAIBAORFKK-UHFFFAOYSA-N 0.000 description 1
- QBTDFSNBBINCIA-UHFFFAOYSA-N ethyl 2-(2,6-dichloropyridine-3-carbonyl)-3-(2,4-difluoroanilino)prop-2-enoate Chemical compound C=1C=C(Cl)N=C(Cl)C=1C(=O)C(C(=O)OCC)=CNC1=CC=C(F)C=C1F QBTDFSNBBINCIA-UHFFFAOYSA-N 0.000 description 1
- OEWIHUFEAFZGBF-UHFFFAOYSA-N ethyl 2-(2,6-dichloropyridine-3-carbonyl)-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=C(Cl)N=C1Cl OEWIHUFEAFZGBF-UHFFFAOYSA-N 0.000 description 1
- GLJKHMRRURRZOH-UHFFFAOYSA-N ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-(cyclopropylamino)prop-2-enoate Chemical compound C=1C=C(F)C(Cl)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 GLJKHMRRURRZOH-UHFFFAOYSA-N 0.000 description 1
- AWMJCEAYEYEAPM-UHFFFAOYSA-N ethyl 2-(3-chloro-2,4-difluorobenzoyl)-3-(ethylamino)prop-2-enoate Chemical compound CCNC=C(C(=O)OCC)C(=O)C1=CC=C(F)C(Cl)=C1F AWMJCEAYEYEAPM-UHFFFAOYSA-N 0.000 description 1
- OPHCSZBDXAIOAT-UHFFFAOYSA-N ethyl 2-(5-chloro-1,4-difluorocyclohexa-2,4-diene-1-carbonyl)-3-(2,4-difluoroanilino)prop-2-enoate Chemical compound C1C(Cl)=C(F)C=CC1(F)C(=O)C(C(=O)OCC)=CNC1=CC=C(F)C=C1F OPHCSZBDXAIOAT-UHFFFAOYSA-N 0.000 description 1
- GDVHCOFRERUXCD-UHFFFAOYSA-N ethyl 2-[2,4-difluoro-3-(trifluoromethyl)benzoyl]-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=C(F)C(C(F)(F)F)=C1F GDVHCOFRERUXCD-UHFFFAOYSA-N 0.000 description 1
- QMNAWBUSDUANLU-UHFFFAOYSA-N ethyl 3-(2,4-difluoroanilino)-2-(2,3,4-trifluorobenzoyl)prop-2-enoate Chemical compound C=1C=C(F)C(F)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1=CC=C(F)C=C1F QMNAWBUSDUANLU-UHFFFAOYSA-N 0.000 description 1
- UFAHWLKYHPRYSY-UHFFFAOYSA-N ethyl 3-(2,4-difluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(F)C=C1F UFAHWLKYHPRYSY-UHFFFAOYSA-N 0.000 description 1
- WVBZLXLYMRZGOY-UHFFFAOYSA-N ethyl 3-(2,6-dichloropyridin-3-yl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)N=C1Cl WVBZLXLYMRZGOY-UHFFFAOYSA-N 0.000 description 1
- QKOLAXGLEDTDRF-UHFFFAOYSA-N ethyl 3-(3-chloro-2,4-difluorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(F)C(Cl)=C1F QKOLAXGLEDTDRF-UHFFFAOYSA-N 0.000 description 1
- OMUYTCWJWMSYAA-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,4-difluoro-3-methylbenzoyl)prop-2-enoate Chemical compound C=1C=C(F)C(C)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 OMUYTCWJWMSYAA-UHFFFAOYSA-N 0.000 description 1
- DQWLIPOKOMMGPU-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,4-difluorobenzoyl)prop-2-enoate Chemical compound C=1C=C(F)C=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 DQWLIPOKOMMGPU-UHFFFAOYSA-N 0.000 description 1
- WXFXYMYBHHIRHD-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,6-dichloropyridine-3-carbonyl)prop-2-enoate Chemical compound C=1C=C(Cl)N=C(Cl)C=1C(=O)C(C(=O)OCC)=CNC1CC1 WXFXYMYBHHIRHD-UHFFFAOYSA-N 0.000 description 1
