DD236523A5 - Verfahren zur herstellung von chinolon- und naphtyridoncarbonsaeuren - Google Patents

Verfahren zur herstellung von chinolon- und naphtyridoncarbonsaeuren Download PDF

Info

Publication number: DD236523A5
Authority: DD; German Democratic Republic
Prior art keywords: chloride; item; cyclocondensation; nitro; yield
Prior art date: 1984-07-18

Application number

DD85278631A

Other languages

German (de)

English (en)

Inventor

Klaus Grohe

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-07-18

Filing date

1985-07-16

Publication date

1986-06-11

1985-07-16 Application filed by ��@��k�� filed Critical ��@��k��

1986-06-11 Publication of DD236523A5 publication Critical patent/DD236523A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 8
238000007363 ring formation reaction Methods 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 9
230000015572 biosynthetic process Effects 0.000 claims abstract description 4
238000003786 synthesis reaction Methods 0.000 claims abstract description 4
-1 amino, methylamino Chemical group 0.000 claims description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 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 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
HETVWNJEAWTHHK-UHFFFAOYSA-N 2,4-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C([N+]([O-])=O)=C1 HETVWNJEAWTHHK-UHFFFAOYSA-N 0.000 claims description 3
ROKOJFJDMZGGHK-UHFFFAOYSA-N 2,6-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1C(Cl)=O ROKOJFJDMZGGHK-UHFFFAOYSA-N 0.000 claims description 3
RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 claims description 3
JJVRWECYWMHJCY-UHFFFAOYSA-N 2-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=CC=C1C(Cl)=O JJVRWECYWMHJCY-UHFFFAOYSA-N 0.000 claims description 3
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 claims description 3
RHUKWLMZLMITBI-UHFFFAOYSA-N 5-chloro-2,4-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(C(Cl)=O)C=C1Cl RHUKWLMZLMITBI-UHFFFAOYSA-N 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
239000012312 sodium hydride Substances 0.000 claims description 3
NNGOTAZYPIEKRC-UHFFFAOYSA-N 2-methoxypyridine-3-carbonyl chloride Chemical compound COC1=NC=CC=C1C(Cl)=O NNGOTAZYPIEKRC-UHFFFAOYSA-N 0.000 claims description 2
AAWPBDPLOOSGGF-UHFFFAOYSA-N 2-methylsulfanylbenzoyl chloride Chemical compound CSC1=CC=CC=C1C(Cl)=O AAWPBDPLOOSGGF-UHFFFAOYSA-N 0.000 claims description 2
VEZPIKNMMOCDRD-UHFFFAOYSA-N 3,5-dichloro-2-methoxybenzoyl chloride Chemical compound COC1=C(Cl)C=C(Cl)C=C1C(Cl)=O VEZPIKNMMOCDRD-UHFFFAOYSA-N 0.000 claims description 2
OKEFBVALFLRAFV-UHFFFAOYSA-N 4-chloro-2-methoxybenzoyl chloride Chemical compound COC1=CC(Cl)=CC=C1C(Cl)=O OKEFBVALFLRAFV-UHFFFAOYSA-N 0.000 claims description 2
MMJYSVRCFSCVCI-UHFFFAOYSA-N 4-chloro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(Cl)=O MMJYSVRCFSCVCI-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 abstract description 8
239000002253 acid Substances 0.000 abstract description 6
150000007513 acids Chemical class 0.000 abstract description 5
YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical class N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 3
229940124350 antibacterial drug Drugs 0.000 abstract description 2
238000007127 saponification reaction Methods 0.000 abstract description 2
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
101150035983 str1 gene Proteins 0.000 abstract 1
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
239000000203 mixture Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
AOEPGTRCCDWMFG-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2-nitrobenzoyl)prop-2-enoate Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(=O)C(C(=O)OCC)=CNC1CC1 AOEPGTRCCDWMFG-UHFFFAOYSA-N 0.000 description 3
ITQFPVUDTFABDH-UHFFFAOYSA-N ethyl 3-ethoxyprop-2-enoate Chemical compound CCOC=CC(=O)OCC ITQFPVUDTFABDH-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
229960003405 ciprofloxacin Drugs 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
YOCKDJIIEWQKQJ-UHFFFAOYSA-N 1-(dimethylamino)-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(N(C)C)C=C(C(O)=O)C(=O)C2=C1 YOCKDJIIEWQKQJ-UHFFFAOYSA-N 0.000 description 1
NWXIFEIWKSUTLL-UHFFFAOYSA-N 1-cyclopropyl-5-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC=CC([N+]([O-])=O)=C2C(=O)C(C(=O)O)=CN1C1CC1 NWXIFEIWKSUTLL-UHFFFAOYSA-N 0.000 description 1
WBHKMAPRABNYBR-UHFFFAOYSA-N 1-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(C)C=C(C(O)=O)C(=O)C2=C1 WBHKMAPRABNYBR-UHFFFAOYSA-N 0.000 description 1
XYBHDXJUJXXONM-UHFFFAOYSA-N 1-methylsulfanylcyclohexa-2,4-diene-1-carbonyl chloride Chemical compound CSC1(C(=O)Cl)CC=CC=C1 XYBHDXJUJXXONM-UHFFFAOYSA-N 0.000 description 1
FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
NFODTGKNJTZWLV-UHFFFAOYSA-N 2-methoxy-5-nitrobenzoyl chloride Chemical compound COC1=CC=C([N+]([O-])=O)C=C1C(Cl)=O NFODTGKNJTZWLV-UHFFFAOYSA-N 0.000 description 1
NMOWGWOAPRKWIR-UHFFFAOYSA-N 3-oxo-4h-quinoxaline-2-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=NC2=C1 NMOWGWOAPRKWIR-UHFFFAOYSA-N 0.000 description 1
LGARXMUVKXDQMY-UHFFFAOYSA-N 4,5-dichloro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1C(Cl)=O LGARXMUVKXDQMY-UHFFFAOYSA-N 0.000 description 1
DXKZKYOSLNTYKH-UHFFFAOYSA-N 7-amino-1h-quinolin-2-one Chemical compound C1=CC(=O)NC2=CC(N)=CC=C21 DXKZKYOSLNTYKH-UHFFFAOYSA-N 0.000 description 1
SSZUMRRPCBEXRX-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-nitro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C([N+]([O-])=O)C=C2C(=O)C(C(=O)O)=CN1C1CC1 SSZUMRRPCBEXRX-UHFFFAOYSA-N 0.000 description 1
LJOCLVIVJNNHON-UHFFFAOYSA-N C(C)OC(CC(C1=C(C=CC=C1)S(=O)(=O)C)=O)=O Chemical compound C(C)OC(CC(C1=C(C=CC=C1)S(=O)(=O)C)=O)=O LJOCLVIVJNNHON-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
JRQJGNRFYHXDCG-UHFFFAOYSA-N [O-][N+](=O)C=1C=CC=C([N+]([O-])=O)C=1C(=O)C(C(=O)OCC)=CNC1CC1 Chemical compound [O-][N+](=O)C=1C=CC=C([N+]([O-])=O)C=1C(=O)C(C(=O)OCC)=CNC1CC1 JRQJGNRFYHXDCG-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
JMZJPUZQASEXRD-UHFFFAOYSA-N ethyl 1-(dimethylamino)-4-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CN(N(C)C)C2=C1 JMZJPUZQASEXRD-UHFFFAOYSA-N 0.000 description 1
FMAQGHRNPNTUEA-UHFFFAOYSA-N ethyl 1-cyclopropyl-4-oxoquinoline-3-carboxylate Chemical compound C12=CC=CC=C2C(=O)C(C(=O)OCC)=CN1C1CC1 FMAQGHRNPNTUEA-UHFFFAOYSA-N 0.000 description 1
OUIIOINZTCLLEE-UHFFFAOYSA-N ethyl 1-ethyl-4-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CN(CC)C2=C1 OUIIOINZTCLLEE-UHFFFAOYSA-N 0.000 description 1
YWXSZQRCUSJNGK-UHFFFAOYSA-N ethyl 1-methyl-4-oxoquinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CN(C)C2=C1 YWXSZQRCUSJNGK-UHFFFAOYSA-N 0.000 description 1
FITNXCCBSPTJIH-UHFFFAOYSA-N ethyl 2-(5-chloro-2,4-dinitrobenzoyl)-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC(Cl)=C([N+]([O-])=O)C=C1[N+]([O-])=O FITNXCCBSPTJIH-UHFFFAOYSA-N 0.000 description 1
OROZKPCJZFDPOP-UHFFFAOYSA-N ethyl 3-(2,2-dimethylhydrazinyl)-2-(2-nitrobenzoyl)prop-2-enoate Chemical compound CCOC(=O)C(=CNN(C)C)C(=O)C1=CC=CC=C1[N+]([O-])=O OROZKPCJZFDPOP-UHFFFAOYSA-N 0.000 description 1
CKDXNAXBSAAOGT-UHFFFAOYSA-N ethyl 3-(2,4-dinitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-] CKDXNAXBSAAOGT-UHFFFAOYSA-N 0.000 description 1
RYIAJRQIIXZYQW-UHFFFAOYSA-N ethyl 3-(2,6-dinitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=C(C=CC=C1[N+](=O)[O-])[N+](=O)[O-] RYIAJRQIIXZYQW-UHFFFAOYSA-N 0.000 description 1
KROPYAVVJDXRPH-UHFFFAOYSA-N ethyl 3-(2-methoxyphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1OC KROPYAVVJDXRPH-UHFFFAOYSA-N 0.000 description 1
OWZNCVIBJQPNEF-UHFFFAOYSA-N ethyl 3-(2-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1[N+]([O-])=O OWZNCVIBJQPNEF-UHFFFAOYSA-N 0.000 description 1
MQGPNBDOORDUJE-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,4-dinitrobenzoyl)prop-2-enoate Chemical compound C=1C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1C(=O)C(C(=O)OCC)=CNC1CC1 MQGPNBDOORDUJE-UHFFFAOYSA-N 0.000 description 1
FLRVKILABVFASU-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2-methoxybenzoyl)prop-2-enoate Chemical compound C=1C=CC=C(OC)C=1C(=O)C(C(=O)OCC)=CNC1CC1 FLRVKILABVFASU-UHFFFAOYSA-N 0.000 description 1
JCIOHVUHTRYZED-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2-methylsulfanylbenzoyl)prop-2-enoate Chemical compound C=1C=CC=C(SC)C=1C(=O)C(C(=O)OCC)=CNC1CC1 JCIOHVUHTRYZED-UHFFFAOYSA-N 0.000 description 1
MHCIIUZUHVHTBR-UHFFFAOYSA-N ethyl 3-(methylamino)-2-(2-nitrobenzoyl)prop-2-enoate Chemical compound CCOC(=O)C(=CNC)C(=O)C1=CC=CC=C1[N+]([O-])=O MHCIIUZUHVHTBR-UHFFFAOYSA-N 0.000 description 1
ZHKLZTFQQISUDG-UHFFFAOYSA-N ethyl 3-ethoxy-2-(2-methylsulfonylbenzoyl)prop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=CC=C1S(C)(=O)=O ZHKLZTFQQISUDG-UHFFFAOYSA-N 0.000 description 1
YBEOYBKKSWUSBR-UHFFFAOYSA-N ethyl 4-oxo-1h-quinoline-3-carboxylate Chemical compound C1=CC=C2C(=O)C(C(=O)OCC)=CNC2=C1 YBEOYBKKSWUSBR-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum 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
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD85278631A 1984-07-18 1985-07-16 Verfahren zur herstellung von chinolon- und naphtyridoncarbonsaeuren DD236523A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3426486A DE3426486A1 (de)	1984-07-18	1984-07-18	Verfahren zur herstellung von chinolon- und naphthyridoncarbonsaeuren

