DD236524A5 - Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren - Google Patents
Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren Download PDFInfo
- Publication number
- DD236524A5 DD236524A5 DD85278634A DD27863485A DD236524A5 DD 236524 A5 DD236524 A5 DD 236524A5 DD 85278634 A DD85278634 A DD 85278634A DD 27863485 A DD27863485 A DD 27863485A DD 236524 A5 DD236524 A5 DD 236524A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dichloro
- benzoyl
- fluoro
- cyclopropyl
- vacuo
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- -1 CARBOXYL Chemical class 0.000 title description 12
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 238000007127 saponification reaction Methods 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- UTTLJDQCSWMGRE-UHFFFAOYSA-N 3-(2,4-dichloro-5-fluorophenyl)-3-oxopropanenitrile Chemical compound FC1=CC(C(=O)CC#N)=C(Cl)C=C1Cl UTTLJDQCSWMGRE-UHFFFAOYSA-N 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- COWUKWMKJQAZKT-UHFFFAOYSA-N 2-(2,4-dichloro-5-fluorobenzoyl)-3-methoxyprop-2-enenitrile Chemical compound COC=C(C#N)C(=O)C1=CC(F)=C(Cl)C=C1Cl COWUKWMKJQAZKT-UHFFFAOYSA-N 0.000 description 4
- CTKJZQMXACMUBP-UHFFFAOYSA-N 2-(2,4-dichlorobenzoyl)-3-methoxyprop-2-enenitrile Chemical compound COC=C(C#N)C(=O)C1=CC=C(Cl)C=C1Cl CTKJZQMXACMUBP-UHFFFAOYSA-N 0.000 description 4
- JVSPQQKHEQVTFS-UHFFFAOYSA-N 3-(cyclopropylamino)-2-(2,4-dichlorobenzoyl)prop-2-enenitrile Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C(C#N)=CNC1CC1 JVSPQQKHEQVTFS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- AKSMJAXTUMPWCX-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-3-oxopropanenitrile Chemical compound ClC1=CC=C(C(=O)CC#N)C(Cl)=C1 AKSMJAXTUMPWCX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- FHPCKNJINJXSIC-UHFFFAOYSA-N ethyl 2,4-dichloro-5-fluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(Cl)C=C1Cl FHPCKNJINJXSIC-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- KZCWJHUTTSVCRO-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(Cl)C=C1Cl KZCWJHUTTSVCRO-UHFFFAOYSA-N 0.000 description 2
- RPZXUSJCSDQNTE-UHFFFAOYSA-N 2,4-dichloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(Cl)C=C1Cl RPZXUSJCSDQNTE-UHFFFAOYSA-N 0.000 description 2
- UNDNPOOFIRIQKM-UHFFFAOYSA-N 3-amino-3-cyclopropyl-2-(2,4-dichloro-5-fluorobenzoyl)prop-2-enenitrile Chemical compound C=1C(F)=C(Cl)C=C(Cl)C=1C(=O)C(C#N)=C(N)C1CC1 UNDNPOOFIRIQKM-UHFFFAOYSA-N 0.000 description 2
- SCPPRGZLILXXPJ-UHFFFAOYSA-N 3-chloro-1-(2,4-dichloro-5-fluorophenyl)prop-2-en-1-one Chemical compound FC1=CC(C(=O)C=CCl)=C(Cl)C=C1Cl SCPPRGZLILXXPJ-UHFFFAOYSA-N 0.000 description 2
- FJECNZWCPBGFPM-UHFFFAOYSA-N 5-(2,4-dichloro-5-fluorophenyl)-1,2-oxazole Chemical compound C1=C(Cl)C(F)=CC(C=2ON=CC=2)=C1Cl FJECNZWCPBGFPM-UHFFFAOYSA-N 0.000 description 2
- PISYZMAJMMQIRQ-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 PISYZMAJMMQIRQ-UHFFFAOYSA-N 0.000 description 2
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229940124350 antibacterial drug Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960003405 ciprofloxacin Drugs 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000015096 spirit Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- UUVNGFJBAZPFSQ-UHFFFAOYSA-N 2,3-dichloro-5-fluorobenzoyl chloride Chemical compound FC1=CC(Cl)=C(Cl)C(C(Cl)=O)=C1 UUVNGFJBAZPFSQ-UHFFFAOYSA-N 0.000 description 1
- STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YCJIZVSZSOSLHO-UHFFFAOYSA-N 3-(cyclopropylamino)-2-(2,4-dichloro-5-fluorobenzoyl)prop-2-enenitrile Chemical compound C1=C(Cl)C(F)=CC(C(=O)C(=CNC2CC2)C#N)=C1Cl YCJIZVSZSOSLHO-UHFFFAOYSA-N 0.000 description 1
- DQEGAMGTZFDDPN-UHFFFAOYSA-N 3-amino-2-benzoylprop-2-enenitrile Chemical compound NC=C(C#N)C(=O)C1=CC=CC=C1 DQEGAMGTZFDDPN-UHFFFAOYSA-N 0.000 description 1