- ZWFMUONVCCIAOW-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-[2,3,4-trifluoro-6-(trifluoromethyl)benzoyl]prop-2-enoate Chemical compound FC=1C(F)=C(F)C=C(C(F)(F)F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 ZWFMUONVCCIAOW-UHFFFAOYSA-N 0.000 description 1
- GPGYYKSFPDCSGI-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-[2,4-difluoro-4-(trifluoromethyl)cyclohexa-1,5-diene-1-carbonyl]prop-2-enoate Chemical compound FC=1CC(F)(C(F)(F)F)C=CC=1C(=O)C(C(=O)OCC)=CNC1CC1 GPGYYKSFPDCSGI-UHFFFAOYSA-N 0.000 description 1
- NPZGHMKXKFJFPK-UHFFFAOYSA-N ethyl 3-[2,4-difluoro-3-(trifluoromethyl)phenyl]-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(F)C(C(F)(F)F)=C1F NPZGHMKXKFJFPK-UHFFFAOYSA-N 0.000 description 1
- OXBYLEPOTZKAII-WDEREUQCSA-N ethyl 3-[[(1r,2s)-2-fluorocyclopropyl]amino]-2-(2,3,4-trifluorobenzoyl)prop-2-enoate Chemical compound C=1C=C(F)C(F)=C(F)C=1C(=O)C(C(=O)OCC)=CN[C@@H]1C[C@@H]1F OXBYLEPOTZKAII-WDEREUQCSA-N 0.000 description 1
- IUQMSOWINMALDV-UHFFFAOYSA-N ethyl 3-oxo-3-(2,3,4-trifluorophenyl)propanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(F)C(F)=C1F IUQMSOWINMALDV-UHFFFAOYSA-N 0.000 description 1
- FDUQZGWTCCQGRM-UHFFFAOYSA-N ethyl 3-oxo-3-[2,3,4-trifluoro-6-(trifluoromethyl)phenyl]propanoate Chemical compound CCOC(=O)CC(=O)C1=C(F)C(F)=C(F)C=C1C(F)(F)F FDUQZGWTCCQGRM-UHFFFAOYSA-N 0.000 description 1
- JTOZQAGQEZEAPC-UHFFFAOYSA-N ethyl 3-oxo-3-[2,4,6-trifluoro-3-(trifluoromethyl)phenyl]propanoate Chemical compound CCOC(=O)CC(=O)C1=C(F)C=C(F)C(C(F)(F)F)=C1F JTOZQAGQEZEAPC-UHFFFAOYSA-N 0.000 description 1
- VMBYLIPKZSTGAC-UHFFFAOYSA-N ethyl 5-amino-1-cyclopropyl-7,8-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=CC(N)=C2C(=O)C(C(=O)OCC)=CN1C1CC1 VMBYLIPKZSTGAC-UHFFFAOYSA-N 0.000 description 1
- JHVQDLBAUWXOJX-WDEREUQCSA-N ethyl 7,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=CC=C2C(=O)C(C(=O)OCC)=CN1[C@@H]1C[C@@H]1F JHVQDLBAUWXOJX-WDEREUQCSA-N 0.000 description 1
- DJQXXVNZJODYME-UHFFFAOYSA-N ethyl 7-(4-amino-1,3,3a,4,7,7a-hexahydroisoindol-2-yl)-1-cyclopropyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=NC(N3CC4C(N)C=CCC4C3)=CC=C2C(=O)C(C(=O)OCC)=CN1C1CC1 DJQXXVNZJODYME-UHFFFAOYSA-N 0.000 description 1
- VPPMHSXMJAOSQG-UHFFFAOYSA-N ethyl 7-(4-amino-7-methyl-1,3,3a,4,7,7a-hexahydroisoindol-2-yl)-1-cyclopropyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=NC(N3CC4C(C(C=CC4N)C)C3)=CC=C2C(=O)C(C(=O)OCC)=CN1C1CC1 VPPMHSXMJAOSQG-UHFFFAOYSA-N 0.000 description 1
- YLDCLFRHZQOEHY-UHFFFAOYSA-N ethyl 7-chloro-1-(4-fluorophenyl)-5-methyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C12=NC(Cl)=CC(C)=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1 YLDCLFRHZQOEHY-UHFFFAOYSA-N 0.000 description 1
- BCBQHGSVVUUSEW-UHFFFAOYSA-N ethyl 7-chloro-1-ethyl-4-oxoquinoline-3-carboxylate Chemical compound ClC1=CC=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 BCBQHGSVVUUSEW-UHFFFAOYSA-N 0.000 description 1
- KHPNOCNHKUEYRB-UHFFFAOYSA-N ethyl 8-chloro-1-(2,4-difluorophenyl)-7-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F KHPNOCNHKUEYRB-UHFFFAOYSA-N 0.000 description 1