Publications (1)

Publication Number	Publication Date
DD236523A5 true DD236523A5 (de)	1986-06-11

Family

ID=6240970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85278631A DD236523A5 (de)	1984-07-18	1985-07-16	Verfahren zur herstellung von chinolon- und naphtyridoncarbonsaeuren

Country Status (10)

Country	Link
EP (1)	EP0168733A3 (fr)
JP (1)	JPS6144866A (fr)
KR (1)	KR910003617B1 (fr)
DD (1)	DD236523A5 (fr)
DE (1)	DE3426486A1 (fr)
DK (1)	DK325585A (fr)
ES (1)	ES8604521A1 (fr)
HU (1)	HU195643B (fr)
IL (1)	IL75811A (fr)
ZA (1)	ZA855389B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3501247A1 (de) *	1985-01-16	1986-07-17	Bayer Ag, 5090 Leverkusen	Aminoacrylsaeure-derivate
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
ES2059335T3 (es) *	1986-09-12	1994-11-16	Hoffmann La Roche	Derivados de pirido(3,2,1-ij)-1,3,4-benzoxadiazina, procedimiento para su obtencion, preparados farmaceuticos correspondientes y productos intermedios utilizables en el procedimiento.
DE3724466A1 (de) *	1987-07-24	1989-02-02	Bayer Ag	Verfahren zur herstellung von chinoloncarbonsaeuren
WO1992010176A1 (fr) *	1990-12-07	1992-06-25	Taisho Pharmaceutical Co., Ltd.	Agent therapeutique contre les maladies du foie

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2808070A1 (de) *	1978-02-24	1979-08-30	Bayer Ag	Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten

1984
- 1984-07-18 DE DE3426486A patent/DE3426486A1/de not_active Withdrawn
1985
- 1985-07-06 EP EP85108398A patent/EP0168733A3/fr not_active Withdrawn
- 1985-07-11 ES ES545081A patent/ES8604521A1/es not_active Expired
- 1985-07-15 IL IL75811A patent/IL75811A/xx unknown
- 1985-07-16 KR KR1019850005070A patent/KR910003617B1/ko not_active Expired
- 1985-07-16 DD DD85278631A patent/DD236523A5/de not_active IP Right Cessation
- 1985-07-17 JP JP60156169A patent/JPS6144866A/ja active Pending
- 1985-07-17 ZA ZA855389A patent/ZA855389B/xx unknown
- 1985-07-17 HU HU852748A patent/HU195643B/hu not_active IP Right Cessation
- 1985-07-17 DK DK325585A patent/DK325585A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
KR860001071A (ko)	1986-02-22
ES8604521A1 (es)	1986-02-01
HU195643B (en)	1988-06-28
ZA855389B (en)	1986-02-26
JPS6144866A (ja)	1986-03-04
EP0168733A2 (fr)	1986-01-22
HUT38912A (en)	1986-07-28
ES545081A0 (es)	1986-02-01
DK325585D0 (da)	1985-07-17
DK325585A (da)	1986-01-19
KR910003617B1 (ko)	1991-06-07
DE3426486A1 (de)	1986-01-30
IL75811A0 (en)	1985-11-29
EP0168733A3 (fr)	1987-08-26
IL75811A (en)	1988-05-31

Legal Events

Date	Code	Title	Description
2002-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE69221175T2 (de)	1998-01-15	Bizyklische Stickstoffverbindungen, ihre Herstellung, erhaltene Zwischenprodukte, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammensetzungen
EP0117473B1 (fr)	1987-01-28	Acides quinolonecarboxyliques, procédé pour leur préparation et compositions antibactériennes les contenant
EP0520240A1 (fr)	1992-12-30	Dérivés carboxyliques de 7-isoindolinyl-chinolone et naphthylridone
EP0607825A1 (fr)	1994-07-27	Acides 6-H-4-OXO-3-quinoléine-carboxyliques et leurs analoques comme agents antibactériens
EP0078362A2 (fr)	1983-05-11	Acides 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-pipérazino-quinoléine-3-carboxyliques, procédé pour leur préparation et agents bactéricides les contenant
EP0022078B1 (fr)	1984-07-25	Pyrazolo-quinoléines, procédés pour leur préparation, et compositions pharmaceutiques les contenant
EP0310917A2 (fr)	1989-04-12	Acides quinolonecarboxylic fonctionnalisés à C(7) par un atome de carbone et un procédé pour leur préparation
EP0168737A2 (fr)	1986-01-22	Procédé pour la préparation d'acides quinolinone carboxyliques halogénés
EP0117474A1 (fr)	1984-09-05	Acides quinolonecarboxyliques, procédé pour leur préparation et compositions antibactériennes les contenant
DE3688004T2 (de)	1993-06-24	Verfahren zur herstellung herbizider 2-(4,4-disubstituierter-5-oxo-2-imidazolin-2yl)benzoesaeuren, -nicotinsaeuren und chinolin-3-carbonsaeuren, ester und salze.
DE2809720C2 (fr)	1992-01-16
DD236523A5 (de)	1986-06-11	Verfahren zur herstellung von chinolon- und naphtyridoncarbonsaeuren
EP0118854A1 (fr)	1984-09-19	Agent bactéricide contenant des acides quinolinonecarboxyliques
DD281806A5 (de)	1990-08-22	Verfahren zur herstellung von chinoloncarbonsaeuren
DE60316047T2 (de)	2008-05-21	Verfahren zur Herstellung von Olanzapine und ein Zwischenprodukt dafür
FR2632639A1 (fr)	1989-12-15	Derives d'amino-4 carboxy-3 naphtyridines, leur preparation et compositions pharmaceutiques qui les contiennent
DE60122539T2 (de)	2007-05-03	Verfahren zur Herstellung von Chinolincarbonsäuren
EP0121727B1 (fr)	1986-09-24	Agent bactéricide basé en acides quinolinonecarboxyliques
DD223451A5 (de)	1985-06-12	Verfahren zur herstellung von chinolonen
EP0245690A1 (fr)	1987-11-19	Procédé pour la préparation d'acides hydroxy-4 quinoléine-carboxyliques-3
DE69232406T2 (de)	2002-08-22	Verfahren zur Herstellung von Fluoro-Chinolin-3-Carbonsäurederivate
DE60013257T2 (de)	2005-08-11	In 6-stellung substituierte heterochinolincarbonsäure-derivate und ihre additionssalze und verfahren zur herstellung beider
DE60031315T2 (de)	2007-04-26	Verfahren zur Herstellung von Derivaten von i(1,5-Diaryl)pyrazol-3-ylöpropansäure
EP0589318B1 (fr)	1995-11-15	Dérivés antibactériens d'acides de 7-(aminométhyl-oxa-7-azabicyclo(3.3.0)oct-7-yl)quinolone- et -naphthyridone-carboxyliques
EP0345464B1 (fr)	1993-03-17	Procédé pour la préparation d'esters d'acide 3-amino-2-(benzoyl) acrylique substitués ainsi qu'un procédé de préparation d'intermédiaires pour des constituants actifs antibactériens à partir de ces composés