- KKLQSWBHUHTJOI-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-4-oxoquinoline-3-carbonitrile Chemical compound C=1C(Cl)=CC=C(C(C(C#N)=C2)=O)C=1N2C1CC1 KKLQSWBHUHTJOI-UHFFFAOYSA-N 0.000 description 1
- QWHZUXPRYZEKBV-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(F)=CC(C(C(C#N)=C2)=O)=C1N2C1CC1 QWHZUXPRYZEKBV-UHFFFAOYSA-N 0.000 description 1
- 206010073478 Anaplastic large-cell lymphoma Diseases 0.000 description 1
- QZNZTVKYKJFMAE-UHFFFAOYSA-N C1=C(C(=CC(C1C(=O)C2C=C(C(=CC2(C=CCl)Cl)Cl)F)(C=CCl)Cl)Cl)F Chemical compound C1=C(C(=CC(C1C(=O)C2C=C(C(=CC2(C=CCl)Cl)Cl)F)(C=CCl)Cl)Cl)F QZNZTVKYKJFMAE-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical class ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ZBBGAUHWTZKKQQ-UHFFFAOYSA-N ethyl 2,4-dichlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1Cl ZBBGAUHWTZKKQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3426483A DE3426483A1 (de) | 1984-07-18 | 1984-07-18 | Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD236524A5 true DD236524A5 (de) | 1986-06-11 |
Family
ID=6240968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85278634A DD236524A5 (de) | 1984-07-18 | 1985-07-16 | Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US4680401A (ja) |
| EP (1) | EP0168737A3 (ja) |
| JP (1) | JPS6136265A (ja) |
| KR (1) | KR910003616B1 (ja) |
| CA (1) | CA1273936A (ja) |
| DD (1) | DD236524A5 (ja) |
| DE (1) | DE3426483A1 (ja) |
| DK (1) | DK325685A (ja) |
| ES (1) | ES8604522A1 (ja) |
| HU (2) | HU194177B (ja) |
| IL (1) | IL75812A (ja) |
| ZA (1) | ZA855385B (ja) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3426483A1 (de) * | 1984-07-18 | 1986-01-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren |
| JPS61118370A (ja) * | 1985-10-30 | 1986-06-05 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸とその製造方法 |
| US4772706A (en) * | 1986-01-13 | 1988-09-20 | Warner-Lambert Company | Process for quinoline-3-carboxylic acid antibacterial agents |
| DE3615767A1 (de) * | 1986-05-10 | 1987-11-12 | Bayer Ag | Verfahren zur herstellung von 4-hydroxy-chinolin-3-carbonsaeuren |
| JPS6416767A (en) * | 1987-07-09 | 1989-01-20 | Dainippon Pharmaceutical Co | 8-halogenoquinoline derivative, its ester and salt |
| DE3853654T2 (de) * | 1987-08-14 | 1996-01-18 | Asahi Glass Co Ltd | Fluorierte Benzoylverbindungen. |
| JPH0780815B2 (ja) * | 1988-08-26 | 1995-08-30 | 旭硝子株式会社 | 核フッ素化芳香族カルボン酸エステル類及びその製造方法 |
| ES2074065T3 (es) * | 1988-08-26 | 1995-09-01 | Asahi Glass Co Ltd | Carboxilatos aromaticos fluorados en el nucleo y sus procedimientos de preparacion. |
| US5656573A (en) * | 1989-09-11 | 1997-08-12 | Rhone-Poulenc Agriculture Ltd. | Herbicidal 4-substituted isoxazoles |
| US5747424A (en) * | 1989-09-11 | 1998-05-05 | Rhone-Poulenc Agriculture Ltd. | Herbicidal 4-substituted isoxazol |
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
| US5650533A (en) * | 1989-09-11 | 1997-07-22 | Rhone-Poulenc Agriculture Ltd. | Intermediates to herbicidal 4-substituted isoxazoles |
| US5028707A (en) * | 1989-11-20 | 1991-07-02 | Board Of Regents, University Of Texas | 4-hydroxyquinaldic acid derivatives |
| US5059709A (en) * | 1990-11-13 | 1991-10-22 | American Cyanamid Company | Process for the synthesis of α-[(dialkylamino)substituted-methylene]-β-oxo-(substituted)propanentriles |
| ES2036136B1 (es) * | 1991-10-16 | 1994-03-01 | Inke Sa | Procedimiento para la obtencion del acido 1-(2,4-difluorofenil)-6-fluoro-7-(3-metilpiperacinil)-4-oxo-1, 4-dihidroquinolin-3-carboxilico y sus sales. |
| DE10021900A1 (de) * | 2000-05-08 | 2001-11-15 | Bayer Ag | Phenyl-substituierte 2-Enamino-Ketonitrile |