- NQCALTKJASHDST-UHFFFAOYSA-N ethyl 8-chloro-1-cyclopropyl-7-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)OCC)=CN1C1CC1 NQCALTKJASHDST-UHFFFAOYSA-N 0.000 description 1
- BXVLEUAZVOYMBS-UHFFFAOYSA-N ethyl 8-chloro-1-ethyl-7-fluoro-4-oxoquinoline-3-carboxylate Chemical compound FC1=CC=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1Cl BXVLEUAZVOYMBS-UHFFFAOYSA-N 0.000 description 1
- HBMSVHWZTBDGCH-GHMZBOCLSA-N ethyl 8-chloro-7-fluoro-1-[(1r,2r)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)OCC)=CN1[C@@H]1C[C@H]1F HBMSVHWZTBDGCH-GHMZBOCLSA-N 0.000 description 1
- HBMSVHWZTBDGCH-WDEREUQCSA-N ethyl 8-chloro-7-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=C(Cl)C(F)=CC=C2C(=O)C(C(=O)OCC)=CN1[C@@H]1C[C@@H]1F HBMSVHWZTBDGCH-WDEREUQCSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- FFACAHMRMSJQDK-UHFFFAOYSA-N methyl hexa-3,5-dienoate Chemical compound COC(=O)CC=CC=C FFACAHMRMSJQDK-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- ZGHCGRBMRYSXEI-UHFFFAOYSA-N n,5-dimethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound C1C=C(C)C(NC)C2CNCC21 ZGHCGRBMRYSXEI-UHFFFAOYSA-N 0.000 description 1
- UQOQSDFUSIRLCU-UHFFFAOYSA-N n,6,7-trimethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CNC1C=C(C)C(C)C2CNCC12 UQOQSDFUSIRLCU-UHFFFAOYSA-N 0.000 description 1
- DIEWEMZWQWGRNU-UHFFFAOYSA-N n,7a-dimethyl-1,2,3,3a,4,7-hexahydroisoindol-4-amine Chemical compound CNC1C=CCC2(C)CNCC12 DIEWEMZWQWGRNU-UHFFFAOYSA-N 0.000 description 1
- BUYXVBOFHPFEIB-UHFFFAOYSA-N n,n-dimethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CN(C)C1C=CCC2CNCC12 BUYXVBOFHPFEIB-UHFFFAOYSA-N 0.000 description 1
- OSZKJPGPCAAACZ-UHFFFAOYSA-N n-ethyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CCNC1C=CCC2CNCC12 OSZKJPGPCAAACZ-UHFFFAOYSA-N 0.000 description 1
- XBDPVNKGUTWIMJ-UHFFFAOYSA-N n-methyl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine;dihydrochloride Chemical compound Cl.Cl.CNC1C=CCC2CNCC12 XBDPVNKGUTWIMJ-UHFFFAOYSA-N 0.000 description 1
- LYKNTLRUUFDJEK-UHFFFAOYSA-N n-methyl-7-propan-2-yl-2,3,3a,4,7,7a-hexahydro-1h-isoindol-4-amine Chemical compound CNC1C=CC(C(C)C)C2CNCC12 LYKNTLRUUFDJEK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- HSFHMJJDUVEWRQ-UHFFFAOYSA-N penta-2,4-dien-1-amine Chemical compound NCC=CC=C HSFHMJJDUVEWRQ-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
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- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
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- 235000013024 sodium fluoride Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- OEALUTRSNGFHND-UHFFFAOYSA-N tert-butyl n-(3-methylbuta-1,3-dienyl)carbamate Chemical compound CC(=C)C=CNC(=O)OC(C)(C)C OEALUTRSNGFHND-UHFFFAOYSA-N 0.000 description 1
- NXTATKWDIRWILE-UHFFFAOYSA-N tert-butyl n-(4-cyclopropylbuta-1,3-dienyl)carbamate Chemical compound CC(C)(C)OC(=O)NC=CC=CC1CC1 NXTATKWDIRWILE-UHFFFAOYSA-N 0.000 description 1
- IZIHVVDVPIXTBB-UHFFFAOYSA-N tert-butyl n-(5-methylhexa-1,3-dienyl)carbamate Chemical compound CC(C)C=CC=CNC(=O)OC(C)(C)C IZIHVVDVPIXTBB-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
-
- 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
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
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- Wood Science & Technology (AREA)
- Zoology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Fodder In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4301246A DE4301246A1 (de) | 1993-01-19 | 1993-01-19 | Chinolon- und Naphthyridoncarbonsäurederivate |
| DEP4301246.9 | 1993-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1097423A true CN1097423A (zh) | 1995-01-18 |
Family
ID=6478454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101078A Pending CN1097423A (zh) | 1993-01-19 | 1994-01-19 | 喹诺酮-及二氮杂萘酮甲酸衍生物 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5457104A (enExample) |
| EP (1) | EP0607825A1 (enExample) |
| JP (1) | JPH06247962A (enExample) |
| KR (1) | KR940018380A (enExample) |
| CN (1) | CN1097423A (enExample) |
| AU (2) | AU667757B2 (enExample) |
| CA (1) | CA2113513A1 (enExample) |
| CZ (1) | CZ10094A3 (enExample) |
| DE (1) | DE4301246A1 (enExample) |
| FI (1) | FI940216A7 (enExample) |
| HU (1) | HUT68455A (enExample) |
| IL (1) | IL108347A (enExample) |
| MX (1) | MX9400341A (enExample) |
| MY (1) | MY110747A (enExample) |
| NO (1) | NO940039L (enExample) |
| NZ (1) | NZ250681A (enExample) |
| PL (1) | PL301928A1 (enExample) |
| RU (1) | RU2114832C1 (enExample) |
| SK (1) | SK5394A3 (enExample) |
| TW (1) | TW266213B (enExample) |
| ZA (1) | ZA94332B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066245A (zh) * | 2019-04-04 | 2019-07-30 | 山东省联合农药工业有限公司 | 一种喹啉羧酸酯类化合物及其制备方法与用途 |
| CN113929579A (zh) * | 2021-11-22 | 2022-01-14 | 南京一苇医药科技有限公司 | 一种克林沙星关键中间体的制备方法 |
| CN116941624A (zh) * | 2021-04-29 | 2023-10-27 | 山东省联合农药工业有限公司 | 一种杀菌杀虫组合物及其应用 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| DE4230804A1 (de) * | 1992-09-15 | 1994-03-17 | Bayer Ag | 7-Isoindolinyl-chinolon- und -naphthyridon-Derivate |
| DE4427530A1 (de) * | 1994-08-04 | 1996-02-08 | Bayer Ag | Chinolon- und Naphthyridoncarbonsäure-Derivate |
| ES2158963T3 (es) * | 1995-02-09 | 2001-09-16 | Bayer Ag | Derivados de acidos 1,6-naftiridoncarboxilicos. |
| DE19506535A1 (de) * | 1995-02-09 | 1996-08-14 | Bayer Ag | 1,6-Naphthyridoncarbonsäurederivate |
| IL124944A (en) * | 1996-02-09 | 2003-06-24 | Toyama Chemical Co Ltd | Quinolonecarboxylic acid derivatives or their salts and pharmaceutical compositions containing them |
| ATE267191T1 (de) | 1996-10-25 | 2004-06-15 | Daiichi Seiyaku Co | Tricyclische aminderivate |
| US6387928B1 (en) * | 1997-09-15 | 2002-05-14 | The Procter & Gamble Co. | Antimicrobial quinolones, their compositions and uses |