| US7778203B2 (en) | 2008-02-01 | 2010-08-17 | Microsoft Corporation | On-demand MAC address lookup |
| CN101456825B (zh) * | 2008-12-30 | 2012-01-11 | 浙江国邦药业有限公司 | 一种丙烯腈衍生物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2726947A (en) * | 1950-12-22 | 1955-12-13 | Goodrich Co B F | Herbicidal compositions comprising alkyl polychlorobenzoates |
| GB830832A (en) * | 1957-02-15 | 1960-03-23 | Ici Ltd | New quinolones and therapeutic compositions containing them |
| US3047574A (en) * | 1960-03-28 | 1962-07-31 | Searle & Co | 2-cyclohexyl-4-(2-hydroxyethyl)-3-methylmorpholine esters of substituted benzoic acids |
| CA947301A (en) * | 1970-01-28 | 1974-05-14 | Sumitomo Chemical Company | Process for the preparation of compound having antibacterial action |
| US4309566A (en) * | 1979-11-05 | 1982-01-05 | Fmc Corporation | Plant regulator |
| DE3036967A1 (de) * | 1980-10-01 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzylalkohol und neue zwischenprodukte hierfuer |
| DE3141659A1 (de) * | 1981-10-21 | 1983-05-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von in o-stellung substituierten fluoraromaten |
| US4665079A (en) * | 1984-02-17 | 1987-05-12 | Warner-Lambert Company | Antibacterial agents |
| DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3248507A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel auf chinoloncarbonsaeure basis |
| US4529725A (en) * | 1984-04-26 | 1985-07-16 | Abbott Laboratories | 1-Pyridine substituted quino-benzothiazine |
| DE3426483A1 (de) * | 1984-07-18 | 1986-01-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von halogenierten chinoloncarbonsaeuren |
| US4686221A (en) * | 1985-10-01 | 1987-08-11 | Kanebo, Ltd. | Quinolinecarboxylic acid compounds and antimicrobial agent containing the same |
-
1984
- 1984-07-18 DE DE3426483A patent/DE3426483A1/de not_active Withdrawn
-
1985
- 1985-06-28 CA CA000486146A patent/CA1273936A/en not_active Expired - Lifetime
- 1985-07-08 EP EP85108421A patent/EP0168737A3/de not_active Withdrawn
- 1985-07-12 US US06/754,563 patent/US4680401A/en not_active Expired - Fee Related
- 1985-07-15 IL IL75812A patent/IL75812A/xx unknown
- 1985-07-16 KR KR1019850005069A patent/KR910003616B1/ko not_active Expired
- 1985-07-16 ES ES545255A patent/ES8604522A1/es not_active Expired
- 1985-07-16 DD DD85278634A patent/DD236524A5/de not_active IP Right Cessation
- 1985-07-17 HU HU852747A patent/HU194177B/hu not_active IP Right Cessation
- 1985-07-17 JP JP15617085A patent/JPS6136265A/ja active Pending
- 1985-07-17 ZA ZA855385A patent/ZA855385B/xx unknown
- 1985-07-17 HU HU872465A patent/HU195488B/hu not_active IP Right Cessation
- 1985-07-17 DK DK325685A patent/DK325685A/da not_active Application Discontinuation
-
1987
- 1987-03-24 US US07/029,939 patent/US4782156A/en not_active Expired - Fee Related
-
1988
- 1988-06-21 US US07/209,751 patent/US4914228A/en not_active Expired - Fee Related
-
1990
- 1990-01-19 US US07/467,630 patent/US4990646A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0168737A3 (de) | 1987-11-25 |
| DE3426483A1 (de) | 1986-01-30 |
| US4990646A (en) | 1991-02-05 |
| US4782156A (en) | 1988-11-01 |
| DK325685A (da) | 1986-01-19 |
| IL75812A0 (en) | 1985-11-29 |
| ES545255A0 (es) | 1986-02-01 |
| KR860001070A (ko) | 1986-02-22 |
| HU194177B (en) | 1988-01-28 |
| CA1273936A (en) | 1990-09-11 |
| KR910003616B1 (ko) | 1991-06-07 |
| US4914228A (en) | 1990-04-03 |
| DK325685D0 (da) | 1985-07-17 |
| JPS6136265A (ja) | 1986-02-20 |
| HU195488B (en) | 1988-05-30 |
| EP0168737A2 (de) | 1986-01-22 |
| IL75812A (en) | 1988-11-15 |
| HUT38911A (en) | 1986-07-28 |
| US4680401A (en) | 1987-07-14 |
| ZA855385B (en) | 1986-02-26 |
| ES8604522A1 (es) | 1986-02-01 |
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