| CA2303389C (en) * | 1997-09-15 | 2007-07-17 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
| JP3346766B2 (ja) * | 1998-04-06 | 2002-11-18 | 富山化学工業株式会社 | キノロンカルボン酸誘導体またはその塩 |
| ES2249489T3 (es) * | 2000-12-14 | 2006-04-01 | THE PROCTER & GAMBLE COMPANY | Quinolonas antimicrobianas. |
| HUP0303457A3 (en) | 2000-12-14 | 2008-05-28 | Procter & Gamble | Antimicrobial 2-pyridones, compositions containing them and their use |
| DE10108750A1 (de) * | 2001-02-23 | 2002-09-05 | Bayer Ag | Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren |
| KR101084521B1 (ko) * | 2006-03-28 | 2011-11-18 | 워너 칠콧 컴퍼니 엘엘씨 | 퀴놀론 중간체를 제조하기 위한 커플링 방법 |
| US7528264B2 (en) * | 2006-03-28 | 2009-05-05 | The Procter & Gamble Company | Hydride reduction process for preparing quinolone intermediates |
| PL2001862T3 (pl) * | 2006-03-28 | 2011-09-30 | Warner Chilcott Co Llc | Jabłczany oraz odmiany polimorficzne kwasu (3S,5S)-7-[3-amino-5-metylo-piperydynylo]-1-cyklopropylo-1,4-dihydro-8-metoksy-4-okso-3-chinolinokarboksylowego |
| CN102459169B (zh) | 2009-05-15 | 2014-12-31 | 莱德克斯制药有限公司 | 氧化还原药物衍生物 |
| MX344529B (es) | 2011-11-08 | 2016-12-19 | Actelion Pharmaceuticals Ltd | Derivados antibioticos de 2 - oxo -oxazolidin - 3, 5 -diilo. |
| JP2019524722A (ja) | 2016-07-11 | 2019-09-05 | バイエル・ファルマ・アクティエンゲゼルシャフト | ７−置換１−ピリジル−ナフチリジン−３−カルボン酸アミドおよびその使用 |
| EP3296298A1 (de) | 2016-09-14 | 2018-03-21 | Bayer Pharma Aktiengesellschaft | 7-substituierte 1-aryl-naphthyridin-3-carbonsäureamide und ihre verwendung |
| JOP20190045A1 (ar) | 2016-09-14 | 2019-03-14 | Bayer Ag | مركبات أميد حمض 1- أريل-نفثيريدين-3-كربوكسيليك مستبدلة في الموضع 7 واستخدامها. |
| AU2020289459A1 (en) | 2019-06-07 | 2022-01-06 | Elanco Tiergesundheit Ag | Bicyclic derivatives for treating endoparasites |
| CN115261104B (zh) * | 2019-08-14 | 2023-08-25 | 胜牌全球产品知识产权有限公司 | 含有无灰tbn分子的润滑剂组合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
| JPS604820B2 (ja) * | 1979-02-26 | 1985-02-06 | 大塚製薬株式会社 | キノリンカルボン酸誘導体 |
| DE3441788A1 (de) * | 1984-11-15 | 1986-05-15 | Bayer Ag, 5090 Leverkusen | Alkyl-1-cyclopropyl-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3615767A1 (de) * | 1986-05-10 | 1987-11-12 | Bayer Ag | Verfahren zur herstellung von 4-hydroxy-chinolin-3-carbonsaeuren |
| US5270340A (en) * | 1988-12-27 | 1993-12-14 | Bayer Aktiengesellschaft | Substituted 2-cyclohexen-1-yl-amine fungicidal and herbicidal agents |
| CA2012681A1 (en) * | 1989-03-31 | 1990-09-30 | Masayasu Okuhira | Quinolone derivatives, preparation processes thereof, and antibacterial agents containing the same |
| CA2030217A1 (en) * | 1989-11-21 | 1991-05-22 | Jun Imose | Pyridone-carboxylic acid derivatives useful as veterinary medicines |
| CA2076982A1 (en) * | 1990-12-27 | 1992-06-28 | Akira Okura | Pyridonecarboxylic acid derivatives |
| DE4120646A1 (de) * | 1991-06-22 | 1992-12-24 | Bayer Ag | 7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate |
| TW209865B (enExample) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| DE4230804A1 (de) * | 1992-09-15 | 1994-03-17 | Bayer Ag | 7-Isoindolinyl-chinolon- und -naphthyridon-Derivate |
-
1993
- 1993-01-19 DE DE4301246A patent/DE4301246A1/de not_active Withdrawn
- 1993-12-20 AU AU52561/93A patent/AU667757B2/en not_active Ceased
- 1993-12-20 TW TW082110770A patent/TW266213B/zh active
-
1994
- 1994-01-05 NO NO940039A patent/NO940039L/no unknown
- 1994-01-07 EP EP94100204A patent/EP0607825A1/de not_active Withdrawn
- 1994-01-07 MX MX9400341A patent/MX9400341A/es not_active Application Discontinuation
- 1994-01-12 US US08/180,948 patent/US5457104A/en not_active Expired - Fee Related
- 1994-01-12 MY MYPI94000082A patent/MY110747A/en unknown
- 1994-01-14 CA CA002113513A patent/CA2113513A1/en not_active Abandoned
- 1994-01-14 NZ NZ250681A patent/NZ250681A/en unknown
- 1994-01-14 JP JP6014979A patent/JPH06247962A/ja active Pending
- 1994-01-17 PL PL94301928A patent/PL301928A1/xx unknown
- 1994-01-17 FI FI940216A patent/FI940216A7/fi unknown
- 1994-01-17 IL IL108347A patent/IL108347A/en not_active IP Right Cessation
- 1994-01-17 RU RU94000714A patent/RU2114832C1/ru active
- 1994-01-17 CZ CZ94100A patent/CZ10094A3/cs unknown
- 1994-01-17 SK SK53-94A patent/SK5394A3/sk unknown
- 1994-01-18 KR KR1019940000818A patent/KR940018380A/ko not_active Withdrawn
- 1994-01-18 HU HU9400143A patent/HUT68455A/hu unknown
- 1994-01-18 ZA ZA94332A patent/ZA94332B/xx unknown
- 1994-01-19 CN CN94101078A patent/CN1097423A/zh active Pending
-
1996
- 1996-01-16 AU AU42033/96A patent/AU4203396A/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066245A (zh) * | 2019-04-04 | 2019-07-30 | 山东省联合农药工业有限公司 | 一种喹啉羧酸酯类化合物及其制备方法与用途 |
| CN110066245B (zh) * | 2019-04-04 | 2020-09-22 | 山东省联合农药工业有限公司 | 一种喹啉羧酸酯类化合物及其制备方法与用途 |
| CN116941624A (zh) * | 2021-04-29 | 2023-10-27 | 山东省联合农药工业有限公司 | 一种杀菌杀虫组合物及其应用 |
| CN113929579A (zh) * | 2021-11-22 | 2022-01-14 | 南京一苇医药科技有限公司 | 一种克林沙星关键中间体的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| PL301928A1 (en) | 1994-07-25 |
| CZ10094A3 (en) | 1995-03-15 |
| FI940216A7 (fi) | 1994-07-20 |
| FI940216A0 (fi) | 1994-01-17 |
| ZA94332B (en) | 1994-08-26 |
| MX9400341A (es) | 1994-08-31 |
| SK5394A3 (en) | 1994-12-07 |
| RU2114832C1 (ru) | 1998-07-10 |
| IL108347A0 (en) | 1994-04-12 |
| NO940039D0 (no) | 1994-01-05 |
| EP0607825A1 (de) | 1994-07-27 |
| DE4301246A1 (de) | 1994-07-21 |
| JPH06247962A (ja) | 1994-09-06 |
| US5457104A (en) | 1995-10-10 |
| HUT68455A (en) | 1995-06-28 |
| AU4203396A (en) | 1996-04-04 |
| NO940039L (no) | 1994-07-20 |
| AU5256193A (en) | 1994-07-28 |
| TW266213B (enExample) | 1995-12-21 |
| IL108347A (en) | 1998-02-22 |
| CA2113513A1 (en) | 1994-07-20 |
| KR940018380A (ko) | 1994-08-16 |
| HU9400143D0 (en) | 1994-05-30 |
| MY110747A (en) | 1999-02-27 |
| NZ250681A (en) | 1995-06-27 |
| AU667757B2 (en) | 1996-04-04 |
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